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184667

Sigma-Aldrich

(Chloromethyl)cyclopropane

97%

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About This Item

Linear Formula:
C3H5CH2Cl
CAS Number:
Molecular Weight:
90.55
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

refractive index

n20/D 1.435 (lit.)

bp

87-89 °C (lit.)

density

0.98 g/mL at 25 °C (lit.)

functional group

chloro

SMILES string

ClCC1CC1

InChI

1S/C4H7Cl/c5-3-4-1-2-4/h4H,1-3H2

InChI key

ZVTQWXCKQTUVPY-UHFFFAOYSA-N

General description

(Chloromethyl)cyclopropane on reaction with isolable dialkylsilylene affords 5-silaspiro[4.4]nonane derivative.

Application

(Chloromethyl)cyclopropane was used in the synthesis of (lithiomethyl)cyclopropane and homoallyllithium via 4,4′-di-tert-butylbiphenyl or naphthalene-catalysed lithiation reaction.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

28.4 °F - closed cup

Flash Point(C)

-2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Easy selective generation of (lithiomethyl) cyclopropane or homoallyllithium by a chlorine-lithium exchange.
Pastor IM, et al.
Tetrahedron Letters, 49(48), 6870-6872 (2008)
Unexpected reactions of an isolable dialkylsilylene with Haloalkanes.
Ishida S, et al.
Chemistry Letters (Jpn), 11, 1102-1103 (2001)

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