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ジフェニルアミン

Diphenylamine

HCID 11487
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
122-39-4
標準SMILES
c1ccc(Nc2ccccc2)cc1
InChIKey
DMBHHRLKUKUOEG-UHFFFAOYSA-N
分子式
C12H11N
平均分子量
169.22 g/mol
単同位体質量
169.08914935

概要

Diphenylamine is a light tan to brown solid with a pleasant odor. Sinks in water. (USCG, 1999)

名称と識別子

優先名称
Diphenylamine
IUPAC
N-phenylaniline
現地名
ジフェニルアミン
英語名
Diphenylamine
分子式
C12H11N
分子量
169.22

名称と別名

DiphenylamineN-Phenylaniline122-39-4N,N-DIPHENYLAMINEN-PhenylbenzenamineAnilinobenzenePhenylanilineScaldipBig DipperN-PhenylbenzeneamineBenzenamine, N-phenyl-Aniline, N-phenyl-
名称をさらに表示
ジフェニルアミンジフェニルアミン (1mg/ml酢酸エチル溶液) [悪臭規制物質分析用内部標準]N-フェニルベンゼンアミンスカルディプN-フェニルアニリンイミノビスベンゼンノースカルドビックディパージフェニルアミン標準品ジフェニルアミン標準原液N-フェニル アニリンジフェニルアミン, 98+%ジフェニルアミン STANDARDジフェニルアミン 溶液ジフェニルアミン Standard, 100 µg/mL in Dichloromethaneジフェニルアミン Standard, 1000 µg/mL in EtOHジフェニルアミン Standard, 5.0 mg/mL in MeOHジフェニルアミン, 1000 µg/mL in MeOHフェニルアニリンDPADFADiphenylaminBenzenamine,N-phenyl-DiphenylanilineDiphenylamine, synthesis gradeZ-876OA-505CORAZA
No-ScaldBenzene, anilino-DifenylaminDeccoscald 282Naugalube 428LN-FenylanilinShield DPANo-Scald DPA 283

データベース識別子

CAS
122-39-4、68442-68-2
PubChem CID
11487
DTXSID
DTXSID4021975
ChEMBL
CHEMBL38688
ChEBI
CHEBI:4640
UNII
9N3CBB0BIQ
EC Number
204-539-4
Nikkaji
J2.493G

物性

構造計算による物性補完中

XLogP
3.5
極性表面積
12 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
2
重原子数
13
形式電荷
0
複雑度
116

実験および物理化学的性質

Chemical ClassesDye
PolymersNitrogen Compounds -> Amines, Polyaromatic
SpringerMaterials PropertiesAngular frequency
FragrancesFragrance substance (Diphenylamine) -> IFRA amendment 38
Pesticides · 4 件

Pesticide -> EPA IRIS

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticide (Diphenylamine (DPA)) -> USDA PDB

LogP · 4 件

log Kow = 3.50

3.50

3.5

3.57

OdorPleasant, floral odor.
Density · 6 件

1.068 at 141.8 °F (USCG, 1999) - Denser than water; will sink

1.16

1.2 g/cm³

1.16

1.158 @ 22°C

1.16

Color/Form · 3 件

Monoclinic leaflets from dilute alcohol

Crystals

Colorless, tan, amber, or brown crystalline solid.

Solubility

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301+H311+H331 (10.1%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P337+P317, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: Benzenamine, N-phenyl-

Hazard Traits - Carcinogenicity

Commission Regulation (EC) No 33/2008

Benzenamine, N-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, N-phenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Diphenylamine is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2009/859/EC, Reg. (EU) No 578/2012

Other Safety InformationEvaluation - Benzenamine, N-phenyl-
DOT LabelPoison
Fire Hazards · 2 件

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Fire PotentialCombustible when exposed to heat or flame.

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

.../Diphenylamine/ has been converted to 4-hydroxydiphenylamine in rat and man. An antioxidant DPA actually promotes lipid hydroperoxide formation and oxygen consumption while markedly inhibiting generation of thiobarbituric acid reactive substances. /Diphenylamine/ abolishes formation of cyclooxygenase-dependent conversion products of arachidonate.

