3-Phenylprop-2-enoyl azide

Base Information

• Chemical Name: 3-Phenylprop-2-enoyl azide
• CAS No.: 26829-64-1
• Molecular Formula: C9H7N3O
• Molecular Weight: 173.174
• DSSTox Substance ID: DTXSID40707900
• Mol file: 26829-64-1.mol

Synonyms:3-Phenylprop-2-enoyl azide;26829-64-1;DTXSID40707900;1-azido-3-phenylprop-2-ene-1-one

Chemical Property of 3-Phenylprop-2-enoyl azide

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 173.058911855
• Heavy Atom Count: 13
• Complexity: 248

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)N=[N+]=[N-]

Technology Process of 3-Phenylprop-2-enoyl azide

There total 20 articles about 3-Phenylprop-2-enoyl azide 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: 97.3%

Cinnamic acid (621-82-9) → cinnamoyl azide (26829-64-1)

Guidance literature:

Cinnamic acid; With N-Chlorourethan; triethylamine; In acetone; at 0 ℃; for 1h;

With sodium azide; In water; acetone; at 0 ℃; for 7h; Further stages.;

DOI:10.1080/10426500701407441

Reference yield: 95.0%

cinnamoyl chloride (102-92-1,17082-09-6) → cinnamoyl azide (26829-64-1)

Guidance literature:

With polymer-supported azide ion reagent; In chloroform; for 1h; Ambient temperature;

Reference yield: 90.0%

(E)-3-phenylacrylic acid (140-10-3) → (E)-cinnamoyl azide (26829-64-1)

Guidance literature:

With sodium azide; N,N-dimethyl-formamide; trichlorophosphate; at 10 - 15 ℃; for 2h;

DOI:10.1081/SCC-120015815

upstream raw materials:

cinnamoyl chloride

3-phenyl-propenal

Cinnamic acid

cis-cinnamic acid

Downstream raw materials:

(E)-1-isocyanato-2-phenylethene

N-benzyloxycarbonylamino-2-phenyl-(E)-ethylene

cinnamoyl isocyanate

C₁₅H₁₂N₄O

Refernces

• 1、 Elmorsy, Saad S.. "Oxidation of aldehydes to acyl azides using triazidochlorosilane (TACS)-active manganese dioxide reagent". . p. 1341 - 1342. Retrieved 1995.
• 2、 Currie, Iain,Sleebs, Brad E.. "Synthesis of Acyl Phosphoramidates Employing a Modified Staudinger Reaction". supporting information. p. 464 - 468. Retrieved 2021/02/03.
• 3、 Giancotti, Gilda,Cancellieri, Michela,Balboni, Andrea,Giustiniano, Mariateresa,Novellino, Ettore,Delang, Leen,Neyts, Johan,Leyssen, Pieter,Brancale, Andrea,Bassetto, Marcella. "Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus". supporting information. p. 56 - 68. Retrieved 2018/03/06.