aniline
benzene, amino
 
Notes:
Aniline is a weak base. Aromatic amines such as aniline are, in general, much weaker bases than aliphatic amines. Aniline reacts with strong acids to form anilinium (or phenylammonium) ion (C6H5-NH3+). The sulfate forms beautiful white plates. Although aniline is weakly basic, it precipitates zinc, aluminium, and ferric salts, and, on warming, expels ammonia from its salts. The weak basicity is due to a negative inductive effect as the lone pair on the nitrogen is partially delocalised into the pi system of the benzene ring.; Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben , who named it crystalline. In 1834, Friedrich Runge (Pogg. Ann., 1834, 31, p. 65; 32, p. 331) isolated from coal tar a substance that produced a beautiful blue colour on treatment with chloride of lime, which he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that, by treating indigo with caustic potash, it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit n?la, dark-blue, and n?l?, the indigo plant. About the same time N. N. Zinin found that, on reducing nitrobenzene, a base was formed, which he named benzidam. August Wilhelm von Hofmann investigated these variously-prepared substances, and proved them to be identical (1855), and thenceforth they took their place as one body, under the name aniline or phenylamine.; Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals. Its main application is in the manufacture of polyurethane. Like most volatile amines, it possesses the somewhat unpleasant odour of rotten fish and also has a burning aromatic taste; it is a highly-acrid poison. It ignites readily, burning with a smoky flame.; Like phenols, aniline derivatives are highly susceptible to electrophilic substitution reactions. For example, reaction of aniline with sulfuric acid at 180 �C produces sulfanilic acid, NH2C6H4SO3H, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs that were widely used as antibacterials in the early 20th century.; The great commercial value of aniline was due to the readiness with which it yields, directly or indirectly, dyestuffs. The discovery of mauve in 1856 by William Henry Perkin was the first of a series of an enormous range of dyestuffs, such as fuchsine, safranine and induline. In addition to its use as a precursor to dyestuffs, it is a starting-product for the manufacture of many drugs, such as paracetamol (acetaminophen, Tylenol).; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue.
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CAS Number: 62-53-3Picture of molecule3D/inchi
Other(deleted CASRN): 146997-94-6
ECHA EINECS - REACH Pre-Reg: 200-539-3
FDA UNII: SIR7XX2F1K
Nikkaji Web: J2.349C
Beilstein Number: 605631
MDL: MFCD00007629
XlogP3: 0.90 (est)
Molecular Weight: 93.12879000
Formula: C6 H7 N
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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FDA Mainterm (IAUFC):62-53-3 ; ANILINE
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Physical Properties:
Appearance: yellowish to brownish clear oily liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 1.02200 @  25.00 °C.
Melting Point: -7.00 to  -6.00 °C. @ 760.00 mm Hg
Boiling Point: 184.00 to  185.00 °C. @ 760.00 mm Hg
Boiling Point: 102.00 to  103.00 °C. @ 50.00 mm Hg
Vapor Pressure: 0.733000 mmHg @ 25.00 °C. (est)
Vapor Density: 3.3 ( Air = 1 )
Flash Point: 158.00 °F. TCC ( 70.00 °C. )
logP (o/w): 0.900
Soluble in:
 water, 2.082e+004 mg/L @ 25 °C (est)
 water, 3.60E+04 mg/L @ 25 °C (exp)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BASF
Aniline
Indis NV
For experimental / research use only.
Aniline
Santa Cruz Biotechnology
For experimental / research use only.
Aniline
Sigma-Aldrich
For experimental / research use only.
Aniline ACS reagent, ≥99.5%
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-bird - wild LD50  562 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

oral-cat LDLo  100 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1301, 1935.

oral-child TDLo  3125 mg/kg
LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Toxicology, Clinical Toxicology. Vol. 26, Pg. 357, 1988.

oral-dog LD50  195 mg/kg
National Technical Information Service. Vol. PB214-270

intravenous-dog LDLo  200 mg/kg
National Technical Information Service. Vol. PB214-270

intraperitoneal-guinea pig LD50  100 mg/kg
Office of Toxic Substances Report. Vol. OTS

oral-guinea pig LD50  400 mg/kg
Office of Toxic Substances Report. Vol. OTS

oral-mammal (species unspecified) LD50  500 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.