The urinary metabolites include 4-hydroxy-DPA, 4,4'-dihydroxy-DPA, and their conjugates. There is no evidence of N-hydroxylation.

...Fate of diphenylamine in dairy cow has been studied. None of the parent compound was detected in the milk or in urine, but small amount (1.4%) were identified in feces. The major metabolites were mono- and di-hydroxylated derivatives. Diphenylamine was rapidly metabolized by beef-liver microsomes.

Fifty percent of 5 ppm diphenylamine disappeared during a 30-minute incubation with liver extract. It was /suggested/ that microsomal hydroxylation of diphenylamine occurs, followed by conjugation and elimination.

Diphenylamine has known human metabolites that include Diphenylamine N-glucuronide.

Absorption, Distribution and Excretion · 4 件

...Stated to be less readily absorbed through the skin and respiratory tract /than aniline/.

After administration of diphenylamine (5 ppm) in feed to holstein cow for 4 days, 1.4% of dose detected in feces but none in urine or milk.

A Holstein cow was fed diphenylamine at 5 ppm in the diet for 4 days. Residues of diphenylamine were not detected in the milk or urine, and only in small amounts (1.4%) of the total dose were detected in the feces.

Diphenylamine is readily absorbed through inhalation and skin contact.

Cellular LocationsMembrane

用途と製造

Uses · 6 件

Used as an antioxidant, stabilizer of explosives, fungicide, and analytical chemical reagent; also used in the manufacture of dyes and pesticides; [ACGIH] Used to make dyes, to stabilize nitrocellulose explosives and celluloid, to treat screwworm topically (veterinary), and to test for nitrate or nitrite poisoning; [Merck Index]

関連反応

317 件
反応記録を作成
HRID 2403 の反応式
HRID 2403反応物としてuspto-grants-1998_03
HRID 7265 の反応式
HRID 7265反応物としてuspto-grants-2006_08
HRID 13886 の反応式
HRID 13886反応物としてuspto-grants-2010_06
HRID 13905 の反応式
HRID 13905反応物としてuspto-grants-2010_06
HRID 13907 の反応式
HRID 13907反応物としてuspto-grants-2010_06
HRID 13908 の反応式
HRID 13908反応物としてuspto-grants-2010_06
HRID 13909 の反応式
HRID 13909反応物としてuspto-grants-2010_06
HRID 13910 の反応式
HRID 13910反応物としてuspto-grants-2010_06
1 / 40 ページ

化合物ノート

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ノートを作成反応を作成見積依頼を出す
· 6 件

less than 1 mg/mL at 61 °F (NTP, 1992)

1 g dissolves in 2.2 ml of alcohol, 4 ml propyl alcohol; Freely sol in benzene, ether, glacial acetic acid, carbon disulfide.

Very sol in ethanol, acetone, benzene, carbon tetrachloride, pyridine, ethyl acetate; sol in ether, acetic acid; slightly sol in chloroform

Soluble in oxygenated and aromatic solvents

In water, 53 mg/liter @ 20 °C

0.053 mg/mL at 20 °C

Flash Point · 6 件

307 °F (NTP, 1992)

307 °F

153 °C OC

153 °C c.c.

307 °F

307 °F

Human DrugsPharmaceuticals

物理化学的性質

融点
52 °C · 52 °C
沸点
302 °C · 302 °C(lit.)
比重(密度)
1.16 · 1.16
蒸気密度
5.82 · 5.82 (vs air)
蒸気圧
1 mm · 1 mm Hg ( 108 °C)
屈折率
1.5785 · 1.5785 (estimate)
闪点
307 °F · 307 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
アルコール:テストに合格
外見
結晶性
酸解離定数(Pka)
0.79 · 0.79(at 25℃)
色
タン
臭い (Odor)
花の匂い
水溶解度
0.03 g/100mL · やや溶ける。 0.03g/100mL
Merck
14 · 14,3317
BRN
508755 · 508755
Henry's Law Constant
3.7 · 3.7×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Dielectric constant
3.3 · 3.3(11℃)
安定性
安定;光に当たると変色することがあります。強酸、強酸化剤とは相容れない。
InChI
1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
InChIKey
DMBHHRLKUKUOEG-UHFFFAOYSA-N
SMILES
N(c1ccccc1)c2ccccc2
LogP
3.82 at · 3.82 at 20.2℃
CAS データベース
122 · 122-39-4(CAS DataBase Reference)
NISTの化学物質情報
Diphenylamine(122-39-4)
EPAの化学物質情報
Diphenylamine (122-39-4)
化学的性質 · 1 件

