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Home > Encyclopedia > Dimethylcarbamoyl chloride

Dimethylcarbamoyl chloride

Dimethylcarbamoyl chloride structure

Dimethylcarbamoyl chloride 

structure
  • CAS No:

    79-44-7

  • Formula:

    C3H6ClNO

  • Chemical Name:

    Dimethylcarbamoyl chloride

  • Synonyms:

    Carbamic chloride,N,N-dimethyl-;Carbamic chloride,dimethyl-;Carbamoyl chloride,dimethyl-;N,N-Dimethylcarbamic chloride;Dimethylcarbamyl chloride;N,N-Dimethylcarbamyl chloride;N,N-Dimethylcarbamoyl chloride;(Dimethylamino)carbonyl chloride;Dimethylcarbamic acid chloride;Dimethylcarbamoyl chloride;N,N-Dimethylcarbamidoyl chloride;(N,N-Dimethylamino)carbonyl chloride;N,N-Dimethylcarbamic acid chloride;Dimethylchloroformamide;N,N-Dimethylchloroformamide;NSC 122671;1-Chloro-N,N-dimethylformamide;342009-25-0;2283397-74-8

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

Dimethylcarbamoyl chloride is a useful intermediate in the production of pharmaceuticals, pesticides, and dyes. However, due to its high toxicity that may induce both acute effects and be of cancer risk, it is strictly limited for application
[1]
.


Dimethylcarbamoyl chloride appears as a colorless to yellow liquid with a pungent odor. Burns to skin, eyes and mucous membranes. A lachrymator. Used to make dyes and pharmaceuticals.|Clear, colorless liquid.


Dimethylcarbamoyl chloride appears as a colorless to yellow liquid with a pungent odor. Burns to skin, eyes and mucous membranes. A lachrymator. Used to make dyes and pharmaceuticals.|Dimethylcarbamoyl chloride is a halide. It derives from a carbamic acid.|Dimethylcarbamoyl chloride is used as an intermediate in the production of pharmaceuticals, pesticides, and dyes. Acute (short-term) inhalation exposure to dimethylcarbamoyl chloride has been observed to result in damaged mucous membranes of the nose, throat, and lungs, and cause difficulty in breathing in rats. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic health effects of dimethylcarbamoyl chloride in humans. Nasal tract carcinomas have been observed in rats and male hamsters following inhalation exposure. EPA has not classified dimethylcarbamoyl chloride for potential carcinogenicity.|Dimethylcarbamoyl Chloride is a colorless liquid that is rapidly hydrolyzed in water. Dimethylcarbamoyl chloride is used as a chemical intermediate in the production of pharmaceuticals, pesticides and dyes. Exposure to this substance results in eye irritation, damaged mucous membranes of the nose, throat, and lungs and causes liver disturbance. Dimethylcarbamoyl chloride is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. (NCI05)

Dimethylcarbamoyl chloride Basic Attributes

107.54

107.54

878197

201-208-6

5D54S95GT6

122671

2262

DTXSID1020512

C44378

Clear, colorless liquid.

29241990

Characteristics

20.3

0.24

Dimethylcarbamoyl chloride appears as a colorless to yellow liquid with a pungent odor. Burns to skin, eyes and mucous membranes. A lachrymator. Used to make dyes and pharmaceuticals.

1.168 g/cm3 @ Temp: 25 °C

-33 °C

167 °C

155 °F

1.436

Decomposes in water

Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ) that bears appropriate label. An inventory should be kept, showing quantity of carcinogen & date it was acquired Facilities for dispensing should be contiguous to storage area.

1.95 mm Hg @ 25 deg C

3.73

Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.

Hydrolyzed by water and alcohol.

Reacts with water or moisture in the air to form hydrochloric acid and dimethylcarbamic acid.

Acyl Halides, Sulfonyl Halides, and Chloroformates

Water-Reactive

DIMETHYLCARBAMOYL CHLORIDE is water reactive. Incompatible with strong oxidizing agents, alcohols, bases (including amines). May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Gives toxic fumes of NOx and HCl when burned (USCG, 1999).

Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.

Safety Information

II

8

UN 2262 8/PG 2

3

45-22-23-36/37/38

53-45-99

FD4200000

T

Sensitive to moisture.

P201-P261-P280-P304 + P340 + P312-P308 + P313-P403 + P233

H302-H315-H319-H331-H335-H350

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U097, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... Summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for DIMETHYLCARBAMOYL CHLORIDE (7 total), please visit the HSDB record page.

