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Sigma-Aldrich

4-(Phenylazo)benzoic acid

98%

Synonym(s):

4-(2-Phenyldiazenyl)benzoic acid, 4-Carboxyazobenzene, Azobenzene-4-carboxylic acid, Azoic acid, p-Phenylazobenzoic acid

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About This Item

Linear Formula:
C6H5N=NC6H4CO2H
CAS Number:
1562-93-2
Molecular Weight:
226.23
EC Number:
216-347-8
MDL number:
MFCD00020348
UNSPSC Code:
12352100
PubChem Substance ID:
24871636
NACRES:
NA.22

Assay

98%

mp

247-250 °C (lit.)

SMILES string

OC(=O)c1ccc(cc1)\N=N\c2ccccc2

InChI

1S/C13H10N2O2/c16-13(17)10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,(H,16,17)/b15-14+

InChI key

CSPTZWQFHBVOLO-CCEZHUSRSA-N

Related Categories

General description

4-(Phenylazo)benzoic acid (PABA), an azobenzene derivative, is a photo-isomerisable molecule. It can be synthesized by reacting p-aminobenzoic acid with nitrosobenzene. The interaction of PABA with TiO2 and ZnO electrodes has been investigated. A photoreversible switch has been developed using dimethylamino calix[4]arene and PABA. The post functionalization of poly(hydroxyethyl acrylate) core cross-linked star polymers with PABA induces an ability to complex with α-cyclodextrin.

Application

4-(Phenylazo)benzoic acid may be used in the preparation of a novel photochromic ZrO2 precursor solution.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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Azobenzene-Functionalised Core Cross-Linked Star Polymers and their Host-Guest Interactions.
Tan S, et al.
Australian Journal of Chemistry, 67(1), 173-178 (2014)
Chao Luo et al.
Advanced materials (Deerfield Beach, Fla.), 30(23), e1706498-e1706498 (2018-04-25)
Organic compounds are desirable alternatives for sustainable lithium-ion battery electrodes. However, the electrochemical properties of state-of-the-art organic electrodes are still worse than commercial inorganic counterparts. Here, a new chemistry is reported based on the electrochemical conversion of nitro compounds to
New dyes for solar cells based on nanostructured semiconducting metal oxides: Synthesis and characterisation of ruthenium (II) complexes with thiol-substituted ligands.
Ohlsson J, et al.
Journal of Photochemistry and Photobiology A: Chemistry, 148(1), 41-48 (2002)
Synthesis of a new photochromic ZrO2 precursor for preparation of functional thin films.
Nishizawa K, et al.
Key Engineering Materials, 320, 175- 178 (2006)
A photoresponsive wettability switch based on a dimethylamino Calix[4]arene.
Zhang X, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 20(30), 9367-9371 (2014)
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