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Chloroacetamide

Chloroacetamide structure

Chloroacetamide 

structure
  • CAS No:

    79-07-2

  • Formula:

    C2H4ClNO

  • Chemical Name:

    Chloroacetamide

  • Synonyms:

    KM 101;NSC 54286;NSC 8408;2-ChloroacetaMide >=98.0% (HPLC);Piracetam Imp. B;chloroacetylamine;Mergal AF;mergalaf

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

white crystalline powder


COLOURLESS-TO-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.


Chloroacetamide is a preservative used in several applications such as in cutting metalwork fluids, in paints or in glues. It can induce contact dermatitis in hairdressers, or in shoemakers when used as a leather preservative.


Poison by ingestion, intravenous, and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits very toxic Cland NOx. See also N-CHLOROACETAMIDE.


Recrystallise the amide from acetone and dry it under vacuum over P2O5. [Beilstein 2 IV 490.]

Chloroacetamide Basic Attributes

93.51

93.51

878191

201-174-2

2R97846T1L

0640

54286|8408

2811

TSCA listed

DTXSID9041570

White

29241900

Characteristics

43.1

-0.5

COLOURLESS-TO-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.

0.84

116-118 °C(lit.)

224.5 °C

170°C

1.4480 (estimate)

Soluble in water(90g/L).

Separated from strong oxidants, strong bases, strong acids and food and feedstuffs. Ventilation along the floor. Store in an area without drain or sewer access.

0.05 mm Hg ( 20 °C)

Relative vapour density (air = 1): 3.2

LD50 orally in Rabbit: 138 mg/kg LD50 dermal Rat > 2000 mg/kg

Non flammable

Characteristic odor

3.8-4.1 (40g/l, H2O, 20℃)

14.69±0.40(Predicted)

2.5×103mol/(m3Pa) at 25℃, HSDB (2015)

Two isomorphous crystalline structures: alpha form "stable form", obtained by sublimation and crystallization from non polar solvents; beta form "unstable form", obtained by quenching the melt or by crystallization from polar solvents.|Hydroxyl radical reaction rate constant = 2.27X10-12 cu cm/molec-sec at 25 °C (est)|Energy of decomposition (in range 170-300 °C) measured as 0.67 kJ/g

Strong irritant to skin and tissue

Store below +30°C.

Safety Information

III

6.1

UN 2811 6.1/PG 3

2

T

22-36/37-45

AB5075000

T:Toxic

Separated from strong oxidants, strong bases, strong acids and food and feedstuffs. Ventilation along the floor. Store in an area without drain or sewer access.

Two isomorphous crystalline modifications: alpha-form, "stable form", obtained by sublimation and by crystallization from nonpolar solvents; beta-form, "unstable form", obtained by quenching the melt or by crystallization from polar solvents .

P201-P280-P301 + P310 + P330-P308 + P313-P333 + P313

25-43-62

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Reacts with strong oxidants, strong reducing agents, strong acids and strong bases.

Chloracetamide is an indirect food additive for use only as a component of adhesives.

UN 2811 6.1/PG 3

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P280, P281, P301+P310, P302+P352, P308+P313, P321, P330, P333+P313, P363, P405, and P501|H301 (91.37%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 614 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P261, P264, P270, P272, P280, P281, P301+P310, P302+P352, P305+P351+P338, P308+P313, P321, P330, P333+P313, P337+P313, P363, P405, and P501|P201, P202, P261, P264, P270, P272, P280, P281, P301+P310, P302+P352, P305+P351+P338, P308+P313, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P405, and P501

Protective gloves. Protective clothing. ... Wear safety spectacles, face shield or eye protection in combination with breathing protection if powder.

Not combustible.

In case of fire in the surroundings, use appropriate extinguishing media.

Spillage Disposal. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|Do NOT take working clothes home.|Prevent dispersion of dust! Avoid all contact! Use local exhaust or breathing protection.|Do not eat, drink, or smoke during work. Wash hands before eating.

Do not transport with food and feedstuffs.

The substance is irritating to the eyes and skin.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from strong oxidants, strong bases, strong acids and food and feedstuffs. Ventilation along the floor. Store in an area without drain or sewer access.

A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

The substance is irritating to the eyes and skin.

Repeated or prolonged contact may cause skin sensitization. Animal tests show that this substance possibly causes toxicity to human reproduction or development.

Chloroacetamide as a preservative is used in several applications as in cutting metalworking fluids, in paints or in glues. It can induce contact dermatitis in hairdressers or in shoemakers, being used as a leather preservative.

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles, face shield or eye protection in combination with breathing protection if powder.

Toxicity

LD50 Mouse oral 155 mg/kg|LD50 Mouse ip 100 mg/kg|LD50 Rabbit oral 122 mg/kg|LD50 Dog oral 31 mg/kg|For more Non-Human Toxicity Values (Complete) data for CHLOROACETAMIDE (9 total), please visit the HSDB record page.

