ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /化合物

4-ニトロ-1,3-フェニレンジアミン

4-Nitro-1,3-benzenediamine

HCID 21208
ノートを作成反応を作成見積依頼を出す
印刷プレビュー

データを補完しています。しばらくしてからページを更新すると最新の内容を表示できます

基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
5131-58-8
標準SMILES
Nc1ccc([N+](=O)[O-])c(N)c1
InChIKey
DPIZKMGPXNXSGL-UHFFFAOYSA-N
分子式
C6H7N3O2
平均分子量
153.14 g/mol
単同位体質量
153.05382646

概要

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

名称と識別子

優先名称
4-Nitro-1,3-benzenediamine
IUPAC
4-nitrobenzene-1,3-diamine
現地名
4-ニトロ-1,3-フェニレンジアミン
英語名
4-Nitro-1,3-phenylenediamine
分子式
C6H7N3O2
分子量
153.14

名称と別名

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
名称をさらに表示
4-ニトロ-1,3-フェニレンジアミン4-ニトロ-1,3-ベンゼンジアミン4-ニトロベンゼン-1,3-ジアミン4-ニトロ-1,3-ジアミノベンゼン4-ニトロ-m-フェニレンジアミン1,3-ジアミノ-4-ニトロベンゼン2,4-ジアミノ-1-ニトロベンゼン4ニトロmフェニレンジアミン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

データベース識別子

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

物性

構造計算による物性補完中

XLogP
0.5
極性表面積
97.9 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
0
重原子数
11
形式電荷
0
複雑度
156

実験および物理化学的性質

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

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 件

322 °F (NTP, 1992)

161 °C

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

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]

物理化学的性質

融点
161 °C · 161°C
沸点
276.04 °C · 276.04°C (rough estimate)
比重(密度)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 2 件

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 件

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)]

化学と産業

用途と製造

Uses · 5 件

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

応用分野

使用4-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.

一般的な説明Orange prisms with blue luster or yellow crystalline solid.

上流・下流製品情報

上流原料

3-アミノ-6-ニトロベンゼンスルホン酸N,N′-(m-フェニレン)ビス(p-トルエンスルホンアミド)2-Chloro-4,5-dinitro-benzoic acid2,4-ジクロロ-5-ニトロ安息香酸

関連反応

35 件
反応記録を作成
HRID 71421 の反応式
HRID 71421反応物としてuspto-grants-2014_09
HRID 76530 の反応式
HRID 76530反応物としてuspto-grants-2014_09
HRID 142954 の反応式
HRID 142954生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 226689 の反応式
HRID 226689反応物としてuspto-grants-2009_07
HRID 273541 の反応式
HRID 273541反応物としてuspto-grants-2008_11
HRID 405418 の反応式
HRID 405418反応物としてuspto-grants-2014_06
HRID 449238 の反応式
HRID 449238反応物としてuspto-grants-2013_07
HRID 528202 の反応式
HRID 528202反応物としてuspto-grants-2016_05
1 / 5 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
1.3682 · 1.3682 (rough estimate)
蒸気圧
0.007 Pa · 0.007Pa at 25℃
屈折率
1.65 · 1.6500 (estimate)
溶解性
almost transparency in hot Methanol
外見
powder to crystal
酸解離定数(Pka)
0.99 · 0.99±0.10(Predicted)
色
染毛剤中の黄色化合物
水溶解度
0.1 g/100 · <0.1 g/100 mL で 20.5 ºC
BRN
2094904 · 2094904
Henry's Law Constant
1.7 · 1.7×105 mol/(m3Pa) at 25℃, HSDB (2015)
化粧品成分の機能
ヘアカラーリング
LogP
0.55 · 0.55
CAS データベース
5131 · 5131-58-8(CAS DataBase Reference)
EPAの化学物質情報
4 · 4-Nitro-m-phenylenediamine (5131-58-8)

化学的性質

化学的特性Yellow crystal powder

TSCA Requirements · 1 件

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 件

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%)

安全と保護具

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

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 件

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 件

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)

毒性情報

Environmental Fate · 3 件

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 件

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 件

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 件

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 件

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 件

/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 件

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).

法規制情報

TSCA Requirements · 1 件

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.

安全データ

tsca
TSCA listed
rtecs
ST2910000
毒性
LD50 orl-rat: 4500 mg/kg GTPZAB 35(2),42,91
hs_code
2921.51.5000
risk_code
22-36/38
化審法
(3)-402
消防法
危-5-II
safety_code
26-36/37/39
有毒物質データの
5131-58-8(Hazardous Substances Data)
2-クロロ-1,4-ジニトロベンゼン
2,6-ジクロロ-3-ニトロ安息香酸
1,3-ビス(アセチルアミノ)ベンゼン
アニリン
2,5-ジニトロアニリン
1,3-フェニレンジアミン
2-クロロ-4-ニトロ安息香酸
アンモニア

下流製品

CCRIS 25464-(4-Fluorobenzylamino)-1,2-phenylenediamine3-[[4-[[4-[(2,4-ジアミノ-5-ニトロフェニル)アゾ]-2-メチル-5-メトキシフェニル]アゾ]-1-ナフタレニル]アゾ]ナフタレン-1,5-ジスルホン酸二ナトリウム1,4-Benzenedisulfonic acid, 2-[[4-[[4-[(2,4-diamino-5-nitrophenyl)azo]-6-sulfo-1-naphthalenyl]azo]-1-naphthalenyl]azo]-, trisodium salt3-[[3-[(3-アミノ-4-ニトロフェニル)アゾ]-2,4-ジヒドロキシフェニル]アゾ]-4-ヒドロキシベンゼンスルホン酸/ナトリウム/銅,(1:1:1)Acid BrOWN85 (c.i. 34900)