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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:
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)

Quality Level

200

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
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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H332,H412

Hazard Classifications

Acute Tox. 4 Inhalation - Aquatic Chronic 3

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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)
Cyclopropanations of alkenes using dibromomethane.
Friedrich E
The Journal of Organic Chemistry, 50(23), 4640-4642 (1985)
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)
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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