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255858

Sigma-Aldrich

Bromonitromethane

technical grade, 90%

Synonym(s):

α-Bromonitromethane, Nitrobromomethane

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About This Item

Linear Formula:
BrCH2NO2
CAS Number:
563-70-2
Molecular Weight:
139.94
EC Number:
209-258-0
MDL number:
MFCD00007401
UNSPSC Code:
12352100
PubChem Substance ID:
24855488
NACRES:
NA.22

grade

technical grade

Quality Level

100

Assay

90%

form

liquid

refractive index

n20/D 1.496 (lit.)

bp

146-148 °C/750 mmHg (lit.)

density

2.007 g/mL at 25 °C (lit.)

functional group

amine
bromo
nitro

SMILES string

[O-][N+](=O)CBr

InChI

1S/CH2BrNO2/c2-1-3(4)5/h1H2

InChI key

DNPRVXJGNANVCZ-UHFFFAOYSA-N

Related Categories

Application

Bromonitromethane has been used:
  • in production of various protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung amide synthesis
  • in preparation of (Z)-1-bromo-1-nitroalkenes via sodium iodide-catalyzed Henry reaction
  • in diastereo- and enantioselective cyclopropanation of β,γ-unsaturated a-ketoesters via domino Michael-addition/intramolecular-alkylation strategy

Pictograms

Flame over circleExclamation mark
GHS03,GHS07

Signal Word

Danger

Hazard Statements

H272,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Ox. Sol. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

5.1B - Oxidizing hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 5: Self-reactive substances
Nitro compounds
Hazardous rank I
1st self-reactive materials

JAN Code

255858-VAR:
255858-10G:
255858-1G:
255858-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2553
MKCW7015
MKCS8722
MKCQ4057
MKCN5670

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Raquel G Soengas et al.
The Journal of organic chemistry, 78(24), 12831-12836 (2013-11-28)
A novel methodology has been developed to obtain enantiopure 2-C-glycosyl-3-nitrochromenes. First, (Z)-1-bromo-1-nitroalkenes were prepared from the corresponding sugar aldehydes through a sodium iodide-catalyzed Henry reaction with bromonitromethane followed by elimination of the resulting 1-bromo-1-nitroalkan-2-ols. In the next step, reaction of
Haijian Yu et al.
Chemistry, an Asian journal, 8(11), 2859-2863 (2013-08-13)
A highly diastereo- and enantioselective cyclopropanation of β,γ-unsaturated α-ketoesters with bromonitromethane has been successfully developed through a domino Michael-addition/intramolecular-alkylation strategy. Acceptable yields (up to 89%) and enantioselectivities (up to 96% ee) have been obtained.
Ran Yin et al.
Chemosphere, 260, 127644-127644 (2020-08-08)
This study investigated the degradation of eight aliphatic halogenated contaminants (one brominated flame retardant and seven disinfection by-products) in synthetic drinking water by the UVA/TiO2 and UVA/Cu-TiO2 processes. The degradation rate constants of 2,2-bis(bromomethyl)-1,3-propanediol and trichloromethane in the UVA/Cu-TiO2 process
Dawn M Makley et al.
Organic letters, 16(11), 3146-3149 (2014-05-16)
We report that N-(trimethylsilyl)imines serve in the Bis(AMidine)-catalyzed addition of bromonitromethane with a high degree of enantioselection. This allows for the production of a range of protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung Amide Synthesis (UmAS). Hence
Anabela Borges et al.
Biofouling, 33(2), 156-168 (2017-02-01)
Disruption of cell-cell communication or quorum sensing (QS) is considered a stimulating approach for reducing bacterial pathogenicity and resistance. Although several QS inhibitors (QSIs) have been discovered so far their clinical use remains distant. This problem can be circumvented by
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