| Identification | Back Directory | [Name]
VINYL CHLOROFORMATE | [CAS]
5130-24-5 | [Synonyms]
VINYL CHLOROFORMATE
Vinyl chlorocarbonate
Vinylchloroformate99%
Vinyl chloroformate 98%
Vinyloxycarbonyl chloride
Ethenyl carbonochloridoate
VINYL CHLOROFORMATE, STAB.
Chloroformic acid ethenyl ester
Chloridocarbonic acid vinyl ester
VINYL CHLOROFORMATE STABILIZED 99%
Carbonochloridic acid ethenyl ester
Chloridocarbonic acid ethenyl ester
VINYL CHLOROFORMATE, 99%, STABILIZED
Vinyl chloroformate, stabilized, 99%
Ethenyl carbonochloridoate, Ethenyl chloroformate | [EINECS(EC#)]
225-874-2 | [Molecular Formula]
C3H3ClO2 | [MDL Number]
MFCD00000641 | [MOL File]
5130-24-5.mol | [Molecular Weight]
106.51 |
| Chemical Properties | Back Directory | [Appearance]
clear colourless liquid | [Boiling point ]
68-69 °C735 mm Hg(lit.)
| [density ]
1.166 g/mL at 20 °C(lit.)
| [vapor pressure ]
0.88 psi ( 20 °C)
| [refractive index ]
n20/D 1.41(lit.)
| [Fp ]
24 °F
| [storage temp. ]
2-8°C
| [form ]
Liquid | [color ]
Clear colorless | [BRN ]
1741679 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colourless liquid | [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. | [Synthesis]
Two processes have been used commercially to make Vinyl Chloroformate. First, ethylene glycol is converted to its bis(chloroformate) with phosgene. This fragments to VOC-Cl in 30- 40% yield when passed through a hot tube packed with glass helices at 480 °C. More recently, VOC-Cl has been made commercially using a two-step route involving the oxymercuration of vinyl acetate.
| [Purification Methods]
It has been fractionated through a Todd column (p 11, Model A with ~60 plates) under atmospheric pressure and the purity can be checked by gas chromatography. Stabilize it with 0.5% of 2,6-di-tert-butyl-p-cresol. It has IR with at 3100 + 2870 (CH2), 1780 (C=O), 1640 (C=C) and 940 (CH2out-of-plane) and 910 (CH2 wagging) cm-1. [IR: Lee J Org Chem 30 3943 1965, Levaillant Ann Chim (Paris) 6 504 1936.] It is used for protecting NH2 groups in peptide synthesis [Olofson et al. Tetrahedron Lett 1563 1977]. [Beilstein 3 III 28.] | [Precautions]
Vinyl Chloroformate is slightly light-sensitive and more reactive than other chloroformates toward trace moisture. Because hydrolysis products, HCl and acetaldehyde, interfere with some applications, the reagent is often distilled before use. It is a strong lachrymator and skin vesicant; inhalation is hazardous. Use in a fume hood.
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