Skip to Content
Merck
All Photos(2)

Documents

392855

Sigma-Aldrich

4,5-Dimethoxy-2-nitrobenzyl bromide

97%

Synonym(s):

6-Nitroveratryl bromide

Sign Into View Organizational & Contract Pricing
All Photos(2)

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

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service