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137677

Sigma-Aldrich

2-Bromobenzoic acid

97%

Synonym(s):

o-Bromobenzoic acid

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About This Item

Linear Formula:
BrC6H4CO2H
CAS Number:
88-65-3
Molecular Weight:
201.02
Beilstein/REAXYS Number:
971266
EC Number:
201-848-6
MDL number:
MFCD00002402
UNSPSC Code:
12352100
PubChem Substance ID:
24848342
NACRES:
NA.22

vapor pressure

>1 mmHg ( 20 °C)

assay

97%

form

powder

mp

147-150 °C (lit.)

solubility

95% ethanol: soluble 100 mg/mL, clear, colorless to yellow

functional group

bromo

SMILES string

OC(=O)c1ccccc1Br

InChI

1S/C7H5BrO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)

InChI key

XRXMNWGCKISMOH-UHFFFAOYSA-N

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General description

2-Bromobenzoic acid (2-BA) on condensation with aminoquinolines yields phenylquinolylamines. 2-BA is the common building block for synthesis of various nitrogen heterocycles.

Application

2-Bromobenzoic acid was used in the synthesis of new zinc(II) − 2-bromobenzoate complex compounds. It was used as the starting reagent in the synthesis of hemilabile benzimidazolyl phosphine ligands.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

>212.0 °F

flash_point_c

> 100 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK8055
STBJ3697
STBH3169
S19351V
S19351-408

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Thermal decomposition and antimicrobial activity of zinc (II) 2-bromobenzoates with organic ligands.
Krajnikova A, et al.
Journal of Thermal Analysis and Calorimetry, 105(2), 451-460 (2011)
Free radical reactions for heterocycle synthesis. Part 6: 2-Bromobenzoic acids as building blocks in the construction of nitrogen heterocycles.
Zhang W and Pugh G.
Tetrahedron, 59(17), 3009-3018 (2003)
J B Bongui et al.
Chemical & pharmaceutical bulletin, 49(9), 1077-1080 (2001-09-18)
Condensation of either 2-bromobenzoic acid (4) or 2-chloro-3-nitrobenzoic acid (5) with suitable aminoquinolines 6-8 afforded phenylquinolylamines 9-13. Acid mediated cyclization gave the corresponding 12H-benzo[b][1,7]phenanthrolin-7-ones 14 and 15, and 12H-benzo[b][1,10]phenanthrolin-7-ones 16-18. Compounds 14, 16, and 17 were subsequently N-methylated to 6-demethoxyacronycine
Kin Ho Chung et al.
Chemical communications (Cambridge, England), 48(14), 1967-1969 (2012-01-12)
A new class of easily accessible hemilabile benzimidazolyl phosphine ligands has been developed. The ligand skeleton is prepared from commercially available and inexpensive o-phenylenediamine and 2-bromobenzoic acid. With catalyst loading down to 0.5 mol% palladium, excellent catalytic activity towards the
K H Engesser et al.
FEMS microbiology letters, 51(1), 143-147 (1989-07-15)
Pseudomonas putida strain CLB 250 (DSM 5232) utilized 2-bromo-, 2-chloro- and 2-fluorobenzoate as sole source of carbon and energy. Degradation is suggested to be initiated by a dioxygenase liberating halide in the first catabolic step. After decarboxylation and rearomatization catechol

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