2549-51-1

Basic information

• Product Name: Vinyl chloroacetate
• Synonyms: CHLOROACETIC ACID VINYL ESTER;VINYL CHLOROACETATE;chloro-aceticaciethenylester;vinylchloracetate;VINYL CHLOROACETATE, STAB.;Vinylchloroacetate,99%;CHLOROACETICACIDVINYLESTER(STABILIZEDWITHMEHQ);Vinyl Chloroacetate (stabilized with MEHQ)
• CAS NO: 2549-51-1
• Molecular Formula: C₄H₅ClO₂
• Molecular Weight: 120.53
• EINECS: 219-834-3
• Product Categories: C2 to C5;Carbonyl Compounds;Esters
• Mol File: 2549-51-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 37-38°C 16mm
• Flash Point: 51°C
• Appearance: colourless liquid
• Density: 1.192 g/mL at 20 °C
• Vapor Pressure: 13.2mmHg at 25°C
• Refractive Index: n20/D 1.444
• Storage Temp.: 2-8°C
• Water Solubility: Difficult to mix in water.
• BRN: 1741679
• CAS DataBase Reference: Vinyl chloroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Vinyl chloroacetate(2549-51-1)
• EPA Substance Registry System: Vinyl chloroacetate(2549-51-1)

Safety Data

• Hazard Codes: C
• Statements: 10-20/21/22-34-22
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2589 6.1/PG 2
• WGK Germany: 3
• RTECS: AG2850000
• F: 8-10-19-23
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 2549-51-1(Hazardous Substances Data)

Usage

Chemical Properties

Vinyl chloroacetate is a colorless clear liquid, almost insoluble in water, soluble in ethanol, carbon tetrachloride, ether, dimethylformamide and benzene. Irritating to skin and eyes. Corrosive. Slowly hydrolyzed to produce chloroacetic acid, which has an ecological impact. It can be used as a raw material for making methacrylic fibers with good affinity for acid dyes.

Uses

Vinyl chloroacetate was used to study the effect of the electron-withdrawing groups on the ligand in a series of bis(acetylacetonate)cobalt(II) derivatives.

General Description

Vinyl chloroacetate appears as a colorless to light yellow colored liquid. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. Toxic by ingestion, inhalation or skin absorption.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Vinyl chloroacetate reacts with acids to liberate heat. 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 with alkali metals and hydrides.

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

InChI:InChI=1/C4H5ClO2/c1-2-7-4(6)3-5/h2H,1,3H2

Synthetic route

chloroacetic acid (79-11-8) + acetylene (74-86-2) → vinyl chloroacetate (2549-51-1)

Conditions	Yield
With mercury(II) diacetate; boric acid at 10 - 20℃;
With hydroquinone; mercury(II) oxide at 60℃; dann bei 40-50grad;
With mercury(II) oxide

divinylmercury (1119-20-6) + chloroacetic acid (79-11-8) → vinyl chloroacetate (2549-51-1)

Conditions	Yield
for 1h; Ambient temperature;

chloroacetyl chloride + 2-chloromercurio-acetaldehyde → vinyl chloroacetate (2549-51-1)

Conditions	Yield
With benzene

octanol (111-87-5) + vinyl chloroacetate (2549-51-1) → n-octyl chloroacetate (5451-98-9)

Conditions	Yield
With Cp*2Sm(THF)2 In toluene Ambient temperature; further reagent: SmI2;	99%
With 1,3-dichlorotetrabutyldistannoxane at 50℃; for 17h;	96%
With 1,3-dichlorotetrabutyldistannoxane at 50℃; for 17h;	96%

vinyl chloroacetate (2549-51-1) + 1-phenyl-2-cyclohex-2-en-1-ol (60174-90-5) → (R)-3-phenylcyclohex-2-enyl chloroacetate

Conditions	Yield
With Candida antartica lipase B (CAL-B) immobilized on a support (commercial name: Chirazyme L-2 C4); V-MPS4 In acetonitrile at 35℃; for 24h; Inert atmosphere;	99%

vinyl chloroacetate (2549-51-1) + 6-Azauridine (54-25-1) → 6-azauridine 5'-chloroacetate

Conditions	Yield
With Candida antarctica lipase B In 2,2,4-trimethylpentane; acetone at 55℃; for 1h; Enzymatic reaction; regioselective reaction;	99%

vinyl chloroacetate (2549-51-1) + thexyldimethylsilyl 6-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside (320351-47-1) → Chloro-acetic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-{(2R,3S,4R,5R,6S)-2-acetoxymethyl-5-azido-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-4-yloxy}-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

