1-Azidoethenylbenzene

Base Information

• Chemical Name: 1-Azidoethenylbenzene
• CAS No.: 16717-64-9
• Molecular Formula: C8H8N3+
• Molecular Weight: 145.164
• NSC Number: 247556
• DSSTox Substance ID: DTXSID20402007
• Nikkaji Number: J909.469E
• Mol file: 16717-64-9.mol

Synonyms:1-azidoethenylbenzene;(1-azidovinyl)benzene;16717-64-9;(1-Azidoethenyl)benzene;Benzene, (1-azidoethenyl)-;alpha-Azidostyrene;alpha-azido styrene;DTXSID20402007;CAUJWSPJKGGYDW-UHFFFAOYSA-N;NSC247556;NSC-247556;EN300-6740346

Chemical Property of 1-Azidoethenylbenzene

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 145.063997236
• Heavy Atom Count: 11
• Complexity: 186

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1-Azidoethenylbenzene

There total 10 articles about 1-Azidoethenylbenzene 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: 92.0%

(1,2-dibromoethyl)benzene (102921-26-6,93-52-7) → 1-azidostyrene (16717-64-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1039/c5cc01155h

Reference yield: 86.0%

phenylacetylene (536-74-3) → 1-azidostyrene (16717-64-9)

Guidance literature:

With silver(I) azide; trimethylsilylazide; water; In dimethyl sulfoxide; at 80 ℃; Reagent/catalyst;

DOI:10.1021/jacs.0c00836

Reference yield: 85.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → 1-azidostyrene (16717-64-9)

Guidance literature:

styrene; With sodium azide; Iodine monochloride; In dichloromethane; acetonitrile; at -20 - 28 ℃; for 1.5h; Inert atmosphere;

With potassium tert-butylate; In diethyl ether; dichloromethane; acetonitrile; at 0 - 28 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201500694

upstream raw materials:

styrene

1-(1-azido-2-bromoethyl)benzene

(1,2-dibromoethyl)benzene

phenylvinylboronic acid

Downstream raw materials:

3a,4,5,6,7,7a-hexahydro-1-(1-phenylvinyl)-7a-(1-pyrrolidinyl)-1H-1,2,3-benzotriazole

7a-morpholino-1-(1-phenylvinyl)-3a,4,5,6,7,7a-hexahydro-1H-1,2,3-benzotriazole

caprophenone

acetophenone

Refernces

• 1、 Smolinsky,G.. "-". . p. 3557 - 3559. Retrieved 1962.
• 2、 Hassner,A. et al.. "-". . p. 4879 - 4883. Retrieved 1970.
• 3、 Mulina, Olga M.,Ilovaisky, Alexey I.,Opatz, Till,Terent'ev, Alexander O.. "Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates". . . Retrieved 2021/01/11.
• 4、 Mulina, Olga M.,Doronin, Mikhail M.,Terent'ev, Alexander O.. "Electrosynthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates mediated by NH4I". . . Retrieved 2021/10/16.