1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea

Base Information

• Chemical Name: 1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea
• CAS No.: 1060-92-0
• Molecular Formula: C17H8F12N2S
• Molecular Weight: 500.311
• DSSTox Substance ID: DTXSID20384410
• Nikkaji Number: J1.874.415E
• Mol file: 1060-92-0.mol

Synonyms:1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea;1060-92-0;1,3-bis(3,5-bis(trifluoromethyl)phenyl)thiourea;Schreiner's thiourea;Thiourea, 1,3-bis(3,5-ditrifluoromethylphenyl)-;Schreiner's Thiourea Catalyst;SCHEMBL11009249;C17H8F12N2S;DTXSID20384410;MFCD00829878;CS-W009618;AS-67290;B3452;T70053;A895858;N,N'-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea #;Carbanilide, thio-3,3',5,5'-tetrakis-(trifluoromethyl)-

Chemical Property of 1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea

Chemical Property:

• Vapor Pressure: 0.000143mmHg at 25°C
• Melting Point: 150.0 to 157.0 °C
• Boiling Point: 332.7oC at 760 mmHg
• PKA: 10.78±0.70(Predicted)
• Flash Point: 155oC
• PSA: 63.19000
• Density: 1.604g/cm3
• LogP: 7.86420
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 2
• Exact Mass: 500.0216574
• Heavy Atom Count: 32
• Complexity: 556

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C=C1C(F)(F)F)NC(=S)NC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)C(F)(F)F
• Uses: Thiourea catalyst, also known as Schreiner′s Thiourea, is commonly used as a hydrogen-bond donor in the activation of carbonyls, nitroolefins, imines etc.

Technology Process of 1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea

There total 9 articles about 1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea 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: 100.0%

3,5-bistrifluoromethylphenylisothiocyanate (23165-29-9) + 3,5-Bis-(trifluoromethyl)aniline (328-74-5) → 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea (1060-92-0)

Guidance literature:

In methanol; for 0.5h;

DOI:10.1002/chem.201200632

Reference yield: 84.0%

thiophosgene (463-71-8) + 3,5-Bis-(trifluoromethyl)aniline (328-74-5) → 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea (1060-92-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; at -5 - 20 ℃;

DOI:10.1016/j.tet.2005.09.079

Reference yield: 61.3%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + 3,5-Bis-(trifluoromethyl)aniline (328-74-5) → 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea (1060-92-0)

Guidance literature:

In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/ejoc.201200739

upstream raw materials:

3,5-bistrifluoromethylphenylisothiocyanate

3,5-Bis-(trifluoromethyl)aniline

thiophosgene

C₂₉H₁₆F₁₂N₂SSi

Downstream raw materials:

C₂₉H₁₆F₁₂N₂SSi

C₁₇H₆Cl₂F₁₂N₂SSi

C₁₇H₈F₁₂N₂S*C₅H₈O₂

C₁₇H₈F₁₂N₂S*C₆H₁₀O

Refernces

• 1、 Ghosh, Titli,Mukherji, Ananya,Kancharla, Pavan K.. "Influence of Anion-Binding Schreiner's Thiourea on DMAP Salts: Synergistic Catalysis toward the Stereoselective Dehydrative Glycosylation from 2-Deoxyhemiacetals". . p. 1253 - 1261. Retrieved 2021.
• 2、 Grill, Kerstin,Dube, Henry. "Supramolecular relay-control of organocatalysis with a hemithioindigo-based molecular motor". . p. 19300 - 19307. Retrieved 2020.
• 3、 Tao, Youhua,Li, Maosheng,Tao, Yue,Tang, Jiadong,Wang, Yanchao,Zhang, Xiaoyong,Wang, Xianhong. "Synergetic Organocatalysis for Eliminating Epimerization in Ring-Opening Polymerizations Enables Synthesis of Stereoregular Isotactic Polyester". supporting information. p. 281 - 289. Retrieved 2019/01/04.