Conditions	Yield
With Candida antarctica lipase In acetonitrile at 40℃; for 12h; Acylation;	91%

vinyl chloroacetate + thexyldimethylsilyl 6-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-β-D-glucopyranoside (320351-46-0) → Chloro-acetic acid (2R,3S,4R,5R,6S)-4-((2R,3R,4S,5R,6R)-6-acetoxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-5-azido-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Conditions	Yield
With Candida antarctica lipase In acetonitrile at 28℃; for 4h; Acylation;	90%

vinyl chloroacetate (2549-51-1) + (3S,5S)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (169437-96-1) → Chloro-acetic acid (1S,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester + Chloro-acetic acid (1S,5S)-3-ethynyl-5-hydroxy-2-methyl-cyclohex-2-enyl ester

Conditions	Yield
In tetrahydrofuran for 23h; Ambient temperature; Chromobacterium viscosum lipase;	A 86% B 7 % Spectr.

vinyl chloroacetate (2549-51-1) + (3R,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (169437-97-2) → Chloro-acetic acid (1R,5R)-5-(2-chloro-acetoxy)-3-ethynyl-2-methyl-cyclohex-2-enyl ester + Chloro-acetic acid (1R,5R)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester + Chloro-acetic acid (1R,5R)-3-ethynyl-5-hydroxy-2-methyl-cyclohex-2-enyl ester

Conditions	Yield
In tetrahydrofuran for 92h; Ambient temperature; Chromobacterium viscosum lipase;	A 6.5% B 2.5% C 85%

2-Hydroxy-1,4-naphthoquinone (83-72-7) + vinyl chloroacetate (2549-51-1) + tert-butylisonitrile (119072-55-8, 7188-38-7) → 2-(tert-butylamino)-3-methylnaptho[2,3-b]furan-4,9-dione

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 120℃; for 0.166667h; Microwave irradiation;	85%

vinyl chloroacetate (2549-51-1) → vinyl iodoacetate (52590-49-5)

Conditions	Yield
With sodium iodide In acetone at 20℃; for 1h;	85%

6-Monoacetylated D-glucal (63914-24-9) + vinyl chloroacetate (2549-51-1) → 6-O-acetyl-3-O-chloroacetyl-glucal (118356-99-3, 118455-48-4)

Conditions	Yield
With lipase from Pseudomonas fluorescens In 1,2-dimethoxyethane for 3h; Ambient temperature;	83%

vinyl chloroacetate (2549-51-1) + tert-butylisonitrile (119072-55-8, 7188-38-7) + 4-hydroxy-2H-pyran-2-one → 2-(tert-butylamino)-3-methyl-4H-furo[3,2-c]pyran-4-one

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 120℃; for 0.166667h; Microwave irradiation;	83%

vinyl chloroacetate (2549-51-1) + 6-O-Benzoyl-D-glucal (58871-05-9) → 6-O-benzoyl-3-O-chloroacetyl-glucal (118357-00-9, 118396-89-7, 126453-38-1)

Conditions	Yield
With lipase from Pseudomonas fluorescens In 1,2-dimethoxyethane for 2h; Ambient temperature;	82%

Lipase P + 6-Monoacetylated D-glucal (63914-24-9) + vinyl chloroacetate (2549-51-1) → 6-O-acetyl-3-O-chloroacetyl-glucal (118356-99-3, 118455-48-4)

Conditions	Yield
In 1,2-dimethoxyethane	80%

Lipase P + vinyl chloroacetate (2549-51-1) + 1-O-acetyl-2,6-anhydro-5-deoxy-D-arabino-hex-5-enitol (63914-24-9, 118396-85-3) → 6-O-acetyl-3-O-chloroacetyl-galactal (118356-99-3, 118455-48-4)

Conditions	Yield
In 1,2-dimethoxyethane	80%

benzyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside (18404-72-3) + vinyl chloroacetate (2549-51-1) → benzyl (6-O-chloroacetyl-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside (183296-89-1)

Conditions	Yield
With lipase from Candida antarctica In tetrahydrofuran at 20℃; for 48h; Acylation; Enzymatic reaction;	78%
With immobilized Candida antarctica lipase In tetrahydrofuran at 40℃; for 48h;	78%

vinyl chloroacetate (2549-51-1) + 2-benzyloxy-3-pentanol → (2S,3R)-2-benzyloxy-3-pentyl chloroacetate

Conditions	Yield
With tert-butyl methyl ether; 4 A molecular sieve; Novo Lipozyme IM-20 for 160h; Ambient temperature;	74.7%

vinyl chloroacetate (2549-51-1) + (3R,5S)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (146728-48-5) → Chloro-acetic acid (1S,5R)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester + Chloro-acetic acid (1R,5S)-3-ethynyl-5-hydroxy-2-methyl-cyclohex-2-enyl ester

Conditions	Yield
In tetrahydrofuran for 21h; Ambient temperature; Chromobacterium viscosum lipase; Yields of byproduct given;	A 71% B n/a
In tetrahydrofuran for 21h; Ambient temperature; Chromobacterium viscosum lipase; Yield given;	A 71% B n/a

vinyl chloroacetate (2549-51-1) + (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (113375-51-2) → Chloro-acetic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester + Chloro-acetic acid (1S,5R)-3-ethynyl-5-hydroxy-2-methyl-cyclohex-2-enyl ester

