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4-メチルアミノフェノール

n-Methyl-p-aminophenol

HCID 5931
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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
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基本情報

CAS
150-75-4
標準SMILES
CNc1ccc(O)cc1
InChIKey
ZFIQGRISGKSVAG-UHFFFAOYSA-N
分子式
C7H9NO
平均分子量
123.15 g/mol
単同位体質量
123.06841391

概要

4-methylaminophenol is the phenol that is the N-methyl derivative of 4-aminophenol. It has a role as an allergen. It is functionally related to a 4-aminophenol.

名称と識別子

優先名称
n-Methyl-p-aminophenol
IUPAC
4-(methylamino)phenol
現地名
4-メチルアミノフェノール
英語名
4-(Methylamino)phenol
分子式
C7H9NO
分子量
123.15

名称と別名

150-75-44-MethylaminophenolN-Methyl-4-aminophenolN-METHYL-P-AMINOPHENOLParamethylaminophenolPhenol, p-(methylamino)-N-methyl-4-hydroxyanilineCHEBI:5541611W1883EFBDTXSID80437834-N-methylaminophenolRefChem:163709
名称をさらに表示
p-(メチルアミノ)フェノールp-メチルアミノフェノール4-(メチルアミノ)フェノールN-メチル-4-ヒドロキシアニリン4-メチルアミノフェノールSULFURIC ACID COMPOUND WITH 4-(メチルアミノ)フェノール (1:1)4-(Methylamino)p-(methylamino)-phenoPARA-METHYLAMINOPHENOL4-(methylamino)phenol[qr]p-(methylamino)phenol[qr]
DTXCID6023783205-768-24-(Methylamino)phenolp-MethylaminophenolPhenol, 4-(methylamino)-p-(Methylamino)phenol4-methylamino-phenolMFCD00042043

データベース識別子

CAS
150-75-4
PubChem CID
5931
DTXSID
DTXSID8043783
ChEMBL
CHEMBL1741003
ChEBI
CHEBI:55416
UNII
11W1883EFB
EC Number
205-768-2
Nikkaji
J53.762D

物性

構造計算による物性補完中

XLogP
1.9
極性表面積
32.3 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
1
重原子数
9
形式電荷
0
複雑度
77

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Amino Phenols
Cosmetics · 2 件

Cosmetic ingredients (p-Methylaminophenol) -> CIR (Cosmetic Ingredient Review)

Hair dyeing

LogP · 2 件

log Kow = 0.79

0.974

Color/FormColorless needles
Solubility · 3 件

Soluble in alcohol, ether

Slightly soluble in ethanol; insoluble in diethyl ether

Solubility in water, g/100ml at 25 °C: 1.17

Boiling Point209-211 °C at 1.6 kPa
DecompositionThe substance decomposes on burning producing toxic fumes including nitrogen oxides.
Melting Point · 2 件

87 °C

87 °C

Vapor Pressure · 2 件

0.05 [mmHg]

3.07X10-3 mm Hg at 25 °C

Physical Description · 2 件

Colorless solid; [ICSC]

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 · 6 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P273, P280, P301+P317, P304+P340, P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory InformationChemical: Phenol, 4-(methylamino)-
Other Safety InformationIMAP assessments - p-Methylaminophenol and its sulfate: Human health tier II assessment
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
Fire PotentialCombustible.
Hazards Summary · 2 件

A mutagen; [RTECS] A skin and eye irritant; May cause skin sensitization; May have adverse effects on blood cells; [ICSC] Emergency treatment: Methemoglobinemia; A skin and eye irritant; May cause allergic dermatitis; [HSDB]

