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242306

Sigma-Aldrich

Allyl chloroformate

97%, for peptide synthesis

Synonym(s):

2-Propen-1-yl chloroformate, Allyloxycarbonyl chloride

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About This Item

Linear Formula:
ClCOOCH2CH=CH2
CAS Number:
2937-50-0
Molecular Weight:
120.53
Beilstein/REAXYS Number:
773915
EC Number:
220-916-6
MDL number:
MFCD00000648
UNSPSC Code:
12190000
PubChem Substance ID:
24854549
NACRES:
NA.22

product name

Allyl chloroformate, 97%

vapor pressure

3.67 psi ( 20 °C)

assay

97%

form

liquid

refractive index

n20/D 1.422 (lit.)

bp

~27 °C/11 mmHg (lit.)

density

1.134 g/mL at 20 °C (lit.)

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

ClC(=O)OCC=C

InChI

1S/C4H5ClO2/c1-2-3-7-4(5)6/h2H,1,3H2

InChI key

CAEWJEXPFKNBQL-UHFFFAOYSA-N

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General description

Allyl chloroformate is an organic compound used to synthesize numerous compounds like allyl carbamates and allyl carbonates. Additionally, it can be used for the preparation of α-allyl carbonyls and α, β-unsaturated carbonyls.

Application

Allyl chloroformate is used in the synthesis of:
  • Histones and their analogs.
  • Alloc-TL monomer (N-(allyloxy)carbonylhomocysteine thiolactone) from cyclic thioester (d,l-homocysteine thiolactonehydrochloride).

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

87.8 °F - closed cup

flash_point_c

31 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP4647
SHBN5915
SHBN4259
SHBN2550
SHBM4450

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Sigma-Aldrich

227781

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Carlos E Cuevas-Suárez et al.
Journal of the mechanical behavior of biomedical materials, 87, 148-154 (2018-08-03)
Over the past years, significant effort has been dedicated to synthesizing low-shrinking formulations, however, development of dental composites with low volumetric shrinkage continues to be challenging. The purpose of this study was to synthesize a bisphenol allylic derivate (BPhADAC) and
Palladium-catalyzed synthesis of substituted cycloheptane-1,4-diones by an asymmetric ring-expanding allylation (AREA).
Sabrina R Schulz et al.
Angewandte Chemie (International ed. in English), 46(21), 3966-3970 (2007-04-20)
Allyl Chloroformate
Herrinton PM
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
William R Cantrell et al.
Nucleosides, nucleotides & nucleic acids, 27(8), 901-913 (2008-08-13)
Degradation of clofarabine (3) in 0.9% saline solution at 100 degrees C afforded three degradation products which were determined to be formamidopyrimidines 4-6. Compounds 4 and 5 were assigned as C(1') anomers on the basis of one-dimensional and two-dimensional NMR
[Toxic action of allylchloroformate].
E F Oskerko et al.
Gigiena truda i professional'nye zabolevaniia, (5)(5), 51-52 (1984-05-01)
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