Conditions	Yield
In tetrahydrofuran at 45℃; for 45h; Chromobacterium viscosum lipase; Yields of byproduct given;	A 70% B n/a
In tetrahydrofuran at 45℃; for 45h; Chromobacterium viscosum lipase; Yield given;	A 70% B n/a

vinyl chloroacetate (2549-51-1) + thexyldimethylsilyl 6-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-β-D-glucopyranoside (320351-46-0) → Chloro-acetic acid (2R,3S,4R,5R,6S)-4-((2R,3R,4S,5R,6R)-6-acetoxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-5-azido-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester + Chloro-acetic acid (2R,3S,4R,5R,6S)-4-[(2R,3R,4S,5R,6R)-6-acetoxymethyl-3-(2-chloro-acetoxy)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-5-azido-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Conditions	Yield
With Candida antarctica lipase In acetonitrile at 35℃; for 1h; Acylation;	A 67% B 29%

tributylphosphine (998-40-3) + vinyl chloroacetate (2549-51-1) → Vinyloxycarbonylmethyl-tributyl-phosphoniumhydroxid

Conditions	Yield
In diethyl ether at 20℃; for 22.5h; Schlenk technique;	63%
In benzene

vinyl chloroacetate (2549-51-1) + benzyl (6-O-acetyl-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside (183296-88-0) → Chloro-acetic acid (2S,3R,4S,5R,6R)-6-acetoxymethyl-2-((2R,3S,4R,5R,6R)-6-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

Conditions	Yield
With immobilized Candida antarctica lipase In acetonitrile at 45℃; for 120h;	62%

vinyl chloroacetate + 2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-cyclopent-3-enol (606495-99-2) → (1S,2R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-cyclopent-3-enol (180187-46-6) + Chloro-acetic acid (1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopent-3-enyl ester

Conditions	Yield
With Lipase PS In di-isopropyl ether at 30℃; for 1h;	A 50% B 46%

vinyl chloroacetate (2549-51-1) + (Z)-2-phenylbut-2-ene-1,4-diol → (Z)-4-hydroxy-3-phenylbut-2-en-1-yl chloroacetate

Conditions	Yield
With Porcine pancreas lipase type II In 1,4-dioxane at 20℃; for 24h; Enzymatic reaction;	50%

vinyl chloroacetate (2549-51-1) + (4-hydroxy-3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanone (24206-41-5) → (R)-1-benzoyl-1,2,3,4-tetrahydroquinolin-4-yl 2-chloroacetate + (S)-(4-hydroxy-3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanone

Conditions	Yield
With Novozyme 435 lipase In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction; enantioselective reaction;	A 49% B 34%

vinyl chloroacetate (2549-51-1) + tert-butyl 6-chloro-4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate → (R)-tert-butyl 6-chloro-4-(2-chloroacetoxy)-3,4-dihydroquinoline-1(2H)-carboxylate + (S)-tert-butyl 6-chloro-4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions	Yield
With Novozyme 435 lipase In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction; enantioselective reaction;	A 42% B 48%

vinyl chloroacetate (2549-51-1) + tert-butyl 6-bromo-4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate → (R)-tert-butyl 6-bromo-4-(2-chloroacetoxy)-3,4-dihydroquinoline-1(2H)-carboxylate + (S)-tert-butyl 6-bromo-4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions	Yield
With Novozyme 435 lipase In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction; enantioselective reaction;	A 47% B 29%

vinyl chloroacetate (2549-51-1) + phenyl 4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate → (R)-phenyl 4-(2-chloroacetoxy)-3,4-dihydroquinoline-1(2H)-carboxylate + (S)-phenyl 4-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions	Yield
With Novozyme 435 lipase In tert-butyl methyl ether at 30℃; for 8h; Enzymatic reaction; enantioselective reaction;	A 43% B 46%

Upstream product

• 79-04-9 chloroacetyl chloride 
• 1119-20-6 divinylmercury 
• 79-11-8 chloroacetic acid 
• 74-86-2 acetylene 

Downstream Products

• 1192-81-0 5-chloromethyl-3-methyl-1,2,4-oxadiazole 
• 75024-00-9 (R,R)-(-)-2-fluorocyclohexanol 
• 292150-03-9 (1S,2S)-(+)-2-fluorocyclohexanol 
• 433305-00-1 (R,R)-(-)-2-fluorocyclooctanol 
• 433305-00-1 (S,S)-(+)-2-fluorocyclooctanol 
• 52590-49-5 vinyl iodoacetate 
• 63058-25-3 (2E,6E)-farnesyl chloroacetate