ContaminantDB: 1,2-Diphenylhydrazine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:12 UTC

Update Date

2026-04-03 12:54:30 UTC

Accession Number

CHEM000153

Identification

Common Name

1,2-Diphenylhydrazine

Class

Small Molecule

Description

1,2-Diphenylhydrazine is a white solid. It dissolves only slightly in water and does not change into a gas unless it is heated to very high temperatures. It sticks to soil and can be carried into the air along with windblown dust. Once in water or exposed to air it is changed into other chemicals within minutes. These chemicals include the toxic chemicals azobenzene and benzidine. 1,2-Diphenylhydrazine is used to make fabric dyes in other countries, and to make certain medicines. (2)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Aromatic Hydrocarbon
Hydrazine
Industrial/Workplace Toxin
Lachrymator
Organic Compound
Organochloride
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Hydrazobenzene	MeSH

Chemical Formula

C₁₂H₁₂N₂

Average Molecular Mass

184.237 g/mol

Monoisotopic Mass

184.100 g/mol

CAS Registry Number

122-66-7

IUPAC Name

1,2-diphenylhydrazine

Traditional Name

hydrazobenzene

SMILES

N(NC1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H12N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10,13-14H

InChI Key

YBQZXXMEJHZYMB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylhydrazines. Phenylhydrazines are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylhydrazines

Direct Parent

Phenylhydrazines

Alternative Parents

Substituents

Phenylhydrazine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Hydrazine derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	131°C
Boiling Point	Not Available
Solubility	0.221 mg/mL at 25 °C [KUHNE,R et al. (1995)]

Predicted Properties

Property	Value	Source
Water Solubility	0.58 g/L	ALOGPS
logP	2.88	ALOGPS
logP	3.76	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	19.22	ChemAxon
pKa (Strongest Basic)	1.29	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	24.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.96 m³·mol⁻¹	ChemAxon
Polarizability	20.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1900000000-ff7fc7e452da47e1d4cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-6900000000-585ccdbb89931863ff59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9100000000-292c3e31b59b6ed72bb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-a30070f306c4a8c7b8dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900000000-a317f40733db3adc46fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d24c9ea196896869d171	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00lu-9400000000-651a67b3ed4972e5e837	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Two of the known metabolites, aniline and benzidine, may contribute to the toxicity and/or carcinogenicity of 1,2-diphenylhydrazine. Nonneoplastic liver lesions, hepatocellular carcinomas and/or neoplastic liver nodules indicate that the liver is a target of 1,2-diphenylhydrazine toxicity. As aniline and other aromatic amino metabolites of 1,2-diphenylhydrazine (e.g., aminophenols) are methemoglobinforming compounds by either oral or inhalation routes of exposure, it is possible that 1,2-diphenylhydrazine may cause methemoglobinemia in humans. (2)

Metabolism

Unchanged 1,2-diphenylhydrazine was detected following treatment by all routes, and aniline and benzidine were identified following oral and intraperitoneal treatments. Other metabolites included two unspecified hydroxy derivatives of benzidine (oral route), 2- and 4- aminophenol (intraperitoneal route), and unidentified compounds (oral, intravenous, and intratracheal routes). Aniline is oxidized by hydroxylation of a ring carbon to form 2-or 4-aminophenol or of the nitrogen to form phenylhydroxylamine, and then is conjugated to glucuronic or sulfuric acid. Benzidine is formed readily from 1,2-diphenylhydrazine by acid rearrangement. It has been suggested that benzidine may be produced from 1,2-diphenylhydrazine by acidity in the stomach. (2)

Toxicity Values

LD50: 959 mg/kg (Oral, Rat) (2)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC. Benzidine, a metabolite of 1,2-diphenylhydrazine, is carcinogenic to humans (Group 1). Aniline, another metabolite, is not classifiable as to its carcinogenicity to humans (Group 3). (1)

Uses/Sources

1,2-Diphenylhydrazine is used to make fabric dyes in other countries, and to make certain medicines. Exposure may result from breathing in dust coated with 1,2-diphenylhydrazine and eating dirt or smearing contaminated dirt on the skin. (2)

Minimum Risk Level

Not Available

Health Effects

Nonneoplastic liver lesions, hepatocellular carcinomas and/or neoplastic liver nodules; seizures and coma. (2)

Symptoms

Irritatinon to the eyes, nose and respiratory system, depending on the route of exposure. Cough, redness of the exposed surface. (2)

Treatment

Consider gastric lavage after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion. Following inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If the exposure occurs through dermal contact remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. (3)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Hydrazobenzene

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

31222

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

1,2-Diphenylhydrazine (CHEM000153)

Structure for CHEM000153: 1,2-Diphenylhydrazine