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Chloroacetamide

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Name

Chloroacetamide

EINECS 201-174-2
CAS No. 79-07-2 Density 1.268 g/cm3
PSA 43.09000 LogP 0.41080
Solubility Soluble in water(90g/L). Melting Point 116-118 °C(lit.)
Formula C2H4ClNO Boiling Point 256 °C at 760 mmHg
Molecular Weight 93.5129 Flash Point 108.6 °C
Transport Information UN 2811 6.1/PG 3 Appearance White crystal
Safety 22-36/37-45 Risk Codes 25-43-62
Molecular Structure Molecular Structure of 79-07-2 (Chloroacetamide) Hazard Symbols ToxicT
Synonyms

Acetamide, a-chloro- (4CI);2-Chloroacetamide;Chloracetamide;KM 101;KM 101 (fungicide);Mergal AF;Microcide;NSC 54286;NSC 8408;a-Chloroacetamide;

Article Data 108

Chloroacetamide Synthetic route

112-41-4

1-dodecene

35070-77-0

N-chloro-alpha-chloroacetamide

A

35077-34-0

2-Chloro-N-(2-chloro-dodecyl)-acetamide

B

79-07-2

Chloroacetamide

Conditions
ConditionsYield
In dichloromethane at 15 - 20℃; Irradiation;A 95%
B 3%
120158-03-4

tert-butyl (2-chloroacetyl)carbamate

79-07-2

Chloroacetamide

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 1h; Ambient temperature;94%
35070-77-0

N-chloro-alpha-chloroacetamide

79-07-2

Chloroacetamide

Conditions
ConditionsYield
With n-octyne In dichloromethane at 15 - 20℃; Irradiation;93%
107-14-2

chloroacetonitrile

79-07-2

Chloroacetamide

Conditions
ConditionsYield
With Amberlyst A-26 (OH- form); dihydrogen peroxide In methanol at 20℃; for 2h; Hydrolysis;93%
With [RuCl2(η6-p-cymene)(P(4-C6H4F)2Cl)]; water at 40℃; for 1h; Sealed tube; Inert atmosphere;93%
With C19H23Cl2N6PRuS3*3ClH; water at 100℃; for 1h; Inert atmosphere; Schlenk technique;88%
35077-11-3

α-chloro-N-bromoacetamide

79-07-2

Chloroacetamide

Conditions
ConditionsYield
With 1,2-dimethylcyclohexene In dichloromethane at 15 - 20℃; Irradiation;92%
With perchloric acid; water; potassium hydrogen phthalate; potassium nitrate; potassium bromide at 25℃; for 1h; Equilibrium constant;
591-49-1

1-methylcyclohex-1-ene

35070-77-0

N-chloro-alpha-chloroacetamide

35077-36-2, 64226-98-8

2-Chloro-N-((1S,2R)-2-chloro-2-methyl-cyclohexyl)-acetamide

B

79-07-2

Chloroacetamide

Conditions
ConditionsYield
In dichloromethane at 15 - 20℃; Irradiation;A 88%
B 7%
67-56-1

methanol

70737-12-1

methyl 2-chloroacetimidate hydrochloride

A

74974-54-2

2-chloro-1,1,1-trimethoxyethane

B

79-07-2

Chloroacetamide

Conditions
ConditionsYield
at 20℃; for 24h;A 65%
B n/a
112-41-4

1-dodecene

35077-11-3

α-chloro-N-bromoacetamide

A

35077-35-1

N-(2-Bromo-dodecyl)-2-chloro-acetamide

B

79-07-2

Chloroacetamide

Conditions
ConditionsYield
In dichloromethane at 15 - 20℃; Irradiation;A 62%
B 30%
35070-77-0

N-chloro-alpha-chloroacetamide

930-66-5

1-chlorocyclohexene

A

78174-21-7

2-Chloro-N-(2,2-dichloro-cyclohexyl)-acetamide

B

79-07-2

Chloroacetamide

Conditions
ConditionsYield
In dichloromethane at 15 - 20℃; Irradiation;A 35%
B 59%
35070-77-0

