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183660

Sigma-Aldrich

3,3-Dimethylacryloyl chloride

97%, contains 400 ppm phenothiazine as inhibitor

Synonym(s):

3-Methyl-2-butenoyl chloride, 3-Methylcrotonoyl chloride, Senecioyl chloride

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About This Item

Linear Formula:
(CH3)2C=CHCOCl
CAS Number:
3350-78-5
Molecular Weight:
118.56
Beilstein:
1560268
EC Number:
222-109-4
MDL number:
MFCD00000730
UNSPSC Code:
12352100
PubChem Substance ID:
24851067
NACRES:
NA.22

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

Signal Word

Danger

Hazard Statements

H226,H314,H335

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

123.8 °F - closed cup

Flash Point(C)

51 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reaction of silylketene acetals with 3, 3-dimethylacryloyl chloride.
Rousseau G and Blanco L.
Tetrahedron Letters, 26(35), 4195-4196 (1985)
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
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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