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Documentos Principais

392855

Sigma-Aldrich

4,5-Dimethoxy-2-nitrobenzyl bromide

97%

Sinônimo(s):

6-Nitroveratryl bromide

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About This Item

Fórmula linear:
O2NC6H2(OCH3)2CH2Br
Número CAS:
Peso molecular:
276.08
Número MDL:
Código UNSPSC:
12352100
ID de substância PubChem:
NACRES:
NA.22

Ensaio

97%

pf

131-133 °C (lit.)

grupo funcional

bromo
nitro

cadeia de caracteres SMILES

COc1cc(CBr)c(cc1OC)[N+]([O-])=O

InChI

1S/C9H10BrNO4/c1-14-8-3-6(5-10)7(11(12)13)4-9(8)15-2/h3-4H,5H2,1-2H3

chave InChI

UEKFEYNZISYRRH-UHFFFAOYSA-N

Descrição geral

4,5-Dimethoxy-2-nitrobenzyl bromide (DMNBB, 1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene) is a 4,5-dimethoxy-2-nitrobenzyl derivative. 4,5-Dimethoxy-2-nitrobenzyl (DMNB) group of DMNBB is used as a photolabile protecting group in caging technology to develop pro-drugs. Synthesis of 1-(bromomethyl)-4,5-dimethoxy-2-nitrobenzene by using 6-nitroveratraldehyde as starting reagent has been reported.

Aplicação

4,5-Dimethoxy-2-nitrobenzyl bromide (DMNB bromide, 6-nitroveratryl bromide) is suitable reagent used in the synthesis of N-(4,5-dimethoxy-2-nitrobenzyl)vanillylamine which forms caged vanilloid. It may be used in the synthesis of the following:
  • 4-(4′,5′-dimethoxy-2-nitrobenzyloxy)benzaldehyde, a DMNB-caged aldehyde
  • N-[4-[(4,5-dimethoxy-2-nitrobenzyl)oxy]-3-methoxybenzyl]acetamide
  • caged derivative of pyridostatin ([C]-PDS)
  • photosensitive polyimide (PI-DMNB)
  • caged β-ecdysone
  • 4-tert-butyldimethylsilyloxy-1-(2-deoxy-3,5-di-O-toluoyl-β-D-ribofuranosyl)-2-(6-nitroveratrylthio)-1H-benzimidazole, an intermediate in synthesis of phosphoramidite bearing 4-hydroxy-2-mercaptobenzimidazole (SBNV) nucleobase
  • alkylation of dihydrofluorescein
  • 4-(4′,5′-Dimethoxy-2′-nitrobenzyloxy)benzaldehyde

Pictogramas

Corrosion

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

Eye Dam. 1 - Skin Corr. 1B

Código de classe de armazenamento

8A - Combustible corrosive hazardous materials

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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


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