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Diazomethane

Diazomethane structure

Diazomethane 

structure
  • CAS No:

    334-88-3

  • Formula:

    CH2N2

  • Chemical Name:

    Diazomethane

  • Synonyms:

    Methane,diazo-;Azimethylene;Diazomethane;Diazirine;Diazonium methylide;Diazyne,methylene-;463-60-5;16835-99-7;62024-16-2;908094-01-9

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Diazomethane is a flammable, yellow gas or a liquid under pressure. Musty odor.


Diazomethane is a yellow gas with a musty odor that is shipped as a liquid under pressure. (NIOSH, 2016) Highly toxic by inhalation.|YELLOW GAS WITH CHARACTERISTIC ODOUR.|Yellow gas with a musty odor.|Yellow gas with a musty odor. [Note: Shipped as a liquefied compressed gas.]


Diazomethane is a yellow gas with a musty odor that is shipped as a liquid under pressure. (NIOSH, 2016) Highly toxic by inhalation.|Diazomethane is the simplest diazo compound, in which a diazo group is attached to a methylene group. It has a role as an alkylating agent, an antineoplastic agent, a carcinogenic agent and a poison.|The major source of exposure to diazomethane is occupational. Diazomethane is a strong respiratory irritant. Acute (short-term) inhalation exposure of humans to diazomethane may cause irritation of the eyes, cough, wheezing, asthmatic symptoms, pulmonary edema, pneumonia, dizziness, weakness, headache, and chest pains. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic effects of diazomethane in humans. Increased incidences of lung tumors have been observed in rats and mice exposed to diazomethane by inhalation and in dermally exposed mice. EPA has not classified diazomethane with respect to its potential carcinogenicity.|A diazonium compound with the formula CH2N2.

Diazomethane Basic Attributes

42.04000

42.02180

206-382-7

60A625P70P

1256

1953

DTXSID0024008

Yellow gas [Note: Shipped as a liquefied compressed gas]

Characteristics

37.39000

log Kow = 2.00 (est)

Diazomethane is a yellow gas with a musty odor that is shipped as a liquid under pressure. (NIOSH, 2016) Highly toxic by inhalation.

1.45 g/cm3

-145 °C

-23 °C

Flammable gas|NA (Gas)

1.684

Reacts with water (NIOSH, 2016)

diazomethane should preferably be handled in solution using glassware specially designated for diazomethane (e.g., with Clear-Seal joints) and should be used as soon as possible after preparation. Storage of diazomethane solutions (even at low temperature) is not advisable. All work with diazomethane should be conducted in a fume hood behind a safety shield, and appropriate impermeable gloves, protective clothing, and safety goggles should be worn at all times.

greater than 1 atm (NIOSH, 2016)

1.45 (Air = 1)|Relative vapor density (air = 1): 1.4|1.45

LCLO inhal (cat) 175 ppm (10 min) PEL (OSHA) 0.2 ppm (0.4 mg/m3) TLV-TWA (ACGIH) 0.2 ppm (0.4 mg/m3)

Musty odor

Henry's Law constant: 3.37X10-2 atm-cu m/mole at 25 °C (est)

Undiluted liquid and concentrated solutions may explode violently, especially if impurities are present. Gaseous diazomethane may explode on heating to 100 °C or on rough glass surfaces. Ground glass apparatus and glass stirrers with glass sleeve bearings where grinding may occur, should not be used. Alkali metals also produce explosions with diazomethane. Soluble in ether, dioxane. Such solutions decompose only slowly at low temperatures. Decomposition is more rapid if alcohols or water are present. Copper powder causes active decomposition with the evolution of nitrogen and the formation of insoluble white flakes of polymethylene (CH2)x. Solid calcium chloride or boiling stones have the same effect. This phenomenon appears to occur always during the action of diazomethane on solid substances.|Incompatible with alkali metals, water, drying agents such as calcium arsenate [Note: May explode violently on heating, exposure to sunlight, or contact with rough edges such as ground glass.]|Severe explosion risk when shocked|Dipole moment = 1.50|For more Other Experimental Properties (Complete) data for DIAZOMETHANE (9 total), please visit the HSDB record page.

