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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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5 G
$50.93
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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

$50.93

List Price$55.60Save 8%
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Available to ship onApril 15, 2025Details

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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.[1]

Application

Allyl chloroformate is used in the synthesis of:
  • Histones and their analogs.[2]
  • Alloc-TL monomer (N-(allyloxy)carbonylhomocysteine thiolactone) from cyclic thioester (d,l-homocysteine thiolactonehydrochloride).[3]

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

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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)
[Toxic action of allylchloroformate].
E F Oskerko et al.
Gigiena truda i professional'nye zabolevaniia, (5)(5), 51-52 (1984-05-01)
Total chemical synthesis of histones and their analogs, assisted by native chemical ligation and palladium complexes
Maity SK, et al.
Nature Protocols, 11(12), 2293-2322 (2017)
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
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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