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diphenyl amine
benzenamine, N-phenyl-

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Name:N-phenylaniline
CAS Number: 122-39-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:204-539-4
FDA UNII: 9N3CBB0BIQ
Nikkaji Web:J2.493G
MDL:MFCD00003014
XlogP3:3.50 (est)
Molecular Weight:169.22667000
Formula:C12 H11 N
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:herbicides / pesticides
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
FDA Mainterm (IAUFC):122-39-4 ; DIPHENYLAMINE
 
Physical Properties:
Appearance:light tan to brown solid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 52.90 °C. @ 760.00 mm Hg
Boiling Point: 302.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.001000 mmHg @ 25.00 °C. (est)
Vapor Density:5.82 ( Air = 1 )
Flash Point: 307.00 °F. TCC ( 152.80 °C. ) (est)
logP (o/w): 3.500
Soluble in:
 water, 53 mg/L @ 20 °C (exp)
 water, 63.61 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor Description:sweet floral faint
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
ECSA Chemicals
DIPHENYLAMINE RPE-ACS-FOR ANALYSIS-REAG. PH.
ECSA TRADE THE MOST UPDATED FINANCIAL PUBLICATION ON THE WORLD OF CHEMISTRY
EMD Millipore
For experimental / research use only.
Diphenylamine
sds
Glentham Life Sciences
Diphenylamine
Penta International
DIPHENYLAMINE
Santa Cruz Biotechnology
For experimental / research use only.
Diphenylamine ≥98%
Sigma-Aldrich
For experimental / research use only.
Diphenylamine ACS reagent, ≥99%
Silver Fern Chemical
Diphenylamine
Odor: characteristic
Use: Diphenylamine is a plant growth regulator used post-harvest to control storage scold on apples. It has applications in mining and energy related products. Diphenylamine derivatives are also useful. Ring-alkylated derivatives of diphenylamine are used as "antiozinates" in the manufacture of rubber products, reflecting the antioxidant nature of aniline derivatives.
TCI AMERICA
For experimental / research use only.
Diphenylamine Zone Refined (number of passes:40)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-guinea pig LD50 300 mg/kg
Farm Chemicals Handbook. Vol. -, Pg. C112, 1991.

oral-mammal (species unspecified) LD50 3200 mg/kg
LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 40(10), Pg. 114, 1975.

oral-mouse LD50 1230 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 104, 1999.

oral-rat LD50 1120 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 104, 1999.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
herbicides / pesticides
IFRA Critical Effect:
Toxicity and teratogenicity
 View the IFRA Standard
Recommendation for diphenyl amine usage levels up to:
 PROHIBITED: Should not be used as a fragrance ingredient.
 
Recommendation for diphenyl amine flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Conclusion on the peer review of the pesticide risk assessment of the active substance diphenylamine
View page or View pdf

EPI System: View
EPA-Iris:IRIS
NIOSH International Chemical Safety Cards:search
NIOSH Pocket Guide:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):122-39-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11487
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
N-phenylaniline
Chemidplus:0000122394
EPA/NOAA CAMEO:hazardous materials
RTECS:122-39-4
 
References:
 N-phenylaniline
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:122-39-4
Pubchem (cid):11487
Pubchem (sid):134973710
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Indirect Additives used in Food Contact Substances:View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C11016
HMDB (The Human Metabolome Database):HMDB32562
FooDB:FDB010494
Export Tariff Code:2921.44.7000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 celery plant
Search Trop Picture
 coriander fruit
Search Trop Picture
 coriander plant
Search Trop Picture
 coriander seed
Search Trop Picture
 lemon plant
Search Trop Picture
 onion bulb
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 onion plant
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 tea leaf
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Synonyms:
 aniline, N-phenyl-
 benzenamine, N-phenyl-
 benzene, (phenylamino)-
 deccoscald 282
 diphenyl-amine
 diphenylamine
 naugalube 428L
 no-scald
(phenylamino)benzene
N-phenylaniline
N-phenylbenzenamine
 scaldip
 shield DPA
 

Articles:

