5-Amino-2-methylphenol
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5-Amino-2-methylphenol
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CAS No:
2835-95-2
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Formula:
C7H9NO
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Chemical Name:
5-Amino-2-methylphenol
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Synonyms:
Phenol,5-amino-2-methyl-;o-Cresol,5-amino-;5-Amino-2-methylphenol;3-Hydroxy-4-methylaniline;3-Amino-6-methylphenol;4-Amino-2-hydroxytoluene;2-Methyl-5-aminophenol;3-Hydroxy-p-toluidine;5-Amino-o-cresol;1-Methyl-2-hydroxy-4-aminobenzene;2-Hydroxy-4-aminotoluene;6-Methyl-3-aminophenol;5-Amino-2-cresol
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CAS No:
Description
Beige crystals
3-amino-6-methylphenol is a brown powder. (NTP, 1992)
3-amino-6-methylphenol is a brown powder. (NTP, 1992)
5-Amino-2-methylphenol Basic Attributes
123.15
123.15
220-618-6
UBB8XEB10B
2512
DTXSID9024489
Plates from water
2922299090
Characteristics
46.2
1.3
Pale brown Powder
1.2±0.1 g/cm3
161 °C
268.6°C at 760 mmHg
116.3±21.8 °C
1.616
In water, 2,427 mg/L @ 25 deg C /Estimated/
Store in a cool, dry place. Store in a tightly closed container.
2.6X10-4 mm Hg @ 25 deg C /Estimated/
Oral-rat LD50: 3600 mg/kg
Flammable; burning produces toxic nitrogen oxide fumes
Henry's Law constant: 2.19X10-10 atm-cu m/mole @ 25 °C /Estimated/
Hydroxyl radical reaction rate constant: 2.00X10-10 cu cm/molecule-sec @ 25 °C /Estimated/
Insoluble in water.
Phenols and Cresols
3-AMINO-6-METHYLPHENOL reacts with strong oxidizing agents. (NTP, 1992)
Safety Information
III
6.1
NONH for all modes of transport
1
36/37/38-20/21/22
26-36-37/39
SJ6090000
Xi,Xn
Warehouse ventilated, low temperature and dry
Stable
P261-P305 + P351 + P338
H315-H319-H335
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.
Incompatible with strong oxidizing agents.
Flash point data are not available for this chemical, but it is probably combustible. (NTP, 1992)
|Warning|H315 (83.26%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 233 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, and P501
Fires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: 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. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
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)|Safety glasses, adequate ventilation.
Combustible
Drug Information
/Percutaneous absorption of 5-amino-o-cresol in a hair dye was studied under the conditions of usage. Radiolabeled 5-amino-o-cresol was added to a commercial dye containing 0.69% non-radioactive 5-amino-o-cresol; the mixture was applied to dry hair of three volunteers, worked in to the hair mass for 5-8 min, and rinsed off after an additional 20 min; the urine samples were collected for as long as radioactivity was detected, approximately 144 hr. The total urinary excretion of radioactivity was 0.2% with 50% of the radioactivity excreted in 24 hr./|/A/ ...series of experiments /compared/ the skin permeability of a number of hair dyes obtained in two different laboratories. /Both pig skin (in vitro) and rat skin (in vivo) are permeable to 5-amino-o-cresol, the latter being more permeable.|A 94% recovery of radioactivity (corrected for incomplete excretion from internal application) in human urine after oral administration of radioactive 4-amino-2-hydroxytoluene /was reported/.