unreported-man LDLo  150 mg/kg
"Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.

unreported-man LDLo  350 mg/kg
Journal of Industrial Hygiene. Vol. 13, Pg. 87, 1931.

intraperitoneal-mouse LD50  492 mg/kg
Izvestiya Sibirskogo Otdeleniya Akademii Nauk SSSR, Seriya Biologomeditsinskikh Nauk. Vol. 3, Pg. 91, 1965.

oral-mouse LD50  464 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 13(5), Pg. 29, 1969.

oral-quail LD50  750 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

intravenous-rabbit LD50  64 mg/kg
National Technical Information Service. Vol. PB214-270

oral-rabbit LDLo  500 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1301, 1935.

intraperitoneal-rat LD50  420 mg/kg
Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 15, Pg. 447, 1957.

oral-rat LD50  250 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 260, 1947.

Dermal Toxicity:
skin-cat LD50 254 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 13(5), Pg. 29, 1969.

subcutaneous-cat LDLo 100 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1301, 1935.

skin-dog LDLo 1540 mg/kg
National Technical Information Service. Vol. PB214-270

skin-guinea pig LD50 1290 mg/kg
Toxicology and Applied Pharmacology. Vol. 7, Pg. 559, 1965.

subcutaneous-mouse LD50 200 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 107, 1958.

skin-rabbit LD50 820 uL/kg
Toxicology and Applied Pharmacology. Vol. 7, Pg. 559, 1965.

subcutaneous-rabbit LDLo 1000 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Medicina del Lavoro. Industrial Medicine. Vol. 28, Pg. 112, 1937.

skin-rat LD50 1400 mg/kg
Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 15, Pg. 447, 1957.

Inhalation Toxicity:
inhalation-cat LCLo 180 ppm/8H
U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 4, 1941.

inhalation-mammal (species unspecified) LC50 2500 mg/m3
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.

inhalation-mouse LC50 175 ppm/7H
National Technical Information Service. Vol. PB214-270

inhalation-rat LCLo 250 ppm/4H
Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 343, 1949.

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Safety in Use Information:
Category: pharmaceuticals / chemical synthisis
Recommendation for aniline usage levels up to:
 not for fragrance use.
 
Recommendation for aniline flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
ECHA (ESR): View
EPA-Iris: IRIS
NIOSH International Chemical Safety Cards: search
NIOSH Pocket Guide: search
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Carcinogenic Potency Database: Search
EPA GENetic TOXicology: Search
EPA Substance Registry Services (TSCA): 62-53-3
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 6115
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 aniline
Chemidplus: 0000062533
EPA/NOAA CAMEO: hazardous materials
RTECS: 62-53-3
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References:
 aniline
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 62-53-3
Pubchem (cid): 6115
Pubchem (sid): 134971372
Pherobase: View
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Indirect Additives used in Food Contact Substances:View
CHEBI: View
CHEMBL: View
UM BBD: Search
KEGG (GenomeNet): C00292
HMDB (The Human Metabolome Database): HMDB03012
FooDB: FDB003571
Export Tariff Code: 2921.41.1000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
Formulations/Preparations:
•grades: commercial; chemically pure •typical commercial grade contains 99.9% (min) aniline, 0.0002% (max) nitrobenzene & 0.1% (max) moisture •aniline oil •huile d'aniline (french) •blue oil
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 apple fruit
Search Trop  Picture
 apple pericarp
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 cabbage leaf
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 cabbage leaf
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 carrot root
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 celery plant
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 corn seed
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 garlic bulb
Search Trop  Picture
 not found in nature
 tea leaf
Search Trop  Picture
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Synonyms:
1-aminobenzene
 anilin
 anyvim
 arylamine
 benzamine
 benzenamine
 benzene, amino
 benzeneamine
 benzidam
 cyanol
 kyanol
 phenyl amine
 phenyleneamine
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