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Merck
CN

183660

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24851067
EC Number:
222-109-4
Beilstein/REAXYS Number:
1560268
MDL number:
MFCD00000730
Assay:
97%
Form:
liquid

Key Documents

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Product Name

3,3-Dimethylacryloyl chloride, 97%, contains 400 ppm phenothiazine as inhibitor

InChI key

BDUBTLFQHNYXPC-UHFFFAOYSA-N

InChI

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

SMILES string

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

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.)

functional group

acyl chloride

Quality Level

100

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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

General description

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCL4532
MKBZ7833V
MKBP6211V
MKBL5355V
MKBD4440V

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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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