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873-74-5

Basic Information
CAS No.: 873-74-5
Name: 4-Aminobenzonitrile
Article Data: 402
Cas Database
Molecular Structure:
Molecular Structure of 873-74-5 (4-Aminobenzonitrile)
Formula: C7H6N2
Molecular Weight: 118.138
Synonyms: Aniline, p-cyano-;benzonitrile, 4-amino-;1-Amino-4-cyanobenzene;Benzonitrile, p-amino- (8CI);4-14-00-01158 (Beilstein Handbook Reference);p-Cyanoaniline;Benzonitrile, p-amino-;4-Cyanoaniline;
EINECS: 212-850-1
Density: 1.14 g/cm3
Melting Point: 83-85 °C(lit.)
Boiling Point: 286.5 °C at 760 mmHg
Flash Point: 127.1 °C
Solubility: Soluble in ethyl acetate, dichloromethane and chloroform. Insoluble in water.
Appearance: off-white or beige to orange-yellow crystalline
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36-36/37/38-20/21/22
Safety: 26-36
Transport Information: UN 2811 6.1/PG 3
PSA: 49.81000
LogP: 1.72168
Synthetic route
1321455-55-3

4-(tert-butyldimethylsilylamino)benzonitrile

873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With silica gel In ethanol; water at 20℃; for 2h;100%

2-oxo-2-phenylethyl (4-cyanophenyl)carbamate

873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2h; Sealed tube; Irradiation; Inert atmosphere;100%
619-72-7

4-nitrobenzonitrile

873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With trimethylamine-borane; palladium hydroxide - carbon In methanol for 1.5h; Heating;99%
With 1-butyl-3-methylimidazolium Tetrafluoroborate; tin(ll) chloride at 20℃; for 0.25h; sonification;99%
With 1,1,3,3-Tetramethyldisiloxane In ethanol at 20℃; for 1h; Inert atmosphere; Sonication; chemoselective reaction;99%
18523-41-6

4-azidobenzonitrile

873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With D-glucose; potassium hydroxide In water at 85℃; for 0.166667h; Reagent/catalyst; Temperature; Solvent; Green chemistry; chemoselective reaction;99%
With triethylsilane; indium(III) chloride In acetonitrile at 0℃; for 0.25h;97%
With methyltriphenylphosphonium tetrahydroborate In dichloromethane for 0.333333h; Reduction; Heating;96%
623-00-7

4-bromobenzenecarbonitrile

873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
Stage #1: 4-bromobenzenecarbonitrile With 2,2,2-trifluoroacetamide; potassium carbonate; N,N`-dimethylethylenediamine; copper(l) iodide In 1,4-dioxane at 75℃;
Stage #2: With methanol In 1,4-dioxane at 75℃; Further stages.;
99%
Stage #1: 4-bromobenzenecarbonitrile With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 0.75h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
97%
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 12h; Sealed tube; Inert atmosphere;97%
3058-39-7

4-iodobenzonitrile

873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With copper acetylacetonate; ammonium hydroxide; 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate In water; N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere;99%
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; liquid NH3;98%
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 4h;97%
773837-37-9

sodium cyanide

106-40-1

4-bromo-aniline

873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With tri-tert-butyl phosphine; [Pd2(dba)5]; zinc In tetrahydrofuran; acetonitrile at 70℃; for 2h;99%

N-(2,2,2-trichloroethoxycarbonyl)-4-aminobenzonitrile

873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With indium; ammonium chloride In ethanol for 3h; Heating;98%
540-37-4

p-aminoiodobenzene

potassium ferrocyanide

873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With copper(l) iodide; sodium carbonate In N,N-dimethyl acetamide for 2h; Reflux;98%
With triethylamine In water; N,N-dimethyl-formamide Catalytic behavior; Sealed tube; Inert atmosphere;80%
With palladium diacetate; sodium carbonate; isopropyl alcohol In 1-methyl-pyrrolidin-2-one; water at 140℃; for 0.7h; open-air conditions;72%
64-17-5

ethanol

51029-20-0

1-(4-cyanophenyl)-3-methyltriazene

A

540-67-0

ethyl methyl ether

B

873-74-5

4-Aminobenzonitrile

C

N2

N2

Conditions
ConditionsYield
copper(II) ion at 20℃; Kinetics; Mechanism; effect of added water on the velocity constant, other temperatures up to 40 deg C, other catalysts Fe(2+), Zn(2+);A n/a
B 97%
C n/a
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Chemistry

Molecular Structure of 4-Cyanoaniline (CAS NO.873-74-5):

Molecular Formula: C7H6N2
Molecular Weight: 118.1359
IUPAC Name: 4-Aminobenzonitrile
Synonyms of 4-Cyanoaniline (CAS NO.873-74-5): 1-Amino-4-cyanobenzene ; 4-14-00-01158 (Beilstein Handbook Reference) ; 4-Aminobenzonitrile ; AI3-24185 ; Aniline, p-cyano- ; BRN 0774507 ; Benzonitrile, 4-amino- ; EINECS 212-850-1 ; NSC 7625 ; p-Aminobenzonitrile ; p-Cyanoaniline ; Benzonitrile, p-amino- (8CI)
CAS NO: 873-74-5
Classification Code: Drug / Therapeutic Agent ; Mutation data ; Skin / Eye Irritant
Melting point: 83-85 °C 
Index of Refraction: 1.59
Molar Refractivity: 34.93 cm3
Molar Volume: 103.4 cm3
Surface Tension: 54.3 dyne/cm
Density: 1.14 g/cm3
Flash Point: 127.1 °C
Enthalpy of Vaporization: 52.56 kJ/mol
Boiling Point: 286.5 °C at 760 mmHg
Vapour Pressure: 0.00263 mmHg at 25°C

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 23700ug/kg (23.7mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mouse LD50 intraperitoneal 155mg/kg (155mg/kg)   Journal of Medicinal Chemistry. Vol. 17, Pg. 900, 1974.
mouse LD50 oral 168mg/kg (168mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
National Technical Information Service. Vol. OTS0555306,
quail LD50 oral 23700ug/kg (23.7mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
rat LD50 oral 283mg/kg (283mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
National Technical Information Service. Vol. OTS0555306,

Consensus Reports

EPA Genetic Toxicology Program. 4-Cyanoaniline (CAS NO.873-74-5) is reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

Safety Profile

Hazard Codes of 4-Cyanoaniline (CAS NO.873-74-5): HarmfulXn,Xi
Risk Statements: 36/37/38-20/21/22 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: BX2320000
Hazard Note: Harmful
TSCA: T
HazardClass: 6.1
PackingGroup: III
HS Code: 29269095
 

Specification

First Aid Measures of 4-Cyanoaniline (CAS NO.873-74-5)
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. If irritation develops, get medical aid. 
Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. 
Ingestion: Get medical aid. Wash mouth out with water. 
Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. 
Notes to Physician: Treat symptomatically and supportively.