The major hazards encountered in the use and handling of N-methyl-4-aminophenol stem from its toxicologic properties. Exposure to this colorless crystalline substance may occur through dermal contact or inhalation at sites where it is commercially produced or used. Exposure to N-methyl-4-aminophenol may cause eye and skin irritation, including a persistent allergic dermatitis. In case of contact, immediately flush skin or eyes with running water for at least 15 minutes. Contaminated clothing and shoes should be removed and isolated at the site. When engaged in emergency activities involving N-methyl-4-aminophenol, wear a self-contained breathing apparatus and chemical protective clothing specifically recommended by the shipper or producer. N-methyl-4-aminophenol does not ignite easily, however, it may burn producing irritating or poisonous gases. Also, containers of the substance may explode in the heat of a fire. For small fires involving N-methyl-4-aminophenol, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Dike runoff from fire control water because it may give off poisonous gases and cause pollution. N-methyl-4-aminophenol may be shipped via air, rail, road, and water, in containers bearing the label, "Keep away from food." Prior to implementing permanent land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance.

化学と産業

薬理情報

Metabolism/MetabolitesYields p-methylaminophenyl-beta-d-glucuronide in rabbit /From table/

用途と製造

Uses · 6 件

CIR ingredient: p-Methylaminophenol

Used as a photographic developer, corrosion inhibitor for steel in acid chloride solutions, and developer for hair dyes; [HSDB]

Photographic Processing [Category: Other]

Organic synthesis, photographic developer

Photographic developer; corrosion inhibitor for steel in acid chloride solutions; developer for hair dyes

Reducing agent used in development of silver sensitized films and papers. /N-methyl-p-aminophenol sulfate/

U.S. Production · 2 件

(1977) Probably more than 4.54x10+5 g-sulfate

(1979) Probably more than 4.54x10+5 g-sulfate

Methods of Manufacturing · 4 件

Industrial synthesis involves the decarboxylation of N-(4-hydroxyphenyl)glycine at elevated temperature in such solvents as chlorobenzene- cyclohexanone. It also can be prepared by the methylation of 4-aminophenol or from methylamine by heating with 4-chlorophenol and copper sulfate at 135 °C in aqueous solution or with hydroquinone at 200-250 °C in alcoholic solution.

Decarboxylation of N-(4-hydroxyphenyl)glycine in an aliphatic ketone solvent; heating of hydroquinone with an alcoholic solution of methylamine; methylation of 4-aminophenol.

... Methylation of p-aminophenol hydrochloride.

Heating of 4-chlorophenol with methylamine solution in presence of copper sulfate /N-Methyl-p-aminophenol sulfate/

Use ClassificationCosmetics -> Hair dyeing
応用分野 · 1 件

使用4-Hydroxy-N-methylaniline is a useful synthetic intermediate. It is used to synthesize arylidene amino azolones with anticancer activity. It is also used to prepare N-(4-hydroxyphenyl)retinamide analogs with antitumor and apoptosis-inducing activities.

関連反応

25 件
反応記録を作成
HRID 63659 の反応式
HRID 63659反応物としてuspto-grants-2016_09
HRID 112758 の反応式
HRID 112758反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 140924 の反応式
HRID 140924反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 157880 の反応式
HRID 157880反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 159120 の反応式
HRID 159120反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 162272 の反応式
HRID 162272反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 208192 の反応式
HRID 208192反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 260345 の反応式
HRID 260345反応物としてuspto-grants-1996_06
1 / 4 ページ

化合物ノート

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COLOURLESS CRYSTALS.

物理化学的性質

融点
87 °C · 87 °C
沸点
262.7 · 262.7±23.0 °C(Predicted)
比重(密度)
1.147 · 1.147±0.06 g/cm3(Predicted)
酸解離定数(Pka)
11.31 · 11.31±0.26(Predicted)
Henry's Law Constant
2.2 · 2.2×104 mol/(m3Pa) at 25℃, HSDB (2015)
化粧品成分の機能
ヘアカラーリング
InChI
InChI=1S/C7H9NO/c1-8-6-2-4-7(9)5-3-6/h2-5,8-9H,1H3
InChIKey
ZFIQGRISGKSVAG-UHFFFAOYSA-N
SMILES
C1(O)=CC=C(NC)C=C1
CAS データベース
150 · 150-75-4
EPAの化学物質情報
4 · 4-(Methylamino)phenol (150-75-4)
UN ClassificationUN Hazard Class: 9; UN Pack Group: III
Chemical DangersDecomposes on burning. This produces toxic fumes including nitrogen oxides.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
DOT Emergency Guidelines · 5 件

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Aminophenols/

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Aminophenols/

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Aminophenols/

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Aminophenols/

For more DOT Emergency Guidelines (Complete) data for N-Methyl-4-aminophenol (8 total), please visit the HSDB record page.

