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A2898

Sigma-Aldrich

4-Aminobiphenyl

≥98%

Synonym(s):

4-Aminodiphenyl, 4-Biphenylamine, 4-Biphenylylamine, 4-Phenylaniline, Biphenyl-4-ylamine, NSC 7660, Xenylamine

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About This Item

Linear Formula:
C6H5C6H4NH2
CAS Number:
92-67-1
Molecular Weight:
169.22
Beilstein:
386533
EC Number:
202-177-1
MDL number:
MFCD00007879
UNSPSC Code:
12352100
PubChem Substance ID:
57653839
NACRES:
NA.22

Assay

≥98%

form

solid

autoignition temp.

842 °F

bp

191 °C/15 mmHg (lit.)

mp

52-54 °C (lit.)

SMILES string

Nc1ccc(cc1)-c2ccccc2

InChI

1S/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2

InChI key

DMVOXQPQNTYEKQ-UHFFFAOYSA-N

Gene Information

human ... UGT1A4(54657)

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Application

  • Induces DNA damage (carcinogen) in human bladder carcinoma cells and bladder tissue in mouse
  • Synthetic amine ligand for enrichment, depletion and one-step purification of leech proteins

Biochem/physiol Actions

Hepatic tumor initiator in experimental animal model.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H350

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1A

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Dexian Dong et al.
Journal of molecular recognition : JMR, 21(3), 163-168 (2008-04-29)
Although the concept of affinity purification using synthetic ligands had been utilized for many years, there are few articles related to this research area, and they focus only on the affinity purification of specific protein by a defined library of
K L Dooley et al.
Cancer letters, 62(3), 205-209 (1992-03-15)
The tumorigenic activities of four representative heterocyclic amine food pyrolysates, 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole (Glu-P-1), 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,8-dimethylimidazo[4,5f]quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), were assessed in the neonatal male B6C3F1 mouse and were compared with that of the potent human carcinogen, 4-amino-biphenyl (4-ABP). These
Samuel M Cohen et al.
Critical reviews in toxicology, 36(10), 803-819 (2006-11-23)
The IPCS Human Relevance Framework was evaluated for a DNA-reactive (genotoxic) carcinogen, 4-aminobiphenyl, based on a wealth of data in animals and humans. The mode of action involves metabolic activation by N-hydroxylation, followed by N-esterification leading to the formation of
Moinuddin et al.
Environmental toxicology, 29(5), 568-576 (2012-05-23)
4-Aminobiphenyl (4-ABP), an aromatic amine is a major environmental carcinogen found mainly in cigarette smoke. It has been vastly implicated in mutagenesis and cancer development. In this study, commercially available human placental DNA was exposed to 4-ABP (1.3 mM) in
Alan M Birch et al.
Journal of medicinal chemistry, 55(8), 3923-3933 (2012-04-06)
We describe how we have been able to design 4-aminobiphenyls that are nonmutagenic (inactive in the Ames test). No such 4-aminobiphenyls were known to us, but insights provided by quantum mechanical calculations have permitted us to design and synthesize some
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