P-Anisidine

HCID 7732CAS 104-94-9

Basic information

Standard SMILES
COc1ccc(N)cc1
InChIKey
BHAAPTBBJKJZER-UHFFFAOYSA-N
Molecular formula
C7H9NO
Average molar mass
123.15 g/mol
Monoisotopic mass
123.06841391

Names & identifiers

Preferred name
P-Anisidine
IUPAC
4-methoxyaniline
English name
p-Anisidine
Molecular formula
C7H9NO
Molecular weight
123.15

Names & synonyms

p-Anisidine4-Methoxyaniline104-94-94-Methoxybenzenamine4-Anisidine4-Aminoanisolep-MethoxyanilineBenzenamine, 4-methoxy-p-Aminoanisolepara-Anisidine4-Methoxybenzeneamine1-Amino-4-methoxybenzene
Show more names
PARA ANISIDINE4-Methoxy-phenylamine4-[4-(4-Aminophenyl)phenyl]anilinep-Anisylamine4-METHOXY-BENZENAMINE
p-MethoxyphenylamineAnisole, p-amino-p-DianisidineAniline, p-methoxy-4-Methoxy-1-aminobenzeneAniline, 4-methoxy-DTXSID7024532NSC 7921

Database identifiers

CAS
104-94-9、29191-52-4
PubChem CID
7732
DTXSID
DTXSID7024532
ChEMBL
CHEMBL295652
ChEBI
CHEBI:82388
UNII
575917SNR4
EC Number
203-254-2、249-496-2
Nikkaji
J4.027D

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
35.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
9

Experimental & physicochemical properties

LogP · 3 items

log Kow = 0.95

0.95

0.95

OdorAmine-like odor
Density · 6 items

1.071 at 135 °F (NTP, 1992) - Denser than water; will sink

1.071 at 57 °C/4 °C

1.07 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

1.071 @ 57°C

1.07

Color/Form · 4 items

White solid

Fused crystalline mass

Crystals, plates from aqueous solution

Yellow to brown, crystalline solid

Solubility · 6 items

less than 1 mg/mL at 68 °F (NTP, 1992)

Soluble in acetone, benzene; very soluble in ether, ethanol

In water, 2.10X10+4 mg/L at 20 °C

21 mg/mL at 20 °C

Solubility in water, g/100ml at 20 °C: 2.2 (moderate)

Moderate

Flash Point · 4 items

41 °F (NTP, 1992)

5 °C

122 °C (251.6 °F) (closed cup)

122 °C

Physicochemical properties

Melting point
56 · 56-59 °C(lit.)
Boiling point
240 · 240-243 °C(lit.)
Density
1.06 · 1.06
bulk density
700 kg/m3 · 700kg/m3
vapor density
4.28 · 4.28
vapor pressure
0.02 hPa · 0.02 hPa (20 °C)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral];H310: Fatal in contact with skin [Danger Acute toxicity, dermal];H330: Fatal if inhaled [Danger Acute toxicity, inhalation];H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

Hazard information

Regulatory Information · 4 items

Chemical: Benzenamine, 4-methoxy-

Status: Active Update: 18-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17660;Status: Active Update: 03-07-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19981

4-Anisidine: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - p-Anisidine and its hydrochloride: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 items

This chemical is flammable. (NTP, 1992)

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

Fire PotentialCombustible.
Health Hazards · 1 item

Excerpt from NIOSH Pocket Guide for p-Anisidine:;Exposure Routes: Inhalation, skin absorption, ingestion, skin and/or eye contact;Symptoms: Headache, dizziness; cyanosis; red blood cell Heinz bodies;Target Organs: Blood, kidneys, liver, cardiovascular system, central nervous system (NIOSH, 2024)

Safety & protection

Fire Fighting · 2 items

Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use water spray, foam, powder, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

First Aid · 2 items

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. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure 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)

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Soap wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageSeparated from strong oxidants, strong bases, acids, chloroformates and food and feedstuffs. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.
Firefighting HazardsProvision to contain effluent from fire extinguishing.
Exposure Control and Personal ProtectionBiological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]

Toxicology

Target OrgansBlood, kidneys, liver, cardiovascular system, central nervous system
Health EffectsP-Anisidine is the most toxic of the three isomers of anisidine and causes blood damage upon oral ingestion, inhalation or skin contact. If heated strongly, it may release very toxic fumes of nitrogen oxides. (Wikipedia)
Ecotoxicity Values · 5 items

EC50; Species: Daphnia magna (water flea); Conditions: freshwater, static; Concentration: 180 ug/L for 48 hr; Effect: intoxication, immobilization /formulated product/

EC50; Species: Daphnia magna (water flea, age 6-24 hr); Conditions: freshwater, static, 20 °C, pH > or =7.0; Concentration: 52000 ug/L (25000-109000 ug/L) for 24 hr; Effect: intoxication, immobilization /formulated product/

EC50; Species: Daphnia magna (water flea, age 6-24 hr); Conditions: freshwater, static, 20 °C, pH > or =7.0; Concentration: 1900 ug/L (1300-2800 ug/L) for 48 hr; Effect: intoxication, immobilization /formulated product/