Hazard Classes and Categories · 2 件

Acute Tox. 4 (100%)

Acute toxicity - category 4

Shipment Methods and Regulations · 3 件

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Shipping Name/ Number DOT/UN/NA/IMO · 3 件

UN 2512; Aminophenols

IMO 6.1; Aminophenols

UN 2512; Aminophenols (o-,m-,p-).

安全と保護具

Fire FightingUse water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink.

Fire Fighting Procedures · 3 件

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. /4-(Methylamino)phenol hemisulfate salt/

Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary. /4-(Methylamino)phenol hemisulfate salt/

Powder, alcohol-resistant foam, water spray, carbon dioxide.

Storage ConditionsStore in cool place. Keep container tightly closed in a dry and well-ventilated place. /4-(Methylamino)phenol hemisulfate salt/
Cleanup Methods · 5 件

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation. /4-(Methylamino)phenol hemisulfate salt/

Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. /4-(Methylamino)phenol hemisulfate salt/

Methods for cleaning up: Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal. /4-(Methylamino)phenol hemisulfate salt/

Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers; if appropriate, moisten first to prevent dusting.

Disposal Methods · 2 件

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. /4-(Methylamino)phenol hemisulfate salt/

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 件

Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance.

Preventive Measures · 5 件

Handling: Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection. /4-(Methylamino)phenol hemisulfate salt/

In case of skin contact: Wash off with soap and plenty of water. Consult a physician. /4-(Methylamino)phenol hemisulfate salt/

In case of eye contact: Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. /4-(Methylamino)phenol hemisulfate salt/

Hygiene measures: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. /4-(Methylamino)phenol hemisulfate salt/

For more Preventive Measures (Complete) data for N-Methyl-4-aminophenol (7 total), please visit the HSDB record page.

Eye PreventionWear safety goggles or eye protection in combination with breathing protection.
Fire PreventionNO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
Inhalation RiskNo indication can be given whether a harmful concentration in the air will be reached.
Skin PreventionProtective gloves. Protective clothing.

毒性情報

Ecotoxicity Values · 4 件

LC50; Species: Goldfish; Concentration: 0.5 mg/L for 48 hr /Conditions of bioassay not specified in source/

LC50; Species: Oncorhynchus mykiss (Rainbow trout, weight 1.2-3.8 g, length 4.6-6.4 cm); Conditions: freshwater, flow through, 14.1-16.5 °C, pH 7.60-8.19, alkalinity 86 mg/L CaCO3, dissolved oxygen 5.6-9.4 mg/L; Concentration: 300 ug/L for 96 hr

LD50; Species: Oncorhynchus mykiss (Rainbow trout, weight 9.1-43.2 g, length 7.9-9.6 cm) oral (by gavage) 0.72 mmol/kg

LD50; Species: Oncorhynchus mykiss (Rainbow trout, weight 9.0-30.4 g, length 7.0-9.9 cm) ip 0.58 mmol/kg

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 110(SRC), determined from a structure estimation method(2), indicates that N-methyl-4-aminophenol is expected to have high mobility in soil(SRC). Volatilization of N-methyl-4-aminophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.4X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). N-Methyl-4-aminophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.1X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2009).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 110(SRC), determined from a structure estimation method(2), indicates that N-methyl-4-aminophenol 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 4.4X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.79(SRC) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Aromatic amines in the water column may be susceptible to significant photooxidation via hydroxyl and peroxy radicals; half-lives for these photooxidations may be on the order of 19-30 sunlight hours(7). Biodegradation data for N-methyl-4-aminophenol were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-methyl-4-aminophenol, which has an estimated vapor pressure of 3.07X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N-methyl-4-aminophenol 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 6.9 hours(SRC), calculated from its rate constant of 5.6X10-11 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). N-Methyl-4-aminophenol contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC); typical half-lives for hydroxyl radical and peroxy radical reactions are on the order of 19-30 sunlight hours(5).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Exposure RoutesThe substance can be absorbed into the body by ingestion.
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Ecotoxicity Excerpts · 1 件

