Benzyl cyanide

Benzyl cyanide

Names
Preferred IUPAC name Phenylacetonitrile [1]
Other names Benzyl cyanide [1] 2-Phenylacetonitrile α-Tolunitrile Benzylnitrile
Identifiers
CAS Number	140-29-4  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:25979  Y
ChemSpider	13839308  Y
ECHA InfoCard	100.004.919
KEGG	C16074  Y
PubChem CID	8794
UNII	23G40PRP93  Y
CompTox Dashboard (EPA)	DTXSID2021492
InChI InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 Y Key: SUSQOBVLVYHIEX-UHFFFAOYSA-N Y InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 Key: SUSQOBVLVYHIEX-UHFFFAOYAJ
SMILES N#CCc1ccccc1
Properties
Chemical formula	C8H7N
Molar mass	117.15 g/mol
Appearance	Colorless oily liquid
Density	1.015 g/cm3
Melting point	−24 °C (−11 °F; 249 K)
Boiling point	233 to 234 °C (451 to 453 °F; 506 to 507 K)
Solubility in water	0.1 g/L (25 °C)
log P	1.56
Vapor pressure	1 mmHg (60 °C)
Magnetic susceptibility (χ)	−76.87·10−6 cm3/mol
Refractive index (nD)	1.52105 (25 °C)
Hazards [2]
Occupational safety and health (OHS/OSH):
Main hazards	Poisonous. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes.
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H311, H330
Precautionary statements	P260, P262, P264, P270, P271, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)	3 1 0
Flash point	102 °C (216 °F; 375 K) [3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	270 mg/kg (rat, oral)
LDLo (lowest published)	74.982 mg/kg (rat, intraperitoneal) 50 mg/kg (rabbit, subcutaneous) 120 mg/kg (pigeon, intramuscular)
LC50 (median concentration)	100 mg/m3 (mouse, 2h) 430 mg/m3 (rat, 2h)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

Benzyl cyanide (abbreviated BnCN), also known as phenylacetonitrile, is an organic compound with the chemical formula C₆H₅CH₂CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. ^[4] It is also an important pheromone in certain species. ^[5]

Preparation

Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide ^[6] and by oxidative decarboxylation of phenylalanine. ^[7]

Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile. ^[8]

Reactions

Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be hydrolyzed to give phenylacetic acid ^[9] or it can be used in the Pinner reaction to yield phenylacetic acid esters. ^[10] Hydrogenation gives β-phenethylamine. ^[11]

The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN. ^[12] A variety of base-induced reactions result in the formation of new carbon-carbon bonds. ^{[13] [14] [15]}

Uses

Benzyl cyanide is used as a solvent ^[16] and as a starting material in the synthesis of fungicides (e.g. Fenapanil), ^[17] fragrances (phenethyl alcohol), antibiotics, ^[4] and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide. ^[18]

Pharmaceuticals

Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include: ^[19]

• Antiarrhythmics (e.g. disopyramide) ^[19]
• Antidepressants: E.g. Milnacipran & Lomevactone
• Antihistamines (e.g. levocabastine (para-fluoro), ^{[19] [20]} Pheniramine & Azatadine.
• Antitussives (e.g. isoaminile, oxeladin, butethamate, pentapiperide, and pentoxyverine) ^[21]
• Diuretics (e.g. triamterene) ^[22]
• Hypnotics (e.g. alonimid and phenobarbital) ^{[19] [23]} & Phenglutarimide
• Spasmolytics (e.g. pentapiperide and drofenine) ^{[19] [24]}
• Stimulants (e.g. methylphenidate), ^[19] mazindol & gamfexine.
• Opioids (e.g. ethoheptazine, pethidine, and phenoperidine) ^[19] & methadone

Regulation

Because benzyl cyanide is a useful precursor to numerous drugs with recreational use potential, many countries strictly regulate the compound.

United States

Benzyl cyanide is regulated in the United States as a DEA List I chemical.

