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Vinyl chloroacetate

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Name

Vinyl chloroacetate

EINECS 219-834-3
CAS No. 2549-51-1 Density 1.153 g/cm3
PSA 26.30000 LogP 0.91190
Solubility Insoluble in water Melting Point -68oC
Formula C4H5ClO2 Boiling Point 123.7 °C at 760 mmHg
Molecular Weight 120.535 Flash Point 39 °C
Transport Information UN 2589 Appearance colourless liquid
Safety 26-36/37/39-45 Risk Codes 10-20/21/22-34
Molecular Structure Molecular Structure of 2549-51-1 (Vinyl chloroacetate) Hazard Symbols CorrosiveC
Synonyms

Aceticacid, chloro-, ethenyl ester (9CI);Acetic acid, chloro-, vinyl ester(6CI,8CI);Vinyl monochloroacetate;

Article Data 14

Vinyl chloroacetate Synthetic route

79-11-8

chloroacetic acid

74-86-2

acetylene

2549-51-1

vinyl chloroacetate

Conditions
ConditionsYield
With mercury(II) diacetate; boric acid at 10 - 20℃;
With hydroquinone; mercury(II) oxide at 60℃; dann bei 40-50grad;
With mercury(II) oxide
1119-20-6

divinylmercury

79-11-8

chloroacetic acid

2549-51-1

vinyl chloroacetate

Conditions
ConditionsYield
for 1h; Ambient temperature;
chloroacetyl chloride

chloroacetyl chloride

2-chloromercurio-acetaldehyde

2-chloromercurio-acetaldehyde

2549-51-1

vinyl chloroacetate

Conditions
ConditionsYield
With benzene
111-87-5

octanol

2549-51-1

vinyl chloroacetate

5451-98-9

n-octyl chloroacetate

Conditions
ConditionsYield
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%
2549-51-1

vinyl chloroacetate

60174-90-5

1-phenyl-2-cyclohex-2-en-1-ol

(R)-3-phenylcyclohex-2-enyl chloroacetate

Conditions
ConditionsYield
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%
2549-51-1

vinyl chloroacetate

54-25-1

6-Azauridine

6-azauridine 5'-chloroacetate

Conditions
ConditionsYield
With Candida antarctica lipase B In 2,2,4-trimethylpentane; acetone at 55℃; for 1h; Enzymatic reaction; regioselective reaction;99%
2549-51-1

vinyl chloroacetate

320351-47-1

thexyldimethylsilyl 6-O-acetyl-β-D-galactopyranosyl-(1->3)-6-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside

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
ConditionsYield
With Candida antarctica lipase In acetonitrile at 40℃; for 12h; Acylation;91%
vinyl chloroacetate

vinyl chloroacetate

320351-46-0

thexyldimethylsilyl 6-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-β-D-glucopyranoside

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
ConditionsYield
With Candida antarctica lipase In acetonitrile at 28℃; for 4h; Acylation;90%
2549-51-1

vinyl chloroacetate

169437-96-1

(3S,5S)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene

A

Chloro-acetic acid (1S,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester

B

Chloro-acetic acid (1S,5S)-3-ethynyl-5-hydroxy-2-methyl-cyclohex-2-enyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 23h; Ambient temperature; Chromobacterium viscosum lipase;A 86%
B 7 % Spectr.
2549-51-1

vinyl chloroacetate

169437-97-2

(3R,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene

A

Chloro-acetic acid (1R,5R)-5-(2-chloro-acetoxy)-3-ethynyl-2-methyl-cyclohex-2-enyl ester

B

Chloro-acetic acid (1R,5R)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester

C

Chloro-acetic acid (1R,5R)-3-ethynyl-5-hydroxy-2-methyl-cyclohex-2-enyl ester

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

Vinyl chloroacetate Specification

The Vinyl chloroacetate with the CAS number 2549-51-1 is also called Acetic acid, 2-chloro-,ethenyl ester. The IUPAC name is ethenyl 2-chloroacetate. Its molecular formula is C4H5ClO2. The EINECS registry number is 219-834-3. This chemical belongs to the following product categories: (1)C2 to C5; (2)Carbonyl Compounds; (3)Esters.

The properties of the chemical are: (1)ACD/LogP: 0.96; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.96; (4)ACD/LogD (pH 7.4): 0.96; (5)ACD/BCF (pH 5.5): 3.17; (6)ACD/BCF (pH 7.4): 3.17; (7)ACD/KOC (pH 5.5): 79.53; (8)ACD/KOC (pH 7.4): 79.53; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.428; (14)Molar Refractivity: 26.92 cm3; (15)Molar Volume: 104.5 cm3; (16)Polarizability: 10.67×10-24cm3; (17)Surface Tension: 29.4 dyne/cm; (18)Enthalpy of Vaporization: 36.17 kJ/mol; (19)Vapour Pressure: 13.2 mmHg at 25°C.

Uses: This chemical can react with octan-1-ol to prepare chloro-acetic acid octyl ester. This reaction needs reagent 1,3-dichlorotetrabutyldistannoxane at temperature of 50°C. The reaction time is 17 hours. The yield is 96%.

While using this chemical, you should be very cautious. This chemical is flammable and harmful by inhalation, in contact with skin and if swallowed. It can cause burns.. Therefore, you should take the following instructions. Firstly, you should wear suitable protective clothing, gloves and eye/face protection. Then in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Finally in case of accident or if you feel unwell, you should seek medical advice immediately (show the label whenever possible).

You can still convert the following datas into molecular structure:
(1)SMILES: ClCC(=O)O\C=C
(2)InChI: InChI=1/C4H5ClO2/c1-2-7-4(6)3-5/h2H,1,3H2
(3)InChIKey: XJELOQYISYPGDX-UHFFFAOYAH

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