EXTREMELY REACTIVE|WILL REACT WITH WATER OR STEAM TO PRODUCE TOXIC & CORROSIVE FUMES.|Acids, water [Note: Rapidly hydrolyzes in water to dimethylamine, carbon dioxide, and hydrogen chloride].

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Dimethylcarbamoyl Chloride (79-44-7) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s076dime.pdf]

Special Hazards of Combustion Products: Toxic fumes of NO x and HCl (USCG, 1999)|Carcinogens, Corrosives, Mutagens, Flammable - 2nd degree, Reactive - 1st degree

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P320, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 334 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P261, P264, P270, P271, P280, P281, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|H227: Combustible liquid [Warning Flammable liquids]|P201, P202, P210, P260, P264, P270, P271, P280, P281, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P320, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P260, P261, P264, P270, P271, P280, P281, P284, P301+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P320, P330, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: Note: Most foams will react with the material and release corrosive/toxic gases. SMALL FIRE: CO2, dry chemical, dry sand, alcohol-resistant foam. LARGE FIRE: Water spray, fog or alcohol-resistant foam. FOR CHLOROSILANES, DO NOT USE WATER; use AFFF alcohol-resistant medium-expansion foam. Move containers from fire area if you can do it without risk. Use water spray or fog; do not use straight streams. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor-suppressing foam may be used to reduce vapors. FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors. DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|IN MANUFACTURING PLANT IN ... GERMANY, PRODN OF DIMETHYLCARBAMOYL CHLORIDE IS CARRIED OUT IN CLOSED SYSTEM; DURING EVACUATION & CLEANING, WORKERS WEAR RESPIRATORS & GLOVES. ... IT IS POSSIBLE THAT LEVELS OF EXPOSURE MIGHT BE CONSIDERABLY HIGHER IN FACILITIES IN WHICH CHEMICAL IS USED FOR FURTHER SYNTHESIS.|... /WORKERS/ SHOULD BE SUPPLIED WITH WORK CLOTHING & UNDERWEAR KEPT IN LOCKERS SEPARATE FROM ORDINARY CLOTHING. ... RESPIRATORS, PROTECTIVE GLOVES & GOGGLES SHOULD BE AVAILABLE FOR DAILY USE. WHEN SUBSTANCE IS HANDLED, NOT ONLY SHOULD THE PROTECTIVE EQUIPMENT SUITABLE FOR THE OPERATIONS INVOLVED BE WORN, BUT THE EQUIPMENT USED FOR TRANSFERRING SUBSTANCE SHOULD ALSO HAVE BEEN PREVIOUSLY CLEANED & DECONTAMINATED.|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/|Wear appropriate personal protective clothing to prevent skin contact.|For more Personal Protective Equipment (PPE) (Complete) data for DIMETHYLCARBAMOYL CHLORIDE (9 total), please visit the HSDB record page.|(See protection codes)

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

THE PROCESSES SHOULD ... TAKE PLACE IN WELL VENTILATED PREMISES UNDER A SLIGHT NEGATIVE PRESSURE TO AVOID ANY DIFFUSION OF POLLUTANTS. THE PROCESS PLANT SHOULD BE EQUIPPED WITH LOCAL EXHAUST DEVICES, IN PARTICULAR AT FLANGES, VALVES, ETC, WHERE LEAKS ARE MORE LIKELY TO ARISE.|PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for DIMETHYLCARBAMOYL CHLORIDE (13 total), please visit the HSDB record page.

/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.|/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for DIMETHYLCARBAMOYL CHLORIDE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.|PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

A powerful lacrimator.

NIOSH recommends that dimethyl carbamoyl chloride be regulated as a potential human carcinogen.|NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Dimethyl carbamoyl chloride is included on this list.

Dimethylcarbamoyl chloride is used as an intermediate in the production of pharmaceuticals, pesticides, and dyes. Acute (short-term) inhalation exposure to dimethylcarbamoyl chloride has been observed to result in damaged mucous membranes of the nose, throat, and lungs, and cause difficulty in breathing in rats. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic health effects of dimethylcarbamoyl chloride in humans. Nasal tract carcinomas have been observed in rats and male hamsters following inhalation exposure. EPA has not classified dimethylcarbamoyl chloride for potential carcinogenicity.

U097; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U097; As stipulated in 40 CFR 261.33, when dimethylcarbamoyl chloride, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Toxicity

LD50 Rat oral 1 g/kg|LC50 Rat inhalation 180 ppm/6 hr|LD50 Mouse ip 300 mg/kg

Human exposure is limited to but not restricted to chemical workers, pesticide formulators, dye makers, and pharmaceutical workers. OSHA estimated that 200 workers exposed to DMCC, primarily through inhalation.

