Thiarubrine A

Base Information

• Chemical Name: Thiarubrine A
• CAS No.: 63543-09-9
• Molecular Formula: C13H8S2
• Molecular Weight: 228.3326
• Hs Code.: 2934999090
• UNII: DVV5W0EG1Z
• DSSTox Substance ID: DTXSID80212947
• Nikkaji Number: J489.431F
• Wikidata: Q27108431
• Metabolomics Workbench ID: 67881
• Mol file: 63543-09-9.mol

Synonyms:1-(2-methyleth-1-yn)-4-(hex-1,3-diyn-5-ene)-2,3-dithiacyclohex-1,3-diene;thiarubrine A

Chemical Property of Thiarubrine A

Chemical Property:

• Vapor Pressure: 0.00033mmHg at 25°C
• Boiling Point: 329.9°Cat760mmHg
• Flash Point: 188.3°C
• PSA: 50.60000
• Density: 1.24g/cm³
• LogP: 3.36530
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 228.00674260
• Heavy Atom Count: 15
• Complexity: 521

Purity/Quality:

97% ^*data from raw suppliers

THIARUBRINE A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CC1=CC=C(SS1)C#CC#CC=C

Technology Process of Thiarubrine A

There total 8 articles about Thiarubrine A 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:

hexadiynedial (114843-16-2) → Thiarubrine A (63543-09-9)

Guidance literature:

Multi-step reaction with 8 steps

1: KOH / dimethylformamide / 3 h / Ambient temperature

2: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) n-BuLi, 3.) BF₃*Et₂O

4: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

5: 54 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C

6: 41 percent / Pd(PPh₃)4, CuI, NEt₃ / toluene / 4 h / Ambient temperature

7: TBAF, 3A molecular sieves / tetrahydrofuran / 1 h / Ambient temperature

8: I₂ / 0.5 h / Ambient temperature

With potassium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00102a058

Reference yield:

(5Z,7Z)-5,8-Bis-(2-trimethylsilanyl-ethylsulfanyl)-undeca-5,7-diene-1,3,9-triyne → Thiarubrine A (63543-09-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 41 percent / Pd(PPh₃)4, CuI, NEt₃ / toluene / 4 h / Ambient temperature

2: TBAF, 3A molecular sieves / tetrahydrofuran / 1 h / Ambient temperature

3: I₂ / 0.5 h / Ambient temperature

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3 A molecular sieve; tetrabutyl ammonium fluoride; iodine; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/ja00102a058

Reference yield:

(4Z,6Z)-4,7-Bis-(2-trimethylsilanyl-ethylsulfanyl)-deca-4,6-diene-2,8-diynal → Thiarubrine A (63543-09-9)

Guidance literature:

Multi-step reaction with 5 steps

1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: 54 percent / n-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C

3: 41 percent / Pd(PPh₃)4, CuI, NEt₃ / toluene / 4 h / Ambient temperature

4: TBAF, 3A molecular sieves / tetrahydrofuran / 1 h / Ambient temperature

5: I₂ / 0.5 h / Ambient temperature

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 3 A molecular sieve; tetrabutyl ammonium fluoride; iodine; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja00102a058

upstream raw materials:

hexadiynedial

(2Z,4Z)-2,5-Bis-benzylsulfanyl-hexa-2,4-dienedial

C₂₂H₁₈Br₄S₂

Downstream raw materials:

2-hex-5-ene-1,3-diynyl-5-prop-1-ynyl-thiophene