Cinnamonitrile

Cinnamonitrile
Names
IUPAC name
(E)-3-phenylprop-2-enenitrile
Other names
    • trans-Cinnamonitrile
    • trans-β-Phenylacrylonitrile
    • (E)-3-Phenyl-2-propenenitrile
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.015.957 Edit this at Wikidata
EC Number
  • 217-552-5
UNII
  • InChI=1S/C9H7N/c10-8-4-7-9-5-2-1-3-6-9/h1-7H/b7-4+
    Key: ZWKNLRXFUTWSOY-QPJJXVBHSA-N
  • C(=C/C#N)\C1=CC=CC=C1
Properties
C9H7N
Molar mass 129.162 g·mol−1
Density 1.0374 (15.2 °C)
Melting point 22 °C (72 °F; 295 K)
Boiling point 263.8 °C (506.8 °F; 537.0 K)
log P 1.96
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
Danger
H301, H312, H317
P261, P264, P270, P272, P280, P301+P316, P302+P352, P317, P321, P330, P333+P313, P362+P364, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(E)-Cinnamonitrile is an organic compound approved for use as a fragrance in products such as air fresheners. It has a spicy cinnamon/cassia aroma.

Synthetic routes include an aldol-like condensation of benzaldehyde with acetonitrile under alkaline conditions, an elimination reaction of various oximes derived from cinnamaldehyde, and oxidative coupling of benzene to acrylonitrile.

References

  1. ↑ "Cinnamonitrile". pubchem.ncbi.nlm.nih.gov.
  2. ↑ "IFRA Standard, Amendment 49: Cinnamyl nitrile" (PDF). International Fragrance Association. 2020. Retrieved 2022-06-23.
  3. ↑ "Cinnamonitrile". Consumer Product Information Database. Retrieved 2022-06-23.
  4. ↑ "cinnamyl nitrile". Scents and Flavors. Scents and Flavors. Retrieved 29 March 2026.
  5. ↑ Yu, Chao-sheng; Pan, Cheng-jun; Xie, Jin; Li, Bin (2007). "Quick synthesis of trans-cinnamyl nitrile". CNKI.
  6. ↑ An, Xiao-De; Yu, Shouyun (2015). "Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source". Organic Letters. 17 (20): 5064–5067. doi:10.1021/acs.orglett.5b02547. PMID 26418564.
  7. ↑ Obora, Yasushi; Okabe, Yoshihisa; Ishii, Yasutaka (2010). "journal Direct oxidative coupling of benzenes with acrylonitriles to cinnamonitriles catalyzed by Pd(OAc)2/HPMoV/O2 system". Organic & Biomolecular Chemistry. 8 (18): 4071–4073. doi:10.1039/c0ob00176g. PMID 20652185.