Reacts with water, releasing nitrogen, more stable in ether or dioxane.

Azo, Diazo, Azido, Hydrazine, and Azide Compounds

Explosive

DIAZOMETHANE undergoes violent thermal decomposition. Above 200°C. the vapors may explode violently if rough glass surfaces are present. Explosions at low temperatures can occur if traces of organic matter are present. [J. Phys. Chem. 35:1403(1931)]. Produces explosions with alkali metals. Reacts with copper powder and to some extent all solid surfaces to produce nitrogen and solid white polymethylene. Reacts with dimethylaminodimethylarsine and trimethyltin in ether with vigorous foaming.

Explodes at 100 °C (212 °F) or if impurities are present, at lower temperatures. Vapor may explode at temperatures above 200 °C (392 °F).|100 °C (explosion)

9.00 eV

Flammable Gas [EXPLOSIVE!]

The gas is heavier than air and may travel along the ground; distant ignition possible.

Safety Information

2.3

1953

3

45

53-45

PA7000000

Xi,Xn

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|DIAZOMETHANE MAY BE DISPOSED OF BY BURNING AT SAFE LOCATION OR IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH AN APPROPRIATE EFFLUENT GAS CLEANING DEVICE.

Contact between diazomethane and alkali metals, calcium sulfate, calcium chloride, boiling stones, or copper powder will cause explosions.|Incompatibilities: Alkale metals; calcium sulfate.|Alkali metals, water, drying agents such as calcium arsenate [Note: May explode violently on heating, exposure to sunlight, or contact with rough edges such as ground glass].

Excerpt from ERG Guide 119 [Gases - Toxic - Flammable]: Flammable; may be ignited by heat, sparks or flames. May form explosive mixtures with air. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Vapors from liquefied gas are initially heavier than air and spread along ground. Vapors may travel to source of ignition and flash back. Some of these materials may react violently with water. Cylinders exposed to fire may vent and release toxic and flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket. Runoff may create fire or explosion hazard. (ERG, 2016)|Extremely flammable. Many reactions may cause fire or explosion. Gives off irritating or toxic fumes (or gases) in a fire. Gas/air mixtures are explosive.|Flammable - 4th degree, Reactive - 3rd degree

|Danger|H350: May cause cancer [Danger Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|H220: Extremely flammable gas [Danger Flammable gases]|P210, P260, P261, P264, P270, P272, P280, P285, P302+P352, P304+P341, P305+P351+P338, P307+P311, P309+P311, P310, P321, P332+P313, P333+P313, P342+P311, P362, P363, P377, P381, P403, P405, and P501

Excerpt from ERG Guide 119 [Gases - Toxic - Flammable]: As an immediate precautionary measure, isolate spill or leak area for at least 100 meters (330 feet) in all directions. SPILL: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 1953 datasheet. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 1600 meters (1 mile) in all directions; also, consider initial evacuation for 1600 meters (1 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 119 [Gases - Toxic - Flammable]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Do not direct water at spill or source of leak. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors. If possible, turn leaking containers so that gas escapes rather than liquid. Prevent entry into waterways, sewers, basements or confined areas. Isolate area until gas has dispersed. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin from becoming frozen from contact with the liquid or from contact with vessels containing the liquid. Eyes: Wear appropriate eye protection to prevent eye contact with the liquid that could result in burns or tissue damage from frostbite. Wash skin: No recommendation is made specifying the need for washing the substance from the skin (either immediately or at the end of the work shift). Remove: Work clothing that becomes wet should be immediately removed due to its flammability hazard(i.e. for liquids with flash point Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Quick drench facilities and/or eyewash fountains should be provided within the immediate work area for emergency use where there is any possibility of exposure to liquids that are extremely cold or rapidly evaporating. (NIOSH, 2016)|Workers should use appropriate personal protective clothing and equipment that must be carefully selected, used, and maintained to be effective in preventing skin contact with diazomethane. The selection of the appropriate personal protective equipment (PPE) (e.g., gloves, sleeves, encapsulating suits) should be based on the extent of the worker's potential exposure to diazomethane. There are no published reports on the resistance of various materials to permeation by diazomethane.|To evaluate the use of PPE materials with diazomethane, users should consult the best available performance data and manufacturers' recommendations. Significant differences have been demonstrated in the chemical resistance of generically similar PPE materials (e.g., butyl) produced by different manufacturers. In addition, the chemical resistance of a mixture may be significantly different from that of any of its neat components.|Any chemical-resistant clothing that is used should be periodically evaluated to determine its effectiveness in preventing dermal contact. Safety showers and eye wash stations should be located close to operations that involve diazomethane.|Splash-proof chemical safety goggles or face shields (20 to 30 cm long, minimum) should be worn during any operation in which a solvent, caustic, or other toxic substance may be splashed into the eyes.|For more Personal Protective Equipment (PPE) (Complete) data for DIAZOMETHANE (13 total), please visit the HSDB record page.|(See protection codes)

