Methyl chloroacetate

Methyl chloroacetate Basic information
Product Name:Methyl chloroacetate
Synonyms:Chloroacetic acid methyl;Methyl chloroacetate,98%;Methyl chloroacetate, 98% 1LT;METHYL CHLOROACETATE FOR SYNTHESIS;Methyl chloroacetate, AR,99.0%;Chlorine Methyl acetate;IHT-FC MCA;Mathyl Chloroacetate
CAS:96-34-4
MF:C3H5ClO2
MW:108.52
EINECS:202-501-1
Product Categories:Pyridines ,Halogenated Heterocycles;organic chemical;C2 to C5;Carbonyl Compounds;Esters;Pesticides&Metabolites;Organics;Alpha sort;H-MAlphabetic;M;META - METH;500 Series Drinking Water Methods;EPA;Method 552;bc0001
Mol File:96-34-4.mol
Methyl chloroacetate Structure
Methyl chloroacetate Chemical Properties
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.)
Fp 125 °F
storage temp. Store at <= 20°C.
solubility 51.6g/l (slow decomposition)
form Liquid
color Clear colorless
PH4.6 (28g/l, H2O, 20℃)
explosive limit4.6-18.5%(V)
Water Solubility 28 g/L (20 ºC)
Merck 14,6042
BRN 506255
LogP0.63 at 20℃
CAS DataBase Reference96-34-4(CAS DataBase Reference)
NIST Chemistry ReferenceAcetic acid, chloro-, methyl ester(96-34-4)
EPA Substance Registry SystemAcetic acid, 2-chloro-, methyl ester (96-34-4)
Safety Information
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
19
Autoignition Temperature869 °F
TSCA Yes
HS Code 2915 40 00
HazardClass 6.1
PackingGroup I
Hazardous Substances Data96-34-4(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 107 mg/kg
MSDS Information
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SigmaAldrich English
ALFA English
Methyl chloroacetate Usage And Synthesis
Chemical Propertiesclear colorless liquid with a slight irritating odor. It is miscible with organic solvents such as ethanol, ether, acetone and benzene. Slightly soluble in water.
UsesMethyl 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.
ApplicationMethyl 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.
PreparationMethyl 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 DescriptionA 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 ReactionsHighly flammable. Insoluble in water.
Reactivity ProfileMethyl 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.
HazardToxic by ingestion and inhalation.
Health HazardExtremely 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 HazardSpecial Hazards of Combustion Products: Toxic fumes of hydrogen chloride
Safety ProfilePoison 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 MethodsShake 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.]
METHYL OXALYL CHLORIDE Methylparaben Methyl Ethyl oxalyl monochloride DICHLOROACETIC ANHYDRIDE TRICHLOROACETIC ANHYDRIDE Acetonitrile Chloroacetic acid METHYL CHLORODIFLUOROACETATE Chloroacetic anhydride Ethyl trichloroacetate Methyl trichloroacetate tert-Butyl chloroacetate Methanol CHLORODIFLUOROACETIC ANHYDRIDE Methyl 2-chloropropionate Ethyl 2-chloropropionate Methyl chloroacetate

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