Tefludazine

Base Information

• Chemical Name: Tefludazine
• CAS No.: 80273-79-6
• Molecular Formula: C₂₂H₂₄F₄N₂O
• Molecular Weight: 408.439
• UNII: 2XUS19W8FE
• DSSTox Substance ID: DTXSID20878607
• Nikkaji Number: J317.014D
• Wikidata: Q27255779
• NCI Thesaurus Code: C90626
• ChEMBL ID: CHEMBL95636
• Mol file: 80273-79-6.mol

Synonyms:4-(3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl)-1-piperazineethanol;tefludazine;tefludazine dihydrochloride, (cis-(+-))-isomer;tefludazine dihydrochloride, (trans-(+-))-isomer;tefludazine, (1R,3S)-isomer;tefludazine, (1S,3R)-isomer;tefludazine, cis-(+-)-isomer

Chemical Property of Tefludazine

Chemical Property:

• Boiling Point: 476.4°Cat760mmHg
• Flash Point: 241.9°C
• PSA: 26.71000
• Density: 1.285g/cm³
• LogP: 3.90690
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 408.18247604
• Heavy Atom Count: 29
• Complexity: 529

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CCO)C2CC(C3=C2C=C(C=C3)C(F)(F)F)C4=CC=C(C=C4)F
• Isomeric SMILES: C1CN(CCN1CCO)[C@@H]2C[C@H](C3=C2C=C(C=C3)C(F)(F)F)C4=CC=C(C=C4)F

Technology Process of Tefludazine

There total 7 articles about Tefludazine 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: 51.0%

1-(2-hydroxyethyl)piperazine (103-76-4) + 1-chloro-3-(4-fluorophenyl)-6-(trifluoromethyl)indan (85118-26-9) → tefludazine (80273-79-6,85663-48-5,111768-75-3,111768-76-4,80680-06-4) + cis-4-<3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl>-1-piperazineethanol (85663-48-5,80680-06-4)

Guidance literature:

In butanone; for 16h; Heating;

DOI:10.1021/jm00361a002

Reference yield:

3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-one (80272-38-4) → tefludazine (80273-79-6,85663-48-5,111768-75-3,111768-76-4,80680-06-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / sodium borohydride / methanol / 1 h / Ambient temperature

2: 100 percent / SOCl₂ / toluene / 1.) RT, 30 min, 2.) from 50 deg C to 55 deg C, 1 h

3: 51 percent / butan-2-one / 16 h / Heating

With sodium tetrahydroborate; thionyl chloride; In methanol; toluene; butanone;

DOI:10.1021/jm00361a002

Reference yield:

2-bromo-4-(trifluoromethyl)benzaldehyde (85118-24-7) → tefludazine (80273-79-6,85663-48-5,111768-75-3,111768-76-4,80680-06-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / piperidine / toluene / 0.5 h / Heating

2: 1.) Mg / 1.) ether, 2.) ether, toluene, reflux, 30 min

3: aq. H₂SO₄, CH₃COOH / 24 h / Heating

4: 82 percent / n-butyllithium / hexane; diethyl ether / 0.5 h / 0 °C

5: 75 percent / sodium borohydride / methanol / 1 h / Ambient temperature

6: 100 percent / SOCl₂ / toluene / 1.) RT, 30 min, 2.) from 50 deg C to 55 deg C, 1 h

7: 51 percent / butan-2-one / 16 h / Heating

With piperidine; sodium tetrahydroborate; n-butyllithium; thionyl chloride; sulfuric acid; magnesium; acetic acid; In methanol; diethyl ether; hexane; toluene; butanone;

DOI:10.1021/jm00361a002

upstream raw materials:

1-(2-hydroxyethyl)piperazine

1-chloro-3-(4-fluorophenyl)-6-(trifluoromethyl)indan

3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-one

2-bromo-4-(trifluoromethyl)benzaldehyde

Refernces