Benzonitrile

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.

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

DOT Classification:  6.1; Label: Poison

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.

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.

Physical properties about Benzonitrile are: (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.

Preparation: this chemical 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%.

Uses of Benzonitrile: it 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%.

When you are using this chemical, 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).

You can still convert the following datas into molecular structure:
(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

The toxicity data is as follows:

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,