Benzyl cyanide

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Benzyl cyanide
Benzyl-cyanide.png
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Names
Preferred IUPAC name
Phenylacetonitrile [1]
Other names
Benzyl cyanide [1]
2-Phenylacetonitrile
α-Tolunitrile
Benzylnitrile
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.919 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 Yes check.svgY
    Key: SUSQOBVLVYHIEX-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
    Key: SUSQOBVLVYHIEX-UHFFFAOYAJ
  • N#CCc1ccccc1
Properties
C8H7N
Molar mass 117.15 g/mol
AppearanceColorless 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)
-76.87·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. [2] It is also an important pheromone in certain species. [3]

Contents

Preparation

Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide [4] and by oxidative decarboxylation of phenylalanine. [5]

Benzyl cyanides can also be prepared by arylation of silyl-substituted acetonitrile. [6]

Reactions

Benzyl cyanide undergoes many reactions characteristic of nitriles. It can be hydrolyzed to give phenylacetic acid [7] or it can be used in the Pinner reaction to yield phenylacetic acid esters. [8] Hydrogenation gives β-phenethylamine. [9]

The compound contains an "active methylene unit". Bromination occurs gives PhCHBrCN. [10] A variety of base-induced reactions result in the formation of new carbon-carbon bonds. [11] [12] [13]

Uses

Benzyl cyanide is used as a solvent [14] and as a starting material in the synthesis of fungicides (e.g. Fenapanil), [15] fragrances (phenethyl alcohol), antibiotics, [2] and other pharmaceuticals. The partial hydrolysis of BnCN results in 2-phenylacetamide. [16]

Pharmaceuticals

Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include: [17]

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. [23]

Safety

Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes. [2]

See also

Related Research Articles

In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

In chemistry, a dehydration reaction is a chemical reaction that involves the loss of water from the reacting molecule or ion. Dehydration reactions are common processes, the reverse of a hydration reaction.

<span class="mw-page-title-main">Benzoyl chloride</span> Organochlorine compound (C7H5ClO)

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring with an acyl chloride substituent. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

<span class="mw-page-title-main">Glutaric acid</span> Chemical compound

Glutaric acid is the organic compound with the formula C3H6(COOH)2. Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50% (w/w).

The Tishchenko reaction is an organic chemical reaction that involves disproportionation of an aldehyde in the presence of an alkoxide. The reaction is named after Russian organic chemist Vyacheslav Tishchenko, who discovered that aluminium alkoxides are effective catalysts for the reaction.

<span class="mw-page-title-main">Phenylacetic acid</span> Chemical compound

Phenylacetic acid, also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogenously, it is a catabolite of phenylalanine. As a commercial chemical, because it can be used in the illicit production of phenylacetone, it is subject to controls in countries including the United States and China.

<span class="mw-page-title-main">Ethyl acetoacetate</span> Chemical compound

The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is a colorless liquid. It is widely used as a chemical intermediate in the production of a wide variety of compounds.

<span class="mw-page-title-main">1,3,5-Trioxane</span> Chemical compound

1,3,5-Trioxane, sometimes also called trioxane or trioxin, is a chemical compound with molecular formula C3H6O3. It is a white, highly water-soluble solid with a chloroform-like odor. It is a stable cyclic trimer of formaldehyde, and one of the three trioxane isomers; its molecular backbone consists of a six-membered ring with three carbon atoms alternating with three oxygen atoms.

<span class="mw-page-title-main">Benzyl benzoate</span> Chemical compound

Benzyl benzoate is an organic compound which is used as a medication and insect repellent. As a medication it is used to treat scabies and lice. For scabies either permethrin or malathion is typically preferred. It is applied to the skin as a lotion. Typically two to three applications are needed. It is also present in Balsam of Peru, Tolu balsam, and in a number of flowers.

Chlorotoluenes are aryl chlorides based on toluene in which at least one aromatic hydrogen atom is replaced with a chlorine atom. They have the general formula C7H8–nCln, where n = 1–5 is the number of chlorine atoms.

2-Cyanoguanidine is a nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in water, acetone, and alcohol, but not nonpolar organic solvents.

