Product Name

  • Name

    VINYL CHLOROFORMATE

  • EINECS 225-874-2
  • CAS No. 5130-24-5
  • Article Data10
  • CAS DataBase
  • Density 1.21 g/cm3
  • Solubility
  • Melting Point
  • Formula C3H3ClO2
  • Boiling Point 72.1 °C at 760 mmHg
  • Molecular Weight 106.509
  • Flash Point 24 °F
  • Transport Information UN 3390 6
  • Appearance clear colourless liquid
  • Safety 16-26-36-45-36/37
  • Risk Codes 23/24/25-34-11
  • Molecular Structure Molecular Structure of 5130-24-5 (VINYL CHLOROFORMATE)
  • Hazard Symbols FlammableF;ToxicT
  • Synonyms Formicacid, chloro-, vinyl ester (7CI,8CI);Vinyl chlorocarbonate;Vinylchloroformate;Vinyloxycarbonyl chloride;ethenyl carbonochloridate;carbonochloridic acid, ethenyl ester;
  • PSA 26.30000
  • LogP 1.50530

Synthetic route

phosgene
75-44-5

phosgene

trimethylsiloxyethene
6213-94-1

trimethylsiloxyethene

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

Conditions
ConditionsYield
palladium diacetate In hexanedinitrile at -2 - 2℃; for 63h; Product distribution / selectivity;85.2%
With palladium diacetate In acetonitrile
ethylenebis(chloroformate)
124-05-0

ethylenebis(chloroformate)

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

Conditions
ConditionsYield
at 425 - 460℃; Pyrolysis;
ethylenebis(chloroformate)
124-05-0

ethylenebis(chloroformate)

A

1,1-dichloroethane
75-34-3

1,1-dichloroethane

B

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

C

carbonochloridic acid 1-chloro-ethyl ester
50893-53-3

carbonochloridic acid 1-chloro-ethyl ester

D

2-Chloroethyl chloroformate
627-11-2

2-Chloroethyl chloroformate

Conditions
ConditionsYield
at 460℃; Produkt 5: 1.2-Dichlor-aethan.Pyrolysis;
2-Chloroethyl chloroformate
627-11-2

2-Chloroethyl chloroformate

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

Conditions
ConditionsYield
Pyrolysis;
at 425 - 460℃; Pyrolysis;
phosgene
75-44-5

phosgene

bis(formylmethyl)mercury
4387-13-7

bis(formylmethyl)mercury

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

Conditions
ConditionsYield
In diethyl ether; diethylene glycol dimethyl ether
phosgene
75-44-5

phosgene

ethenol
557-75-5

ethenol

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

Conditions
ConditionsYield
With pyridine In diethyl ether 1.) 1 h, 0 deg C, 2.) 8 h, 25 deg C;
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

2-Benzyl-4,4-diphenyl-octahydro-2-aza-4-sila-inden-7-one
203570-57-4

2-Benzyl-4,4-diphenyl-octahydro-2-aza-4-sila-inden-7-one

7-Oxo-4,4-diphenyl-octahydro-2-aza-4-sila-indene-2-carboxylic acid vinyl ester
203570-62-1

7-Oxo-4,4-diphenyl-octahydro-2-aza-4-sila-indene-2-carboxylic acid vinyl ester

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane for 2.5h; Ambient temperature;100%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

2-(3,4-dimethoxyphenyl)-2-cyclohexen-1-ol
189363-85-7

2-(3,4-dimethoxyphenyl)-2-cyclohexen-1-ol

carbonic acid 2-(3,4-dimethoxy-phenyl)-cyclohex-2-enyl ester vinyl ester

carbonic acid 2-(3,4-dimethoxy-phenyl)-cyclohex-2-enyl ester vinyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃;100%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

2-(3,4-methylenedioxyphenyl)-2-cyclohexen-1-ol
215609-91-9

2-(3,4-methylenedioxyphenyl)-2-cyclohexen-1-ol

carbonic acid 2-benzo[1,3]dioxol-5-yl-cyclohex-2-enyl ester vinyl ester
335371-05-6

carbonic acid 2-benzo[1,3]dioxol-5-yl-cyclohex-2-enyl ester vinyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃;100%
Ethyl diphenylphosphinite
719-80-2

