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Merck
CN

392855

Sigma-Aldrich

4,5-二甲氧基-2-硝基溴苄

97%

别名:

6-硝基藜芦基溴化物

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About This Item

线性分子式:
O2NC6H2(OCH3)2CH2Br
CAS号:
分子量:
276.08
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22

方案

97%

mp

131-133 °C (lit.)

官能团

bromo
nitro

SMILES字符串

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

InChI key

UEKFEYNZISYRRH-UHFFFAOYSA-N

一般描述

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.

应用

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

象形图

Corrosion

警示用语:

Danger

危险声明

危险分类

Eye Dam. 1 - Skin Corr. 1B

储存分类代码

8A - Combustible corrosive hazardous materials

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

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


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G Marriott et al.
Biochemistry, 35(10), 3170-3174 (1996-03-12)
An understanding of the molecular mechanism of muscle contraction will require a complete description of the kinetics of the myosin motor in vitro and in vivo. To this end chemical relaxation studies employing light-directed generation of ATP from caged ATP
Surface functionalization of PEEK films using photochemical routes.
Henneuse-Boxus C, et al.
Eur. Polymer J., 37(1), 9-18 (2001)
Pierre Murat et al.
Chemical communications (Cambridge, England), 49(76), 8453-8455 (2013-08-21)
The use of a caged G-quadruplex ligand allows for transcriptional control of quadruplex-containing genes using UV light as an external trigger. An important oncogene, SRC, involved in the initiation and proliferation of epithelial tumours is shown to be significantly downregulated
Light-triggered strand exchange reaction using the change in the hydrogen bonding pattern of a nucleobase analogue.
Morihiro K, et al.
Chemical Science, 5(2), 744-750 (2014)
Weiying Lin et al.
Chemistry & biology, 9(12), 1347-1353 (2002-12-25)
Transgene-based inducible expression systems offer the potential to study the influence of any gene at any point during an organism's lifetime. However, the expression of individual genes is both temporally and spatially (i.e., cell/tissue)-regulated. The inducible gene expression systems devised

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