There are no known natural sources of dimethylcarbamoyl chloride(1).

Dimethylcarbamoyl chloride's production and former use as a chemical intermediate in the production of dyes, pharmaceuticals, and pesticides(1) may have resulted in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: If dimethylcarbamoyl chloride is released to soil, it will be expected to rapidly hydrolyze if the soil is moist, based upon a half-life of 54 sec at 14 °C(SRC) calculated from a measured hydrolysis rate constant(1). Since it rapidly hydrolyzes, adsorption to and volatilization from moist soil are not expected to be significant processes, although no data specifically regarding the fate of dimethylcarbamoyl chloride in soil were located(SRC). The potential for volatilization of dimethylcarbamoyl chloride from dry soil surfaces may exist(SRC) based upon a vapor pressure of 1.95 mm Hg(2). Biodegradation should not be an important process since hydrolysis is such a rapid process(SRC).|AQUATIC FATE: If dimethylcarbamoyl chloride is released to water, it will be expected to rapidly hydrolyze, based upon a half-life of 54 sec at 14 °C(SRC) calculated from a measured hydrolysis rate constant(1). The products of hydrolysis are dimethylamine, carbon dioxide, and hydrogen chloride(2). Since it rapidly hydrolyzes, bioconcentration, volatilization, and adsorption to sediment and suspended solids are not expected to be significant processes(SRC). No data were located concerning biodegradation, but dimethylcarbamoyl chloride probably abiotically degrades via hydrolysis significantly faster than via biodegradation(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethylcarbamoyl chloride, which has a vapor pressure of 1.95 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase dimethylcarbamoyl chloride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 24 hours(SRC), calculated from its rate constant of 16X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). The hydrolysis half-life for dimethylcarbamoyl chloride is 54 sec(SRC), calculated from its rate constant of 12.76X10-3 sec-1(4), which suggests that vapor-phase dimethylcarbamoyl chloride will rapidly hydrolyze in fog and rain(SRC).

The rate constant for the vapor-phase reaction of dimethylcarbamoyl chloride with photochemically-produced hydroxyl radicals has been estimated as 16X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 24 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The measured overall rate constant for hydrolysis of dimethylcarbamoyl chloride in aqueous solution at approx 14 °C is 12.76X10-3 sec-1(2). This corresponds to a half-life of 54 sec for hydrolysis(SRC). A half-life of 6 minutes has been reported for hydrolysis at 0 °C(3). The products of hydrolysis are dimethylamine, carbon dioxide, and hydrogen chloride(3).

Since dimethylcarbamoyl chloride rapidly hydrolyzes in water(1), bioconcentration of dimethylcarbamoyl chloride in aquatic organisms is not expected to be an important environmental fate process(SRC).

Since dimethylcarbamoyl chloride rapidly hydrolyzes in water and moist soil(1), adsorption to soil is not expected to be an important environmental fate process(SRC).

Dimethylcarbamoyl chloride rapidly hydrolyzes in water with a half-life of 54 sec at 14 °C(SRC) calculated from a measured hydrolysis rate constant(1). Due to rapid hydrolysis in water, volatilization of dimethylcarbamoyl chloride from water and moist soil surfaces is not expected to be an important environmental fate process(SRC). The potential for volatilization of dimethylcarbamoyl chloride from dry soil surfaces may exist(SRC) based upon a vapor pressure of 1.95 mm Hg(2).

Occupational exposure to dimethylcarbamoyl chloride may have occurred through inhalation and dermal contact with this compound at workplaces where dimethylcarbamoyl chloride was produced or used(SRC). Concns as high as 1.5 ppm have been measured in the air of a plant where dimethylcarbamoyl chloride was manufactured(1). Workers in this plant apparently wore respirators and gloves during evacuation and cleaning of the closed systems used to make the chemical(1).

