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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:
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).

Signal Word

Danger

Hazard Statements

H226,H301,H314,H330

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

87.8 °F - closed cup

Flash Point(C)

31 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN4259
SHBN2550
SHBM4450
SHBM0749
SHBL8870

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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)
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
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)
Di-Wei Zheng et al.
Nature communications, 9(1), 1680-1680 (2018-04-28)
Bacteria preferentially accumulating in tumor microenvironments can be utilized as natural vehicles for tumor targeting. However, neither current chemical nor genetic approaches alone can fully satisfy the requirements on both stability and high efficiency. Here, we propose a strategy of
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