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Sigma-Aldrich

4-Bromomethyl-3-nitrobenzoic acid

97%

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About This Item

Fórmula lineal:
BrCH2C6H3(NO2)CO2H
Número de CAS:
55715-03-2
Peso molecular:
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

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

Certificados de análisis (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
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
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
Syntheses of nucleosides designed for combinatorial DNA sequencing.
Welch MB, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 5, 951-960 (1999)
Jinfang Zhang et al.
Molecular diversity, 6(1), 13-17 (2003-08-30)
A method utilizing polymer-bound 4-(bromomethyl)-3-nitrobenzoic acid as a key precursor leading to 1,4-benzodiazepin-2,3-dione scaffold is described. It involves a four-step sequence including nucleophilic displacement, acylation, simultaneous reduction-cyclization and alkylation, providing rapid access to the title compounds in excellent yield and
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