771058
4-(4′-Hydroxyphenylazo)benzoic acid
97%
Synonym(s):
(E)-4-[(4-Hydroxyphenyl)azo]benzoic acid
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About This Item
Empirical Formula (Hill Notation):
C13H10N2O3
CAS Number:
Molecular Weight:
242.23
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22
Quality Level
Assay
97%
form
solid
reaction suitability
reagent type: cross-linking reagent
mp
270-280 °C
functional group
carboxylic acid
hydroxyl
storage temp.
2-8°C
SMILES string
OC(C1=CC=C(/N=N/C2=CC=C(O)C=C2)C=C1)=O
InChI
1S/C13H10N2O3/c16-12-7-5-11(6-8-12)15-14-10-3-1-9(2-4-10)13(17)18/h1-8,16H,(H,17,18)/b15-14+
InChI key
HLVCZTOFOWHIJZ-CCEZHUSRSA-N
Application
4-(4′-Hydroxyphenylazo)benzoic acid may be used to synthesize 4-(4-propyloxyphenylazo)benzoic acid via Williamson synthesis by reacting with 1-bromopropane.
Azobenzene cleavable linker. Treatment with sodium dithionite (sodium hydrosulfite) reduces azo functionality, cleaving the N-N bond to yield two primary amines.
Has been used in proteomic and affinity chromatography applications.
Has been used in proteomic and affinity chromatography applications.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Molecular imprinting of azobenzene carboxylic acid on a TiO2 ultrathin film by the surface sol-gel process
Lee SW, et al.
Langmuir, 14(10), 2857-2863 (1998)
Felicetta Landi et al.
Organic & biomolecular chemistry, 8(1), 56-59 (2009-12-22)
A new chemically-cleavable linker has been synthesised for the affinity-independent elution of biomolecules by classical affinity chromatography. This azo-based linker is shown to couple efficiently with "click" derivatised ligands such as biotin propargyl amide through a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition
A mild chemically cleavable linker system for functional proteomic applications.
Steven H L Verhelst et al.
Angewandte Chemie (International ed. in English), 46(8), 1284-1286 (2007-01-06)
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