Drug Information

Material is extremely destructive to the mucous membranes, upper respiratory tract, eyes, and skin. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)|(See procedures)

ONE CASE OF EYE IRRITATION & ONE OF LIVER DISTURBANCES HAVE BEEN OBSERVED IN WORKERS EXPOSED TO DIMETHYLCARBAMOYL CHLORIDE.|NO CHROMOSOMAL ABERRATION WAS REPORTED IN 10 WORKERS EXPOSED TO THIS CMPD FOR 4-17 YEARS.|AN ESTIMATE OF TOTAL NUMBER OF WORKERS AT RISK OF DMCC EXPOSURE, MADE IN 1976, WAS < 200. THIS DID NOT INCLUDE POTENTIAL EXPOSURES TO DMCC FORMED IN SIDE REACTIONS DURING THE SYNTHESIS OF OTHER PRODUCTS. NO CASES OF HUMAN CANCER ATTRIBUTABLE TO DMCC HAVE BEEN REPORTED. DUE TO HIGH TOXICITY, HOWEVER, EXPOSURES HAVE APPARENTLY BEEN WELL CONTROLLED.|NO CANCER DEATHS (OUT OF A TOTAL OF SIX DEATHS) OR X-RAY INDICATIONS OF LUNG CANCER WERE REPORTED IN AN INVESTIGATION OF 39 DMCC PRODUCTION WORKERS...26 PROCESSING WORKERS & 42 EX-WORKERS, AGED 17-65 & EXPOSED FOR PERIODS RANGING FROM 6 MO TO 12 YR.|Chromosomal analysis of peripheral lymphocytes from 10 people who had been occupationally exposed to dimethylcarbamoyl chloride (and diethylcarbamoyl chloride) for periods ranging from 4 to 17 years showed differences in the frequency of chromosomal aberrations (inclusive and exclusive gaps), when compared with a control group of 10 people matched for age, although statistical evaluation revealed no significant increase.

dimethylcarbamoyl chloride

inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, skin, nose, throat, respiratory system; eye, skin burns; cough, wheezing, larnygitis, dyspnea (breathing difficulty); headache, nausea, vomiting; liver injury; [potential occupational carcinogen]

Eyes, skin, respiratory system, liver

Dimethylcarbamoyl chloride Use and Manufacturing

Methods of Manufacturing

Dimethylcarbamoyl chloride is prepared by the reaction of dimethylamine and phosgene. Reaction equation: (CH3)2NH+COCl2→(CH3)2NCOCl add toluene into the reaction pot, and pass in phosgene to absorb to the calculated amount under cooling conditions. In another pot, gas dimethylamine is generated from the dimethylamine aqueous solution, and after drying, it is passed into the phosgene toluene solution for reaction. After the completion of the reaction, the hydrochloride was removed by filtration and distillation under reduced pressure. The 75°C (3.33kPa) fraction was collected as dimethylcarbamoyl chloride with a yield of 55%. Dimethylcarbamoyl chloride can also be prepared by reacting N, N-dimethylformamide with phosphorus trichloride and then reacting with thionyl chloride. The reaction equation is as follows: HCON(CH3)2+PCl3→[(CH3)2N+=CHOPCl2]Cl-[SOCl2]→(CH3)2NCOCl In addition, Pd, PdCl2 or RhCl3 can also be used as the catalyst, which is composed of dimethylammonium chloride and Carbon monoxide reaction system. Reaction equation: (CH3)2NCl+CO[catalyst]→(CH3)2NCOCl

Uses

Used in the synthesis of medicines, pesticides, dyes, plastics, synthetic materials and other fine organic chemical products, such as the production of new bromine bromide, neostigmine methylsulfate, pyridostigmine, carbamates Insecticides, etc.

Production

(1978) NOT PRODUCED COMMERCIALLY IN USA|(1982) NOT PRODUCED COMMERCIALLY IN USA

Carbamic chloride, N,N-dimethyl-: ACTIVE|Dimethylcarbamoyl chloride /was/ produced since 1961.

GAS CHROMATOGRAPHY HAS BEEN USED TO MEASURE ATMOSPHERIC LEVELS IN WORKING ENVIRONMENTS.|THROUGH SPECTROSCOPIC DETERMINATIONS OF CONCENTRATION OF THIS PRODUCT IN SAMPLES TAKEN FROM AIR, LEVELS AS LOW AS 17 PPB WERE DETECTED QUANTITATIVELY.|Analyte: Dimethylcarbamoyl chloride; technique: Gas chromatography; Carrier gas: Helium/Hydrogen; range: 0.08 to 1.3 ppb; Limit of detection: 10 ppm; interference: none recorded.

Hazardous Air Pollutants (HAPs)|Fire Hazards -> Carcinogens, Corrosives, Mutagens, Flammable - 2nd degree, Reactive - 1st degree

Computed Properties

Molecular Weight:107.54
XLogP3:0.8
Hydrogen Bond Acceptor Count:1
Exact Mass:107.0137915
Monoisotopic Mass:107.0137915
Topological Polar Surface Area:20.3
Heavy Atom Count:6
Complexity:61.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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