3-phenyl-3H-diazirine

Base Information

• Chemical Name: 3-phenyl-3H-diazirine
• CAS No.: 42270-91-7
• Molecular Formula: C7H6N2
• Molecular Weight: 118.138
• DSSTox Substance ID: DTXSID00445912
• Nikkaji Number: J264.357J
• Mol file: 42270-91-7.mol

Synonyms:3-phenyl-3H-diazirine;42270-91-7;SCHEMBL587341;DTXSID00445912;EN300-33309214

Chemical Property of 3-phenyl-3H-diazirine

Chemical Property:

• PSA: 24.72000
• LogP: 1.02220
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 118.053098200
• Heavy Atom Count: 9
• Complexity: 119

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2N=N2

Technology Process of 3-phenyl-3H-diazirine

There total 8 articles about 3-phenyl-3H-diazirine 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: 80.0%

2,4,6-triphenyl-1,3,5-triazabicyclo(3.1.0)hexane → 3-phenyl-3H-diazirine (42270-91-7)

Guidance literature:

With tert-butylhypochlorite; In methanol; tert-butyl alcohol; 1.) 0 deg C, 1 h, 2.) RT, 20 min.;

DOI:10.1021/ja00242a034

Reference yield: 32.3%

2,4,6-triphenyl-1,3,5-triazabicyclo[3.1.0]hexane (56782-50-4) → 3-phenyl-3H-diazirine (42270-91-7)

Guidance literature:

With tert-butylhypochlorite; In methanol; tert-butyl alcohol; at 0 - 20 ℃;

DOI:10.1039/b310148g

Reference yield: 20.0%

3-bromo-3-phenyl-3H-diazirine (4222-25-7) → benzonitrile (100-47-0) + 3-phenyl-3H-diazirine (42270-91-7)

Guidance literature:

With methyllithium; In tetrahydrofuran; diethyl ether; pentane; at -115 ℃; for 1h;

DOI:10.1021/acs.orglett.6b01753

upstream raw materials:

tetrabutylammonium acetate

3-bromo-3-phenyl-3H-diazirine

Potassium benzoate

benzaldehyde

Downstream raw materials:

phenyldiazomethane

phenylcarbene

allyl(benzyl)sulfide

Triplett-Cycloheptatrienyliden

Refernces

• 1、 Navrátil, Rafael,Tarábek, Ján,Linhart, Igor,Martin?, Tomá?. "Radical and Nitrenoid Reactivity of 3-Halo-3-phenyldiazirines". supporting information. p. 3734 - 3737. Retrieved 2016/08/16.
• 2、 Likhotvorik, Igor R.,Tae, Eunju Lee,Ventre, Celine,Platz, Matthew S.. "A facile one-pot conversion of non-enolizable aldehydes to diazirines". . p. 795 - 796. Retrieved 2007/10/03.