Highly explosive when shocked, exposed to hear, or by chemical reaction. Undiluted liquid or gas may explode on contact with alkali metals, rough surfaces, heat (100 °C), high-intensity light, or shock.|... MAY EXPLODE VIOLENTLY ON HEATING OR IN CONTACT WITH ROUGH SURFACES. IN ETHER OR BENZENE, IN WHICH DIAZOMETHANE IS SOL, THE DANGER OF EXPLOSION IS MUCH DECREASED.|DIAZOMETHANE WILL UNDERGO VIOLENT THERMAL DECOMP. ABOVE 200 °C, VAPOR MAY EXPLODE VIOLENTLY. EXPLOSIONS AT LOW TEMPERATURES CAN OCCUR IF TRACES OF ORGANIC MATTER ARE PRESENT.|CALCIUM SULFATE IS UNSUITABLE DESICCANT FOR DRYING-TUBES IN DIAZOMETHANE SYSTEMS. CONTACT OF DIAZOMETHANE VAPOR & SULFATE CAUSES EXOTHERM WHICH MAY LEAD TO DETONATION.|Above 200 °C, the vapor may explode

If material /is/ on fire or involved in /a/ fire use dry chemical, dry sand, or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.|Fires involving diazomethane should be fought upwind from the maximum distance possible. Diazomethane will explode in a fire. The fire area should be evacuated immediately. Keep unnecessary people away; isolate the hazard area and deny entry. Vapors may travel to a source of ignition and flash back. Vapors are an explosion and poison hazard indoors, outdoors, or in sewers.

... Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. ...

In the event of a spill or leak involving diazomethane, persons not wearing protective equipment and clothing should be restricted from contaminated areas until cleanup has been completed. The following steps should be undertaken following a spill or leak: Notify safety personnel. Remove all sources of heat and ignition. Ventilate potentially explosive atmospheres. Provide and require the use of fully-encapsulating, vapor-protective clothing and equipment for cleanup personnel. If possible without risk, stop flow of gas. If source of leak is a cylinder and cannot be stopped in place, remove the leaking cylinder to a safe place in the open air, and repair leak or allow cylinder to empty. If the leak is in the liquid form, allow diazomethane to evaporate.|Decompose chemically with ceric ammonium nitrate under constant agitation and cooling.

EXPLOSIVE (USE SAFETY SCREEN), INSIDIOUS POISON (WELL-VENTILATED HOOD IS ABSOLUTELY NECESSARY), AVOID VAPOR.|If material /is/ not on fire and not involved in /a/ fire, keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. Do not use water on material itself. Neutralize spilled material with crushed limestone, soda ash, or lime.|Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing.|If diazomethane contacts the skin, workers should flush the affected areas immediately with plenty of water, followed by washing with soap and water. Clothing contaminated with diazomethane should be removed immediately, and provisions should be made for the safe removal of the chemical from the clothing. Persons laundering the clothes should be informed of the hazardous properties of diazomethane, particularly its potential for causing severe irritation.|For more Preventive Measures (Complete) data for DIAZOMETHANE (9 total), please visit the HSDB record page.