Ethyl diphenylphosphinite

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

diphenylvinyloxycarbonylphosphinoxide
1237132-78-3

diphenylvinyloxycarbonylphosphinoxide

Conditions
ConditionsYield
at 0 - 20℃; for 3.25h; Michaelis-Arbuzov reaction;99%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

3-(tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone
144152-46-5

3-(tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone

N-vinyloxycarbonyl-3-(tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone
144152-44-3

N-vinyloxycarbonyl-3-(tbutyldimethylsilyl)-14-acetoxy-7,8-dihydromorphinone

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 72h; Heating;98%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

14β-methoxy-7,8-dihydrocodeinone

14β-methoxy-7,8-dihydrocodeinone

14β-methoxy-7,8-dihydro-N-<(vinyloxy)carbonyl>norcodeinone

14β-methoxy-7,8-dihydro-N-<(vinyloxy)carbonyl>norcodeinone

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 50℃; for 120h;97%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

2,2,4,4-Tetramethyl-1,3-oxazolidine
57822-91-0

2,2,4,4-Tetramethyl-1,3-oxazolidine

vinyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

vinyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

Conditions
ConditionsYield
With sodium carbonate In dichloromethane at 20℃; for 5h;97%
(1R)-9-methyl-9-azabicyclo[4.2.1]nonan-2-one
126811-06-1

(1R)-9-methyl-9-azabicyclo[4.2.1]nonan-2-one

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

(1R,6R)-2-Oxo-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid vinyl ester
200402-26-2

(1R,6R)-2-Oxo-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid vinyl ester

Conditions
ConditionsYield
With potassium carbonate In dichloromethane96%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

9-methyl-9-aza-bicyclo[4.2.1]nonan-2-one

9-methyl-9-aza-bicyclo[4.2.1]nonan-2-one

2-oxo-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid vinyl ester

2-oxo-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid vinyl ester

Conditions
ConditionsYield
With potassium carbonate In dichloromethane Substitution;96%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

2-[(tert-butyldimethylsiloxy)methyl]cyclohex-2-enol
350678-19-2

2-[(tert-butyldimethylsiloxy)methyl]cyclohex-2-enol

1-tert-butyldimethylsilanyloxymethyl-6-vinyloxycarbonyloxy-1-cyclohexene
335371-10-3

1-tert-butyldimethylsilanyloxymethyl-6-vinyloxycarbonyloxy-1-cyclohexene

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 1h;96%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

N,N`-dimethylethylenediamine
110-70-3

N,N`-dimethylethylenediamine

C10H16N2O4
1158919-28-8

C10H16N2O4

Conditions
ConditionsYield
With sodium carbonate In dichloromethane; water at 0 - 20℃; for 2.66667h; Inert atmosphere;96%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

vinylene carbonate
872-36-6

vinylene carbonate

Conditions
ConditionsYield
With triethylamine at 34 - 49℃; for 0.0555556h; Temperature; Flow reactor; Sonication; Inert atmosphere;95.6%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

trans-decahydro-4a-(3-methoxyphenyl)-2-methyl-6-methyleneisoquinoline

trans-decahydro-4a-(3-methoxyphenyl)-2-methyl-6-methyleneisoquinoline

ethenyl (+/-)-trans-3,4,4a,5,8,8a-hexahydro-4a-(3-methoxyphenyl)-2(1H)-isoquinolinecarboxylate
137517-94-3

ethenyl (+/-)-trans-3,4,4a,5,8,8a-hexahydro-4a-(3-methoxyphenyl)-2(1H)-isoquinolinecarboxylate

Conditions
ConditionsYield
With potassium carbonate In 1,2-dichloro-ethane for 1.5h; Heating;95%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

C12H18N2O

C12H18N2O

C14H18N2O3

C14H18N2O3

Conditions
ConditionsYield
With potassium carbonate In dichloromethane Heating;95%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