LC50; Species: Daphnia magna (water flea); Conditions: freshwater, static; Concentration: 330 ug/L for 48 hr /formulated product/

For more Ecotoxicity Values (Complete) data for p-Anisidine (6 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 45(SRC), determined from a log Kow of 0.95(2) and a regression-derived equation(3), indicates that p-anisidine is expected to have very high mobility in soil(SRC). The pKa of p-anisidine is 5.36(4), indicating that it will partially exist in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of the neutral form of p-anisidine from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 6.60X10-8 atm-cu m/mole(6). Volatilization from moist soil is not expected for the cationic form of p-anisidine because cations do not volatilize(SRC). p-Anisidine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.00X10-2 mm Hg at 20 °C(7). p-Anisidine readily biodegrades in aerobic activated sludge as indicated by screening tests with 65.3% degradation after 2 weeks(8) and 100% after 4 weeks using 60 mg/L test concn(9). In a mixed-culture of soil microorganisms, p-anisidine degraded completely after 64 days(10).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 45(SRC), determined from a log Kow of 0.95(2) and a regression-derived equation(3), indicates that p-anisidine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected for the neutral species(4) based upon a Henry's Law constant of 6.60X10-8 atm-cu m/mole(5). According to a classification scheme(6), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). p-Anisidine degraded the 82% in river water and 2% in seawater after 3 days during Cultivation Method screening tests(7-8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-anisidine, which has a vapor pressure of 3.00X10-2 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase p-anisidine 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 4.1 hours(SRC), calculated from its rate constant of 9.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). p-Anisidine absorbs light at 300 nm(4) and therefore it may undergo direct photolysis by sunlight(SRC).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect;ACGIH Carcinogen - Not Classifiable.
Exposure Routes · 3 items

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

oral ingestion, inhalation or skin contact

Regulatory information

Regulatory Information · 4 items

Chemical: Benzenamine, 4-methoxy-

Status: Active Update: 18-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17660;Status: Active Update: 03-07-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19981

4-Anisidine: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, & reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health & environmental impact & energy requirements. Anisidine is produced, as an intermediate or a final product, by process units covered under this subpart. /Anisidine/

Safety data

F
8
OEB
C
OEL
TWA: 0.5 mg/m3 [skin]
wgk
2
IDLA
50 mg/m3
tsca
TSCA listed

Chemistry & industry

Pharmacology

Metabolism/MetabolitesP-METHOXYANILINE YIELDS P-AMINOPHENOL IN RABBIT ... & P-METHOXY-N-METHYLANILINE IN RABBIT. /FROM TABLE/
Absorption, Distribution and ExcretionThe substance can be absorbed into the body by inhalation of its vapor, through the skin and by ingestion.
Cellular LocationsCytoplasm;Extracellular

Uses & manufacturing

Uses · 3 items

Both ortho and para isomers are used to produce azo dyes, while only the ortho form is used to produce synthetic guaiacol; [ACGIH]

Azo dyestuffs, intermediate

CHEM INTERMED FOR VAT RED 29 (CI 71140), DISPERSE ORANGE 15 (CI 10350) & AZOIC COUPLING COMPONENT 13 (CI 37595)

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3301]
Methods of Manufacturing · 5 items

Reduction of p-nitroanisole; methylation of p-nitrophenol followed by reduction; or the action of methanol and caustic on p-nitrochlorobenzene with subsequent reduction

p-Chloronitrobenzene and methanol ether formation and nitro reduction.

Reduction of p-nitroanisole with iron filings and hydrochloric acid or methylation of p-aminophenol.

Mn3+ - or Ce4+ -mediated oxidation of nitrobenzene.

For its industrial production 4-nitroanisole is reduced either with sodium sulfide or with hydrogen in the presence of precious-metal catalysts or Raney nickel.

General Manufacturing InformationBenzenamine, 4-methoxy-: ACTIVE

Applications

Usesp-Anisidine is used mostly for producing dyes, and some smaller quantities are employed in making pharmaceuticals and liquid crystals.

General DescriptionP-anisidine appears as brown crystals or dark brown solid. Characteristic amine odor. (NTP, 1992)

Preparation methods · 1 item

Preparationp-Anisidine is an important intermediate for synthesis of dye, medicine and perfume. Traditional preparation of p-Anisidine uses iron powder or sodium sulfide as reductant, which produces a large amount of waste and results in serious environment pollution problem. Liquid phase catalytic hydrogenation is not only an environmentally benign technique but also of high yield.Synthesis of p-Anisidine by Hydrogenation with Raney-RuNiC as Catalyst

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
Additional notes · 1 item

DefinitionChEBI: P-anisidine is a substituted aniline that is aniline in which the hydrogen para to the amino group has been replaced by a methoxy group. It is used as a reagent for the detection of oxidation products such as aldehydes and ketones in fats and oils. It has a role as a reagent and a genotoxin. It is a member of methoxybenzenes, a substituted aniline and a primary amino compound.

Related reactions

2,038 records

Linked notes

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