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392855

Sigma-Aldrich

4,5-Dimethoxy-2-nitrobenzyl bromide

97%

Synonym(s):

6-Nitroveratryl bromide

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About This Item

Linear Formula:
O2NC6H2(OCH3)2CH2Br
CAS Number:
53413-67-5
Molecular Weight:
276.08
MDL number:
MFCD00192064
UNSPSC Code:
12352100
PubChem Substance ID:
24864490
NACRES:
NA.22

assay

97%

mp

131-133 °C (lit.)

SMILES string

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

Related Categories

General description

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.

Application

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

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

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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
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
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)
Synthesis and Characterizations of Positive-Working Photosensitive Polyimides Having 4, 5-Dimethoxy-o-Nitrobenzyl Side Group.
Ryu S, et al.
Bull. Korean Chem. Soc., 29(9), 1689-1689 (2008)
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