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255858

Bromonitromethane

Name: Bromonitromethane
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

24855488

UNSPSC Code:

12352100

EC Number:

209-258-0

MDL number:

MFCD00007401

Assay:

90%

Form:

liquid

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Properties

grade

technical grade

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

Description

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

GHS03,GHS07

signalword

Danger

hcodes

H272,H315,H319,H335

pcodes

P210 - P220 - P261 - P264 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

5.1B - Oxidizing hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Silyl imine electrophiles in enantioselective catalysis: a Rosetta Stone for peptide homologation, enabling diverse N-protected aryl glycines from aldehydes in three steps.

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

Synthesis of enantiopure 2-C-glycosyl-3-nitrochromenes.

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

Stereoselective synthesis of highly functionalized nitrocyclopropanes through the organocatalyic Michael-addition-initiated cyclization of bromonitromethane and β,γ-unsaturated α-ketoesters.

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.

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Global Trade Item Number

SKU	GTIN
255858-1G	04061836826048
255858-10G	04061826035467