Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

771058

Sigma-Aldrich

4-(4′-Hydroxyphenylazo)benzoic acid

97%

Synonym(s):

(E)-4-[(4-Hydroxyphenyl)azo]benzoic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

100

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service