... Diazomethane exposure has caused irritation of the eyes ...|Skin exposure has produced irritation and denudation.

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 0.2 ppm (0.4 mg/cu m).

Recommended Exposure Limit: 10 Hour Time-Weighted Average: 0.2 ppm (0.4 mg/cu m).

Evacuate danger area! Consult an expert! Ventilation. Personal protection: complete protective clothing including self-contained breathing apparatus.

Solutions of diazomethane should not be stored.

A harmful concentration of this gas in the air will be reached very quickly on loss of containment.

The substance is very corrosive to the eyes, skin and respiratory tract. Inhalation of the vapour may cause lung oedema. Inhalation of the vapour may cause asthma-like reactions (RADS). The liquid may cause frostbite. Exposure above the OEL could cause death. Medical observation is indicated.

Repeated or prolonged inhalation may cause asthma. This substance is possibly carcinogenic to humans.

NO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Do NOT expose to friction or shock. Prevent build-up of electrostatic charges (e.g., by grounding).

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Cold-insulating gloves.

Wear face shield or eye protection in combination with breathing protection.

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. Diazomethane is included on this list.

The major source of exposure to diazomethane is occupational. Diazomethane is a strong respiratory irritant. Acute (short-term) inhalation exposure of humans to diazomethane may cause irritation of the eyes, cough, wheezing, asthmatic symptoms, pulmonary edema, pneumonia, dizziness, weakness, headache, and chest pains. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic effects of diazomethane in humans. Increased incidences of lung tumors have been observed in rats and mice exposed to diazomethane by inhalation and in dermally exposed mice. EPA has not classified diazomethane with respect to its potential carcinogenicity.

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 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

Toxicity

NO VANCOMYCIN WAS ADSORBED TO CELL WALLS /OF BACILLUS SUBTILIS W23/ THAT HAD BEEN ESTERIFIED BY TREATMENT WITH DIAZOMETHANE.

Diazomethane's production and use as a powerful methylating agent for acidic compounds such as carboxylic acids, phenols, enols(1) used in synthetic organic transformations may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Since diazomethane is a gas and undergoes rapid hydrolysis with water, volatilization from soil is not relevant. Similarly, adsorption to soil and biodegradation are not expected due to the rapid rate of decomposition under environmental conditions. (SRC)|AQUATIC FATE: Since diazomethane is a gas and undergoes rapid hydrolysis with water, volatilization from water is not relevant. Similarly, hydrolysis, adsorption to sediments, bioconcentration, and biodegradation are not expected due to the rapid rate of decomposition under environmental conditions. (SRC)|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diazomethane, which has an estimated vapor pressure of 3.94X10+3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a gas. Gas-phase diazomethane will undergo rapid hydrolysis with atmospheric water vapor but may also be degraded by reaction with photochemically-produced hydroxyl radicals at a much slower rate(SRC); the half-life for this reaction in air is estimated to be 16 days(SRC), calculated from its rate constant of 9.34X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The rate constant for the gas-phase reaction of diazomethane with ozone was 3.3X10-17 cu cm/molecule-sec(4). Diazomethane does not contain chromophores that absorb at wavelengths >290 nm(5), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of diazomethane with photochemically-produced hydroxyl radicals has been estimated as 9.34X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 16 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Diazomethane undergoes rapid hydrolysis with water, releasing nitrogen, and therefore hydrolysis is not expected. Diazomethane does not contain chromophores that absorb at wavelengths >290 nm(3), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).|The reaction between diazomethane and the hydronium ion was studied in a THF-water (60:40 v/v) mixture at 25 °C. When a large excess if diazoalkane was used, the kinetics were zero order in diazoalkane abd first order in acid for the pH range 4

Diazomethane is a gas and undergoes rapid hydrolysis with water; therefore, bioconcentration is not expected to be an important environmental fate process. (SRC)

Diazomethane is a gas and undergoes rapid hydrolysis with water; therefore, adsorption is not expected to be an important environmental fate process. (SRC)

