Vinyl chloroformate

Base Information

• Chemical Name: Vinyl chloroformate
• CAS No.: 5130-24-5
• Molecular Formula: C3H3ClO2
• Molecular Weight: 106.509
• Hs Code.: 29159000
• European Community (EC) Number: 225-874-2
• UNII: 9DJ5DDM7G9
• DSSTox Substance ID: DTXSID30199299
• Nikkaji Number: J203.322D
• Wikidata: Q72516345
• Mol file: 5130-24-5.mol

Synonyms:Vinyl chloroformate;5130-24-5;ethenyl carbonochloridate;vinyl carbonochloridate;vinylchloroformate;9DJ5DDM7G9;Carbonochloridic acid, ethenyl ester;EINECS 225-874-2;ethenyl chloroformate;Chloroformic acid vinyl;UNII-9DJ5DDM7G9;Vinyl chloroformate, 94%;Vinyl chloroformate, 99%;chloroformic acid vinyl ester;SCHEMBL197073;DTXSID30199299;STR07467;AKOS015950674;FT-0635551

Chemical Property of Vinyl chloroformate

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 0.88 psi ( 20 °C)
• Refractive Index: n20/D 1.41(lit.)
• Boiling Point: 72.1 °C at 760 mmHg
• Flash Point: 24 °F
• PSA: 26.30000
• Density: 1.21 g/cm³
• LogP: 1.50530
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 105.9821570
• Heavy Atom Count: 6
• Complexity: 69.2

Purity/Quality:

98%Min ^*data from raw suppliers

Vinyl chloroformate 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F；T
• Hazard Codes: F,T
• Statements: 23/24/25-34-11
• Safety Statements: 16-26-36-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C=COC(=O)Cl
• Uses: Vinyl Chloroformate was used to prepare analogues of the Nicotinic Acetylcholine Receptor Agonist (±)-UB-165. It was also used to synthesize possible antitumor agents such as paclitaxel-2''-carbonates and N-carbamyl triazenes.

Technology Process of Vinyl chloroformate

There total 7 articles about Vinyl chloroformate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.2%

phosgene (75-44-5) + trimethylsiloxyethene (6213-94-1) → Vinyl chloroformate (5130-24-5)

Guidance literature:

palladium diacetate; In hexanedinitrile; at -2 - 2 ℃; for 63h; Product distribution / selectivity;

Reference yield:

ethylenebis(chloroformate) (124-05-0) → 1,1-dichloroethane (75-34-3) + Vinyl chloroformate (5130-24-5) + carbonochloridic acid 1-chloro-ethyl ester (50893-53-3) + 2-Chloroethyl chloroformate (627-11-2)

Guidance literature:

at 460 ℃; Produkt 5: 1.2-Dichlor-aethan.Pyrolysis;

Reference yield:

phosgene (75-44-5) + ethenol (557-75-5) → Vinyl chloroformate (5130-24-5)

Guidance literature:

With pyridine; In diethyl ether; 1.) 1 h, 0 deg C, 2.) 8 h, 25 deg C;

DOI:10.1021/jo00181a005

upstream raw materials:

ethylenebis(chloroformate)

2-Chloroethyl chloroformate

phosgene

bis(formylmethyl)mercury

Downstream raw materials:

diethylene glycol bis-vinyl carbonate

(2S,3S)-3-Vinyl-piperidine-1,2-dicarboxylic acid 2-(2-chloro-2-phenyl-ethyl) ester 1-vinyl ester

(3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-1-vinyloxycarbonylpiperidine

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

Refernces

• 1、 -. "Process for preparing vinyl chloroformate". Page/Page column 11; 12. . Retrieved 2012/10/07.
• 2、 Hoffmann, H.M.R.,Iranshahi, Lotfollah. "Synthesis an CuCN-Promoted Cyanation of Iodoformic Esters". . p. 1174 - 1176. Retrieved 2007/10/02.