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Sigma-Aldrich

4-Bromomethyl-3-nitrobenzoic acid

97%

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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

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

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

Certificates of Analysis (COA)

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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
Yoonho Jun et al.
Journal of the American Chemical Society, 132(29), 9958-9959 (2010-07-02)
We demonstrate an optical interference-based photochemical method for the high-resolution localization of nanoparticles inside colloidal crystals or other porous structures. The method specifically relies on photoinduced inversion of the colloidal crystal surface charge to drive the localized deposition of charged
Eric Besson et al.
Langmuir : the ACS journal of surfaces and colloids, 22(20), 8346-8352 (2006-09-20)
This work describes how selective patterning of hydrophobic and hydrophilic areas inside microchannels of microfluidic devices can be achieved by combining well-known chemical protocols and standard photolithography equipment (365 nm). Two techniques have been performed and compared. The first technique
Hai-Yuan Hsu et al.
Molecular diversity, 16(2), 241-249 (2011-12-20)
An efficient microwave-assisted and water-soluble ionic liquid (IL)-supported synthesis of medicinally important dihydro- and tetrahydroquinazolines has been developed. The protocol involves the S(N)2 substitution reaction of IL-bound 4-bromomethyl-3-nitrobenzoic acid with various primary amines to provide IL-bound 4-((alkylamino) methyl)-3-nitrobenzoate under microwave
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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