Methyl chloroacetate Property

Melting point:

-33 °C

Boiling point:

130 °C740 mm Hg(lit.)

Density 

1.238 g/mL at 25 °C(lit.)

vapor density 

3.8 (vs air)

vapor pressure 

10 mm Hg ( 25 °C)

refractive index 

n20/D 1.422(lit.)

Flash point:

125 °F

storage temp. 

Store at <= 20°C.

solubility 

51.6g/l (slow decomposition)

form 

Liquid

color 

Clear colorless

PH

4.6 (28g/l, H2O, 20℃)

explosive limit

4.6-18.5%(V)

Water Solubility 

28 g/L (20 ºC)

Merck 

14,6042

BRN 

506255

Dielectric constant

12.9（20℃）

LogP

0.63 at 20℃

CAS DataBase Reference

96-34-4(CAS DataBase Reference)

NIST Chemistry Reference

Acetic acid, chloro-, methyl ester(96-34-4)

EPA Substance Registry System

Acetic acid, 2-chloro-, methyl ester (96-34-4)

Safety

Hazard Codes 

T,Xi,F

Risk Statements 

10-23/25-37/38-41-40-36/37/38-38

Safety Statements 

26-37/39-45-36-16

RIDADR 

UN 2295 6.1/PG 1

WGK Germany 

2

RTECS 

AF9500000

F 

19

Autoignition Temperature

869 °F

TSCA 

Yes

HS Code 

2915 40 00

HazardClass 

6.1

PackingGroup 

I

Hazardous Substances Data

96-34-4(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 107 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Methyl chloroacetate Chemical Properties,Usage,Production

Chemical Properties

clear colorless liquid with a slight irritating odor. It is miscible with organic solvents such as ethanol, ether, acetone and benzene. Slightly soluble in water.

Uses

Methyl chloroacetate is used as a solvent and chemical intermediate. It acts as a precursor in the preparation of (carboxymethyl) trimethylammonium chloride esters. Further, it is used in the preparation of octakis-(carbethoxymethoxy)calix[8]arene. It is employed as an extraction solvent during the separation of neutral compounds. In addition to this, it is used in the synthesis of dimethyl carbonate.

Application

Methyl chloroacetate (MC) is a halogenated ester mainly used as a solvent in organic synthesis or in the preparation of several compounds. Typically, MC is used in the preparation of (carboxymethyl) trimethylammonium chloride estersor in the synthesis of octakis- (carbethoxymethoxy)calix[8]arene. Additionally, methyl chloroacetate acts as an extraction solvent during the separation of neutral compounds with concentration enhancement using coupling liquid–liquid semi-microextraction with micellar electrokinetic chromatography through oncapillary decomposition.

Preparation

Methyl chloroacetate is prepared by esterification of chloroacetic acid with methanol.
Reaction: Methanol and chloroacetic acid are uniformly mixed in a weight ratio of 0.366:1, heated with stirring, and the esterification reaction is carried out at 105-110 °C. In the reaction process, the ternary azeotrope of methyl chloroacetate, water and methanol is continuously steamed, layered through the ester separator, the separated methanol and water are returned to the reaction pot, and the separated crude ester is made of sodium carbonate. neutralize. The neutralized crude ester is firstly cut out the 130°C fraction by atmospheric distillation, and then subjected to vacuum distillation to collect the 65°C (8kPa) fraction, which is the finished product of methyl chloroacetate. The yield is about 96%.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 3408, 1985 DOI: 10.1021/jo00218a034

General Description

A crystalline solid or a solid dissolved in a liquid. Insoluble in water and denser than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Methyl chloroacetate is a halogenated ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Hazard

Toxic by ingestion and inhalation.

Health Hazard

Extremely corrosive to the eyes, skin, nose, throat, and upper respiratory tract. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.

Fire Hazard

Special Hazards of Combustion Products: Toxic fumes of hydrogen chloride

Safety Profile

Poison by ingestion. Moderately toxic by inhalation and subcutaneous routes. Flammable when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits toxic fumes of Cl-.

Purification Methods

Shake the ester with saturated aqueous Na2CO3 (three times), aqueous 50% CaCl2 (three times), saturated aqueous NaCl (twice), dry (Na2SO4) and fractionally distil it. Very toxic. [Beilstein 2 IV 480.]