3-(4-Iodophenyl)-3-(trifluoromethyl)diaziridine

Base Information

• Chemical Name: 3-(4-Iodophenyl)-3-(trifluoromethyl)diaziridine
• CAS No.: 210107-37-2
• Molecular Formula: C8H6F3IN2
• Molecular Weight: 314.049
• DSSTox Substance ID: DTXSID30471103
• Wikidata: Q82299522
• Mol file: 210107-37-2.mol

Synonyms:3-(4-Iodophenyl)-3-(trifluoromethyl)diaziridine;210107-37-2;Diaziridine, 3-(4-iodophenyl)-3-(trifluoromethyl)-;SCHEMBL4659859;DTXSID30471103;AKOS015966154

Chemical Property of 3-(4-Iodophenyl)-3-(trifluoromethyl)diaziridine

Chemical Property:

• PSA: 43.88000
• LogP: 2.77170
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 313.95278
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2(NN2)C(F)(F)F)I

Technology Process of 3-(4-Iodophenyl)-3-(trifluoromethyl)diaziridine

There total 4 articles about 3-(4-Iodophenyl)-3-(trifluoromethyl)diaziridine 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%

O-p-tosyloxime 4'-iodo-2,2,2-trifluoroacetophenone (210107-36-1) → 3-(p-iodophenyl)-3-(trifluoromethyl)diaziridine (210107-37-2)

Guidance literature:

With ammonia; In diethyl ether; at -78 - 20 ℃; for 16h;

DOI:10.1021/jm050958a

Reference yield:

oxime 4'-iodo-2,2,2-trifluoroacetophenone (210107-35-0) → 3-(p-iodophenyl)-3-(trifluoromethyl)diaziridine (210107-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / 2 h / Heating

2: 96 percent / NH₃ / diethyl ether / 16 h / -78 - 20 °C

With pyridine; ammonia; In diethyl ether;

DOI:10.1021/jm050958a

Reference yield:

para-diiodobenzene (624-38-4,1032416-46-8) → 3-(p-iodophenyl)-3-(trifluoromethyl)diaziridine (210107-37-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / n-BuLi / diethyl ether / 4 h / -78 - 20 °C

2: 94 percent / NH₂OH*HCl; pyridine / ethanol / 2 h / Heating

3: 94 percent / pyridine / 2 h / Heating

4: 96 percent / NH₃ / diethyl ether / 16 h / -78 - 20 °C

With pyridine; n-butyllithium; hydroxylamine hydrochloride; ammonia; In diethyl ether; ethanol;

DOI:10.1021/jm050958a

upstream raw materials:

O-p-tosyloxime 4'-iodo-2,2,2-trifluoroacetophenone

para-diiodobenzene

2,2,2-trifluoro-1-(4-iodophenyl)ethan-1-one

oxime 4'-iodo-2,2,2-trifluoroacetophenone

Downstream raw materials:

N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)-3H-diazirin-3-yl]-L-phenylalanine tert-butyl ester

(S)-N-(9-fluorenylmethoxycarbonyl)-[4-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine

1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenyl]-1H-pyrimidine-2,4-dione

N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl ester

Refernces

• 1、 Topin, Andrey N.,Gritsenko, Oxana M.,Brevnov, Maxim G.,Gromova, Elisaveta S.,Korshunova, Galina A.. "Synthesis of a new photo-cross-linking nucleoside analogue containing an aryl(trifluoromethyl)diazirine group: Application for EcoRII and MvaI restriction-modification enzymes". . p. 1163 - 1175. Retrieved 2007/10/03.