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Sigma-Aldrich

4-Bromomethyl-3-nitrobenzoic acid

97%

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Linear Formula:
BrCH2C6H3(NO2)CO2H
CAS Number:
55715-03-2
Molecular Weight:
260.04
Beilstein/REAXYS Number:
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.)

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

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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

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

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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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)
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
Solid-phase synthesis of 3, 4-dihydro-2 (1H)-quinazolinones and 3, 4-dihydro-1H-quinazolin-2-thiones.
Sun Q, et al.
Tetrahedron Letters, 42(25), 4119-4121 (2001)
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