In nitrile reduction a nitrile is reduced to either an amine or an aldehyde with a suitable chemical reagent.

The Ritter reaction is a chemical reaction that transforms a nitrile into an N-alkyl amide using various electrophilic alkylating reagents. The original reaction formed the alkylating agent using an alkene in the presence of a strong acid.

<span class="mw-page-title-main">Sodium chloroacetate</span> Chemical compound

Sodium chloroacetate is the organic compound with the formula CH2ClCO2Na. A white, water-soluble solid, it is the sodium salt of chloroacetic acid. Many of its uses are similar to those of the parent acid. It is prepared by treating chloroacetic acid with sodium carbonate.

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

<span class="mw-page-title-main">3-Chloropropionitrile</span> Chemical compound

3-Chloropropionitrile is an organic compound with the formula ClCH2CH2CN. A colorless liquid, it is prepared by the reaction of hydrogen chloride with acrylonitrile. It is used commercially as a precursor to the drug famotidine.

<span class="mw-page-title-main">Cyanoacetic acid</span> Chemical compound

Cyanoacetic acid is an organic compound. It is a white, hygroscopic solid. The compound contains two functional groups, a nitrile (−C≡N) and a carboxylic acid. It is a precursor to cyanoacrylates, components of adhesives.

<span class="mw-page-title-main">Cyanoethylation</span>

Cyanoethylation is a process for the attachment of CH2CH2CN group to another organic substrate. The method is used in the synthesis of organic compounds.

4-Chlorobutyronitrile is the organic compound with the formula ClCH2CH2CH2CN. With both chloro and cyano functional groups, it is a bifunctional molecule. It is a colorless liquid.

References

  1. 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.
  2. 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   3527306730.
  3. ↑ https://www.mpg.de/20278575/0504-choe-chemisches-signal-schuetzt-wanderheuschrecken-vor-kannibalismus [ bare URL ]
  4. ↑ Adams, Roger; Thal, A. F. (1922). "Benzyl cyanide". Organic Syntheses. 2: 9. doi:10.15227/orgsyn.002.0009.
  5. ↑ 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.
  6. ↑ 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. PMID   16277525.
  7. ↑ Adams, Roger; Thal, A. F. (1922). "Phenylacetic acid". Organic Syntheses. 2: 59. doi:10.15227/orgsyn.002.0059.
  8. ↑ Adams, Roger; Thal, A. F. (1922). "Ethyl Phenylacetate". Organic Syntheses. 2: 27. doi:10.15227/orgsyn.002.0027.
  9. ↑ Robinson, John C. Jr.; Snyder, H. R. (1943). "β-Phenylethylamine". Organic Syntheses. 23: 71. doi:10.15227/orgsyn.023.0071.
  10. ↑ Robb, C. M.; Schultz, E. M. (1948). "Diphenylacetonitrile". Organic Syntheses. 28: 55. doi:10.15227/orgsyn.028.0055.
  11. ↑ Makosza, M.; Jonczyk, A (1976). "Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile". Organic Syntheses. 55: 91. doi:10.15227/orgsyn.055.0091.
  12. ↑ 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.
  13. ↑ Wawzonek, Stanley; Smolin, Edwin M. (1955). "α-Phenylcinnamonitrile". Organic Syntheses. 3: 715. doi:10.15227/orgsyn.029.0083.
  14. ↑ 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.
  15. ↑ Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a12_085. ISBN   3527306730.
  16. ↑ "PHENYLACETAMIDE". Organic Syntheses. 32: 92. 1952. doi:10.15227/orgsyn.032.0092. ISSN   0078-6209.
  17. 1 2 3 4 5 6 7 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.
  18. ↑ 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.
  19. ↑ Bub, Oskar; Friedrich, Ludwig (2000). "Cough Remedies". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_013. ISBN   3527306730.
  20. ↑ Hropot, Max; Lang, Hans-Jochen (2000). "Diuretics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_029. ISBN   3527306730.
  21. ↑ 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.
  22. ↑ Bungardt, Edwin; Mutschler, Ernst (2000). "Spasmolytics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a24_515. ISBN   3527306730.
  23. ↑ "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.
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