Benzyl cyanide(abbreviatedBnCN) is anorganic compoundwith thechemical formulaC6H5CH2CN. This colorless oily aromatic liquid is an importantprecursorto numerous compounds inorganic chemistry.[2] It is also an importantpheromonein certain species.[3]
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| Preferred IUPAC name
Phenylacetonitrile[1] | |
| Other names | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.004.919 |
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PubChemCID
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CompTox Dashboard(EPA)
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| Properties | |
| 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) |
| -76.87·10−6cm3/mol | |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Preparation
editBenzyl cyanide can be produced viaKolbe nitrile synthesisbetweenbenzyl chlorideandsodium cyanide[4]and byoxidative decarboxylationofphenylalanine.[5]
Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile.[6]
Reactions
editBenzyl cyanide undergoes many reactions characteristic of nitriles. It can behydrolyzedto givephenylacetic acid[7]or it can be used in thePinner reactionto yield phenylacetic acidesters.[8]Hydrogenation givesβ-phenethylamine.[9]
The compound contains an "activemethylene unit".Bromination occurs gives PhCHBrCN.[10]A variety of base-induced reactions result in the formation of newcarbon-carbon bonds.[11][12][13]
Uses
editBenzyl cyanide is used as a solvent[14]and as a starting material in the synthesis offungicides(e.g.Fenapanil),[15]fragrances (phenethyl alcohol),antibiotics,[2]and otherpharmaceuticals.The partial hydrolysis of BnCN results in2-phenylacetamide.[16]
Pharmaceuticals
editBenzyl cyanide is a usefulprecursorto numerous pharmaceuticals. Examples include: [17]
- Antiarrhythmics(e.g.disopyramide)[17]
- Antidepressants: E.g.Milnacipran&Lomevactone
- Antihistamines(e.g.levocabastine(para-fluoro),[17][18]Pheniramine&Azatadine.
- Antitussives(e.g.isoaminile,oxeladin,butethamate,pentapiperide,andpentoxyverine)[19]
- Diuretics(e.g.triamterene)[20]
- Hypnotics(e.g.alonimidandphenobarbital)[17][21]&Phenglutarimide
- Spasmolytics(e.g.pentapiperideanddrofenine)[17][22]
- Stimulants(e.g.methylphenidate)[17]
- Opioids(e.g.ethoheptazine,pethidine,andphenoperidine)[17]&methadone
Regulation
editBecause benzyl cyanide is a usefulprecursorto numerousdrugs with recreational use potential,many countries strictly regulate the compound.
United States
editBenzyl cyanide is regulated in the United States as aDEA List I chemical.
China
editBenzyl cyanide is regulated in People's Republic of China as a Class III drug precursor since 7 June 2021.[23]
Safety
editBenzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes.[2]
See also
editReferences
edit- ^abNomenclature 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.ISBN978-0-85404-182-4.
- ^abcPollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles".Ullmann's Encyclopedia of Industrial Chemistry.doi:10.1002/14356007.a17_363.ISBN3527306730.
- ^https://www.mpg.de/20278575/0504-choe-chemisches-signal-schuetzt-wanderheuschrecken-vor-kannibalismus[bare URL]
- ^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.S2CID52208189.
- ^Wu, Lingyun; Hartwig, John F. (2005). "Mild Palladium-Catalyzed Selective Monoarylation of Nitriles".Journal of the American Chemical Society.127(45): 15824–15832.doi:10.1021/ja053027x.PMID16277525.
- ^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.ISBN3527306730.
- ^Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural".Ullmann's Encyclopedia of Industrial Chemistry.doi:10.1002/14356007.a12_085.ISBN3527306730.
- ^"PHENYLACETAMIDE".Organic Syntheses.32:92. 1952.doi:10.15227/orgsyn.032.0092.ISSN0078-6209.
- ^abcdefgWilliam 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.ISBN9780815515265.
- ^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.ISBN3527306730.
- ^Hropot, Max; Lang, Hans-Jochen (2000). "Diuretics".Ullmann's Encyclopedia of Industrial Chemistry.doi:10.1002/14356007.a09_029.ISBN3527306730.
- ^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.ISBN9780582462366.
- ^Bungardt, Edwin; Mutschler, Ernst (2000). "Spasmolytics".Ullmann's Encyclopedia of Industrial Chemistry.doi:10.1002/14356007.a24_515.ISBN3527306730.
- ^"Quốc vụ viện bạn công thính quan vu đồng ý tương α- bổn ất tiên ất toan giáp chỉ đẳng 6 chủng vật chất liệt nhập dịch chế độc hóa học phẩm phẩm chủng mục lục đích hàm"(in Simplified Chinese). The State Council - The People's Republic of China. 7 June 2021.Retrieved11 October2021.