化学的特性Diphenylamine is a colorless monoclinic leafl et substance. It is used in the manufacture of a variety of substances, i.e., dyestuffs and their intermediates, pesticides, antihelmintic drugs, and as reagents in analytical chemistry laboratories.

Health HazardsInhalation may irritate mucous membranes. Overexposure, including ingestion of solid or skin contact, may cause fast pulse, hypertension, and bladder trouble. Contact with dust irritates eyes. (USCG, 1999)
Hazards Summary · 1 件

The toxicity of diphenylamine is similar to that of aniline. Hepatotoxic effects have been demonstrated in animals. It can cause bladder irritation and induce methemoglobinemia in workers. As a skin sensitizer it cross-reacts with p-phenylene diamine. [ACGIH] May have effects on the kidneys and blood; A skin, eye, and respiratory tract irritant; [ICSC]

Reactive GroupAmines, Aromatic
EC ClassificationSymbol: T, N; R: 23/24/25-33-50/53; S: (1/2)-28-36/37-45-60-61
UN ClassificationUN Hazard Class: 9; UN Pack Group: III; UN Pack Group: II
TSCA Requirements · 2 件

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Diphenylamine is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

FIFRA Requirements · 3 件

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Diphenylamine is found on List B. Case No: 2210; Pesticide type: fungicide, herbicide; Case Status: RED Approved 9/1997; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): diphenylamine; Data Call-in (DCI) Date(s): 01/10/1991, 10/13/1995; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Tolerances for residues of the plant growth regulator diphenylamine are established in or on the following commodities: Apple, wet pomace; apple from preharvest or postharvest use, including use of impregnated wraps; cattle, fat; cattle, liver; cattle, meat byproducts, except liver; cattle, meat; goat, fat; goat, liver; goat, meat byproducts, except liver; goat, meat; horse, fat; horse, liver; horse, meat byproducts, except liver; horse, meat; milk; sheep, fat; sheep, liver; sheep, meat byproducts, except liver; and sheep, meat.

A time-limited tolerance is established for the indirect or inadvertent residues of diphenylamine in or on the following commodity: pear (Expiration/Revocation Date: 12/1/01).

安全と保護具

Fire Fighting · 2 件

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest.

Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink.

First Aid · 2 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

Safe StorageProvision to contain effluent from fire extinguishing. Separated from strong acids and oxidants. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 2 件

Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]

5.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]

Fire Fighting ProceduresFoam, dry chemical, carbon dioxide. ...Water or foam may cause frothing
Storage Conditions · 3 件

In general, materials which are toxic as stored or which can decompose into toxic components...should be stored in a cool, well-ventilated place, out of direct rays of the sun, away from areas of high fire hazard, and should be periodically inspected... Incompatible materials should be isolated from each other.

Keep protected from light.

/Store/ separated from strong acids, oxidants.

Cleanup MethodsSweep spilled substance into containers; if appropriate, moisten first to prevent dusting, then remove to safe place
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 2 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Burn in admixture with flammable solvent in furnace equipped with afterburner and scrubber. Recommendable methods: Incineration ... .

Spillage Disposal · 1 件

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Then store and dispose of according to local regulations.

Preventive Measures · 4 件

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

The worker should wash daily at the end of each work shift.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

毒性情報

Interactions · 3 件

Diphenylamine (5 mg) together with sodium nitrite (15 mg) fed to rats greatly decreased growth of animals. Kidney and liver toxicities and papillomatous hyperplasia of bladder observed in rats fed diphenylamine and sodium nitrite.