N-chloro-alpha-chloroacetamide

932-66-1

1-cyclohexenyl methyl ketone

35077-39-5, 35077-40-8

N-((1S,2R)-2-Acetyl-2-chloro-cyclohexyl)-2-chloro-acetamide

35077-39-5, 35077-40-8

N-((1R,2R)-2-Acetyl-2-chloro-cyclohexyl)-2-chloro-acetamide

C

79-07-2

Chloroacetamide

Conditions
ConditionsYield
In dichloromethane at 15 - 20℃; Irradiation;A 16%
B 54%
C 30%

Chloroacetamide Specification

The CAS registry number of Chloroacetamide is 79-07-2. The IUPAC name is 2-chloroacetamide. Its EINECS registry number is 201-174-2. It is also called Acetamide, 2-chloro-. In addition, the molecular formula is C2H4ClNO and the molecular weight is 93.51. It is a colorless or yellow crystalline substance with characteristic smell, readily soluble in water. What's more, it belongs to the classes of Amides; Carbonyl Compounds; Organic Building Blocks. It should be stored in a airtight, cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: -0.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.85; (4)ACD/LogD (pH 7.4): -0.85; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 8.18; (8)ACD/KOC (pH 7.4): 8.18; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 20.31 Å2; (13)Index of Refraction: 1.447; (14)Molar Refractivity: 19.72 cm3; (15)Molar Volume: 73.7 cm3; (16)Polarizability: 7.82 ×10-24cm3; (17)Surface Tension: 39 dyne/cm; (18)Density: 1.268 g/cm3; (19)Flash Point: 108.6 °C; (20)Enthalpy of Vaporization: 49.35 kJ/mol; (21)Boiling Point: 256 °C at 760 mmHg; (22)Vapour Pressure: 0.0158 mmHg at 25°C.

Preparation of Chloroacetamide: it can be prepared by ethyl chloroacetate and ammonia. At first, cool the ethyl chloroacetate to 10 °C, slowly add ammonia (relative density is 0.9) with stirring. After finish adding ammonia, continue to stir for 1 hour, filter and crystal the product, use ammonia to wash chloride, drained the product as far as possible, use ethanol for recrystallization at last.

Chloroacetamide can be prepared by ethyl chloroacetate and ammonia.

Uses of Chloroacetamide: it can be used in organic synthesis, pharmaceutical intermediates. It can produce organic compounds such as chloroacetonitrile, sulfanilyl-3-methoxypyrazine and sulfanilylmethylpyrazine. In addition, it can be used as preservative of shampoo, cutting oils, plastics, coatings slab and shower gel. What's more, it can react with 1-phenyl-piperazine to get (4-phenyl-piperazino)-acetic acid amide. This reaction will need reagent K2CO3 and solvent toluene. The yield is about 75% by heating.

Chloroacetamide can react with 1-phenyl-piperazine to get (4-phenyl-piperazino)-acetic acid amide

When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed and may cause sensitization by skin contact. And it has risk of impaired fertility. During using it, do not breathe dust and wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure:
(1)SMILES: ClCC(=O)N
(2)InChI: InChI=1/C2H4ClNO/c3-1-2(4)5/h1H2,(H2,4,5)
(3)InChIKey: VXIVSQZSERGHQP-UHFFFAOYAM

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 31mg/kg (31mg/kg)   Zhonghua Yixue Zazhi. Chinese Medical Journal. Vol. 58, Pg. 462, 1978.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03764,
mouse LD50 oral 155mg/kg (155mg/kg)   Zhonghua Yixue Zazhi. Chinese Medical Journal. Vol. 58, Pg. 462, 1978.
rabbit LD50 oral 122mg/kg (122mg/kg)   Zhonghua Yixue Zazhi. Chinese Medical Journal. Vol. 58, Pg. 462, 1978.
rat LD50 oral 138mg/kg (138mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0536947,
rat LD50 unreported 70mg/kg (70mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1073, 1969.

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