4-Nitrodiphenylamine (HCID 13271)

Names & identifiers

Preferred name: 4-Nitrodiphenylamine
IUPAC: 4-nitro-N-phenylaniline
English name: 4-Nitrodiphenylamine
Molecular formula: C12H10N2O2
Molecular weight: 214.22

Names & synonyms

4-NITRODIPHENYLAMINE836-30-64-Nitro-N-phenylanilinep-Nitrodiphenylamine(4-nitrophenyl)phenylamineBenzenamine, 4-nitro-N-phenyl-Diphenylamine, 4-nitro-p-Nitrophenylphenylamine4-Nitrodifenylamin4-NdpaN-(4-Nitrophenyl)benzenamineAmine, diphenyl, 4-nitro-

Show more names

NSC 33836TIMTEC-BB SBB0080554-nitro-diphenylaminGlycerol Impurity 77diphenyl,4-nitro-aminLABOTEST-BB LT01487848

4-Nitro-diphenylamineMFCD000073014-nitro-N-phenyl-anilineEINECS 212-646-2BRN 2051910MLS000584664DTXSID8027323AI3-02915

Database identifiers

CAS: 836-30-6
PubChem CID: 13271
DTXSID: DTXSID8027323
ChEMBL: CHEMBL1323785
UNII: 5ZOC179N5D
EC Number: 212-646-2
Nikkaji: J38.267A

Properties

Computed structural properties

XLogP: 3.7
Topological polar surface area: 57.9 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 16
Formal charge: 0
Complexity: 226

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)

SpringerMaterials PropertiesBoiling point

LogP · 2 items

3.82

3.74

Color/FormYELLOW NEEDLES OR TABLETS FROM CARBON TETRACHLORIDE

Solubility · 3 items

INSOL IN WATER; VERY SOL IN ALCOHOL, ACETIC ACID

SOL IN CONCN SULFURIC ACID

Solubility in water: none

Flash Point · 2 items

190 °C

190 °C o.c.

Physicochemical properties

Melting point: 132 · 132-135 °C (lit.)
Boiling point: 211 °C · 211 °C (30 mmHg)
Density: 1.2042 · 1.2042 (rough estimate)
refractive index: 1.666 · 1.6660 (estimate)
Flash point: 190 °C · 190°C
storage temp.: Refrigerator
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: -2.6 · -2.60±0.20(Predicted)
color: Orange to Brown
Water Solubility: INSOLUBLE
BRN: 2051910 · 2051910
Henry's Law Constant: 2.4 · 2.4×103 mol/(m3Pa) at 25℃, Zhang et al. (2010)
InChI: 1S/C12H10N2O2/c15-14(16)12-8-6-11(7-9-12)13-10-4-2-1-3-5-10/h1-9,13H
InChIKey: XXYMSQQCBUKFHE-UHFFFAOYSA-N
SMILES: [O-][N+](=O)c1ccc(Nc2ccccc2)cc1
CAS DataBase Reference: 836 · 836-30-6(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 5 ZOC179N5D · 5ZOC179N5D
NIST Chemistry Reference: N-(4-Nitrophenyl)-N-phenylamine(836-30-6)
EPA Substance Registry System: 4 · 4-Nitrodiphenylamine (836-30-6)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-37/39-36
RIDADR: 3077 · 3077
WGK Germany: 3 · 3
RTECS: 9600000 · JJ9600000
Hazard Note: Irritant
TSCA: TSCA listed
HazardClass: 9 · 9
PackingGroup: III
HS Code: 29214400 · 29214400
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Hazardous Substances Data: 836 · 836-30-6(Hazardous Substances Data)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 3.6% (3 of 83) of reports.

Warning

H315 (91.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 83 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory InformationChemical: Benzenamine, 4-nitro-N-phenyl-

Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire.

Hazards SummaryCan induce methemoglobinemia; [ICSC] Emergency treatment: Methemoglobinemia; [HSDB] An irritant; [Alfa Aesar MSDS]

UN ClassificationUN Hazard Class: 4.1; UN Pack Group: III

Chemical DangersDecomposes on heating and on burning. This produces toxic fumes of nitrogen oxides. Reacts with strong oxidants.

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (91.6%)

Specific target organ toxicity - Repeated exposure - Category 1 (blood system), Category 2 (kidney)

Safety & protection

Fire FightingUse water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

Safe StorageSeparated from strong oxidants and strong bases. Cool. Dry.

Spillage Disposal · 1 item

Personal protection: self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Eye PreventionWear safety goggles or eye protection in combination with breathing protection.

Fire PreventionNO open flames.

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.

Signs and Symptoms · 2 items

Blue lips, fingernails and skin. Dizziness. Headache. Confusion. Convulsions. Nausea. Unconsciousness.

See Inhalation.

ICSC Environmental DataThe substance is very toxic to aquatic organisms. It is strongly advised not to let the chemical enter into the environment. The substance may cause long-term effects in the aquatic environment.

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: JJ9600000
ridadr: 3077
hs_code: 29214400
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-37/39-36
hazard_class: 9
Storage Class: 11 - Combustible Solids
packing_group: III
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazardous Substances Data: 836-30-6(Hazardous Substances Data)

Chemistry & industry

Uses & manufacturing

UsesUsed as a chemical intermediate; [OECD SIDS: Benzenamine, 4-nitro-N-phenyl - 1998]

General Manufacturing InformationBenzenamine, 4-nitro-N-phenyl-: ACTIVE

Applications

Uses4-Nitrodiphenylamine was used to study reduction of nitrated diphenylamine derivatives in sediment water batch enrichments and dense cell suspensions of anaerobic, aromatic-compound-mineralizing pure bacterial cultures.

General Description4-Nitrodiphenylamine undergoes heterogeneous catalytic transfer hydrogenation to form p-phenylenediamines. 4-Nitrodiphenylamine is used as stabilizer for propellants and explosives.