China

Benzyl cyanide is regulated in People's Republic of China as a Class III drug precursor since 7 June 2021. ^[25]

Safety

Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes. ^[4]

See also

• Bromobenzyl cyanide

References

1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 16. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
2. "Phenylacetonitrile". pubchem.ncbi.nlm.nih.gov. Retrieved 4 May 2025.
3. "Phenylacetonitrile". pubchem.ncbi.nlm.nih.gov. Retrieved 24 December 2025.
4. Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_363. ISBN   3527306730.
5. "Toxin Protects Migratory Locusts from Cannibalism". Max Planck Society. 4 May 2023. Retrieved 8 December 2024.
6. Adams, Roger; Thal, A. F. (1922). "Benzyl cyanide". Organic Syntheses. 2: 9. doi:10.15227/orgsyn.002.0009.
7. Hiegel, Gene; Lewis, Justin; Bae, Jason (2004). "Conversion of α-Amino Acids into Nitriles by Oxidative Decarboxylation with Trichloroisocyanuric Acid". Synthetic Communications. 34 (19): 3449–3453. doi:10.1081/SCC-200030958. S2CID   52208189.
8. Wu, Lingyun; Hartwig, John F. (2005). "Mild Palladium-Catalyzed Selective Monoarylation of Nitriles". Journal of the American Chemical Society. 127 (45): 15824–15832. Bibcode:2005JAChS.12715824W. doi:10.1021/ja053027x. PMID   16277525.
9. Adams, Roger; Thal, A. F. (1922). "Phenylacetic acid". Organic Syntheses. 2: 59. doi:10.15227/orgsyn.002.0059.
10. Adams, Roger; Thal, A. F. (1922). "Ethyl Phenylacetate". Organic Syntheses. 2: 27. doi:10.15227/orgsyn.002.0027.
11. Robinson, John C. Jr.; Snyder, H. R. (1943). "β-Phenylethylamine". Organic Syntheses. 23: 71. doi:10.15227/orgsyn.023.0071.
12. Robb, C. M.; Schultz, E. M. (1948). "Diphenylacetonitrile". Organic Syntheses. 28: 55. doi:10.15227/orgsyn.028.0055.
13. Makosza, M.; Jonczyk, A (1976). "Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile". Organic Syntheses. 55: 91. doi:10.15227/orgsyn.055.0091.
14. Itoh, Masumi; Hagiwara, Daijiro; Kamiya, Takashi (1988). "New Reagent for tert-Butoxycarbonylation: 2-tert-Butoxycarbonyloxyimino-2-phenylacetonitrile". Organic Syntheses. 6: 199. doi:10.15227/orgsyn.059.0095.
15. Wawzonek, Stanley; Smolin, Edwin M. (1955). "α-Phenylcinnamonitrile". Organic Syntheses. 3: 715. doi:10.15227/orgsyn.029.0083.
16. Bien, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2000). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry: 29. doi:10.1002/14356007.a02_355. ISBN   3527306730.
17. Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a12_085. ISBN   3527306730.
18. "PHENYLACETAMIDE". Organic Syntheses. 32: 92. 1952. doi:10.15227/orgsyn.032.0092. ISSN   0078-6209.
19. William Andrew Publishing (2008). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Norwich, NY: Elsevier Science. pp. 182, 936, 1362, 1369, 1505, 2036, 2157, 2259, 2554, 2620, 2660, 2670, 2924, 3032, & 3410. ISBN   9780815515265.
20. Berkoff, Charles E.; Rivard, Donald E.; Kirkpatrick, David; Ives, Jeffrey L. (1980). "The Reductive Decyanation of Nitriles by Alkali Fusion". Synthetic Communications. 10 (12): 939–945. doi:10.1080/00397918008061855.
21. Bub, Oskar; Friedrich, Ludwig (2000). "Cough Remedies". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_013. ISBN   3527306730.
22. Hropot, Max; Lang, Hans-Jochen (2000). "Diuretics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_029. ISBN   3527306730.
23. Furniss, Brian; Hannaford, Antony; Smith, Peter & Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. pp. 1174–1179. ISBN   9780582462366.
24. Bungardt, Edwin; Mutschler, Ernst (2000). "Spasmolytics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a24_515. ISBN   3527306730.
25. "国务院办公厅关于同意将α-苯乙酰乙酸甲酯等6种物质列入易制毒化学品品种目录的函" (in Simplified Chinese). The State Council - The People's Republic of China. 7 June 2021. Retrieved 11 October 2021.

External links

• EPA Chemical Profile for phenylacetonitrile