Benzyl cyanide
Benzyl cyanide
Names
Preferred IUPAC name
Other names
Benzyl cyanide
[ 1] 2-Phenylacetonitrile
α-Tolunitrile
Benzylnitrile
Identifiers
ChEBI
ChemSpider
ECHA InfoCard 100.004.919
KEGG
UNII
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
Properties
C8 H7 N
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)
0.1 g/L (25 °C)
log P 1.56
Vapor pressure 1 mmHg (60 °C)
−76.87·10−6 cm3 /mol
1.52105 (25 °C)
Hazards[ 2]
Occupational safety and health
Main hazards
Poisonous. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes.
GHS labelling
Danger
H301 , H302 , H311 , H330
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 diamond)
Flash point 102 °C (216 °F; 375 K)[ 3]
Lethal dose or concentration (LD, LC):
270 mg/kg (rat, oral)
74.982 mg/kg (rat, intraperitoneal)
100 mg/m3 (mouse, 2h)3 (rat, 2h)
Except where otherwise noted, data are given for materials in their
standard state (at 25
°C [77
°F], 100
kPa).
Chemical compound
Benzyl cyanide (abbreviated BnCN ), also known as phenylacetonitrile , is an organic compound with the chemical formula C6 H5 CH2 CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry .[ 4] pheromone in certain species.[ 5]
Regulation
Because benzyl cyanide is a useful precursor to numerous drugs with recreational use potential , many countries strictly regulate the compound.
China
Benzyl cyanide is regulated in People's Republic of China as a Class III drug precursor since 7 June 2021.[ 33]
Safety
Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.[ 4]
References
1 2 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 ↑ "Phenylacetonitrile" . pubchem.ncbi.nlm.nih.gov . Retrieved 4 May 2025 .↑ "Phenylacetonitrile" . pubchem.ncbi.nlm.nih.gov . Retrieved 24 December 2025 .1 2 3 Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry . doi :10.1002/14356007.a17_363 . ISBN 3-527-30673-0 ↑ "Toxin Protects Migratory Locusts from Cannibalism" . Max Planck Society . 4 May 2023. Retrieved 8 December 2024 .↑ Adams, Roger; Thal, A. F. (1922). "Benzyl cyanide". Organic Syntheses . 2 : 9. doi :10.15227/orgsyn.002.0009 . ↑ 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 . ↑ 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 . ↑ Adams, Roger; Thal, A. F. (1922). "Phenylacetic acid". Organic Syntheses . 2 : 59. doi :10.15227/orgsyn.002.0059 . ↑ Adams, Roger; Thal, A. F. (1922). "Ethyl Phenylacetate". Organic Syntheses . 2 : 27. doi :10.15227/orgsyn.002.0027 . ↑ Robinson, John C. Jr.; Snyder, H. R. (1943). "β-Phenylethylamine". Organic Syntheses . 23 : 71. doi :10.15227/orgsyn.023.0071 . ↑ Robb, C. M.; Schultz, E. M. (1948). "Diphenylacetonitrile". Organic Syntheses . 28 : 55. doi :10.15227/orgsyn.028.0055 . ↑ Makosza, M.; Jonczyk, A (1976). "Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile". Organic Syntheses . 55 : 91. doi :10.15227/orgsyn.055.0091 . ↑ 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 . ↑ Wawzonek, Stanley; Smolin, Edwin M. (1955). "α-Phenylcinnamonitrile". Organic Syntheses . 3 : 715. doi :10.15227/orgsyn.029.0083 . ↑ 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 3-527-30673-0 ↑ Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural". Ullmann's Encyclopedia of Industrial Chemistry . doi :10.1002/14356007.a12_085 . ISBN 3-527-30673-0 ↑ "PHENYLACETAMIDE". Organic Syntheses . 32 : 92. 1952. doi :10.15227/orgsyn.032.0092 . ISSN 0078-6209 . 1 2 3 4 5 6 7 William Andrew Publishing (2008). Pharmaceutical Manufacturing Encyclopedia ed.). Norwich, NY: Elsevier Science. pp. 182, 936, 1362, 1369, 1505, 2036, 2157, 2259, 2554, 2620, 2660, 2670, 2924, 3032, & 3410. ISBN 978-0-8155-1526-5 ↑ 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 . ↑ Bub, Oskar; Friedrich, Ludwig (2000). "Cough Remedies". Ullmann's Encyclopedia of Industrial Chemistry . doi :10.1002/14356007.a08_013 . ISBN 3-527-30673-0 ↑ Hropot, Max; Lang, Hans-Jochen (2000). "Diuretics". Ullmann's Encyclopedia of Industrial Chemistry . doi :10.1002/14356007.a09_029 . ISBN 3-527-30673-0 ↑ Furniss, Brian; Hannaford, Antony; Smith, Peter & Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed 1174– 1179. ISBN 978-0-582-46236-6 ↑ Bungardt, Edwin; Mutschler, Ernst (2000). "Spasmolytics". Ullmann's Encyclopedia of Industrial Chemistry . doi :10.1002/14356007.a24_515 . ISBN 3-527-30673-0 ↑ "a,b-DIPHENYLCINNAMONITRILE" . Organic Syntheses . 31 : 52. 1951. doi :10.15227/orgsyn.031.0052 ↑ Dore, J. C.; Gilbert, J.; Bignon, E.; Crastes De Paulet, A.; Ojasoo, T.; Pons, M.; Raynaud, J. P.; Miquel, J. F. (February 1992). "Multivariate analysis by the minimum spanning tree method of the structural determinants of diphenylethylenes and triphenylacrylonitriles implicated in estrogen receptor binding, protein kinase C activity, and MCF7 cell proliferation" Journal of Medicinal Chemistry . 35 (3): 573– 583. doi :10.1021/jm00081a021 . ↑ Bignon, E.; Pons, M.; Crastes De Paulet, A.; Dore, J. C.; Gilbert, J.; Abecassis, J.; Miquel, J. F.; Ojasoo, T.; Raynaud, J. P. (September 1989). "Effect of triphenylacrylonitrile derivatives on estradiol-receptor binding and on human breast cancer cell growth" Journal of Medicinal Chemistry . 32 (9): 2092– 2103. doi :10.1021/jm00129a013 . 1 2 Hermans, B., Van Daele, P., Van De Westeringh, C., Van Der Eycken, C., Boey, J., Dockx, J., Janssen, P. (July 1968). "4-Substituted Piperidines. IV. The Synthesis of 4-[ (2,6-Dioxo-3-phenyl)-3-piperidyl] piperidines" . Journal of Medicinal Chemistry . 11 (4): 797– 800. doi :10.1021/jm00310a613 . ↑ Daniel Lednicer & L.A. Mitscher drug synthesis Book 3, Page 191. ↑ Silverman RB, Zieske PA. 1-Phenylcyclobutylamine, the first in a new class of monoamine oxidase inactivators. Further evidence for a radical intermediate. Biochemistry. 1986 Jan 28;25(2):341-6. doi: 10.1021/bi00350a010. PMID: 3955001. ↑ Singer, T.P. (1987). Perspectives in MAO: past, present, and future. In: Oreland, L., Callingham, B.A. (eds) Monoamine Oxidase Enzymes. Journal of Neural Transmission, vol 23. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8901-6_1 ↑ Kalir, A., Pelah, Z. (January 1967). "1‐Phenylcycloakylamine Derivatives I" . Israel Journal of Chemistry . 5 (5): 223– 229. doi :10.1002/ijch.196700039 . ↑ "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 .
