Tivirapine

Base Information

• Chemical Name: Tivirapine
• CAS No.: 137332-54-8
• Molecular Formula: C16H20ClN3S
• Molecular Weight: 321.874
• NSC Number: 636661
• UNII: 7WP69N3Y3Y
• DSSTox Substance ID: DTXSID00160138
• Nikkaji Number: J1.572.197I,J443.656C
• Wikidata: Q27097800
• NCI Thesaurus Code: C76930
• Metabolomics Workbench ID: 151725
• ChEMBL ID: CHEMBL58711
• Mol file: 137332-54-8.mol

Synonyms:8-chloro-TIBO;8-chlorotetrahydroimidazo(4,5,1-jk)(1,4)-benzodiazepin-2(1H)-thione

Chemical Property of Tivirapine

Chemical Property:

• Vapor Pressure: 3.73E-08mmHg at 25°C
• Boiling Point: 446.1°C at 760 mmHg
• Flash Point: 223.6°C
• PSA: 56.62000
• Density: 1.25g/cm³
• LogP: 5.14310
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 321.1066465
• Heavy Atom Count: 21
• Complexity: 449

Purity/Quality:

TIVIRAPINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN2C3=C(C=CC(=C3CN1CC=C(C)C)Cl)NC2=S
• Isomeric SMILES: C[C@H]1CN2C3=C(C=CC(=C3CN1CC=C(C)C)Cl)NC2=S

Technology Process of Tivirapine

There total 15 articles about Tivirapine 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: 54.0%

(S)-6-chloro-2,3,4,5-tetrahydro-3-methyl-4-(3-methyl-2-butenyl)-1H-1,4-benzodiazepin-9-amine (149976-82-9) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → Tivirapine (137332-54-8,257891-65-9)

Guidance literature:

In tetrahydrofuran; for 0.5h; Heating;

DOI:10.1021/jm00005a006

Reference yield:

chloroform (67-66-3,8013-54-5) + (S)-6-chloro-2,3,4,5-tetrahydro-3-methyl-4-(3-methyl-2-butenyl)-1H-1,4-benzodiazepin-9-amine (149976-82-9) → Tivirapine (137332-54-8,257891-65-9)

Guidance literature:

With carbon disulfide; potassium hydroxide; In ethanol; acetonitrile;

Reference yield:

(+)-(S)-6-Chloro-3-methyl-9-nitro-2,3,4,5-tetrahydro-1H-<1,4>benzodiazepine (137332-58-2) → Tivirapine (137332-54-8,257891-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.93 g / Na₂CO₃, KI / dimethylformamide / 16 h / Ambient temperature

2: 1.75 g / LAH / tetrahydrofuran / 8 h / Heating

3: 54 percent / tetrahydrofuran / 0.5 h / Heating

With lithium aluminium tetrahydride; sodium carbonate; potassium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm00005a006

upstream raw materials:

carbon disulfide

(S)-6-chloro-2,3,4,5-tetrahydro-3-methyl-4-(3-methyl-2-butenyl)-1H-1,4-benzodiazepin-9-amine

1,1'-Thiocarbonyldiimidazole

2,6-dichloro-3-nitrobenzaldehyde