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HCID 7573Erstellt: 4. November 2026

N-(1-Methylethyl)-N'-phenyl-1,4-benzoldiamin

IPPD · 4010na · Diafen FP · N-isopropyl-N'-phenyl-p-phenylenediamine · 4010 NA · Antioxidant IPPD · N-isopropyl-N`-phenylenediamine · n-isopropyl-n-phenyl-4-phenylenediamine

https://huagongshe.com/de/chemical/7573

Molekülstruktur von N-(1-Methylethyl)-N'-phenyl-1,4-benzoldiamin

Identifikatoren & physikalische Daten

CAS No.101-72-4
SummenformelC15H18N2
Durchschnittliche Molmasse226,32 g/mol
Monoisotopische Masse226,14699858 g/mol
SMILESCC(C)Nc1ccc(Nc2ccccc2)cc1
InChIKeyOUBMGJOQLXMSNT-UHFFFAOYSA-N
PubChem CID7573
ChEMBLCHEMBL1449018
ChEBICHEBI:63569
EC No.202-969-7
DTXSIDDTXSID1025485
Lokaler NameN-(1-Methylethyl)-N'-phenyl-1,4-benzoldiamin

Chemische & physikalische Eigenschaften

XLogP4
Polarare Oberfläche (TPSA)24,1
H-Brücken-Donoren2
H-Brücken-Akzeptoren2
Frei drehbare Bindungen4
Schwere Atome17
Formalladung0
Komplexität201
PolymersPlastics & Rubber -> Rubber AdditivesNitrogen Compounds -> Amines, Polyaromatic
Dichte1.04 (NTP, 1992) - Denser than waterwill sink1.04 @ 25 °C1.04 g/cm³1,17 g/cm3
Color/FormDark gray to black flakes
Löslichkeitless than 1 mg/mL at 64 °F (NTP, 1992)Soluble in benzene and gasolineinsoluble in water.Insoluble watersoluble in aromatic solventsSolubility in water: noneChloroform (Slightly), DMSO (Slightly, Sonicated)<0.1 g/100 mL at 18 ºC
Flammpunkt303 °F (NTP, 1992)161°C/1mm
Siedepunkt322 °F at 1 mmHg (NTP, 1992)161°C
Schmelzpunkt162 to 169 °F (NTP, 1992)75 °C72-76 °C72-76°C
Dampfdruck0.00343 mmHg at 194 °F (NTP, 1992)0.0000711 [mmHg]0.007Pa at 20℃
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionN-isopropyl-n'-phenyl-p-phenylenediamine appears as dark gray to black flakes or brown-black small chip-like solid with an aromatic odor. (NTP, 1992)Large CrystalsOther SolidDry PowderDark grey to black solid[Hawley] Brown, grey, or dark purple to black solid[CHEMINFO]DARK GREY-TO-BLACK FLAKES.
Collision Cross Section155.4 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID1025485]
Other Experimental PropertiesFP: 72-76 °C
Brechungsindex1.5000 (estimate)
Lagerbedingungen-20°C
AggregatzustandSolid
pKa (Säurekonstante)6.76±0.32(Predicted)
FarbeGrey to Very Dark Grey
Biologische Quellerabbit
Henry-Konstante7.0×103 mol/(m3Pa) at 25℃, HSDB (2015)
StabilitätStable. Combustible. Incompatible with strong oxidizing agents.
LogP (Verteilungskoeffizient)2.77 at 20℃
CAS Datenbank101-72-4(CAS DataBase Reference)
NIST chemische InformationenP-phenylenediamine, n-isopropyl-n'-phenyl-(101-72-4)
EPA chemische InformationenN-Isopropyl-N'-phenyl-p-phenylenediamine (101-72-4)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Regulatorische InformationenChemical: 1,4-Benzenediamine, N-(1-methylethyl)-N'-phenyl-1,4-Benzenediamine, N1-(1-methylethyl)-N4-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediamine, N1-(1-methylethyl)-N4-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)REACH registered substance: N-isopropyl-N'-phenyl-p-phenylenediamine (EC: 202-969-7)Isopropylphenyl p-phenylenediamine: Does not have an individual approval but may be used under an appropriate group standard
DOT-KennzeichnungPoison
BrandgefahrenThis chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
GesundheitsgefahrenSYMPTOMS: Symptoms of exposure to this compound may include contact dermatitis and occupational eczema. It may be irritating to the eyes, skin and respiratory system.
GefahrenübersichtN-lsopropyl-N'-phenyl Paraphenylenediamine (IPPD) CAS # 101-72-4\\ N-Cyclohexyl-N'-phenyl-Paraphenylenediamine (CPPD)\\ N,N'-Diphenyl Paraphenylenediamine ((DPPD) CAS # 74-31-7\\ These amines are added to rubber products (tires, tubes, pipes, gaskets, flanges, boots, shoes, etc.) during manufacturing to retard degradation by oxidants and ozone. [Marks, p. 68]A skin and eye irritantMay cause skin sensitization[ICSC] Emergency treatment: ParaphenylenediamineParaphenylenediamine can cause angioneurotic edema, the most common cause of death after an overdoseOther effects after ingestion are vomiting, acute tubular necrosis, liver injury, methemoglobinemia, and seizures

