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468479

Sigma-Aldrich

4-Pentenoyl chloride

98%

Synonym(s):

4-Pentenoic acid chloride

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About This Item

Linear Formula:
H2C=CHCH2CH2COCl
CAS Number:
39716-58-0
Molecular Weight:
118.56
MDL number:
MFCD00799572
UNSPSC Code:
12352100
PubChem Substance ID:
24870517
NACRES:
NA.22

assay

98%

bp

125 °C (lit.)

density

1.074 g/mL at 25 °C (lit.)

functional group

acyl chloride
allyl

SMILES string

ClC(=O)CCC=C

InChI

1S/C5H7ClO/c1-2-3-4-5(6)7/h2H,1,3-4H2

InChI key

JDKQTIKEGOOXTJ-UHFFFAOYSA-N

General description

4-Pentenoyl chloride has been identified as a key impurity in 5-chlorovaleroyl chloride (5-CVC). 4-Pentenoyl chloride can be synthesized by reacting thionyl chloride and 4-pentenoic acid.

Application

4-Pentenoyl chloride may be used in the preparation of:
  • D-pro-L-derived cyclic peptides
  • 4-pentenoylcobalt tricarbonyl
  • N-4-pentenoyl-L-cysteine methyl ester

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

80.6 °F - closed cup

flash_point_c

27 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000370381
0000370380
0000329477
0000370381
0000370380

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I Nageshwara Rao et al.
The Journal of organic chemistry, 69(6), 2181-2184 (2004-04-03)
An acyclic tripeptide based on a heterochiral D-pro-L-pro template shows a propensity to exist as a 3(10) helical conformation and can be cyclized, via ring-closing metathesis, to the corresponding cyclic tetrapeptides without disrupting the helical conformations in CDCl(3) as well
Alkyl-and Acyl-cobalt Carbonyls Containing Olefinic Unsaturation. Allylcobalt Tricarbonyl and Related Compounds1.
Heck RF and Breslow DS.
Journal of the American Chemical Society, 83(5), 1097-1102 (1961)
Synthesis and radical polyaddition of optically active monomers derived from cysteine.
Kudo H, et al.
Macromolecules, 32(25), 8370-8375 (1999)
Liya Tang et al.
Journal of pharmaceutical and biomedical analysis, 53(3), 309-314 (2010-05-05)
5-Chlorovaleroyl chloride (5-CVC) is commonly used as an alkylating agent in the synthesis of pharmaceutical intermediates, active ingredients, as well as other specialty chemicals. It is critical to monitor the impurities present in 5-CVC as they may have a direct
Norlaily Ahmad et al.
Biomacromolecules, 20(7), 2506-2514 (2019-06-28)
Inflammatory conditions are frequently accompanied by increased levels of active proteases, and there is rising interest in methods for their detection to monitor inflammation in a point of care setting. In this work, new sensor materials for disposable single-step protease

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