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3,3-Dimethylacryloyl chloride

97%, contains 400 ppm phenothiazine as inhibitor

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Synonym(s):
3-Methyl-2-butenoyl chloride, 3-Methylcrotonoyl chloride, Senecioyl chloride
Linear Formula:
(CH3)2C=CHCOCl
CAS Number:
Molecular Weight:
118.56
Beilstein/REAXYS Number:
1560268
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

liquid

contains

400 ppm phenothiazine as inhibitor

refractive index

n20/D 1.476 (lit.)

bp

145-147 °C (lit.)

density

1.065 g/mL at 25 °C (lit.)

SMILES string

C\C(C)=C\C(Cl)=O

InChI

1S/C5H7ClO/c1-4(2)3-5(6)7/h3H,1-2H3

InChI key

BDUBTLFQHNYXPC-UHFFFAOYSA-N

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General description

3,3-Dimethylacryloyl chloride reacts with silylketene acetals in acetonitrile to give δ-ethylenic β-keto esters.

Application

3,3-Dimethylacryloyl chloride was used in the synthesis of:
  • substituted 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one via condensation with aniline
  • N-(3,3-Dimethylacryloyl)-(S)-leucine methyl ester

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

123.8 °F - closed cup

flash_point_c

51 °C - closed cup

ppe

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


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Marie-Anne Letellier et al.
European journal of medicinal chemistry, 43(8), 1730-1736 (2008-01-01)
A new series of substituted 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one have been prepared via condensation of 3,3-dimethylacryloyl chloride with aniline. Details of synthetic procedures are shown. Our aim was to investigate the potency of our original heterocycle in the inhibition of the Rho-kinase enzyme
Reaction of silylketene acetals with 3, 3-dimethylacryloyl chloride.
Rousseau G and Blanco L.
Tetrahedron Letters, 26(35), 4195-4196 (1985)
Structure and Biosynthesis of Chrysophysarin A, a Plasmodial Pigment from the Slime Mould Physarum polycephalum (Myxomycetes).
Eisenbarth S and Steffan B.
Tetrahedron, 56(3), 363-365 (2000)
Vishal Nanavaty et al.
Molecular cell, 78(4), 752-764 (2020-04-26)
Dysregulation of DNA methylation and mRNA alternative cleavage and polyadenylation (APA) are both prevalent in cancer and have been studied as independent processes. We discovered a DNA methylation-regulated APA mechanism when we compared genome-wide DNA methylation and polyadenylation site usage
Seon-Mi Seo et al.
Pesticide biochemistry and physiology, 113, 55-61 (2014-07-24)
This study investigated the fumigant toxicity of 4 Asteraceae plant essential oils and their constituents against the Japanese termite Reticulitermes speratus Kolbe. Fumigant toxicity varied with plant essential oils or constituents, exposure time, and concentration. Among the tested essential oils

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