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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)
-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).
Chemical compound
Benzyl cyanide (abbreviated BnCN ) 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 .
[2]
It is also an important
pheromone in certain species.
[3]
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
References
^
a
b 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 .
^
a
b
c 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 .
^
https://www.mpg.de/20278575/0504-choe-chemisches-signal-schuetzt-wanderheuschrecken-vor-kannibalismus
^ 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.
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
3527306730 .
^ Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural". Ullmann's Encyclopedia of Industrial Chemistry .
doi :
10.1002/14356007.a12_085 .
ISBN
3527306730 .
^ "PHENYLACETAMIDE". Organic Syntheses . 32 : 92. 1952.
doi :
10.15227/orgsyn.032.0092 .
ISSN
0078-6209 .
^
a
b
c
d
e
f
g 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 .
^ 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
3527306730 .
^ Hropot, Max; Lang, Hans-Jochen (2000). "Diuretics". Ullmann's Encyclopedia of Industrial Chemistry .
doi :
10.1002/14356007.a09_029 .
ISBN
3527306730 .
^ 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 .
^ Bungardt, Edwin; Mutschler, Ernst (2000). "Spasmolytics". Ullmann's Encyclopedia of Industrial Chemistry .
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10.1002/14356007.a24_515 .
ISBN
3527306730 .
^
"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