Cinnamyl formate

Base Information

• Chemical Name: Cinnamyl formate
• CAS No.: 23510-72-7
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Hs Code.: 2942000000
• European Community (EC) Number: 203-223-3
• NSC Number: 21737
• UNII: 896AGS89RD
• DSSTox Substance ID: DTXSID401265889
• Nikkaji Number: J141.582D,J35.356F
• Wikidata: Q27270010
• Mol file: 23510-72-7.mol

Synonyms:cinnamyl formate

Chemical Property of Cinnamyl formate

Chemical Property:

• Boiling Point: 252 °C at 760 mmHg
• Flash Point: 127.668 °C
• PSA: 26.30000
• Density: 1.077 g/cm³
• LogP: 2.50870
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 146

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CCOC=O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/COC=O

Technology Process of Cinnamyl formate

There total 5 articles about Cinnamyl formate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) + formic acid ethyl ester (109-94-4) → (2E)-3-phenylprop-2-en-1-yl formate (23510-72-7)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; for 1.08333h; Heating;

Reference yield: 75.0%

formic acid (64-18-6) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (2E)-3-phenylprop-2-en-1-yl formate (23510-72-7)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 80 ℃; for 12h; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201701971

Reference yield:

(E)-3-phenylpropenal (14371-10-9) → (2E)-3-phenylprop-2-en-1-yl formate (23510-72-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 0 °C / Schlenk technique; Inert atmosphere

2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 12 h / 80 °C / Schlenk technique; Inert atmosphere

With sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In methanol; toluene;

DOI:10.1002/chem.201701971

upstream raw materials:

formic acid

(2E)-3-phenyl-2-propen-1-ol

carbon disulfide

formic acid ethyl ester

Downstream raw materials:

1,4-dimethyl-2-[(2E)-3-phenylprop-2-en-1-yl]benzene

ethyl (3-phenyl-propyl)phosphinate

(2E)-3-phenyl-2-propen-1-ol

1-(triethylsilyl)oxy-3-phenyl-2-propene

Refernces

• 1、 Iranpoor, Nasser,Firouzabadi, Habib,Jamalian, Arezu. "Silphos [PCl3-n(SiO2)n]: A heterogeneous phosphine reagent for formylation and acetylation of alcohols and amines with ethyl formate and acetate". . p. 7963 - 7966. Retrieved 2007/10/03.
• 2、 Mohammadpoor-Baltork,Khosropour,Aliyan. "A convenient and chemoselective acetylation and formylation of alcohols and phenols using acetic acid and ethyl formate in the presence of Bi(III) salts". . p. 280 - 282. Retrieved 2007/10/03.