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N,N-Diethyl-p-phenylendiamin

N,N-Diethyl-p-phenylenediamine

HCID 7120
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Grundinformationen

CAS
93-05-0
Standard-SMILES
CCN(CC)c1ccc(N)cc1
InChIKey
QNGVNLMMEQUVQK-UHFFFAOYSA-N
Summenformel
C10H16N2
Durchschnittliche Molmasse
164,25 g/mol
Monoisotopische Masse
164,13134851

Überblick

Reddish brown or black liquid. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
N,N-Diethyl-p-phenylenediamine
IUPAC
4-N,4-N-diethylbenzene-1,4-diamine
Lokaler Name
N,N-Diethyl-p-phenylendiamin
Englischer Name
N,N-Diethyl-1,4-phenylenediamine
Summenformel
C10H16N2
Molmasse
164.25

Namen und Synonyme

93-05-0N,N-DIETHYL-P-PHENYLENEDIAMINEN,N-Diethyl-1,4-phenylenediamine4-Amino-N,N-diethylaniline4-(Diethylamino)anilinep-(Diethylamino)anilinep-Amino-N,N-diethylanilineN,N-Diethyl-4-aminoanilineDiethylaminoanilineN,N-Diethyl-1,4-benzenediamineDTXSID20250581,4-Benzenediamine, N1,N1-diethyl-
Weitere Namen anzeigen
DPDN1,N1-diethylbenzene-1,4-diamineHept-1-yn-3-ol1,4-Benzenediamine, N,N-diethyl-DPYD4-DiethylaminoanilineDiethyl-p-phenylenediamineDHPDHASE
p-Phenylenediamine, N,N-diethyl-Diethyl-para-phenylenediaminepara-AminodiethylanilineN,N-Diethyl 4-phenylenediamine0QQA4DFV2JN,N-Diethyl-para-phenylenediamineDTXCID205058NSC-147488

Datenbank-Bezeichner

CAS
93-05-0

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
2,2
Polarare Oberfläche (TPSA)
29,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
3
Schwere Atome
12
Formalladung
0
Komplexität
113

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
Density · 2 Einträge

0.988 (NTP, 1992) - Less dense than water; will float

0.988

Color/Form · 2 Einträge

Liquid

Pale yellow liquid

Solubility · 3 Einträge

less than 1 mg/mL at 66 °F (NTP, 1992)

Insol in water; sol in alcohol and ether

Very soluble in benzene

Flash Pointgreater than 230 °F (NTP, 1992)
Boiling Point · 2 Einträge

500 to 504 °F at 760 mmHg (NTP, 1992)

260-262 °C

Melting Point79 to 82 °F (NTP, 1992)
Vapor Pressure0.00298 [mmHg]
Refractive IndexIndex of refraction: 1.5710 @ 20 °C/D

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

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

P260, P264, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: 1,4-Benzenediamine, N,N-diethyl-

Status: Active Update: 02-06-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/7727

4-Amino-N,N-diethylaniline: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Chemicals with limited data availability that may be used in hair dyes overseas: Human health tier II assessment
DOT LabelPoison
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include skin irritation, dermatitis, and hemorrhaging.
Hazards Summary · 1 Eintrag

May cause allergic dermatitis, irritation, and hemorrhage on skin contact; May induce methemoglobinemia; [HSDB] A severe eye irritant, based on animal studies; May cause skin sensitization after prolonged contact, based on a related compound; [CHEMINFO] Can cause burns; [eChemPortal: ESIS] A severe eye irritant; Causes general anesthesia, convulsions, and cyanosis in dermal lethal-dose study of rabbits; Causes convulsions in oral lethal-dose study of cats; [RTECS] Causes burns; Toxic if ingested; May be harmful if absorbed through skin; [Aldrich MSDS]

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesAN AZOTOBACTER VINELANDII ELECTRON TRANSPORT-ACTIVE 0 R3 FRACTION RAPIDLY OXIDIZED N,N-DIETHYL-P-PHENYLENEDIAMINE.
Absorption, Distribution and ExcretionFOLLOWING IN VIVO APPLICATION OF 1-(14)C-LABELED 4-AMINO-N,N-DIETHYLANILINE TO GUINEA PIG SKIN, BINDING TO EPIDERMAL PROTEINS WAS DEMONSTRATED, ALTHOUGH IT WAS RELATIVELY LABILE, & NO HAPTEN-AMINO ACID ADDUCT COULD BE ISOLATED.

