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D41686

Sigma-Aldrich

Dibromomethane

99%

Synonym(s):

Methylene bromide

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About This Item

Empirical Formula (Hill Notation):
CH2Br2
CAS Number:
74-95-3
Molecular Weight:
173.83
Beilstein/REAXYS Number:
969143
EC Number:
200-824-2
MDL number:
MFCD00000168
UNSPSC Code:
12352100
PubChem Substance ID:
24893828
NACRES:
NA.22

vapor density

6.05 (vs air)

vapor pressure

34.9 mmHg ( 20 °C)

assay

99%

form

liquid

refractive index

n20/D 1.541 (lit.)

bp

96-98 °C (lit.)

mp

−52 °C (lit.)

density

2.477 g/mL at 25 °C (lit.)

SMILES string

BrCBr

InChI

1S/CH2Br2/c2-1-3/h1H2

InChI key

FJBFPHVGVWTDIP-UHFFFAOYSA-N

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Application

Dibromomethane may be used for the cyclopropanation of alkenes via Simmons-Smith type reaction. It may also be used in a novel methodology for the preparation of reaction intermediates such as α-substituted acroleins, α-methylene esters, α-keto esters, α-methylene lactones, α-methylene lactams, and α-keto lactones.

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Description
Pricing

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H332,H412

Hazard Classifications

Acute Tox. 4 Inhalation - Aquatic Chronic 3

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

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Dibromomethane as one-carbon source in organic synthesis: microwave-accelerated ?-methylenation of ketones with dibromomethane and diethylamine.
Hon Y, et. Al.
Tetrahedron, 59(9), 1509-1520 (2003)
Dibromomethane as one-carbon source in organic synthesis: total synthesis of (?)-and (?)-methylenolactocin.
Hon Y, et. Al.
Tetrahedron, 61(10), 2713-2723 (2005)
Dibromomethane as one-carbon source in organic synthesis: a versatile methodology to prepare the cyclic and acyclic ?-methylene or ?-keto acid derivatives from the corresponding terminal alkenes.
Hon Y, et. Al.
Tetrahedron, 60(22), 4837-4860 (2004)
Cyclopropanations of alkenes using dibromomethane.
Friedrich E
The Journal of Organic Chemistry, 50(23), 4640-4642 (1985)
Cyclopropanes from an Easily Prepared, Highly Active Zinc?Copper Couple, Dibromomethane, and Olefins.
LeGoff E
The Journal of Organic Chemistry, 29(7), 2048-2050 (1964)
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