Chloroacetamide's production and use as a chemical intermediate for the production of herbicides and insecticides(1) may result in its release to the environment through various waste streams(SRC). The compound was formerly used as a preservative in various cosmetics(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4.2(SRC), determined from a log Kow of -0.53(2) and a regression-derived equation(3), indicates that chloroacetamide is expected to have very mobility in soil(SRC). Volatilization of chloroacetamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Chloroacetamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-2 mm Hg mm Hg at 25 deg (SRC), determined from a fragment constant method(2). Utilizing the Zahn-Wellens test, 90% biodegradation was reached in 6 days(5) indicating that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4.2(SRC), determined from a log Kow of -0.53(2) and a regression-derived equation(3), indicates that chloroacetamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 3.9X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(3) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A hydrolysis half-life of 53 days at pH 8(7) suggests that hydrolysis may be an important environmental fate process for chloroacetamide in alkaline waters(SRC). Utilizing the Zahn-Wellens test, 90% biodegradation was reached in 6 days(8) indicating that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloroacetamide, which has an estimated vapor pressure of 1.1X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroacetamide 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 5 days(SRC), calculated from its rate constant of 2.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Chloroacetamide does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of chloroacetamide with photochemically-produced hydroxyl radicals has been estimated as 2.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base catalyzed hydrolysis rate constant of 540 L/mol-hr was reported for chloroacetamide(2), which corresponds to hydrolysis half-lives of approximately 53 days at pH 8 and 1.5 years at pH 7(SRC). Chloroacetamide 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).

An estimated BCF of 3 was calculated in fish for chloroacetamide(SRC), using a log Kow of 0.53(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of chloroacetamide is estimated as 4.2(SRC), using a log Kow of -0.53(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that chloroacetamide is expected to have very high mobility in soil.

The Henry's Law constant for chloroacetamide is estimated as 3.94X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that chloroacetamide is expected to be essentially nonvolatile from water surfaces(2). Chloroacetamide's Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). Chloroacetamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimate) vapor pressure of 1.1X10-2 mm Hg(SRC), determined from a fragment constant method(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 90 workers (none of these were female) were potentially exposed to chloroacetamide in the US(1). Occupational exposure to chloroacetamide may occur through inhalation and dermal contact with this compound at workplaces where chloroacetamide is produced or used. The general population may have been exposed to chloracetamide via dermal contact due to its former use in cosmetic products(SRC).

Drug Information

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

/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/

/HUMAN EXPOSURE STUDIES/ Six subjects were used in a study of the effect of elicitation concentration in contact dermatitis testing. All of the subjects had positive reactions to a 1% solution of chloroacetamide in a Draize test conducted 6 months before the study reported here. Chloroacetamide at four concentrations in petrolatum (0.5, 0.1, 0.05, and 2%) was applied to the upper back of the subjects, and the reactions were scored. Four of the six subjects had positive reactions to the 2% concentration, and 1 subject had a positive reaction to the 0.5% concentration. None of the subjects had reactions to the 0.1 and 0.05% concentrations.|/HUMAN EXPOSURE STUDIES/ Chloroacetamide was patch tested on 465 dermatological patients ranging in age from 2 to 80 years, with an average age of 37 years. Chloroacetamide, 0.1% in petrolatum, was applied using the ICDRG procedure and scored at 24, 48, and 72 hr. Seven of the 465 subjects had a positive reaction to chloroacetamide. Of the 7 subjects who had positive reactions, 5 were younger women who had mainly facial lesions.|/HUMAN EXPOSURE STUDIES/ A mixture of 70% chloroacetamide and 30% sodium benzoate was tested for ocular irritation in humans. A 5% solution of this mixture was instilled without rinse into the human eye and caused slight discomfort, lacrimation, and blurred vision lasting 15 to 30 minutes.|/HUMAN EXPOSURE STUDIES/ From February 1989 to January 1990, the Swiss Contact Dermatitis Research Group conducted a 1-year study to examine the frequency of sensitization to a series of 13 common preservatives. A group of 2295 consecutive outpatients with suspected allergic contact dermatitis (age range 7-90 years, with a mean age of 42; 911 males, 1384 females) was tested. The %s of positive reactions to the preservatives studied are as follows, in descending order: formaldehyde 5.7%, benzalkonium chloride 5.5%, Kathon CG 5.5%, thimerosal 4.2%, chlorhexidine digluconate 2.0%, DMDM hydantoin 1.7%, paraben mix 1.7%, chloroacetamide 1.5%, Bronopol 1.2%, imidazolidinyl urea 1.0%, quaternium 15 1.0%, triclosan 0.8%, 2,4-dichlorobenzyl alcohol 0.4%. These relatively high values suggest a heavy exposure of the Swiss population to topical preservatives.|For more Human Toxicity Excerpts (Complete) data for CHLOROACETAMIDE (16 total), please visit the HSDB record page.

chloracetamide

The substance can be absorbed into the body in hazardous amounts by ingestion. The substance can be absorbed into the body through the skin.

Cough.


Redness. Pain.


Redness. Pain.

Chloroacetamide Use and Manufacturing

Methods of Manufacturing

Prepared from ethyl chloroacetate and ammonia; ... from chloroacetyl chloride and ammonium acetate ... .|... Obtained on an industrial scale by reaction of methylchloroacetate with ammonia at low temperature. Manufacture from chloroacetic acid and cyanamide at 150 to 200 °C also has been described.

Uses

A component of herbicidal mixtures of cellulose biosynthesis inhibitors with VLCFA inhibitors. preservative in cosmetic and pharmaceutical creams, shampoos, bath lotions, etc.; preservative in glues, cooling fluids.


2-Chloroacetamide is used as surface-active agent in home laundry, cleaning products & household formulated cleaners, other industrial uses, petroleum production, polymer processing.

Production

(1986) 10 thousand-500 thousand pounds|(1990) 10 thousand-500 thousand pounds|(1998) 10 thousand-500 thousand pounds|Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#7113]

Acetamide, 2-chloro-: ACTIVE

Cosmetics -> Preservative

Computed Properties

Molecular Weight:93.51
XLogP3:-0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:92.9981414
Monoisotopic Mass:92.9981414
Topological Polar Surface Area:43.1
Heavy Atom Count:5
Complexity:44.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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