C12H18N2O

C12H18N2O

C14H18N2O3

C14H18N2O3

Conditions
ConditionsYield
With potassium carbonate In dichloromethane Heating;95%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

C12H18N2O

C12H18N2O

C14H18N2O3

C14H18N2O3

Conditions
ConditionsYield
With potassium carbonate In dichloromethane Heating;95%
oleoyl alcohol
143-28-2

oleoyl alcohol

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

cis-octadec-9-enyl vinyl carbonate
1188536-57-3

cis-octadec-9-enyl vinyl carbonate

Conditions
ConditionsYield
With pyridine at 0 - 50℃; Inert atmosphere;95%
9-methyl-9-azabicyclo[4.2.1]nonan-2-one
70423-78-8

9-methyl-9-azabicyclo[4.2.1]nonan-2-one

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

9-vinyloxycarbonyl-9-azabicyclo[4.2.1]nonan-2-one
284039-55-0

9-vinyloxycarbonyl-9-azabicyclo[4.2.1]nonan-2-one

Conditions
ConditionsYield
Stage #1: 9-methyl-9-azabicyclo[4.2.1]nonan-2-one With potassium carbonate In dichloromethane at 20℃; for 1h;
Stage #2: Vinyl chloroformate In dichloromethane at 20℃; for 48h; Further stages.;
94%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

3-tert-butyl-2,5-dihydroxybenzaldehyde
192803-37-5

3-tert-butyl-2,5-dihydroxybenzaldehyde

3-tert-butyl-4-hydroxy-5-oxomethylphenyl vinyl carbonate

3-tert-butyl-4-hydroxy-5-oxomethylphenyl vinyl carbonate

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 4h;94%
3-{4,5-dimethoxy-2-[2-(4-methylbenzenesulfonylamino)ethyl]phenyl}prop-2-enol
950676-27-4

3-{4,5-dimethoxy-2-[2-(4-methylbenzenesulfonylamino)ethyl]phenyl}prop-2-enol

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

ethenyl (Z)-3-{4,5-dimethoxy-2-[2-(4-methylbenzenesulfonylamino)ethyl]phenyl}prop-2-enyl carbonate

ethenyl (Z)-3-{4,5-dimethoxy-2-[2-(4-methylbenzenesulfonylamino)ethyl]phenyl}prop-2-enyl carbonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 3h;94%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

1,4-bis(vinyloxycarbonyloxy)butane
1158919-26-6

1,4-bis(vinyloxycarbonyloxy)butane

Conditions
ConditionsYield
With pyridine at 0 - 50℃; Inert atmosphere;94%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

(+/-)-6-methoxydimetindene
151562-12-8

(+/-)-6-methoxydimetindene

{2-[6-Methoxy-3-(1-pyridin-2-yl-ethyl)-1H-inden-2-yl]-ethyl}-methyl-carbamic acid vinyl ester
173070-30-9

{2-[6-Methoxy-3-(1-pyridin-2-yl-ethyl)-1H-inden-2-yl]-ethyl}-methyl-carbamic acid vinyl ester

Conditions
ConditionsYield
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In 1,2-dichloro-ethane 15 min, -5 to -10 deg C; 30 min, 60-70 deg C;93%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

(Z)-3-{4,5-dimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enol
640727-43-1

(Z)-3-{4,5-dimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enol

ethenyl (Z)-3-{4,5-dimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate
950676-31-0

ethenyl (Z)-3-{4,5-dimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 3h;93%
(S)-(-)-4-chloro-2-(1-hydroxyethyl)pyridine
872036-41-4

(S)-(-)-4-chloro-2-(1-hydroxyethyl)pyridine

Vinyl chloroformate
5130-24-5

Vinyl chloroformate

(1S)-(-)-1-(4-chloropyridin-2-yl)ethyl vinyl carbonate
1207742-70-8

(1S)-(-)-1-(4-chloropyridin-2-yl)ethyl vinyl carbonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃;93%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

(Z)-3-{4,6-dimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enol
1332523-77-9

