(E)-Cinnamonitrile is an organic compound approved for use as a fragrance in products such as air fresheners.[2][3] It has a spicy cinnamon aroma.
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| Names | |
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| IUPAC name
(E)-3-phenylprop-2-enenitrile
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.015.957 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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:[1] | |
 
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| 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).
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Synthetic routes include an aldol-like condensation of benzaldehyde with acetonitrile under alkaline conditions,[4] an elimination reaction of various oximes derived from cinnamaldehyde,[5] and oxidative coupling of benzene to acrylonitrile.[6]
References
edit- ^ "Cinnamonitrile". pubchem.ncbi.nlm.nih.gov.
- ^ "IFRA Standard, Amendment 49: Cinnamyl nitrile" (PDF). International Fragrance Association. 2020. Retrieved 2022-06-23.
- ^ "Cinnamonitrile". Consumer Product Information Database. Retrieved 2022-06-23.
- ^ Yu, Chao-sheng; Pan, Cheng-jun; Xie, Jin; Li, Bin (2007). "Quick synthesis of trans-cinnamyl nitrile". CNKI.
- ^ 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.
- ^ 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.
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