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100-47-0

Basic Information
CAS No.: 100-47-0
Name: Benzonitrile
Article Data: 2160
Molecular Structure:
Molecular Structure of 100-47-0 (Benzonitrile)
Formula: C7H5N
Molecular Weight: 103.123
Synonyms: Benzene,cyano-;Benzenecarbonitrile;Benzenenitrile;Benzoic acid nitrile;Benzonitril;Cyanobenzene;NSC 8039;Phenyl cyanide;
EINECS: 202-855-7
Density: 1.032 g/cm3
Melting Point: -13 °C
Boiling Point: 191.099 °C at 760 mmHg
Flash Point: 71.667 °C
Solubility: 10 g/L (100 °C)
Appearance: colourless liquid
Hazard Symbols: HarmfulXn
Risk Codes: 21/22
Safety: 23
Transport Information: UN 2224 6.1/PG 2
PSA: 23.79000
LogP: 1.55828
Synthetic route
55-21-0

benzamide

100-47-0

benzonitrile

Conditions
ConditionsYield
With phosphorus pentoxide In methanol at 20℃; for 1h;100%
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide In acetonitrile at 20℃; for 0.166667h; Solvent;98%
With trimethylsilylphosphate for 0.666667h; Heating;97%
100-52-7

benzaldehyde

100-47-0

benzonitrile

Conditions
ConditionsYield
With iron(III) chloride; hydroxylamine hydrochloride In dimethyl sulfoxide Molecular sieve;100%
With [bis(acetoxy)iodo]benzene; ammonium bicarbonate In methanol; water at 36℃; for 12h; Sealed tube;100%
With N-(4-sulphonic acid)butylpyridinium hydrogen sulphate; 1-sulfobutylpyridine hydrogensulfate hydroxylamine In toluene at 100℃; under 760.051 Torr; for 2h; Temperature; Solvent; Reagent/catalyst;100%
932-90-1

Benzaldoxime

100-47-0

benzonitrile

Conditions
ConditionsYield
With nickel(II) chloride dihydrate In acetonitrile at 80℃; Molecular sieve; Inert atmosphere;100%
With oxalyl dichloride; triethylamine In dimethyl sulfoxide; acetonitrile at 20℃; for 0.333333h; Reagent/catalyst; Swern Oxidation;100%
With zinc trifluoromethanesulfonate In toluene at 100℃; for 24h;99%
613-90-1

benzoyl cyanide

100-47-0

benzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In benzene at 120℃; for 12h; Product distribution; other acyl cyanides, var. solvents, temp. and time;100%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 180℃; for 24h; Temperature; Glovebox; Inert atmosphere; Sealed tube;95 %Chromat.
623-03-0

4-Cyanochlorobenzene

100-47-0

benzonitrile

Conditions
ConditionsYield
With potassium tert-butylate; N,N-dimethyl-formamide at 35℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;100%
With C60H48BP3Pd; potassium formate; [2.2.2]cryptande In tetrahydrofuran at 60℃; for 72h; Schlenk technique; Inert atmosphere;99%
With formic acid; Cyclohexanethiol; 10-phenyl-10H-phenothiazine; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; under 2625.26 Torr; for 0.05h; Catalytic behavior; Reagent/catalyst; Time; Wavelength; Irradiation; Flow reactor;96%
Conditions
ConditionsYield
With triethylamine; 2,4-Dichloro-5-nitropyrimidine In acetonitrile for 5h; Ambient temperature;100%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 20℃; Beckmann rearrangement;100%
With oxalyl dichloride; Triphenylphosphine oxide In chloroform at 20℃; for 1h;99%
55-21-0

benzamide

78303-22-7

chloro(tert-butyl)diethylamino(methylene)phosphorane

A

100-47-0

benzonitrile

B

C9H22Cl2NP

C

P-tert-butyl-N,N-diethyl-P-methylphosphinic amide

Conditions
ConditionsYield
In diethyl ether -10 dec C, then +20 deg C.;A 70%
B 100%
C 85%
149540-88-5

(E)-benzaldehyde O-pivaloyloxime

100-47-0

benzonitrile

Conditions
ConditionsYield
With triethylamine In acetonitrile at 25℃; Rate constant; Mechanism; variation of base/solvent system;100%
With diisobutylamine In acetonitrile at 20℃; for 10h;94 %Chromat.
With diisopropylamine In acetonitrile at 25℃; Kinetics;
149540-89-6

C12H14(2)HNO2

100-47-0

benzonitrile

Conditions
ConditionsYield
With triethylamine In acetonitrile at 25℃; Rate constant; variation of base/solvent system;100%
108-90-7

chlorobenzene

potassium ferrocyanide

100-47-0

benzonitrile

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one; Hexadecane at 140℃; for 16h; Product distribution / selectivity;100%
With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.166667h; Microwave irradiation;94%
With sodium carbonate; palladium diacetate; tri-tert-butyl phosphine In 1-methyl-pyrrolidin-2-one; Hexadecane at 140℃; for 16h; Product distribution / selectivity;88%
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History

Benzonitrile(100-47-0) was discovered by Hermann Fehling in 1844. He heated ammonium benzoate until it decomposed, and one of the products was benzonitrile. He was able to determine the structure of the product from the already known analogue reaction of ammonium formate yielding hydrocyanic acid. He also coined the name benzonitrile which gave the name to all the group of nitriles.