(Z)-3-{4,6-dimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enol

ethenyl (Z)-3-{4,6-dimethoxy-2-[2-(trifluoroacetylamino)-ethyl]phenyl}prop-2-enyl carbonate
1332523-71-3

ethenyl (Z)-3-{4,6-dimethoxy-2-[2-(trifluoroacetylamino)-ethyl]phenyl}prop-2-enyl carbonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 3h; Inert atmosphere;93%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

1,3-bis(4-methoxybenzyloxy)-6-[(Z)-3-hydroxyprop-1-enyl]5-[2-(trifluoroacetamido)ethyl]benzene
1314093-93-0

1,3-bis(4-methoxybenzyloxy)-6-[(Z)-3-hydroxyprop-1-enyl]5-[2-(trifluoroacetamido)ethyl]benzene

1,3-bis(4-methoxybenzyloxy)-4-(3-ethenyloxycarbonyloxyprop-1-enyl)-5-[ 2-(trifluoroacetamido)ethyl]benzene

1,3-bis(4-methoxybenzyloxy)-4-(3-ethenyloxycarbonyloxyprop-1-enyl)-5-[ 2-(trifluoroacetamido)ethyl]benzene

Conditions
ConditionsYield
With pyridine at 0℃; for 3h;93%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

sodium chloride
7647-14-5

sodium chloride

Conditions
ConditionsYield
With triethylamine93%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

(2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-2-carboxylic acid ethyl ester
193538-84-0

(2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-2-carboxylic acid ethyl ester

(2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-1,2-carboxylic acid 2-ethyl ester 1-vinyl ester
193538-86-2

(2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-1,2-carboxylic acid 2-ethyl ester 1-vinyl ester

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 192h; Heating;92%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

(3S,5S)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene
169437-96-1

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

(3S,5S)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene
797037-97-9

(3S,5S)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene

Conditions
ConditionsYield
With pyridine In dichloromethane for 1h;92%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

25-ethoxymethyloxyvitamin D3

25-ethoxymethyloxyvitamin D3

3-O-(vinyloxy)carbonyl-25-ethoxymethyloxyvitamin D3

3-O-(vinyloxy)carbonyl-25-ethoxymethyloxyvitamin D3

Conditions
ConditionsYield
With pyridine at 0℃;92%
With triethylamine In dichloromethane at 0 - 20℃; for 12h;92%

Vinyl chlorocarbonate Specification

The Vinyl chlorocarbonate, with the CAS registry number 5130-24-5 and EINECS registry number 225-874-2, has the systematic name and IUPAC name of ethenyl carbonochloridate. It is a kind of clear colourless liquid, and belongs to the followiing product categories: Monomers; Polymer Science; Vinyl Esters. And the molecular formula of the chemical is C3H3ClO2. What' s more, it should bestored at 2-8°C.

The characteristics of Vinyl chlorocarbonate are as followings: (1)ACD/LogP: 1.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.51; (4)ACD/LogD (pH 7.4): 1.51; (5)ACD/BCF (pH 5.5): 8.24; (6)ACD/BCF (pH 7.4): 8.24; (7)ACD/KOC (pH 5.5): 157.52; (8)ACD/KOC (pH 7.4): 157.52; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.42; (14)Molar Refractivity: 22.29 cm3; (15)Molar Volume: 88 cm3; (16)Polarizability: 8.83×10-24cm3; (17)Surface Tension: 28.6 dyne/cm; (18)Density: 1.21 g/cm3; (19)Enthalpy of Vaporization: 31.35 kJ/mol; (20)Boiling Point: 72.1 °C at 760 mmHg; (21)Vapour Pressure: 120 mmHg at 25°C.  

Uses of Vinyl chlorocarbonate: It can react with diazomethane to produce vinyl diazoacetate, and the yield is about 92%.   

You should be cautious while dealing with this chemical. It is highly flammable chemical which may cause burns. And it is toxic by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Keep away from sources of ignition - No smoking; Wear suitable protective clothing and gloves, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible). 

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: ClC(=O)O\C=C
(2)InChI: InChI=1/C3H3ClO2/c1-2-6-3(4)5/h2H,1H2
(3)InChIKey: PQLFROTZSIMBKR-UHFFFAOYAD

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