Cinnamonitrile

Cinnamonitrile

Names
IUPAC name (E)-3-phenylprop-2-enenitrile
Other names trans-Cinnamonitrile trans-β-Phenylacrylonitrile (E)-3-Phenyl-2-propenenitrile
Identifiers
CAS Number	1885-38-7 4360-47-8 (unspecified geometry)
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2387747
ChemSpider	1267328
ECHA InfoCard	100.015.957
EC Number	217-552-5
PubChem CID	1550846
UNII	H475UV3WWH
CompTox Dashboard (EPA)	DTXSID8044385
InChI InChI=1S/C9H7N/c10-8-4-7-9-5-2-1-3-6-9/h1-7H/b7-4+ Key: ZWKNLRXFUTWSOY-QPJJXVBHSA-N
SMILES C(=C/C#N)\C1=CC=CC=C1
Properties
Chemical formula	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]
Pictograms
Signal word	Danger
Hazard statements	H301, H312, H317
Precautionary statements	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). Infobox references

(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.

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

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. Yu, Chao-sheng; Pan, Cheng-jun; Xie, Jin; Li, Bin (2007). "Quick synthesis of trans-cinnamyl nitrile". CNKI.
5. 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.
6. 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.