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242586

Sigma-Aldrich

Diphenylamine

ACS reagent, ≥99%

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Synonym(s):
DPA
Linear Formula:
(C6H5)2NH
CAS Number:
122-39-4
Molecular Weight:
169.22
Beilstein:
508755
EC Number:
204-539-4
MDL number:
MFCD00003014
UNSPSC Code:
12352100
PubChem Substance ID:
24854569
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

vapor density

5.82 (vs air)

vapor pressure

1 mmHg ( 108 °C)

Assay

≥99%

autoignition temp.

1175 °F

ign. residue

≤0.03%

bp

302 °C (lit.)

mp

50-53 °C (lit.)

solubility

alcohol: passes test

anion traces

nitrate (NO3-): passes test

suitability

passes test for sensitivity to nitrate

SMILES string

N(c1ccccc1)c2ccccc2

InChI

1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H

InChI key

DMBHHRLKUKUOEG-UHFFFAOYSA-N

Gene Information

human ... UGT1A4(54657)

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Application

Diphenylamine can undergo palladium-catalyzed intramolecular cyclization to form carbazole. It may also be used as a starting material in the synthesis of triphenylamine.
Diphenylamine may be used in the preparation of diphenylamine reagent, which is employed for the quantitative estimation of nucleic acid (DNA) from various biological sources by colorimetric method.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Target Organs

Kidney,Liver,spleen

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Palladium-promoted cyclization of diphenyl ether, diphenylamine, and related compounds.
Akermark B, et al.
The Journal of Organic Chemistry, 40(9), 1365-1367 (1975)
Triphenylamine
Hager FD
Organic Syntheses, 8(116), 116-116 (1928)
An improved diphenylamine method for the estimation of deoxyribonucleic acid.
Giles KW and Myers A.
Nature, 206(4979), 93-93 (1965)
Soluble and methane sulfonic acid doped poly (diphenylamine)-synthesis and characterization.
Wen T-C, et al.
Materials Letters, 57(2), 280-290 (2002)
Walter J Jessen et al.
The Journal of clinical investigation, 123(1), 340-347 (2012-12-12)
Neurofibromatosis type 1 (NF1) patients develop benign neurofibromas and malignant peripheral nerve sheath tumors (MPNST). These incurable peripheral nerve tumors result from loss of NF1 tumor suppressor gene function, causing hyperactive Ras signaling. Activated Ras controls numerous downstream effectors, but
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