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N,N-디에틸-p-페닐렌디아민

N,N-Diethyl-p-phenylenediamine

HCID 7120
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인쇄 미리보기

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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
93-05-0
표준 SMILES
CCN(CC)c1ccc(N)cc1
InChIKey
QNGVNLMMEQUVQK-UHFFFAOYSA-N
분자식
C10H16N2
평균 분자량
164.25 g/mol
단동위원소 질량
164.13134851

개요

Reddish brown or black liquid. (NTP, 1992)

이름 및 식별자

우선 이름
N,N-Diethyl-p-phenylenediamine
IUPAC
4-N,4-N-diethylbenzene-1,4-diamine
현지명
N,N-디에틸-p-페닐렌디아민
영어명
N,N-Diethyl-1,4-phenylenediamine
분자식
C10H16N2
분자량
164.25

이름 및 동의어

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-
이름 더 보기
N,N-디에틸-p-페닐렌디아민N,N-디에틸-1,4-페닐렌디아민DPDN1,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

데이터베이스 식별자

CAS
93-05-0
PubChem CID
7120
DTXSID
DTXSID2025058
ChEMBL
CHEMBL1452158
UNII
0QQA4DFV2J
EC Number
202-214-1
Nikkaji
J28.419J

물성

구조 계산 물성보충 중

XLogP
2.2
극성 표면적
29.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
3
무거운 원자 수
12
형식 전하
0
복잡도
113

실험 및 물리화학적 성질

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

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

0.988

Color/Form · 2건

Liquid

Pale yellow liquid

Solubility · 3건

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 · 2건

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
Physical Description · 2건

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]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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)

유해성 정보

Regulatory Information · 3건

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 · 1건

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]

화학 및 산업

약리 정보

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.

용도 및 제조

Uses · 4건

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 · 2건

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

응용 분야

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

일반 설명Reddish brown or black liquid.

상·하류 제품 정보

상류 원료

Nitro염화나트륨물N,N-디에틸-4-니트로소아닐린

관련 반응

45건
반응 기록 만들기
HRID 16125 반응식
HRID 16125반응물로uspto-grants-2010_06
HRID 16127 반응식
HRID 16127반응물로uspto-grants-2010_06
HRID 16129 반응식
HRID 16129반응물로uspto-grants-2010_06
HRID 153920 반응식
HRID 153920반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 162938 반응식
HRID 162938반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 193408 반응식
HRID 193408반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 244525 반응식
HRID 244525반응물로uspto-grants-2014_02
HRID 268251 반응식
HRID 268251반응물로uspto-grants-1976_03
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화합물 노트

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

물리화학적 성질

녹는점
19 · 19-21 °C(lit.)
끓는 점
115 · 115-116 °C5 mm Hg(lit.)
밀도
0.988 g/mL · 0.988 g/mL at 25 °C(lit.)
굴절률
20 · n20/D 1.571(lit.)
인화점
230 °F · >230 °F
저장 조건
2 · Keep in dark place,Sealed in dry,2-8°C
용해도
물: 불용성
물리적 상태
액체 또는 저융점 고체
산도 계수 (pKa)
8.21 · 8.21±0.32(Predicted)
색상
투명한 황갈색에서 진한 갈색까지
생물학적 소스
rabbit
수용성
19 · 19ºC에서 <0.1g/100mL
BRN
879361 · 879361
Henry's Law Constant
1.9 · 1.9×102 mol/(m3Pa) at 25℃, HSDB (2015)
안정성
안정성 공기와 빛에 민감합니다. 강한 산화제, 강산과 호환되지 않습니다.
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
NIST
1 · 1,4-Benzenediamine, N,N-diethyl-(93-05-0)
EPA
N,N-Diethyl-p-phenylenediamine (93-05-0)

화학적 성질

dark brown to black solid or liquid, depending upon room temperature

Reactive GroupAmines, Aromatic
Reactivity Profile · 1건

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 · 4건

Acute Tox. 3 (100%)

Acute toxicity - category 3

Acute toxicity (Oral) - Category 3

Acute Tox. 3 *

안전 및 보호

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

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 · 1건

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 · 1건

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) · 1건

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)

독성 정보

Environmental Fate · 3건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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)

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
SS9275000
ridadr
UN 2922 8/PG 2
HS 번호
29215190
risk_code
25-34
hazard_code
T
safety_code
26-36-45
포장분류
III
위험 등급
6.1(b)
Hazard Classifications
Acute Tox. 3 OralEye Dam. 1Skin Corr. 1B
스토리지 클래스
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
유해 물질 데이터
93-05-0(Hazardous Substances Data)
철분
N,N-DIETHYL-4-NITROANILINE
4,4'-비스(디에틸아미노)아조벤젠
Propanedioic acid, 2-[[[4-(diethylamino)phenyl]amino]methylene]-, 1,3-diethyl ester
N,N-디에틸아닐린
N,N-디에틸-p-페닐렌디아민
4-Bromochlorobenzene
p-플루오로미트로벤젠

하류 제품

N,N-Diethyl-p-phenylenediamine sulfatePropanedinitrile, 2-[2-[2-(4-aminophenyl)ethenyl]-4H-1-benzopyran-4-ylidene]-설파닐산 나트륨 염아닐린N,N-디에틸-p-페닐렌디아민N,N-디에틸-P-페닐렌디아민모노히드로클로라이드2-[[4-[에틸(2-하이드록시에틸)아미노]페닐]아조]-6-메톡시-3-메틸벤조티아졸륨Benzo[a]phenazinium, 9-(diethylamino)-5-[[4-(diethylamino)phenyl]amino]-7-phenyl-, chloride4-[[4-(디에틸아미노)페닐]이미노]나프탈렌-1(4H)-온