PubMed:Cell wall, cell membrane, and volatile metabolism are altered by antioxidant treatment, temperature shifts, and peel necrosis during apple fruit storage.
PubMed:A method to detect diphenylamine contamination of apple fruit and storages using headspace solid phase micro-extraction and gas chromatography/mass spectroscopy.
PubMed:Effect of metabolic inhibitors on growth and carotenoid production in Dunaliella bardawil.
PubMed:Design, synthesis, and structure-activity relationship of novel aniline derivatives of chlorothalonil.
PubMed:Hollow fiber liquid-phase microextraction with in situ derivatization combined with gas chromatography-mass spectrometry for the determination of root exudate phenylamine compounds in hot pepper ( Capsicum annuum L.).
PubMed:Effects of route of administration and feeding schedule on pharmacokinetics of robenacoxib in cats.
PubMed:Redox spectrophotometric method involving electrolytically generated manganese(III) sulphate with diphenylamine for the determination of ascorbic acid present in the samples of various fruits, commercial juices and sprouted food grains.
PubMed:Cell wall, cell membrane, and volatile metabolism are altered by antioxidant treatment, temperature shifts, and peel necrosis during apple fruit storage.
PubMed:A novel dsDNA/polydiphenylamine-4-sulfonic acid electrochemical biosensor for selective detection of the toxic catechol and related DNA damage.
PubMed:Determination of fungicide residues in baby food by liquid chromatography-ion trap tandem mass spectrometry.
PubMed:Micronucleus frequency in human lymphocytes after exposure to diphenylamine in vitro.
PubMed:Diphenylamine residues in apples caused by contamination in fruit storage facilities.
PubMed:Antcin B and its ester derivative from Antrodia camphorata induce apoptosis in hepatocellular carcinoma cells involves enhancing oxidative stress coincident with activation of intrinsic and extrinsic apoptotic pathway.
PubMed:Decreases in cocaine self-administration with dual inhibition of the dopamine transporter and σ receptors.
PubMed:Ripening, storage temperature, ethylene action, and oxidative stress alter apple peel phytosterol metabolism.
PubMed:Development of a quantitative high-performance thin-layer chromatographic method for sucralose in sewage effluent, surface water, and drinking water.
PubMed:'Diffuse skin browning' in 1-MCP-treated apples: etiology and systems of control.
PubMed:Short anaerobiosis period prior to cold storage alleviates bitter pit and superficial scald in Granny Smith apples.
PubMed:Screening of agrochemicals in foodstuffs using low-temperature plasma (LTP) ambient ionization mass spectrometry.
PubMed:Profiling of compounds and degradation products from the postharvest treatment of pears and apples by ultra-high pressure liquid chromatography quadrupole-time-of-flight mass spectrometry.
PubMed:Metabolomic change precedes apple superficial scald symptoms.
PubMed:Trial offers early test case for personalized medicine.
PubMed:Diphenylamine metabolism in 'braeburn' apples stored under conditions conducive to the development of internal browning.
PubMed:Pesticide residues in Italian Ready-Meals and dietary intake estimation.
PubMed:Analyses of pesticide residues in fruit-based baby food by liquid chromatography/electrospray ionization time-of-flight mass spectrometry.
PubMed:Development of a high-throughput screening method using a cell-based, lawn format assay for the identification of novel plant defense activators from combinatorial peptide libraries.
PubMed:The indirect detection of bleach (sodium hypochlorite) in beverages as evidence of product tampering.
PubMed:Analysis of sucrose esters--insecticides from the surface of tobacco plant leaves.
PubMed:Oxidative remediation of diphenylamine in wastewater.
PubMed:Influence of ethylene action, storage atmosphere, and storage duration on diphenylamine and diphenylamine derivative content of Granny Smith apple peel.
PubMed:Rapid determination of diphenylamine residues in apples and pears with a single multicommuted fluorometric optosensor.
PubMed:Relationship of superficial scald development and alpha-farnesene oxidation to reactions of diphenylamine and diphenylamine derivatives in Cv. Granny Smith apple peel.
