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N-Methyl-p-aminophenol

N-Methyl-p-aminophenol structure

N-Methyl-p-aminophenol 

structure
  • CAS No:

    150-75-4

  • Formula:

    C7H9NO

  • Chemical Name:

    N-Methyl-p-aminophenol

  • Synonyms:

    Phenol,4-(methylamino)-;Phenol,p-(methylamino)-;4-(Methylamino)phenol;p-(Methylamino)phenol;N-Methyl-p-aminophenol;N-Methyl-4-aminophenol;p-Hydroxy-N-methylaniline;N-Methyl-p-hydroxyaniline;N-Methyl-4-hydroxyaniline;4-Hydroxy-N-methylaniline;NSC 7311

  • Categories:

    Cosmetic Ingredient  >  Hair Dyeing

Description

ChEBI: The phenol that is the N-methyl derivative of 4-aminophenol.


COLOURLESS CRYSTALS.


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

N-Methyl-p-aminophenol Basic Attributes

123.15246

123.15

205-768-2

11W1883EFB

1146

7311

3077

DTXSID8043783

Colorless needles

2922299090

Characteristics

32.26000

0.85

COLOURLESS CRYSTALS.

1.147±0.06 g/cm3(Predicted)

87 °C

262.7±23.0 °C(Predicted)

148.6±13.3 °C

1.621

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

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. /4-(Methylamino)phenol hemisulfate salt/

3.07X10-3 mm Hg at 25 deg C

Finely dispersed particles form explosive mixtures in air.

Henry's Law constant = 4.35X10-10 atm-cu m/mole at 25 °C (est)

pKa = 10.51 (est)

Hydroxyl radical reaction rate constant = 5.60X10-11 cu cm/molec-sec at 25 °C (est)

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

III

9

3077

SL8225000

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.

Materials to avoid: Acids, acid chlorides, acid anhydrides, oxidizing agents /4-(Methylamino)phenol hemisulfate salt/

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P280, P301+P312, P302+P352, P314, P321, P330, P333+P313, P363, and P501

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). /4-(Methylamino)phenol hemisulfate salt/|Hand protection: The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Handle with gloves. /4-(Methylamino)phenol hemisulfate salt/|Eye protection: Face shield and safety glasses. /4-(Methylamino)phenol hemisulfate salt/|Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place. /4-(Methylamino)phenol hemisulfate salt/|Protective gloves. Protective clothing. Safety goggles, or eye protection in combination with breathing protection.

Combustible.

Finely dispersed particles form explosive mixtures in air.

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.

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.

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.

/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.

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.

May be harmful if inhaled. May cause respiratory tract irritation. Skin May be harmful if absorbed through skin. May cause skin irritation. Eyes May cause eye irritation. /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. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance.

No indication can be given whether a harmful concentration in the air will be reached.

The substance is irritating to the eyes and skin.

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in lesions of blood cells.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST! AVOID ALL CONTACT!

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

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.

Toxicity

/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.

N-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).

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).

The rate constant for the vapor-phase reaction of N-methyl-4-aminophenol with photochemically-produced hydroxyl radicals has been estimated as 5.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). N-Methyl-4-aminophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). N-Methyl-4-aminophenol contains chromophores that absorb at wavelengths >290 nm(3) 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(4).|If released to aquatic systems, N-methyl-4-aminophenol will be very soluble in either acidic or alkaline waters since it is both a weak acid and weak base(1).

An estimated BCF of 3.2 was calculated in fish for N-methyl-4-aminophenol(SRC), using an estimated log Kow of 0.79(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).

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.

The Henry's Law constant for N-methyl-4-aminophenol is estimated as 4.4X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that N-methyl-4-aminophenol is expected to be essentially nonvolatile from water(2) and moist soil surfaces(SRC). 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(SRC), determined from a fragment constant method(3).

Occupational exposure to N-methyl-4-aminophenol may occur through inhalation and dermal contact with this compound at workplaces where N-methyl-4-aminophenol is produced or used. (SRC)

Drug Information

Experimental therapy: The efficacy of cobalt edetate (Kelocyanor) was compared with 4-methylaminophenol in experimental cyanide poisoning. 4-Methylaminophenol gave the best survival results.

Yields p-methylaminophenyl-beta-d-glucuronide in rabbit /From table/

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.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. DIRECT PHYSICIAN ORDER ONLY ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Phenols and related compounds/|For more Antidote and Emergency Treatment (Complete) data for N-Methyl-4-aminophenol (6 total), please visit the HSDB record page.

/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.

4-(methylamino)phenol

The substance can be absorbed into the body by ingestion.

Redness.


Redness. Pain.

N-Methyl-p-aminophenol Use and Manufacturing

Methods of Manufacturing

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/

Production

(1977) Probably more than 4.54x10+5 g-sulfate|(1979) Probably more than 4.54x10+5 g-sulfate

NEW DETECTION REAGENT FOR IDENTIFICATION & SEMIQUANTITATIVE DETERMINATION OF AMINOPHENOLS IN POLLUTED WATER USING THIN LAYER CHROMATOGRAPHY IS PRESENTED. /AMINOPHENOLS/|DETERMINATION OF AMINOPHENOL ISOMERS BY HIGH-SPEED LIQUID CHROMATOGRAPHY. /AMINOPHENOLS/|SEMIQUANTITATIVE DETERMINATION OF M-AMINOPHENOL BY THIN-LAYER CHROMATOGRAPHY. /M-AMINOPHENOL/|M-AMINOPHENOL IS REACTED WITH KIO4 TO GIVE INTENSE RED COLOR, WHICH IS MEASURED, COLORIMETRICALLY, @ 500 NM./M-AMINOPHENOL/|THIN LAYER CHROMATOGRAPHIC DETERMINATION OF AMINOPHENOLS. /AMINOPHENOLS/

Cosmetics -> Hair dyeing

Computed Properties

Molecular Weight:123.15
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:123.068413911
Monoisotopic Mass:123.068413911
Topological Polar Surface Area:32.3
Heavy Atom Count:9
Complexity:77
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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