Skip to Content
Merck
CN
All Photos(2)

Key Documents

View All Documentation

423564

Sigma-Aldrich

4-Bromomethyl-3-nitrobenzoic acid

97%

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

About This Item

Linear Formula:
BrCH2C6H3(NO2)CO2H
CAS Number:
55715-03-2
Molecular Weight:
260.04
Beilstein:
1970939
MDL number:
MFCD00216575
UNSPSC Code:
12352100
PubChem Substance ID:
24866507
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

127-130 °C (lit.)

solubility

DMF: soluble(lit.)
dichloromethane: soluble(lit.)

functional group

bromo
carboxylic acid
nitro

SMILES string

OC(=O)c1ccc(CBr)c(c1)[N+]([O-])=O

InChI

1S/C8H6BrNO4/c9-4-6-2-1-5(8(11)12)3-7(6)10(13)14/h1-3H,4H2,(H,11,12)

InChI key

QMAHVAFURJBOFV-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

4-Bromomethyl-3-nitrobenzoic acid (BNBA) is a benzoic acid derivative. It has been synthesized by the nitration of 4-bromomethylbenzoic acid using fuming nitric acid. It participates in the synthesis of 3,4-dihydro-2(1H)-quinazolinones and 3,4-dihydro-1H-quinazolin-2-thiones.

Application

4-Bromomethyl-3-nitrobenzoic acid may be used in the following studies:
  • As a reactant in the synthesis of 4-bromomethyl-3-nitrobenzoic acid succinimide ester (BNBA-SE).
  • As a reactant in the synthesis of 4-(2-hydroxyethylmercaptylmethyl)-3-nitrobenzoic acid.
  • As a reactant in the synthesis of decyl 4-(bromomethyl)-3-nitrobenzoate.
  • As a reactant in the synthesis of 4-((2-(hydroxymethyl)phenylamino)methyl)-3-nitrobenzoic acid.
  • As a thiol photo-deprotection reagent.
  • As a UV-cleavable reagent to functionalize polyacrylamide acryl hydrate (PAAH).
  • As a photocleavable linker to form localized photoinversion of surface charges inside the colloidal crystal.
  • As a starting material in the synthesis of 2H-indazole based library using parallel solution-phase methods.
  • As a reactant in the synthesis of (N-allyloxycarbonyl)-5-aminopent-1-yl 4-bromomethyl-3-nitrobenzoate.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCB2629V
03614EJ
13922HH
02502CE
14608LD

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Margo T Frey et al.
Soft matter, 5, 1918-1924 (2009-08-13)
Recent studies indicate that extracellular mechanical properties, including rigidity, profoundly affect cellular morphology, growth, migration, and differentiation [R. J. Pelham, Jr. and Y. Wang, Proc. Natl. Acad. Sci. U. S. A., 1997, 94(25), 13661-13665; H. B. Wang, M. Dembo and
G Marriott et al.
Biochemistry international, 26(5), 943-951 (1992-04-11)
The ability to generate substrate concentration jumps through photo-deprotection of amine, carboxyl and phosphate groups has been an important development for investigations of protein activity in complex systems. To broaden the versatility and applications of photo-deprotection techniques for the photomodulation
Jeffrey D Butler et al.
The Journal of organic chemistry, 73(1), 234-240 (2007-12-07)
The parent 5H-indazolo[3,2-b]benzo[d]-1,3-oxazine heterocycle as well as a series of novel analogues have been synthesized utilizing two subsequent intramolecular heterocyclizations in one pot. A variety of diversity groups were added to explore the scope of this reaction and to provide
Aaron D Mills et al.
Journal of combinatorial chemistry, 9(1), 171-177 (2007-01-09)
A library of 200 2-alkyl-3-alkyloxy-2H-indazole-6-carboxamides was synthesized using parallel solution-phase methods. The indazole cyclization reaction was optimized for library production with the best yields resulting from controlled alcohol/water solvent ratios. The key step, a heterocyclization reaction, proceeds by N,N-bond formation
Syntheses of nucleosides designed for combinatorial DNA sequencing.
Welch MB, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 5, 951-960 (1999)
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