Verwendung und Herstellung

Uses · 4 Einträge

Used as a dye intermediate and in diazo copying processes; [Hawley] Used as an antioxidant/antiozonant, as a developing agent in color photography, and in organic synthesis; [CHEMINFO]

Photographic Processing [Category: Other]

Dye intermediate; source of diazonium compd in diazo copying process

Color photography /Hydrochloride/

Methods of Manufacturing · 2 Einträge

Treatment of diethylaniline with nitrous acid and subsequent reduction.

Reduction of p-nitro-N,N-dimethylaniline

General Manufacturing Information1,4-Benzenediamine, N1,N1-diethyl-: ACTIVE

Anwendungen

VerwendenDye intermediate, source of diazonium compounds in diazo copying process.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

NitroNatriumchloridWasser

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Weitere Aktionen
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PubChem CID
7120
DTXSID
DTXSID2025058
ChEMBL
CHEMBL1452158
UNII
0QQA4DFV2J
EC Number
202-214-1
Nikkaji
J28.419J
Physical Description · 2 Einträge

Reddish brown or black liquid. (NTP, 1992)

Pale yellow liquid; [HSDB] Reddish-brown or black liquid; [CAMEO] Pale yellow liquid; Turns dark brown on exposure to light and air; [CHEMINFO] Clear very deep brown liquid; [MSDSonline]

Dissociation ConstantspKa= 7.96 (conjugate acid)
Other Experimental PropertiesColorless needles; soluble in water, alcohol; insoluble in ether /Hydrochloride/

Physikochemische Eigenschaften

Schmelzpunkt
19 · 19-21 °C(lit.)
Siedepunkt
115 · 115-116 °C5 mm Hg(lit.)
Dichte
0.988 g/mL · 0.988 g/mL at 25 °C(lit.)
Brechungsindex
20 · n20/D 1.571(lit.)
Flammpunkt
230 °F · >230 °F
storage temp.
2 · Keep in dark place,Sealed in dry,2-8°C
Löslichkeit
water: insoluble
Aggregatzustand
Liquid or Low Melting Solid
pka
8.21 · 8.21±0.32(Predicted)
Farbe
Clear yellow-brown to dark brown
Biologische Quelle
rabbit
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 19 ºC
BRN
879361 · 879361
Henry's Law Constant
1.9 · 1.9×102 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Stability Air and light sensitive. Incompatible with strong oxidizing agents, strong acids.
InChI
1S/C10H16N2/c1-3-12(4-2)10-7-5-9(11)6-8-10/h5-8H,3-4,11H2,1-2H3
InChIKey
QNGVNLMMEQUVQK-UHFFFAOYSA-N
SMILES
CCN(CC)c1ccc(N)cc1
CAS Datenbank
93 · 93-05-0(CAS DataBase Reference)
NIST chemische Informationen
1 · 1,4-Benzenediamine, N,N-diethyl-(93-05-0)
EPA chemische Informationen
N,N-Diethyl-p-phenylenediamine (93-05-0)
Reactive GroupAmines, Aromatic
Reactivity Profile · 1 Eintrag

N,N-DIETHYL-P-PHENYLENEDIAMINE 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.

Air and Water ReactionsInsoluble in water.
Hazard Classes and Categories · 4 Einträge

Acute Tox. 3 (100%)

Acute toxicity - category 3

Acute toxicity (Oral) - Category 3

Acute Tox. 3 *

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

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.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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 · 1 Eintrag

SRP: 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.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Personal Protective Equipment (PPE) · 1 Eintrag

