3-Bromo-3-(4-nitrophenyl)-3H-diazirine

Base Information

• Chemical Name: 3-Bromo-3-(4-nitrophenyl)-3H-diazirine
• CAS No.: 115127-49-6
• Molecular Formula: C7H4BrN3O2
• Molecular Weight: 242.032
• DSSTox Substance ID: DTXSID60471792
• Nikkaji Number: J315.087I
• Mol file: 115127-49-6.mol

Synonyms:3-Bromo-3-(4-nitrophenyl)-3H-diazirine;115127-49-6;3-bromo-3-(4-nitrophenyl)diazirine;3-Bromo-3-(4-nitrophenyl)-3H-diazirene;DTXSID60471792

Chemical Property of 3-Bromo-3-(4-nitrophenyl)-3H-diazirine

Chemical Property:

• Melting Point: 33-35℃
• Boiling Point: 303.3±52.0 °C(Predicted)
• PSA: 70.54000
• Density: 2.00±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 1.96020
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 240.94869
• Heavy Atom Count: 13
• Complexity: 249

Purity/Quality:

99.0%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2(N=N2)Br)[N+](=O)[O-]

Technology Process of 3-Bromo-3-(4-nitrophenyl)-3H-diazirine

There total 2 articles about 3-Bromo-3-(4-nitrophenyl)-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: 11.0%

4-nitrobenzamidine hydrochloride (15723-90-7) → 3-bromo-3-(4-nitrophenyl)diazirine (115127-49-6)

Guidance literature:

With sodium hypobromide; sodium bromide; In water; dimethyl sulfoxide; at 0 ℃; for 3h;

DOI:10.1021/jo00294a010

Reference yield:

4-nitrobenzonitrile (619-72-7) → 3-bromo-3-(4-nitrophenyl)diazirine (115127-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NaOMe, MeOH 2) NH₄Cl / 1) r.t., 55 h 2) 43 deg C, 36 h

2: 11 percent / NaOBr, NaBr / dimethylsulfoxide; H₂O / 3 h / 0 °C

With methanol; sodium hypobromide; sodium methylate; ammonium chloride; sodium bromide; In water; dimethyl sulfoxide;

DOI:10.1021/jo00294a010

Reference yield: 82.0%

3-(2-acetylaminophenyl)acrylic acid ethyl ester (147503-25-1) + 3-bromo-3-(4-nitrophenyl)diazirine (115127-49-6) → ethyl 2-acetyl-1a,6b-dihydro-c-1a-(4-nitrophenyl)cyclopropaindole-r-1-carboxylate

Guidance literature:

With sodium hydride; dimethyl sulfoxide; Product distribution; multistep rection; also with 1,3-dinitrobenzene;

DOI:10.1002/hlca.19930760114

upstream raw materials:

4-nitrobenzamidine hydrochloride

4-nitrobenzonitrile

Downstream raw materials:

N-cyclohexyl-4-nitrobenzamide

4-nitro-N-phenethylbenzamide

N-(adamantan-1-yl)-4-nitrobenzamide

4-nitrobenzamidine

Refernces

• 1、 Creary, Xavier,Sky, Anthony F.,Phillips, Gillian. "SRN1 Reactions of Arylhalodiazirines with Azide Ion". . p. 2005 - 2011. Retrieved 2007/10/02.