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4-나이트로-m-페닐렌다이아민

4-Nitro-1,3-benzenediamine

HCID 21208
새 노트새 반응견적 요청하기
인쇄 미리보기

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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
5131-58-8
표준 SMILES
Nc1ccc([N+](=O)[O-])c(N)c1
InChIKey
DPIZKMGPXNXSGL-UHFFFAOYSA-N
분자식
C6H7N3O2
평균 분자량
153.14 g/mol
단동위원소 질량
153.05382646

개요

4-nitro-1,3-benzenediamine appears as orange prisms with blue luster or yellow crystalline solid. (NTP, 1992)

이름 및 식별자

우선 이름
4-Nitro-1,3-benzenediamine
IUPAC
4-nitrobenzene-1,3-diamine
현지명
4-나이트로-m-페닐렌다이아민
영어명
4-Nitro-1,3-phenylenediamine
분자식
C6H7N3O2
분자량
153.14

이름 및 동의어

5131-58-84-Nitro-1,3-phenylenediamine4-Nitro-m-phenylenediamine2,4-Diaminonitrobenzene4-NITRO-1,3-BENZENEDIAMINE1,3-Benzenediamine, 4-nitro-1,3-Diamino-4-nitrobenzene4-Nitro-1,3-diaminobenzenem-Phenylenediamine, 4-nitro-C.I. 760304-Nitro-1,3-fenylendiaminNSC 9575
이름 더 보기
4-나이트로-m-페닐렌다이아민4-나이트로-m-페닐렌다이아민및그염류(예:p-나이트로-m-페닐렌다이아민설페이트)4-니트로-1,3-페닐렌디아민4-Nitrobenzene-1,3-diaminec.i.760303-Amino-4-nitroanilineLABOTEST-BB LT000537604-NITRO-M-BENZENEDIAMINE4-nitro-3-benzenediamine4-nitro-m-phenylenediamin
CCRIS 4682DTXSID1025770HSDB 6243EINECS 225-876-34-Nitro-1,3-fenylendiamin [Czech]BRN 20949040D5U5EW62ZCI 76030

데이터베이스 식별자

CAS
5131-58-8
PubChem CID
21208
DTXSID
DTXSID1025770
ChEMBL
CHEMBL1427182
ChEBI
CHEBI:192970
UNII
0D5U5EW62Z
EC Number
225-876-3
Nikkaji
J70.162I

물성

구조 계산 물성보충 중

XLogP
0.5
극성 표면적
97.9 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
4
회전 가능 결합 수
0
무거운 원자 수
11
형식 전하
0
복잡도
156

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
Cosmetics · 2건

Cosmetic ingredients (4-Nitro-m-Phenylenediamine) -> CIR (Cosmetic Ingredient Review)

Hair dyeing

Color/FormOrange prisms from water
Solubilityless than 1 mg/mL at 68.9 °F (NTP, 1992)
Melting Point · 2건

322 °F (NTP, 1992)

161 °C

Vapor Pressure0.000056 [mmHg]
Physical Description · 2건

4-nitro-1,3-benzenediamine appears as orange prisms with blue luster or yellow crystalline solid. (NTP, 1992)

Orange solid; [HSDB] Orange solid with blue luster or yellow solid; [CAMEO] Yellow or brown crystalline powder; [Alfa Aesar MSDS]

물리화학적 성질

녹는점
161 °C · 161°C
끓는 점
276.04 °C · 276.04°C (rough estimate)

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Danger

H302 (13%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P321, P330, P332+P317, P337+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 2건

Chemical: 1,3-Benzenediamine, 4-nitro-

Status: Cease Manufacture Update: 10-05-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19463

Other Safety InformationIMAP assessments - Chemicals with limited data availability that may be used in hair dyes overseas: Human health tier II assessment
Fire HazardsFlash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)
Hazards SummaryEmergency treatment: Methemoglobinemia; [HSDB] Causes other liver changes, other changes in urine composition, and hemorrhage in 30-day intermittent oral study of rats; [RTECS] An irritant; [Alfa Aesar MSDS]
Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Special Reports · 1건