The toxicity of halogenated hydrocarbons such as carbon tetrachloride, hexachlorophene, and bithionol sulfoxide, used in veterinary medicine was diminished by the prior or simultaneous administration of diphenylamine (0.1-10% of the admin hydrocarbon).

...Dimethyl sulfoxide lessened the incidence of papillary lesions from diphenylamine.

Target Organs · 2 件

Hepatic

Eyes, skin, respiratory system, cardiovascular system, blood, bladder, reproductive system

Ecotoxicity Values · 4 件

LC50 Brachydanio rerio (Zebrafish) 2.2 mg/L/48 hr /Conditions of bioassay not specified/

LC50 Oryzias latipes (Japanese medaka) 5.1 mg/L/48 hr /Conditions of bioassay not specified/

LC50 Pimephales promelas (Fathead minnow, 31 day old) 3.79 mg/L/96 hr @ 24.9 °C (95% CI: 3.47-4.14 mg/L); flow through, dissolved oxygen 7.3 mg/L, hardness 48.0 mg/L as calcium carbonate, alkalinity 43.1 mg/L as calcium carbonate, pH 7.8 /99+% pure/

EC50 Pimephales promelas (Fathead minnow, 31 day old) affected fish lost schooling behavior, were hypoactive, swam near the tank bottom and were darly colored. 3.63 mg/L/96 hr @ 24.9 °C (95% CI: 3.31-3.99 mg/L); flow through, dissolved oxygen 7.3 mg/L, hardness 48.0 mg/L as calcium carbonate, alkalinity 43.1 mg/L as calcium carbonate, pH 7.8 /99+% pure/

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,900(SRC), determined from a log Kow of 3.50(2) and a regression-derived equation(3), indicates that N,N-diphenylamine is expected to have low mobility in soil(SRC). Volatilization of N,N-diphenylamine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.7X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 6.7X10-4 mm Hg(4), and water solubility, 53 mg/liter(5). N,N-Diphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). N,N-Diphenylamine is not expected to biodegrade in soil based on aqueous screening tests(6). N,N-Diphenylamine, present at 30 mg/l, reached 0% of its theoretical BOD in 2 weeks using an activated sludge innoculum at 100 mg/l and the Japanese MITI test(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,900(SRC), determined from a log Kow of 3.50(2) and a regression-derived equation(3), indicates that N,N-diphenylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.7X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 6.70X10-4 mm Hg(4), and water solubility, 53 mg/l(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 9.4 and 107 days, respectively(SRC). According to a classification scheme(6), BCFs ranging from 51 to 253(7), suggests bioconcentration in aquatic organisms is moderate(SRC). N,N-Diphenylamine was found to be not readily biodegradable in aqueous screening tests(7). N,N-Diphenylamine, present at 30 mg/l, reached 0% of its theoretical BOD in 2 weeks using an activated sludge innoculum at 100 mg/l and the Japanese MITI test(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-diphenylamine, which has a vapor pressure of 6.7X10-4 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase N,N-diphenylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.9 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Food Survey Values · 1 件

N,N-Diphenylamine was found in domestic and imported apples at avg concns of 0.275 ppm (max, 8.1 ppm; detections, 223 out of 769) and 0.232 ppm (max, 5.9 ppm; detections, 402 out of 1,062), respectively(1). N,N-Diphenylamine was detected in fruits and vegetables (15 of 3,962 sample) at concns between <0.01 and <5 ug/g from samples collected in Ontario, Canada between the years 1991 to 1995(2). As part of the Danish Pesticide Monitoring Program conducted between the years 1995-96, N,N-diphenylamine was detected in 5 of 96 apples and 1 of 33 pear samples(3). In selected agricultural commodities available in Canada, the concn of N,N-diphenylamine ranged from <0.05 to 2.0 ppm in 16 of 676 samples analyzed(4).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Toxicity Summary · 1 件

Diphenylamine uncouples mitochondrial oxidative phosphorylation, resulting in a decrease in hepatocellular ATP content and consequently hepatocyte injury (A15350). Short-term and long-term exposure in animal models results in altered haematological parameters, splenic erythropoiesis, splenic congestion and haemosiderosis (L2078).

Average Daily Intake · 1 件

Based on a FDA Total Diet Study analysis conducted between the years 1986 to 1991, the avg daily intake of N,N-diphenylamine was determined for eight age groups as follows (all ug/kg body wt/day): 6-11 month old (0.0034), 2 year old (0.0410), 14-16 year old female (0.0073), 14-16 year old male (0.0099), 25-30 female (0.0074), 25-30 male (0.0051), 60-65 year old female (0.0079), and 60-65 year old male (0.0065)(1,2).

Signs and Symptoms · 5 件

Cough. Sore throat.

Redness.

Redness.

Sore throat.

irritation eyes, skin, mucous membrane; eczema; tachycardia, hypertension; cough, sneezing; methemoglobinemia; increased blood pressure, heart rate; proteinuria, hematuria (blood in the urine), bladder injury; In Animals: teratogenic effects

Effluent Concentrations · 1 件

N,N-Diphenylamine had been detected as a volatile organic compound released from textile floor coverings(1). N,N-Diphenylamine was detected in 3 samples of municipal landfill leachate from Gryta, Vasteras, Sweden at concns of 2.3, 3.5, and <2 ug/liter (quantification limit = 2 ug/liter)(2).

ICSC Environmental DataThe substance is 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.

法規制情報

TSCA Requirements · 2 件

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Diphenylamine is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

FIFRA Requirements · 3 件

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Diphenylamine is found on List B. Case No: 2210; Pesticide type: fungicide, herbicide; Case Status: RED Approved 9/1997; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): diphenylamine; Data Call-in (DCI) Date(s): 01/10/1991, 10/13/1995; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Tolerances for residues of the plant growth regulator diphenylamine are established in or on the following commodities: Apple, wet pomace; apple from preharvest or postharvest use, including use of impregnated wraps; cattle, fat; cattle, liver; cattle, meat byproducts, except liver; cattle, meat; goat, fat; goat, liver; goat, meat byproducts, except liver; goat, meat; horse, fat; horse, liver; horse, meat byproducts, except liver; horse, meat; milk; sheep, fat; sheep, liver; sheep, meat byproducts, except liver; and sheep, meat.

A time-limited tolerance is established for the indirect or inadvertent residues of diphenylamine in or on the following commodity: pear (Expiration/Revocation Date: 12/1/01).

Atmospheric Standards · 1 件

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diphenylamine is produced, as an intermediate or a final product, by process units covered under this subpart.

State Drinking Water Guidelines · 2 件

(ME) MAINE 175 ug/l

(FL) FLORIDA 175 ug/l

Federal Drinking Water GuidelinesEPA 200 ug/l

安全データ

F
8-10-23
OEB
B
OEL
TWA: 10 mg/m3
wgk
3
tsca
TSCA listed
rtecs
JJ7800000
ridadr
UN 3077 9/PG 3
毒性
LD50 orally in Rabbit: 1120 mg/kg LD50 dermal Rabbit > 5000 mg/kg
PRTR法
第一種指定化学物質
hs_code
2921 44 00
risk_code
23/24/25-33-50/53-52/53-39/23/24/25-11-51/53
化審法
(3)-133
安衛法
有機溶剤中毒予防規則:第2種有機溶剤,57,57-2
消防法
危-4-1-II
hazard_code
T,N,F
safety_code
28-36/37-45-60-61-28A-16-7
hazard_class
6.1
packing_group
III
自然発火温度
630 °C DIN 51794
環境リスク評価
ジフェニルアミン(122-39-4)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
122-39-4(Hazardous Substances Data)

For diphenylamine (USEPA/OPP Pesticide Code: 038501) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Manufacture of dyes; stabilizing nitrocellulose explosives and celluloid; in analytical chemistry for detection of nitrates, chlorates and other oxidizing substances with which, in presence of sulfuric acid, it gives a deep-blue color.

VET: Topically in anti-screwworm mixtures; in test for nitrate or nitrate poisoning.