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from a structure estimation method(2), indicates that the non-protonated form of N,N-diethyl-p-phenylenediamine is expected to have moderate mobility in soil(SRC). Volatilization of N,N-diethyl-p-phenylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.3X10-8 atm-cu m/mole(3), using a fragment constant estimation method(3). A pKa of 7.96(5) indicates N,N-diethyl-p-phenylenediamine will exist primarily in the protonated form at pH values of 5 to 9.Cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts. N,N-Diethyl-p-phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-3 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from an estimation method(2), indicates that the non-protonated form of N,N-diethyl-p-phenylenediamine 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 5.3X10-8 atm-cu m/mole(4), developed using a fragment constant estimation method(4). A pKa of 7.96(5) indicates N,N-diethyl-p-phenylenediamine will exist primarily in the ionized form at pH values of 5 to 9. According to a classification scheme(6), an estimated BCF of 11(SRC), from an estimated log Kow of 2.2(7),and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-diethyl-p-phenylenediamine, which has an estimated vapor pressure of 3.0X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the vapor-phase in the ambient atmosphere. Vapor-phase N,N-diethyl-p-phenylenediamine 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). N,N-Diethyl-p-phenylenediamine absorbs light in the environmental spectrum and has the potential for direct photolysis(4).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc for N,N-diethyl-p-phenylenediamine can be estimated to be 470(SRC). According to a classification scheme(2), this estimated Koc value suggests that the non-protonated form of N,N-diethyl-p-phenylenediamine is expected to have moderate mobility in soil. The pKa of N,N-diethyl-p-phenylenediamine is 7.96(3), indicating that this compound will exist in the cation form. Cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process because the cation is not expected to volatilize(SRC).

Artificial Pollution SourcesN,N-Diethyl-p-phenylenediamine's production and use as a dye(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 11 was calculated for N,N-diethyl-p-phenylenediamine(SRC), using an estimated log Kow of 2.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for N,N-diethyl-p-phenylenediamine is estimated as 5.3X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that N,N-diethyl-p-phenylenediamine is expected to be essentially nonvolatile from water surfaces(2). N,N-Diethyl-p-phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-3 mm Hg(SRC) determined from a fragment constant method(3).

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of N,N-diethyl-p-phenylenediamine 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).

Probable Routes of Human ExposureOccupational exposure to N,N-diethyl-p-phenylenediamine may occur through inhalation and dermal contact with this compound at workplaces where N,N-diethyl-p-phenylenediamine is produced or used.(SRC)
Environmental Fate/Exposure Summary · 1 Eintrag

N,N-Diethyl-p-phenylenediamine's production and use as a dye may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 3.0X10-3 mm Hg at 25 °C indicates N,N-diethyl-p-phenylenediamine will exist solely in the vapor-phase. Vapor-phase N,N-diethyl-p-phenylenediamine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2 hours. N,N-Diethyl-p-phenylenediamine absorbs light in the environmental UV spectrum and has the potential for direct photolysis. If released to soil, N,N-diethyl-p-phenylenediamine is expected to have moderate mobility based upon an estimated Koc of 470. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 5.3X10-8 atm-cu m/mole. The pKa of N,N-diethyl-p-phenylenediamine is 7.96, indicating that this compound will exist in the cation form. Cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process because the cation is not expected to volatilize. If released into water, N,N-diethyl-p-phenylenediamine is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 11 suggests the potential for bioconcentration in aquatic organisms is low. The general population may be exposed to N,N-diethyl-p-phenylenediamine via dermal contact with this compound and consumer products containing N,N-diethyl-p-phenylenediamine. (SRC)

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 2922 8/PG 2
hs_code
29215190
RTECS-Nr.
SS9275000
risk_code
25-34
hazard_code
T
safety_code
26-36-45
hazard_class
6.1(b)
packing_group
III
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Giftige Stoffe Daten
93-05-0(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 OralEye Dam. 1Skin Corr. 1B
N,N-Diethyl-4-nitrosoanilin
Eisen
N,N-Diethyl-4-nitroanilin
4,4'-Bis(diethylamino)azobenzene
Propanedioic acid, 2-[[[4-(diethylamino)phenyl]amino]methylene]-, 1,3-diethyl ester
N,N-Diethylanilin
N,N-Diethyl-p-phenylendiamin
1-Brom-4-chlorbenzol
1-Fluor-4-nitrobenzol

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