Diazomethane is a gas and undergoes rapid hydrolysis with water; therefore, volatilization from water or moist soil surfaces is not expected to be an important environmental fate process. (SRC)

Occupational exposure to diazomethane may occur through inhalation if the gas supplied in its pure form or when it is formed in situ during organic syntheses. Dermal contact with solutions of this compound in organic solvents may also occur at workplaces where diazomethane is produced or used. The general population is not likely to be exposed to diazomethane since it is primarily used in a laboratory setting. (SRC)

Drug Information

Exposure Routes: inhalation, skin and/or eye contact (liquid) Symptoms: Irritation eyes; cough, shortness breath; headache, lassitude (weakness, exhaustion); flush skin, fever; chest pain, pulmonary edema, pneumonitis; asthma; liquid: frostbite Target Organs: Eyes, respiratory system (NIOSH, 2016)

Eye: If eye tissue is frozen, seek medical attention immediately; if tissue is not frozen, immediately and thoroughly flush the eyes with large amounts of water for at least 15 minutes, occasionally lifting the lower and upper eyelids. If irritation, pain, swelling, lacrimation, or photophobia persist, get medical attention as soon as possible. Skin: If frostbite has occurred, seek medical attention immediately; do NOT rub the affected areas or flush them with water. In order to prevent further tissue damage, do NOT attempt to remove frozen clothing from frostbitten areas. If frostbite has NOT occurred, immediately and thoroughly wash contaminated skin with soap and water. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. (NIOSH, 2016)|(See procedures)


Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.


ON FROSTBITE: rinse with plenty of water, do NOT remove clothes. Refer immediately for medical attention. Wear protective gloves when administering first aid.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. Keep rinsing during transport for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/SIGNS AND SYMPTOMS/ ON SKIN ... /IT/ CAUSES SEVERE, DELAYED INFLAMMATORY REACTION.|/SIGNS AND SYMPTOMS/ ... Inhalation can cause severe lung damage with symptoms of coughing, chest pain, shortness of breath, fever and fatigue. Exposure to the gas or liquid can cause severe skin burns and eye damage. Contact with liquid can cause frostbite.|/SIGNS AND SYMPTOMS/ The toxic effects of diazomethane advance insidiously. Diazomethane exposure has caused irritation of the eyes, dizziness, denudation of mucus membranes, and sensitization in laboratory workers. Chest pain, fever, and sever asthmatic attacks have been reported|/SIGNS AND SYMPTOMS/ Inhalation of diazomethane by man, depending on degree of exposure caused chest pains, asthmatic symptoms, cough and fever, fulminating pneumonia, moderate cyanosis, shock and death.|For more Human Toxicity Excerpts (Complete) data for DIAZOMETHANE (12 total), please visit the HSDB record page.

Diazirine

The substance can be absorbed into the body by inhalation.|inhalation, skin and/or eye contact (liquid)

irritation eyes; cough, short breath; headache, lassitude (weakness, exhaustion); flush skin, fever; chest pain, pulmonary edema, pneumonitis; asthma; liquid: frostbite


Sore throat. Headache. Laboured breathing. Shortness of breath. Nausea. Vomiting. Symptoms may be delayed.


Redness. Pain. Skin burns. Burning sensation. ON CONTACT WITH LIQUID: FROSTBITE.


Burning sensation. Redness. Pain. Burns. Loss of vision. ON CONTACT WITH LIQUID: FROSTBITE.

Eyes, respiratory system

Diazomethane Use and Manufacturing

Methods of Manufacturing

REACTION OF N-NITROSOMETHYL-P-TOLUENESULFONAMIDE WITH AN ALKALI SUCH AS POTASSIUM HYDROXIDE OR POTASSIUM CARBONATE|Ether solns of diazomethane: From N-nitroso-beta-methylaminoisobutyl methyl ketone in ether and isopropanol by reaction with sodium isopropoxide or from the same ketone in ether by reaction with sodium cyclohexoxide; ... By potassium hydroxide saponification of nitrosomethylurea in ether; ... or of nitrosomethylurethan in ether. /Ether solutions of diazomethane/|Prepared from chloroform and hydrazine by reaction with potassium hydroxide; ... from potassium hydroxide and nitrosomethylurea. /Gaseous diazomethane/

