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C31104

Sigma-Aldrich

3-Chloro-2-chloromethyl-1-propene

99%

Synonym(s):

1,1-Bis(chloromethyl)ethylene, Methallyl dichloride

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About This Item

Linear Formula:
CH2=C(CH2Cl)2
CAS Number:
1871-57-4
Molecular Weight:
125.00
Beilstein/REAXYS Number:
1560178
EC Number:
217-489-3
MDL number:
MFCD00000952
UNSPSC Code:
12352100
PubChem Substance ID:
24892333
NACRES:
NA.22

vapor density

3.12 (vs air)

assay

99%

form

liquid

autoignition temp.

896 °F

expl. lim.

8.1 %

refractive index

n20/D 1.4753 (lit.)

bp

138 °C (lit.)

mp

−14 °C (lit.)

density

1.08 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClCC(=C)CCl

InChI

1S/C4H6Cl2/c1-4(2-5)3-6/h1-3H2

InChI key

XJFZOSUFGSANIF-UHFFFAOYSA-N

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Application

3-Chloro-2-chloromethyl-1-propene can be used in the synthesis of 2,11-bis(methylidene)spermine, an inhibitor of spermine oxidase and branched side chains of conjugated polymers. It can also be used in the intermolecular [2+2] photocycloaddition during the total synthesis of (−)-grandisol.

pictograms

FlameSkull and crossbones
GHS02,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

96.8 °F

flash_point_c

36 °C

ppe

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

Certificates of Analysis (COA)

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Synthesis of 2, 11-bis (methylidene) spermine, a new inhibitor of spermine oxidase.
Grigorenko N A, et al.
Russian Journal of Bioorganic Chemistry, 42(4), 423-427 (2016)
Synthesis of well-defined three-and four-armed cage-shaped polymers via ?topological conversion? from trefoil-and quatrefoil-shaped polymers.
Satoh Y, et al.
Macromolecules, 50(1), 97-106 (2016)
Diketopyrrolopyrrole?based Conjugated Polymers Bearing Branched Oligo (Ethylene Glycol) Side Chains for Photovoltaic Devices.
Chen X, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 128(35), 10532-10536 (2016)
Enantioselective Intermolecular [2+ 2] Photocycloaddition Reaction of Cyclic Enones and Its Application in a Synthesis of (−)-Grandisol.
Poplata S and Bach T
Journal of the American Chemical Society, 140(9), 3228-3231 (2018)
Matthew K McBride et al.
Science advances, 4(8), eaat4634-eaat4634 (2018-08-29)
Liquid crystalline (LC) elastomers (LCEs) enable large-scale reversible shape changes in polymeric materials; however, they require intensive, irreversible programming approaches in order to facilitate controllable actuation. We have implemented photoinduced dynamic covalent chemistry (DCC) that chemically anneals the LCE toward

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