EVIDENCE IS GIVEN SUPPORTING TESTING OF THE CLASS OF COMPOUNDS PHENYLENEDIAMINES FOR THEIR TOXIC EFFECTS ON HUMAN HEALTH AND THE ENVIRONMENT. THE RESULTS OF TOXICITY TESTING OF 22 COMPOUNDS ARE TABULATED AS ARE THE EFFECTS FOR WHICH TESTING IS BEING CONSIDERED FOR 13 COMPOUNDS, AND THE USES OR POTENTIAL USES OF 47 PHENYLENEDIAMINES.[UNITED STATES EPA; PHENYLENEDIAMINES; RESPONSE TO INTERAGENCY TESTING COMMITTEE; FED REGIST 47(5) 973 (1982)]

화학 및 산업

용도 및 제조

Uses · 5건

CIR ingredient: 4-Nitro-m-Phenylenediamine

Used as a disperse dye intermediate and hair colorant; [HSDB]

Dressing Hair [Category: Other]

Disperse dye intermediate

... Used as a hair colorant in cosmetic products.

Methods of ManufacturingA wide variety of reaction types, including direct nitration, selective reduction, electrophilic substitution, alkylation, and molecular rearrangement are used in the manufacture of the commercially used nitro dyes.
Use ClassificationCosmetics -> Hair dyeing
General Manufacturing Information1,3-Benzenediamine, 4-nitro-: INACTIVE

응용 분야

용도4-Nitro-1,3-diaminobenzene is a general chemical reagent used in the synthesis of pharmaceuticals. Used in the synthesis of potent and selective Chk-1 inhibitors in the treatment of various cancers.

일반 설명Orange prisms with blue luster or yellow crystalline solid.

상·하류 제품 정보

상류 원료

4-니트로아닐린-3-설폰산4-니트로아닐린-3-설폰산4-methyl-N-[3-[(4-methylphenyl)sulfonylamino]phenyl]benzenesulfonamide2-Chloro-4,5-dinitro-benzoic acid2,4-디클로로-5-니트로벤조산

관련 반응

35건
반응 기록 만들기
HRID 71421 반응식
HRID 71421반응물로uspto-grants-2014_09
HRID 76530 반응식
HRID 76530반응물로uspto-grants-2014_09
HRID 142954 반응식
HRID 142954생성물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 226689 반응식
HRID 226689반응물로uspto-grants-2009_07
HRID 273541 반응식
HRID 273541반응물로uspto-grants-2008_11
HRID 405418 반응식
HRID 405418반응물로uspto-grants-2014_06
HRID 449238 반응식
HRID 449238반응물로uspto-grants-2013_07
HRID 528202 반응식
HRID 528202반응물로uspto-grants-2016_05
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
밀도
1.3682 · 1.3682 (rough estimate)
증기압
0.007 Pa · 0.007Pa at 25℃
굴절률
1.65 · 1.6500 (estimate)
용해도
almost transparency in hot Methanol
물리적 상태
powder to crystal
산도 계수 (pKa)
0.99 · 0.99±0.10(Predicted)
색상
머리 염색약의 노란색 화합물
수용성
20.5 · 20.5&C에서 <0.1g/100mL
BRN
2094904 · 2094904
Henry's Law Constant
1.7 · 1.7×105 mol/(m3Pa) at 25℃, HSDB (2015)
화장품 원료 기능
머리 염색
LogP
0.55 · 0.55
EPA
4 · 4-Nitro-m-phenylenediamine (5131-58-8)

화학적 성질

Yellow crystal powder

TSCA Requirements · 1건

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. 1,3-Benzenediamine, 4-nitro is included on this list. Effective date 4/29/83; Sunset date 12/29/88.

Reactivity Profile · 1건

4-NITRO-1,3-BENZENEDIAMINE is an amine/organonitrate. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (13%)

안전 및 보호

Fire FightingFires involving this compound can be controlled using a carbon dioxide, dry chemical 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 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.

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 85(SRC), determined from a structure estimation method(2), indicates that 4-nitro-1,3-benzenediamine is expected to have high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 4-nitro-1,3-benzenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 4-Nitro-1,3-benzenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.6X10-5 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2007).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 85(SRC), determined from a structure estimation method(2), indicates that 4-nitro-1,3-benzenediamine is not 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 5.8X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.55(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-nitro-1,3-benzenediamine, which has an estimated vapor pressure of 5.6X10-5 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-nitro-1,3-benzenediamine 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 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 4-nitro-1,3-benzenediamine may be removed from the air by wet or dry deposition(SRC). The compound contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Toxicity Summary · 2건

The safety of 4-Nitro-m-Phenylenediamine has not been documented and substantiated. The CIR Expert Panel cannot conclude that this ingredient is safe for use in cosmetic products until the appropriate safety data have been obtained and evaluated.

