Benzyl cyanide

Last updated
Benzyl cyanide
Benzyl-cyanide.png
Benzyl-cyanide-3D-balls.png
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

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

Sodium cyanide is a poisonous compound with the formula NaCN. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its high reactivity toward metals. It is a moderately strong base.

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">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.

Geminal halide hydrolysis is an organic reaction. The reactants are geminal dihalides with a water molecule or a hydroxide ion. The reaction yields ketones from secondary halides or aldehydes from primary halides.

1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

<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.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

Chlorotoluene is a group of three isomeric chemical compounds. They consist of a disubstituted benzene ring with one chlorine atom and one methyl group.

Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic.

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.

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

Phenylpyruvic acid is the organic compound with the formula C6H5CH2C(O)CO2H. It is a keto 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">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">2-Methylanthraquinone</span> Chemical compound

2-Methylanthraquinone, also known as β-methylanthraquinone and tectoquinone, is an organic compound which is a methylated derivative of anthraquinone. An off-white solid, it is an important precursor to many dyes. It is present in the wood of the teak tree, where it gives the tree resistance to insects.

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.

<span class="mw-page-title-main">2-Acetylthiophene</span> Chemical compound

2-Acetylthiophene is an organosulfur compound with the formula CH3C(O)C4H3S. A yellow liquid, it is the more useful of the two isomers of acetylthiophene. It is of commercial interest as a precursor to both thiophene-2-carboxylic acid and thiophene-2-acetic acid. It is prepared by the reaction of thiophene with acetyl chloride in the presence of stannic chloride.

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
  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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.