/The total urinary excretion of radioactivity was 0.2% with 50% of the radioactivity excreted in 24 hr./
SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes. ACUTE/CHRONIC HAZARDS: This compound is a local irritant. When heated to decomposition it emits toxic fumes. (NTP, 1992)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . 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 normal saline 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 patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
/HUMAN EXPOSURE STUDIES/ Ten volunteers (males and females) each had their hair dyed 13 times at intervals of 3-6 wk. Each volunteer used a single commercial preparation throughout the study. /Five of the preparations contained 2-hydroxy-4-aminotoluene./ ...Lymphocytes of the hair-dyed volunteers and of ten controls matched for age and sex were scored for chromosomal aberrations. The incidence of aberrations did not differ significantly between the controls and the hair-dyed volunteers at any of the nine sampling times.|/HUMAN EXPOSURE STUDIES/ A modified Draize repeat insult patch test (RIPT) procedure was used to evaluate the irritation and sensitization potential of two aqueous solutions, each containing 2% of 4-amino-2-hydroxytoluene as supplied. An initial challenge (100% applied for 1 hr) was made to aid in the interpretation of the challenge following the rest period. For the induction exposure, semiocclusive patches containing 0.3 ml of the solution were applied to the same site on the upper arm of each subject on Mondays, Wednesdays, and Fridays for 3 consecutive weeks. The first solution for induction was a 3.0% v/v aqueous solution and the second was a 10% w/v aqueous solution. Patches were left in place for 24 hr and scored 48 or 72 hr after application. The challenge was made after a 2 wk nontreatment period. A patch containing 100% of the test solution was applied to a previously untreated site for 1 hr. Sites were scored 48 and 96 hr after application. Another challenge patch was also applied simultaneously to the induction site using the induction concentration. Twenty-three of the 27 subjects completed testing with the first solution. The initial challenge produced 21 negative and 5 slight reactions; the induction period elicited reactions from one subject only, who had a score of 4 (maximum=7) at the sixth induction patch and was subsequently patched on a different site. The challenge solution produced 20 negative, 2 slight (score of 1), and 1 significant (score of 3) reactions. The significant reaction was seen in the same subject who had reacted during the induction phase. No reactions were produced by the challenge patch applied to the induction site. A rechallenge was conducted with 11 of the subjects at a naive site on the upper back using a concentration of 25% of the test solution; 10 negative (including the 1 patient with the significant reaction at challenge) and 1 slight reactions were observed. /It was/ concluded that the test solution had produced one case of significant dermatitis, although it was not reproduced at rechallenge. Thirty-one subjects completed testing with the second solution. The initial challenge failed to produce a reaction in any of the subjects. During the induction period, very slight reactions (scores of 1 or less) were observed in 4 subjects and strong reactions (scores of up to 3 and 5) in two subjects. Challenge at a previously untreated site produced two slight reactions and one strong reaction (scores of 5 at both 48 and 96 hr), the latter being a delayed challenge due to residual reactions from the induction phase. The challenge patches applied to the induction site produced three slight and two strong reactions; however, only one of these five subjects had a reaction when challenged at a previously untreated site. A rechallenge of two subjects produced one negative and one significant response, the latter being from one of those with a strong reaction to challenge at the induction site. In the investigator's opinion, two cases of significant dermatitis had been observed, one each during challenge and rechallenge; therefore, these were cases of induced contact allergic eczema.
5-amino-o-cresol
5-Amino-2-methylphenol Use and Manufacturing
In a 4800L autoclave, 1700 kg of 50percent sodium hydroxide solution was added, 1850 kg of an ethanol solution containing 1000 kg of 3-chloro-4-methylaniline was added, 50 kg of cuprous chloride and 15 kg of copper powder were added, and the reaction vessel was sealed and replaced with nitrogen 5 times. Warm up to 175°C, incubate for 4 hours, sample and analyze. After passing the test, cool down. Ethanol is recovered under reduced pressure, filtered into an 8000L tank, neutralized by adding 1450 kg of industrial hydrochloric acid to weak acidity, extracted with 2000 L of ethyl acetate and extracted three times, and ethyl acetate is recovered under reduced pressure. , get crude. The crude product was added with 1000 kg of ethanol, heated to 60° C., and 50 kg of activated carbon was added. After stirring for 1 hour, the mixture was filtered and cooled to 5° C. to obtain 707 kg of a product with a yield of 85.36percent and a purity of 99.8percent.
Used as dyes and pharmaceutical intermediates
Phenol, 5-amino-2-methyl-: ACTIVE
Cosmetics -> Hair dyeing
Computed Properties
Molecular Weight:123.15
XLogP3:1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:123.068413911
Monoisotopic Mass:123.068413911
Topological Polar Surface Area:46.2
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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