Ingredients for which the data are insufficient and their use in cosmetics is not supported

Medical SurveillanceRoutine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases.
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 4-nitro-1,3-benzenediamine can be estimated to be 85(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4-nitro-1,3-benzenediamine is expected to have high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3), suggesting that mobility may be much lower in some soils(SRC).

Human Toxicity Excerpts/OTHER TOXICITY INFORMATION/ POTENTIAL METHEMOGLOBIN FORMER
Artificial Pollution Sources4-Nitro-1,3-benzenediamine's production and use as a disperse dye intermediate(1) and hair colorant(2) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1건

An estimated BCF of 3 was calculated in fish for 4-nitro-1,3-benzenediamine(SRC), using an estimated log Kow of 0.55(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 4-nitro-1,3-benzenediamine is estimated as 5.8X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-nitro-1,3-benzenediamine is expected to be essentially nonvolatile from water surfaces(2). 4-Nitro-1,3-benzenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.6X10-5 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 2건

/GENOTOXICITY/ The mutagenicity of 4-nitro-m-phenylenediamine in DMSO in Salmonella typhimurium strains TA97, TA98, TA100, TA1535, and TA1537 was evaluated with and without metabolic activation ... The test substance (0.0-10,000 ug/plate) was incubated with each Salmonella culture for 20 min (37 °C) prior to plating. Two different S-9 mixes (rat and hamster liver) were used. ... 4-Nitro-m-phenylenediamine was mutagenic in strain TA98 both with and without metabolic activation, but was not mutagenic in strains TA100 and TA1535. In strain TA1537, positive (S-9 mix, hamster liver) and negative (S-9 mix, rat liver) results were obtained with metabolic activation, and, negative results, without metabolic activation. In strain TA97, 4-nitro-m-phenylenediamine was mutagenic only in the presence of metabolic activation (10.0% S-9, hamster liver). ... 4-nitro-m-phenylenediamine was mutagenic.

/OTHER TOXICITY INFORMATION/ ... Review of the 4-nitro-1,3 -Benzenediamine toxicological properties revealed a median lethal dose of 500 mg/kg in an acute oral toxicity study in mice. /This coumpound/ was mutagenic in the Ames/Salmonella assay and a chromosome aberrations test. Equivocal results were demonstrated in a sister chromatid exchange assay. No carcinogenicity data existed. ... no data on the skin irritation and sensitization and dermal toxicity potential ...

Populations at Special RiskRoutine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases.
Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of 4-nitro-1,3-benzenediamine with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Nitro-1,3-benzenediamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). The compound contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

규제 정보

TSCA Requirements · 1건

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. 1,3-Benzenediamine, 4-nitro is included on this list. Effective date 4/29/83; Sunset date 12/29/88.

안전 데이터

tsca
TSCA listed
rtecs
ST2910000
독성
LD50 orl-rat: 4500 mg/kg GTPZAB 35(2),42,91
HS 번호
2921.51.5000
risk_code
22-36/38
safety_code
26-36/37/39
기존화학 물질
KE-26022
유해 물질 데이터
5131-58-8(Hazardous Substances Data)
2-클로로-1,4-디니트로벤젠
2,6-디클로로-3-니트로벤조산
N,N'-(m-페닐렌)디(아세트아미드)
아닐린
2,5-Dinitroaniline
M-페닐렌다이아민
2-클로로-4-니트로벤조산
암모니아(가스)

하류 제품

CCRIS 25464-(4-플루오로벤질아미노)-1,2-페닐렌디아민듀라졸브라운4RNS1,4-Benzenedisulfonic acid, 2-[[4-[[4-[(2,4-diamino-5-nitrophenyl)azo]-6-sulfo-1-naphthalenyl]azo]-1-naphthalenyl]azo]-, trisodium saltsodium [3-[[3-[(3-amino-4-nitrophenyl)azo]-2,4-dihydroxyphenyl]azo]-4-hydroxybenzenesulphonato(3-)]cuprate(1-)Acid BrOWN85 (c.i. 34900)