Consensus Reports

Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

Standards and Recommendations

DOT Classification:  6.1; Label: Poison

Specification

1. Introduction of Benzonitrile
The Benzonitrile is an organic compound with the formula C7H5N. The IUPAC name of this chemical is benzonitrile. With the CAS registry number 100-47-0, it is also named as benzoic acid nitrile. The product's categories are Industrial/Fine Chemicals; Intermediates; Organics. Besides, it is colourless liquid, which should be stored in a cool and well-ventilated place.

2. Properties of Benzonitrile
(1)ACD/LogP: 1.58; (2)ACD/LogD (pH 5.5): 1.584; (3)ACD/LogD (pH 7.4): 1.584; (4)ACD/BCF (pH 5.5): 9.413; (5)ACD/BCF (pH 7.4): 9.413; (6)ACD/KOC (pH 5.5): 173.222; (7)ACD/KOC (pH 7.4): 173.222; (8)#H bond acceptors: 1; (9)Polar Surface Area: 23.79 Å2; (10)Index of Refraction: 1.539; (11)Molar Refractivity: 31.32 cm3; (12)Molar Volume: 99.952 cm3; (13)Polarizability: 12.416×10-24cm3; (14)Surface Tension: 41.066 dyne/cm; (15)Density: 1.032 g/cm3; (16)Flash Point: 71.667 °C; (17)Enthalpy of Vaporization: 42.73 kJ/mol; (18)Boiling Point: 191.099 °C at 760 mmHg; (19)Vapour Pressure: 0.524 mmHg at 25°C.

3. Structure Descriptors of Benzonitrile
(1)SMILES: c1ccc(cc1)C#N
(2)InChI: InChI=1/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H
(3)InChIKey: JFDZBHWFFUWGJE-UHFFFAOYAY
(4)Std. InChI: InChI=1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H
(5)Std. InChIKey: JFDZBHWFFUWGJE-UHFFFAOYSA-N

4. Toxicity of Benzonitrile

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 800mg/kg (800mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Food and Cosmetics Toxicology. Vol. 17, Pg. 723, 1979.
frog LDLo subcutaneous 1700mg/kg (1700mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

CARDIAC: OTHER CHANGES
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 5, Pg. 161, 1899.
mammal (species unspecified) LD50 oral 800mg/kg (800mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
mouse LC50 inhalation 1800mg/m3 (1800mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(6), Pg. 34, 1977.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 723, 1979.
mouse LD50 oral 971mg/kg (971mg/kg)   Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. Vol. 39, Pg. 423, 1984.
pigeon LDLo subcutaneous 500mg/kg (500mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 723, 1979.
rabbit LD50 intraperitoneal 1250mg/kg (1250mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 723, 1979.
rabbit LD50 oral 800mg/kg (800mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Food and Cosmetics Toxicology. Vol. 17, Pg. 723, 1979.
rabbit LD50 skin 1250mg/kg (1250mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 723, 1979.
rabbit LDLo subcutaneous 200mg/kg (200mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 5, Pg. 161, 1899.
rat LCLo inhalation 950ppm/8H (950ppm) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Aerospace Medical Research Laboratory Report. Vol. TR-74-78, Pg. 1974,
rat LD50 intraperitoneal 740mg/kg (740mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Annales Pharmaceutiques Francaises. Vol. 48, Pg. 23, 1990.
rat LD50 skin 1200mg/kg (1200mg/kg)   Aerospace Medical Research Laboratory Report. Vol. TR-74-78, Pg. 1974,
rat LDLo oral 720mg/kg (720mg/kg)   Aerospace Medical Research Laboratory Report. Vol. TR-74-78, Pg. 1974,

5. Safety Information of Benzonitrile
Hazard Symbols:HarmfulXn
Risk Codes:
R21/22:Harmful in contact with skin and if swallowed.
Safety Description:
S23:Do not breathe vapour.

6. Preparation of Benzonitrile
Benzonitrile can be prepared by benzaldehyde. This reaction will need reagent TMSA, catalyst ZnCl2 and solvent CHCl3. The reaction time is 4 hours at ambient temperature. The yield is about 2%.



7. Use of Benzonitrile
Benzonitrile can be used to produce 2,5-diphenyl-1H-thieno[2,3-d]pyrimidin-4-one at ambient temperature. It will need reagent HCl. The yield is about 35.5%.


The Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis. It is a precursor to Ph2C=NH (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by methanolysis. Benzonitrile can form coordination complexes with late transition metals that are both soluble in organic solvents and conveniently labile. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.

8. Other details of Benzonitrile
When you are using Benzonitrile, please be cautious about it as the following:
It is harmful in contact with skin and if swallowed. When you are using it, do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer).