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4-Nitro-m-phenylendiamin

4-Nitro-1,3-benzenediamine

HCID 21208
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Grundinformationen

CAS
5131-58-8
Standard-SMILES
Nc1ccc([N+](=O)[O-])c(N)c1
InChIKey
DPIZKMGPXNXSGL-UHFFFAOYSA-N
Summenformel
C6H7N3O2
Durchschnittliche Molmasse
153,14 g/mol
Monoisotopische Masse
153,05382646

Überblick

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

Namen und Bezeichner

Bevorzugter Name
4-Nitro-1,3-benzenediamine
IUPAC
4-nitrobenzene-1,3-diamine
Lokaler Name
4-Nitro-m-phenylendiamin
Englischer Name
4-Nitro-1,3-phenylenediamine
Summenformel
C6H7N3O2
Molmasse
153.14

Namen und Synonyme

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
Weitere Namen anzeigen
4-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

Datenbank-Bezeichner

CAS
5131-58-8
PubChem CID
21208
DTXSID
DTXSID1025770

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0,5
Polarare Oberfläche (TPSA)
97,9 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
0
Schwere Atome
11
Formalladung
0
Komplexität
156

Experimentelle und physikochemische Eigenschaften

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

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 · 2 Einträge

322 °F (NTP, 1992)

161 °C

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

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]

Physikochemische Eigenschaften

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 · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 2 Einträge

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 · 1 Eintrag

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)]

Chemie und Industrie

Verwendung und Herstellung

Uses · 5 Einträge

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

Anwendungen

Verwenden4-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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

4-Nitroaniline-3-sulfonicacid4-methyl-N-[3-[(4-methylphenyl)sulfonylamino]phenyl]benzenesulfonamide2-Chloro-4,5-dinitro-benzoic acid2,4-Dichloro-5-nitrobenzoic acid2-Chloro-1,4-dinitrobenzene

Zugehörige Reaktionen

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Reaktionsgleichung von HRID 142954
HRID 142954als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 226689
HRID 226689als Eduktuspto-grants-2009_07
Reaktionsgleichung von HRID 273541
HRID 273541als Eduktuspto-grants-2008_11
Reaktionsgleichung von HRID 405418
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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
ChEMBL
CHEMBL1427182
ChEBI
CHEBI:192970
UNII
0D5U5EW62Z
EC Number
225-876-3
Nikkaji
J70.162I
Schmelzpunkt
161 °C · 161°C
Siedepunkt
276.04 °C · 276.04°C (rough estimate)
Dichte
1.3682 · 1.3682 (rough estimate)
Dampfdruck
0.007 Pa · 0.007Pa at 25℃
Brechungsindex
1.65 · 1.6500 (estimate)
Löslichkeit
almost transparency in hot Methanol
Aggregatzustand
powder to crystal
pka
0.99 · 0.99±0.10(Predicted)
Farbe
Yellow compound in hair dyes
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 20.5 ºC
BRN
2094904 · 2094904
Henry's Law Constant
1.7 · 1.7×105 mol/(m3Pa) at 25℃, HSDB (2015)
Kosmetik-Inhaltsstoffe Funktionen
HAIR DYEING
LogP
0.55 · 0.55
CAS Datenbank
5131 · 5131-58-8(CAS DataBase Reference)
EPA chemische Informationen
4 · 4-Nitro-m-phenylenediamine (5131-58-8)
TSCA Requirements · 1 Eintrag

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 · 1 Eintrag

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%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this compound can be controlled using a carbon dioxide, dry chemical 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 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) · 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 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 · 2 Einträge

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 · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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 · 2 Einträge

/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 · 1 Eintrag

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).

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

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.

Sicherheitsdaten

tsca
TSCA listed
hs_code
2921.51.5000
RTECS-Nr.
ST2910000
risk_code
22-36/38
Toxizität
LD50 orl-rat: 4500 mg/kg GTPZAB 35(2),42,91
safety_code
26-36/37/39
Giftige Stoffe Daten
5131-58-8(Hazardous Substances Data)
2,6-Dichloro-3-nitrobenzoic acid
N,N'-(m-Phenylen)di(acetamid)
Anilin
2,5-Dinitroaniline
m-Phenylendiamin
2-Chlor-4-nitrobenzoesure
Ammoniak, wasserfrei

Nachgelagerte Produkte

CCRIS 25464-(4-Fluorobenzylamino)-1,2-phenylenediamineDurazol Brown 4RNS1,4-Benzenedisulfonic acid, 2-[[4-[[4-[(2,4-diamino-5-nitrophenyl)azo]-6-sulfo-1-naphthalenyl]azo]-1-naphthalenyl]azo]-, trisodium saltNatrium-[3-[[3-[(3-amino-4-nitrophenyl)azo]-2,4-dihydroxyphenyl]azo]-4-hydroxybenzolsulfonato(3-)]cuprat(1-)Acid BrOWN85 (c.i. 34900)