Rubber antioxidants and accelerators, solid rocket propellants, pesticides, dyes, pharmaceuticals, storage preservation of apples, stabilizer for nitrocellulose.

For more Uses (Complete) data for N,N-DIPHENYLAMINE (10 total), please visit the HSDB record page.

Impurities · 3 件

Six commercial brands of DPA were analyzed for these impurities: o-cyclohexylaniline was in all samples; p-biphenylamine in 4; o-biphenylamine in 3 and p-cyclohexylaniline in 1.

A number of primary and secondary amines have been reported as impurities in commercial DPA, including p-biphenylamine.

...The carcinogen 4-aminodiphenyl may be present as an impurity during manufacturing process. This may be concentrated to significant proportions in tars... At distillation stage... hazard of bladder cancer.

U.S. Exports(1986) No Data
U.S. Imports(1983) 2.78X10+8 g
U.S. Production · 2 件

2023: 50,000,000 - <100,000,000 lb

(1984) LESS THAN 2.27X10+6 g

Consumer UsesLubricating agent
Industry UsesStabilizing agent
IFRA Fragrance Standards · 6 件

Diphenylamine

Benzeneamine, N-phenyl-

IFRA_STD_135.pdf

38

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Prohibition: This material should not be used as a fragrance ingredient

Methods of Manufacturing · 2 件

By heating equal formula weights of aniline and aniline hydrochloride in an autoclave. The product is boiled with dilute hydrochloric acid to remove the unaltered aniline, and the residue is distilled.

... Manufactured by heating aniline by itself, or with phenol, and with an acid catalyst at high temperatures.

Formulations/Preparations · 5 件

GRADES: TECHNICAL; REFINED, FLAKE & FUSED

NO SCALD

SCALDIP

BIG DIPPER

DECCOSCALD EC 282 (25% AI), NO SCALD DPA EC 283 (31% AI), NO SCALD DPA POWDER NO. 31 (83% AI)

Household ProductsInformation on 9 consumer products that contain N,N-Diphenylamine in the following categories is provided:
Use ClassificationPharmaceuticals
応用分野 · 9 件

解説芳香族アミンの一つ。ジフェニルアミンは,芳香をもつ無色の結晶。弱塩基性。アニリンから合成される。糖類の呈色反応、硝酸塩やDNAの定量のほか、硝煙反応に用いられる。アニリンの塩酸塩と小過剰のアニリンの混合物を、圧力をかけながら加熱すると得られる無色の結晶。芳香がある。塩基性は弱い。水には溶けないが、エタノール(エチルアルコール)、エーテル、ベンゼンなどによく溶ける。濃硫酸溶液に硝酸イオンや亜硝酸イオンを加えると濃青色を呈するので、これらのイオンの検出剤として使われる(ジフェニルアミン反応)。また核酸の定量試薬としても使われる。アゾ染料の合成中間体、ニトロセルロースやセルロイドの安定剤として用いられる。発癌(はつがん)性が認められている。

解説C12H11N(169.22).(C6H5)2NH.アニリンと塩酸アニリンとの等モル混合物をオートクレーブ中で加熱すると得られる芳香族第二級アミン.葉状晶.融点54 ℃,沸点302 ℃.密度1.16 g cm-3.アルコール類に易溶.その濃硫酸水溶液は,微量の硝酸または亜硝酸によって青色を呈するので,これらの検出に用いる.工業的には,染料や医薬品の中間物として用いられる.[CAS 122-39-4]森北出版「化学辞典(第2版)

用途有機ゴム薬品、染料、火薬安定剤、塩素系溶剤の安定剤、医薬品

用途硝酸塩の検出試薬、有機合成原料(染料、医薬品)、安定剤(火薬、塩素系溶剤)。

用途染料中間体、媒染剤

説明Solutions of diphenylamine are used to treat apples a few days before harvest. Residue on apples’ surfaces of 10 ppm is permitted by regulation in Australia, Canada, and the United States.

使用Diphenylamine is an aromatic amine that was shown to exhibit antioxidant activities and is now used as an anti-scald agent. It is also used in the manufacture of a variety of substances, for instance, dye stuffs and their intermediates, pesticides, anthelmintic drugs, and as reagents in analytical chemistry laboratories.

