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771058

Sigma-Aldrich

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:
105299-45-4
Molecular Weight:
242.23
MDL number:
MFCD00225268
UNSPSC Code:
12352106
PubChem Substance ID:
329767468
NACRES:
NA.22

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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

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