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

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

Uses

Used in Chemical Synthesis:
Vinyl chloroacetate is used as a raw material for the production of methacrylic fibers, which exhibit good affinity for acid dyes. This application takes advantage of its chemical properties to create a valuable material in the textile industry.
Used in Research and Development:
In the field of research, vinyl chloroacetate is utilized to study the effects of electron-withdrawing groups on the ligand in a series of bis(acetylacetonate)cobalt(II) derivatives. This application highlights its importance in understanding and advancing chemical reactions and compound development.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, vinyl chloroacetate can also be used in the pharmaceutical industry as an intermediate for the synthesis of various drugs and pharmaceutical compounds due to its reactive nature and ability to form different chemical bonds.
Used in Environmental Studies:
Given its ecological impact when hydrolyzed to produce chloroacetic acid, vinyl chloroacetate can be used in environmental studies to understand the effects of chemical compounds on ecosystems and to develop methods for mitigating their potential harm.

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

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

Downstream Products

• 1192-81-0 5-chloromethyl-3-methyl-1,2,4-oxadiazole 
• 1822-94-2 5-(chloromethyl)-3-phenyl-1,2,4-oxadiazole 
• 118357-00-9 6-O-benzoyl-3-O-chloroacetyl-galactal 
• 72681-54-0 (Toluene-4-sulfonyl)-acetic acid vinyl ester 
• 5451-98-9 n-octyl chloroacetate 
• 183296-89-1 benzyl (6-O-chloroacetyl-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside 

Relevant articles and documents

A novel synthesis of vinyl esters from vinylversatate-10

Vinylversatate-10 (VV10)1 1 VV 10 Vinyl Monomer, Development Product, Shell Chemical Company has successfully been used to synthesise a large number of lower vinyl esters by transvinylation in presence of mercuric acetate and sulfuric acid. The synthesis of vinylhalo esters proceeds with more difficulty. It has been observed that neither Hg(OAc)2 nor H2SO4 alone is capable of initiating the transvinylation. Furthermore, it has been found that a molar ratio 2:1 of VV10 to carboxylic acid is sufficient to drive the reaction to the right by continuous distillation of the vinyl ester formed, and as a result a high yield of vinyl ester is obtained. A mechanism for this reaction and for the formation of side products has been proposed.