PubMed:1-Methylcyclopropene interactions with diphenylamine on diphenylamine degradation, alpha-farnesene and conjugated trienol concentrations, and polyphenol oxidase and peroxidase activities in apple fruit.
PubMed:Production of volatile compounds by Fuji apples following exposure to high CO2 or low O2.
PubMed:Carbendazim and metalaxyl residues in post-harvest treated apples.
PubMed:Sphingoid bases and ceramide induce apoptosis in HT-29 and HCT-116 human colon cancer cells.
PubMed:Conjugated triene oxidation products of alpha-farnesene induce symptoms of superficial scald on stored apples.
PubMed:Fate of apple peel phenolics during cool storage.
PubMed:Fate of
PubMed:Multivariate analysis of superficial scald susceptibility on Granny Smith apples dipped with different postharvest treatments.
PubMed:Effect of superficial scald suppression by diphenylamine application on volatile evolution by stored Cortland apple fruit.
PubMed:UVA-induced oxidative damage to rat liver nuclei: reduction of iron ions and the relationship between lipid peroxidation and DNA damage.
PubMed:Monitoring of domestic and imported apples and rice by the U.S. Food and Drug Administration pesticide program.
PubMed:Ascorbic acid inhibits lipid peroxidation but enhances DNA damage in rat liver nuclei incubated with iron ions.
PubMed:Determination of o-phenylphenol, diphenylamine, and propargite pesticide residues in selected fruits and vegetables by gas chromatography/mass spectrometry.
PubMed:Oxidative liver DNA damage in rats treated with pesticide mixtures.
PubMed:Effectiveness of intramuscularly administered cyanide antidotes on methemoglobin formation and survival.
PubMed:Investigation of regional glutathione levels in a model of chemically-induced renal papillary necrosis.
PubMed:Cytogenetic effects on human lymphocytes of a mixture of fifteen pesticides commonly used in Italy.
PubMed:Effect of Vicia faba and bran feeding on nitrosamine carcinogenesis and formation.
PubMed:Genetic toxicity of a mixture of fifteen pesticides commonly found in the Italian diet.
PubMed:Decreased incidence of diphenylamine-induced renal papillary necrosis in Syrian hamsters given dimethylsulphoxide.
PubMed:Reverse-phase liquid chromatographic determination of clioquinol in cream and ointment preparations: collaborative study.
PubMed:Monitoring Ontario-grown apples for pest control chemicals used in their production, 1978-86.
PubMed:Determination of diphenylamine residues in apples, and 4-aminobiphenyl residues in diphenylamine, by high-performance liquid chromatography and electrochemical detection.
PubMed:Conformation and configuration at the central amine nitrogen of a nucleotide adduct of the carcinogen 2-(acetylamino)fluorene as studied by 13C and 15N NMR spectroscopy.
PubMed:Effect of anti-oxidants on growth and lactic acid production by Streptococcus mutans.
PubMed:Effect of micronutrients, antioxidants and related compounds on the mutagenicity of 3,2'-dimethyl-4-aminobiphenyl, a colon and breast carcinogen.
PubMed:Methods for the determination of diphenylamine residues in apples.
PubMed:[Thin-layer chromatography of sugars (author's transl)].
PubMed:An Action Spectrum for Light-induced Primordium Formation in a Basidiomycete, Favolus arcularius (Fr) Ames.
PubMed:Superficial scald, a functional disorder of stored apples. IV. Effect of variety, maturity, oiled wraps and diphenylamine on the concentration of alpha-farnesene in the fruit.
PubMed:Superficial scald, a functional disorder of stored apples. 3. Concentration of diphenylamine in the fruit after treatment.
PubMed:Metabolism of diphenylamine in the rat, rabbit and man.
 
Notes:
in humans it may be irritating to mucous membranes. methemoglobinemia has been produced experimentally. in veterinary use, it is one of active ingredients in topical agents for prevention and treatment of screwworm infestation. an indicator in tests for nitrate poisoning. Used for control of superficial scald in stored apples Diphenylamine is the organic compound with the formula (C6H5)2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities.; It is a weak base, with a KB of 10?14. With strong acids, it forms the water soluble salt.
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