一般的な説明Light tan to brown solid with a pleasant odor. Sinks in water.

使用用途ジフェニルアミンの主な使用用途は、硝酸塩の検出試薬、各種有機合成原料・中間体、火薬・塩素系溶剤の安定剤などです。特に、硝酸塩の検出は硝煙反応として知られています。また、DNAの抽出にも使われる物質です。 合成原料としては、 医薬・染料・有機ゴム薬品や、重合禁止剤であるフェノチアジンなどの合成中間体・原料物質として使用されます。また、有機ゴム薬品の老化防止剤 (N-(1,3)-ジメチルブチル-N'-フェニル-p-フェニレンジアミンなど) の合成原料でもあります。染料では、酸性および硫化系およびセリトン染料に用いられる物質です。

調製方法

純化方法Crystallise diphenylamine from pet ether, MeOH, or EtOH/water. Dry it under vacuum. [Beilstein 12 H 174, 12 IV 271.]

上流・下流製品情報

上流原料

エタノールアニリン

下流製品

1,3-ジヒドロ-7-クロロ-5-フェニル-2H-1,4-ベンゾジアゼピン-2-チオンメタニル エロータンプラミンβ-アラニンN-[4-[[4-(ジメチルアミノ)フェニル][4-(エチルアミノ)ナフタレン-1-イル]メチレン]-2,5-シクロヘキサジエン-1-イリデン]-N-メチルメタンアミニウム·クロリド5-[[4-(アミノスルホニル)-2-ニトロフェニル]アミノ]-2-[[4-[[4-(アミノスルホニル)-2-ニトロフェニル]アミノ]フェニル]アミノ]ベンゼンスルホン酸Direct Blending Navy Blue D-RN,N'-ジ-1-ナフチル-N,N'-ジフェニルベンジジン (昇華精製品)ダイレクト ブラック22Direct Blend Blueα-アミルシンナムアルデヒドフェノチアジン9-メチルアクリジンノルダゼパム4,4'-ビス(α,α-ジメチルベンジル)ジフェニルアミンN,N'-ジフェニルベンジジン4-ニトロソジフェニルアミン9,10-ジヒドロ-9,9-ジメチルアクリジン3-アミノプロピオニトリル2,2'-[(2,4-ジヒドロキシ-1,3-フェニレン)ビス(アゾ-4,1-フェニレンイミノ)]ビス[5-ニトロベンゼンスルホン酸ナトリウム]エリオ グリーン Bジフェニルアミン-4-スルホン酸ナトリウム4-ジアゾジフェニルアミンスルファート4-[[4-[(4-ヒドロキシ-2-メチルフェニル)アゾ]フェニル]アミノ]-3-ニトロベンゼンスルホン酸ナトリウム4-アミノ-3-[[4-[[4-[(2-アミノ-4-ヒドロキシフェニル)アゾ]フェニル]アミノ]-3-(ソジオオキシスルホニル)フェニル]アゾ]-5-ヒドロキシ-6-(フェニルアゾ)-2,7-ナフタレンジスルホン酸ジナトリウムC.I.サルファーブルー7lithium base grease2-アミノ-5-ニトロベンゾフェノンN-ニトロソジフェニルアミンSulphur Dark Blue 3RN,N'-ジフェニル-N,N'-ジ(m-トリル)ベンジジン1,1-ジフェニル-2-ピクリルヒドラジル フリーラジカルMolybdenum disulfide lithium-based greasephotosensitive polyimide photoresist (PSPI)N,N,N',N'-テトラフェニルベンジジン4,4`-di(a-methylbenzyl)diphenylamine
補足説明 · 1 件

定義diphenylamine: A colourless crystallinearomatic compound,(C6H5)2NH; m.p. 54°C. It is made byheating phenylamine (aniline) withphenylamine hydrochloride. It is asecondary amine and is both slightlyacidic (forming an N-potassium salt)and slightly basic (forming salts withmineral acids). Its derivatives are employedas stabilizers for syntheticrubber and rocket fuels.