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255858

溴代硝基甲烷

Name: 溴代硝基甲烷
Brand: ALDRICH

technical grade, 90%

别名:

α-溴硝基甲烷, 硝基溴甲烷

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关于此项目

线性分子式:

BrCH₂NO₂

化学文摘社编号:

563-70-2

分子量:

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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属性

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

说明

Application

溴代硝基甲烷已被用于：

生产各种受保护的α-溴代硝基烷烃供体（包括Fmoc），用于Umpolung酰胺合成
通过碘化钠催化的亨利反应，制备（Z）-1-溴-1-硝基烯烃
通过domino Michael加成/分子内烷基化策略，用于β,γ-不饱和a-酮酯的非对映体和对映体选择性环丙烷化反应中

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

存储类别

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

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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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全球贸易项目编号

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