Anwendungen & Verwendung

Verwenden

Protection of rubbers against oxidation, ozone, flex-cracking, and poisoning by copper and manganese.

p-Phenylenediamine is a skin and respiratory tract sensitizer
[HSDB] A skin, eye, and respiratory tract irritant
May cause contact dermatitis
[CAMEO] Does not readily penetrate intact skin
Not an eye or skin irritant based on animal studies
No data available on inhalation toxicity, respiratory sensitization, or carcinogenicity
[OECD SIDS: N-Isopropyl-N'-phenyl-p-phenylenediamine (IPPD) - 2000] See p-Phenylenediamine.
Reaktive GruppeAmines, Aromatic
EG-EinstufungSymbol: Xn, NR: 22-43-50/53S: (2)-24-37-60-61
Reactivity ProfileN-ISOPROPYL-N'-PHENYL-P-PHENYLENEDIAMINE reacts with oxidizing agents (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Chemical DangersDecomposes on burning. This produces toxic fumes including nitrogen oxides.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
Packaging and LabellingDo not transport with food and feedstuffs.
Air and Water ReactionsMay be sensitive to heat, air, light and moisture during long term storage. Insoluble in water.
BrandbekämpfungFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)Use water spray, powder.
Erste-Hilfe-MaßnahmenFresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth.
Erste HilfeEYES: 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.
Sichere LagerungWell closed.
Expositionsschutz und Persönliche Schutzausrüstung2.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Freisetung ohne BrandSMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Verschüttetes entsorgenPersonal protection: chemical protection suit. 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.
Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Eye PreventionWear safety goggles or face shield.
Fire PreventionNO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
KörperbelastungThe level of 4-(iso-propylamino)diphenylamine in the urine of rubber vulcanization workers were noted to be higher in the end-shift than in the before-shift sample, respective concentrations being 83.57 and 19.55 ug/l(1).
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.3X10+4(SRC), determined from a structure estimation method(2), indicates that 4-(iso-propylamino)diphenylamine is expected to be immobile in soil(SRC). Volatilization of 4-(iso-propylamino)diphenylamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The estimated pKa of 4-(iso-propylamino)diphenylamine is 5.1(5), indicating that this compound will exist only slightly in the cation form(SRC). Cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts. 4-(Iso-propylamino)diphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(4).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.3X10+4(SRC), determined from an estimation method(2), indicates that the non-protonated form of 4-(iso-propylamino)diphenylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.4X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An estimated pKa of 5.1(8) indicates 4-(iso-propylamino)diphenylamine will exist only slightly in the cation form at pH values of 5 to 9(SRC). Cations generally adsorb to suspended solids and sediment more strongly thantheir neutral counterparts. According to a classification scheme(5), an estimated BCF of 67(SRC), from an estimated log Kow of 3.3(6), and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-(iso-propylamino)diphenylamine, which has an estimated vapor pressure of 3.5X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4-(iso-propylamino)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 2 hours(SRC), calculated from its rate constant of 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase 4-(iso-propylamino)diphenylamine may be removed from the air by wet and dry deposition(SRC).
Unerwünschte WirkungenSkin Sensitizer - An agent that can induce an allergic reaction in the skin.Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
ExpositionspfadeThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Signs and SymptomsRedness.Redness. Pain.
ICSC Environmental DataThe substance is very toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment.
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc for 4-(iso-propylamino)diphenylamine can be estimated to be 1.3X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4-(iso-propylamino)diphenylamine is expected to be immobile in soil(SRC). The estimated pKa of 4-(iso-propylamino)diphenylamine is 5.1(3), indicating that this compound will exist only slightly in the cation form and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts.
Human Toxicity ExcerptsA study of the prevalence of HLA antigens in persons sensitized to N-isopropyl-N'-phenyl-p-phenylenediamine was conducted to determine if an association between N-isopropyl-N'-phenyl-p-phenylenediamine sensitivity and the gene product of theHLA complex exists. The cohort consisted of 32 Czech patients sensitized to N-isopropyl-N'-phenyl-p-phenylenediamine, as determined by patch tests. The comparisons consisted of 159 persons from the general Slovak population who were unrelated to the patients. Blood samples were collected and serological typing for HLA-A, HLA-B, HLA-C and the HLA-Dw antigens HLA-Dw1, HLA-Dw2, HLA-Dw3, HLA-Dw4, HLA-Dw5, HLA-Dw7, HLA-Dw8, hLA-Dw9, HLA-Dw10, and HLA-Dw11 was performed. The prevalence of HLA-Dw3 in thecohort was significantly elevated relative to the comparisons, 37.5 versus 8.7%.The increased HLA-Dw3 prevalence was associated with a relative risk of 6.3 of developing allergy to N-isopropyl-N'-phenyl-p-phenylenediamine. The prevalence of the HLA-Dw4 antigen was nonsignificantly elevated in the cohort. The prevalence of the other HLA antigens did not differ significantly between the two groups. The authors conclude that allergy to N-isopropyl-N'-phenyl-p-phenylenediamine has a polygenetic background and that genes of theHLA antigen complex are involved.DERMATITIS WAS CAUSED BY N-ISOPROPYL-N-PHENYL-P-PHENYLENEDIAMINE (SANTOFLEX IP).CONTACT ALLERGIC ECZEMA AT WRIST REGION IN 9 PROFESSIONALS & 36 HOUSEWIVES IN CONTACT WITH RUBBER PARTS OF ELECTRIC IRONS PRODUCED CHARACTERISTIC COLOR CAUSED BY PETECHIAE & HEMOSIDERIN PIGMENTATION. EXAM REVEALED CAPILLARITIS. IN 5 CASES PURPURA SPREAD TO WHOLE BODY.51 PATIENTS ALLERGIC TO IPPD WERE REVIEWED & CLINICAL FEATURES & PROGNOSIS DISCUSSED. IN 38 OF 51 PATIENTS, THE DERMATITIS WAS CONSIDERED OCCUPATIONAL, MAJORITY BEING EMPLOYED IN TRANSPORT INDUSTRY.For more Human Toxicity Excerpts (Complete) data for 4-(ISOPROPYLAMINO)DIPHENYLAMINE (10 total), please visit the HSDB record page.
Artificial Pollution Sources4-(Iso-propylamino)diphenylamine's production and use as an antiozonant and antioxidant may result in its release to the environment through various waste streams(SRC).
Environmental BioconcentrationAn estimated BCF of 67 was calculated for 4-(iso-propylamino)diphenylamine(SRC), using an estimated log Kow of 3.3(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.
Volatilization from Water/SoilThe Henry's Law constant for 4-(iso-propylamino)diphenylamine is estimated as 1.4X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-(iso-propylamino)diphenylamine is expected to be essentially nonvolatile from water and moist soil surfaces(2). 4-(Iso-propylamino)diphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(3).
Environmental Abiotic DegradationThe rate constant for the vapor-phase reaction of 4-(iso-propylamino)diphenylamine with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of approximately 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).
TSCA-Inventar-StatusTSCA listed
UN-Transportnummer3077
Zollcode29215900
RTECS-Nr.ST2650000
R-Sätze (R)36/37/38-50/53-43-22
ToxizitätLD50 oral in rat: 720mg/kg
GefahrensymboleXi,N,Xn
hazard_noteIrritant
Sicherheitshinweise (S)26-36-61-60-37-24
Gefahrenklasse9
VerpackungsgruppeIII
Gefahrstoffdaten101-72-4(Hazardous Substances Data)