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Benzyl Cyanide

Benzyl cyanide (BnCN) is an organic compound used as a precursor in the synthesis of various pharmaceuticals, including analgesics and antidepressants. It can be produced through nitrile synthesis and oxidative decarboxylation, and has chemical properties that allow it to form new carbon-carbon links. Due to its potential for recreational use, benzyl cyanide is strictly regulated in many countries, including the United States.

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48 views3 pages

Benzyl Cyanide

Benzyl cyanide (BnCN) is an organic compound used as a precursor in the synthesis of various pharmaceuticals, including analgesics and antidepressants. It can be produced through nitrile synthesis and oxidative decarboxylation, and has chemical properties that allow it to form new carbon-carbon links. Due to its potential for recreational use, benzyl cyanide is strictly regulated in many countries, including the United States.

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Benzyl cyanide

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Benzyl cyanide (abbreviated BnCN) is aorganic compoundwith


thechemical formulaCHCHCN. This colorless oily aromatic liquid is
aprecursorI amimportant in numerous compounds inorganic chemistry. [2]
Preparation
Benzyl cyanide can be produced by thenitrile synthesis of
Kolbebetweenbenzyl chlorideand thesodium cyanide[3] and by
theoxidative decarboxylationfrom thephenylalanine. [4]
Chemical properties
Benzyl cyanide canhydrolyzeto givephenylacetic acid[5] o
to be used in thePinner reactionto produceesters ofacid
phenylacetic. [6] The compound also forms a 'methylene unitaactive
in the carbon between the ringaromaticand thenitrile functional group. This carbon
active, denominatednitrile anion, it is areactive intermediaryuseful for the
formation of newcarbon-carbon links. [7] [8] [9]
Uses
Benzyl cyanide is used as a solvent [10] and as a starting material.
in the synthesis offungicides, [11] fragrances (alcohol
phenethylic), antibiotics, [2] and otherspharmaceutical productsHydrolysis
BnCN partial results in 2-
phenylacetamide, [12] aanticonvulsantcoknown.
Pharmaceutical products
Benzyl cyanide is aprecursoruseful for numerous products
pharmaceuticals. Examples include:

Anorectics(for example,sibutramine) [13]


Analgesics(p.Ex., Etoheptazine, cetobemidone, petidineyfenoperidine)
[13]
Antiarrhythmics(e.g.,Disopyramide
Antidepressants(e.g.,Venlafaxine13
Antihistamines(e.g.,Levocabastineychlorpheniramine
Antimalarial drugs(e.g.Pyrimethamine
Antitussives(p.Ej. , Isoamineoxeladina
butetamatopentapiperidaypentoxiverine
Diuretics(e.g.,Triamterene) [16]
Hypnotics(e.g., Alonimid andphenobarbital
Antispasmodics(e.g., Pentapiperide and drofenine) [13] [18]
Stimulants(e.g.Methylphenidate
Azatadine

Regulation
Due to the fact that benzyl cyanide is aprecursoruseful for
numerousmedications with potential for recreational use, many countries
they strictly regulate the compound.
United States
Benzyl cyanide is regulated in the United States as achemical of
the DEA List I.
Security
Benzyl cyanide, like related benzyl derivatives, is a
irritating to the skin and eyes. It is toxic and produces the deadly poison.cyanide
of hydrogenwhen it burns.
References

1. Nomenclature of Organic Chemistry: Recommendations of the IUPAC and


Preferential Names 2013 (Blue Book). Cambridge:the Royal Society of
Chemistry2014. p. 16.doi: 10.1039 / 9781849733069-FP001. ISBN978-
0-85404-182-4.
2. Pollak, Peter; Romeder, Gérard; Hagedorn, Fernando; Gelbke, Heinz-Peter
(2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry
Industrial.doi: 10.1002 / 14356007.a17_363.
Benzyl Cyanide
Organics.2: 9.doi: 10.15227 / orgsyn.002.0009.
4. Hiegel, Gene; Lewis, Justin; Bae, Jason (2004). "Conversion of α-
amino acids in nitriles by oxidative decarboxylation with acid
trichloroisocyanuric acid. Synthetic communications.34(19): 3449-
3453.doi: 10.1081 / SCC-200030958.
Phenylacetic Acid
Organics.2: 59.doi: 10.15227 / orgsyn.002.0059.
6. Adams, Roger; Thal, AF (1922). "Ethyl phenylacetate". Synthesizers
Organics.2: 27.doi: 10.15227 / orgsyn.002.0027.
7. Makosza, M.; Jonczyk, A (1976). "Phase transfer alkylation of
nitriles: 2-phenylbutyronitrile. Organic Synthesizers.55: 91.doi: 10.15227
/ orgsyn.055.0091.
8. Itoh, Masumi; Hagiwara, Daijiro; Kamiya, Takashi (1988). "New reagent
for the tert-butoxycarbonylation: 2-tert-butoxycarbonylamino-2-
phenylacetonitrile. Organic Synthesizers. 6: 199.doi: 10.15227 /
.
9. Wawzonek, Stanley; Smolin, Edwin M. (1955). "α-
"phenylcinnamitrile". Organic Synthesizers.3: 715.doi: 10.15227 /
orgsyn.029.0083.
10. Well, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2000). "Colorants and
intermediates of anthraquinone. Ullmann's Encyclopedia of Industrial Chemistry:
29.doi: 10.1002 / 14356007.a02_355.
11.Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides,
"Agricultural". Ullmann's Encyclopedia of Industrial Chemistry.doi: 10.1002 /
14356007.a12_085.
12. "PHENYLACETAMIDE". Organic Synthesizers. 32: 92.
1952doi: 10.15227 / orgsyn.032.0092. ISSN0078-6209.
13. 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, y
3410.ISBN9780815515265
14. Berkoff, Charles E.; Rivard, Donald E.; Kirkpatrick, David; Ives, Jeffrey L.
(1980). "Decyanation Reductive of Nitriles by Alkali
"Fusion". Synthetic Communications. 10(12): 939 - 945.doi: 10.1080 /
00397918008061855.
Remedies for Cough
from Ullmann's Industrial Chemistry.doi: 10.1002 / 14356007.a08_013.
16. Hropot, Max; Lang, Hans-Jochen (2000). "Diuretics". Encyclopedia of
Ullmann's Encyclopedia of Industrial Chemistry.doi: 10.1002 / 14356007.a09_029.
17.Furniss, Brian; Hannaford, Antony; Smith, Peter y Tatchell, Austin
(1996).Vogel's Textbook of Practical Organic Chemistry 5th EdLondon:
Longman Science & Technical. pp. 1174-1179.ISBN9780582462366.
18. Bungardt, Edwin; Mutschler, Ernst (2000). "Spasmolytics". Encyclopedia of
Ullmann's Encyclopedia of Industrial Chemistry.doi: 10.1002 / 14356007.a24_515.

external links

Chemical profile of EPA for phenylacetonitrile

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