Uses

It is used as a methylating agent especially for acidic compounds which may include enols, phenols, and carboxylic acids. Powerful methylating agent for acidic Compounds such as carboxylic acids, phenols, enols. For syntheses with diazomethane see the reviews by Smith, Chem. Rev. 23, 193 (1938); Eistert, Z. Angew. Chem. 54, 99, 124 (1941) translated by Spangler in Newer Methods of Preparative Organic Chemistry (New York, 1948) p 513; J. S. Pizey, Synthetic Reagents vol. 2 (John Wiley, New York, 1974) pp 65-142. It is used in organic synthesis as a methylating agent to methylate acidic compoundssuch as carboxylic acids and phenols. Itis used in trace environmental analysis tomethylate chlorophenoxy acid herbicides.

Diazomethane generators are generally used to produce this compound in situ for laboratory use.|Because of its toxicity and its explosive nature, diazomethane is not manufactured for distribution and sale. When used as methylating agent in the laboratory, it is produced and used in situ. Thus, there is no available information on technical products and impurities.|In the laboratory diazomethane may be prepared most simply by the action of alkali on the commercially available N-methyl-N-nitroso-N'-nitroguanidine.|One USA company offers a self-contained reaction kit for generating ether solutions of diazomethane as needed without exposing the user to the diazomethane or to the N-nitrosomethyl-p-toluenesulfonamide.

NIOSH Method 2515. Analyte: Diazomethane. Matrix: Air. Procedure: Gas chromatography, flame ionization detector. For diazomethane this method has an estimated detection limit that was (not determined)/sample. The overall precision/RSD is 0.024. Applicability: The working range is 0.1 to 0.6 ppm (0.2 to 1 mg/cu m) diazomethane for a 10 liter air sample. Interferences: None reported.|NIOSH Method S127. Analyte: Diazomethane. Matrix: Air. Procedure: Gas chromatography analysis. Method Evaluation: Method was validated over the range of 0.17 to 0.80 mg/cu m using a 10 liter sample. Precision (CVt): 0.084. Applicability: Under the conditions of sample size (10 liter) the useful range is 0.10 to 1.2 mg/cu m. Interferences: A compound with the same retention time as the analyte is an interference.|Determination of a worker's exposure to airborne diazomethane is made using a coated XAD-2 tube (100/50 mg sections, 20/50 mesh). Coating is 1 percent (w/w) octanoic acid. Samples are collected at a maximum flow rate of 0.2 liter/minute until a maximum collection volume of 30 liters is reached. The sample is then treated with carbon disulfide. Analysis is conducted by gas chromatography using a flame ionization detector (GC/FID). This method (NIOSH # 2515) is described in the OSHA Computerized Information System and the NIOSH Manual of Analytical Methods and is fully validated.|A modified procedure is described for the preparation of diazomethane for methyl esterification of environmental samples analysis by gas chromatography. Presently, the USA Environmental Protection Agency recommends the bubbler method and the Diazald kit for methyl esterification of acidic herbicides and other related compounds. The proposed modified procedure will be more convenient and safer to operate than either of these two methods, thus eliminating their tedious nature and potential hazards. In this study, the Aldrich MNNG (N-methyl-N'-nitro-N-nitrosoguanidine) Diazomethane Kit is modified. Diazald is the reagent used instead of N-methyl-N'-nitro-N-nitrosoguanidine because of its large scale production of diazomethane, fast reaction time, safety, and stability. The whole esterification procedure takes about 40 min. It can simultaneously esterify many samples and it yields consistent results.

Hazardous Air Pollutants (HAPs)|Fire Hazards -> Flammable - 4th degree, Reactive - 3rd degree

Computed Properties

Molecular Weight:42.040
XLogP3:1.6
Hydrogen Bond Acceptor Count:1
Exact Mass:42.021798072
Monoisotopic Mass:42.021798072
Topological Polar Surface Area:2
Heavy Atom Count:3
Complexity:25.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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