Allyl cyanide

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Structural formula
Structural formula of allyl cyanide
General
Surname Allyl cyanide
other names
  • 3-butenenitrile
  • Vinyl acetonitrile
  • 3-cyano-1-propene
Molecular formula C 4 H 5 N
Brief description

colorless liquid with an unpleasant odor

External identifiers / databases
CAS number 109-75-1
EC number 203-701-1
ECHA InfoCard 100.003.366
PubChem 8009
Wikidata Q1321290
properties
Molar mass 67.09 g · mol -1
Physical state

liquid

density

0.83 g cm −3 (20 ° C)

Melting point

−87 ° C

boiling point

118.6 ° C

solubility

practically insoluble in water

Refractive index

1.406 (20 ° C)

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 06 - Toxic or very toxic

danger

H and P phrases H: 226-301-331-312-315-319
P: 261-280-301 + 310-305 + 351 + 338-311
Toxicological data
Thermodynamic properties
ΔH f 0

117.8 kJ / mol

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Allyl cyanide is a chemical compound from the group of alkenes and nitriles .

history

Allyl cyanide was first discovered in mustard oil by H. Will and W. Körner in 1863 . It was first synthesized in 1864 by A. Claus or in pure form in 1871 by A. Rinne and B. Tollens from allyl iodide and potassium cyanide .

synthesis

Allyl cyanide, by reaction of allyl bromide with copper (I) cyanide are produced.

Production of allyl cyanide from allyl bromide and copper cyanide

properties

Allyl cyanide is colorless liquid with an unpleasant odor. Their flash point is 23 ° C, the ignition temperature 455 ° C.

An isomeric compound is crotononitrile .

Individual evidence

  1. ↑ a b Allyl cyanide data sheet from AlfaAesar, accessed on May 20, 2010 ( PDF )(JavaScript required) .
  2. ↑ a b c d e f g h Entry on 3-butenenitrile in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  3. ^ Entry on allyl cyanide at ChemicalBook , accessed on September 19, 2011.
  4. ↑ Data sheet Allyl cyanide, 98% from Sigma-Aldrich , accessed on January 19, 2020 ( PDF ).
  5. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-25.
  6. ↑ H. Will, W. Körner: On the knowledge of the formation of mustard oil from the seeds of black mustard , in: Justus Liebigs Annalen der Chemie , 1863 , 125  (3), pp. 257–281; doi : 10.1002 / jlac.18631250302 .
  7. ↑ a b C. Pomeranz: About allyl cyanide and allyl mustard oil , in: Justus Liebigs Annalen der Chemie , 1906 , 351  (1-3), pp. 354-362: doi : 10.1002 / jlac.19073510127 .
  8. ^ A. Claus: Ueber Crotonsäure , in: Justus Liebigs Annalen der Chemie , 1864 , 131  (1), pp. 58-66; doi : 10.1002 / jlac.18641310106 .
  9. ↑ A. Rinne, B. Tollens: Ueber das Allylcyanür or Crotonitril , in: Justus Liebigs Annalen der Chemie , 1871 , 159  (1), pp. 105-109; doi : 10.1002 / jlac.18711590110 .
  10. ↑ JV Supniewski, PL Salzberg: Allyl cyanide In: Organic Syntheses . 8, 1928, p. 4, doi : 10.15227 / orgsyn.008.0004 ; Coll. Vol. 1, 1941, p. 46 ( PDF ).