/AQUATIC SPECIES/ The cytotoxicity of 12 chemicals to rainbow trout (Salmo gairdneri) cells (RTG-2) was determined in culture. The indicator of cytotoxicity was the inability of cells to attach to a growth surface after chemical exposure. From most toxic to least toxic, these chemicals were pentachlorophenol, p-methylaminophenol, 2,4-dichlorophenol, p-chlorophenol, p-cyanophenol, p-nitrophenol, benzene, p-methylphenol, aniline, phenol, p-methoxyphenol, and 1,2,4-trichlorobenzene. Cytotoxicity was significantly correlated to systemic toxicity in rainbow trout.

Signs and Symptoms · 2 件

Redness.

Redness. Pain.

ICSC Environmental DataThe substance is very toxic to aquatic organisms.
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of N-methyl-4-aminophenol can be estimated to be 110(SRC). According to a classification scheme(2), this estimated Koc value suggests that N-methyl-4-aminophenol is expected to have high mobility in soil.

Human Toxicity Excerpts · 3 件

/SIGNS AND SYMPTOMS/ Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood, resulting in lesions of blood cells.

/SIGNS AND SYMPTOMS/ N-Methyl-p-aminophenol causes a persistence of allergic dermatitis.

/SURVEILLANCE/ During the period January 1980-June 1981, an investigation was made of skin diseases among employees of a film laboratory. The investigation was carried out in 5 stages. (I) Questionnaire (II) Clinical examination and interview with all employees who stated that they had had skin disease at some time (III) Patch testing at the laboratory of all cases of suspected occupational dermatoses, and control tests in hospital of 200 non-exposed eczema patients (IV) Investigation of protective gloves by patch testing and in a chemical bath (V) Allergy test on guinea pigs (GPMT) of one agent (PBA-1). The firm had 114 employees and the questionnaire was answered by 103. Altogether 43 persons at some time had been exposed to chemicals in their work, and 21 of them had had occupational dermatoses. In 12 cases, contact allergy was found to one or more of the photographic chemicals CD-2, CD-3, Metol and PBA-1. GPMT with PBA-1 showed it to be a potent sensitizer. The color developing agents may also give rise to lichenoid reactions and 2 such cases were seen in this investigation. Other causes of occupational dermatoses are indicated, as well as the occurrence of non-occupational skin diseases.

Artificial Pollution SourcesN-Methyl-4-aminophenol's production and use as in organic synthesis and as a photodeveloper(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

AEROBIC: The BOD of a five-day BOD test was 0.2 with a BOD/COD ratio of 0.17 for 4-methylaminophenol sulfate, a compound similar to 4-methylaminophenol. This salt proved to be strongly inhibitory to an unacclimated system at concentrations as low as 50 mg/L; acclimation of the biomass to the compound eliminated any inhibitory effects. The data indicated biodegradation of 4-methylaminophenol sulfate proceeded at a moderate rate(1). /4-Methylaminophenol sulfate/

安全データ

ridadr
3077
hazard_class
9
packing_group
III
有毒物質データの
150-75-4 (Hazardous Substances Data)

上流・下流製品情報

下流製品

6-キノリンカルボン酸, 4-クロロ-7-メトキシ-, メチルエステル1,3-Dihydro-5-hydroxy-1,3-dimethyl-2H-indol-2-one

補足説明

定義ChEBI: 4-methylaminophenol is the phenol that is the N-methyl derivative of 4-aminophenol. It has a role as an allergen. It is functionally related to a 4-aminophenol.