(+)-Benzotetramisole

Base Information

• Chemical Name: (+)-Benzotetramisole
• CAS No.: 885051-07-0
• Molecular Formula: C₁₅H₁₂N₂S
• Molecular Weight: 252.34
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60468566
• Nikkaji Number: J2.301.100J
• Wikidata: Q82295824
• Mol file: 885051-07-0.mol

Synonyms:benzotetramisole

Chemical Property of (+)-Benzotetramisole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 95.0-95.5℃ (ethyl ether hexane )
• Refractive Index: 1.736
• Boiling Point: 428.075°C at 760 mmHg
• PKA: 7.53±0.40(Predicted)
• Flash Point: 212.692°C
• PSA: 45.53000
• Density: 1.328g/cm³
• LogP: 2.79400
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 252.07211956
• Heavy Atom Count: 18
• Complexity: 348

Purity/Quality:

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

(+)-Benzotetramisole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(N=C2N1C3=CC=CC=C3S2)C4=CC=CC=C4
• Isomeric SMILES: C1[C@H](N=C2N1C3=CC=CC=C3S2)C4=CC=CC=C4

Technology Process of (+)-Benzotetramisole

There total 25 articles about (+)-Benzotetramisole 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: 98.0%

(S)-N-(2-benzothiazolyl)-2-hydroxy-1-phenylethylamine (1235891-51-6) → (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole (950194-37-3,885051-07-0)

Guidance literature:

(S)-N-(2-benzothiazolyl)-2-hydroxy-1-phenylethylamine; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

With methanol; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at 55 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo1020344

Reference yield: 97.0%

(R)-(-)-2-(benzo[d]thiazol-2-ylamino)-2-phenylethanol → (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole (885051-07-0)

Guidance literature:

(R)-(-)-2-(benzo[d]thiazol-2-ylamino)-2-phenylethanol; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃;

With triethylamine; In methanol; dichloromethane; Heating;

DOI:10.1021/ol060065s

Reference yield: 89.0%

(R)-2-[N-(benzo[d]thiazol-2-yl)methylsulfonamido]-2-phenylethylmethanesulfonate → (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole (885051-07-0)

Guidance literature:

With triethylamine; In methanol; dichloromethane; Reflux;

DOI:10.1055/s-0034-1378931

upstream raw materials:

2-(2-imino-benzothiazol-3-yl)-1-phenyl-ethanol

2-amino-benzthiazole

2-imino-3-phenacyl-2,3-dihydrobenzothiazole hydrobromide

α-bromoacetophenone

Refernces

Nonenzymatic kinetic resolution of racemic 2,2,2-trifluoro-1-aryl ethanol via enantioselective acylation

10.1016/j.tet.2009.01.058

The study focuses on the nonenzymatic kinetic resolution of racemic 2,2,2-trifluoro-1-aryl ethanols, utilizing (R)-benzotetramisole as a catalyst. The aim was to achieve enantioselective acylation, which is crucial for obtaining chiral 1-substituted 2,2,2-trifluoro-ethanols, important intermediates in the synthesis of biologically active molecules. Various aryl-substituted ethanols were tested to evaluate the system's ability to differentiate between enantiomers, with a focus on the impact of different aryl groups on the enantioselectivity, as indicated by the s value. The study also optimized reaction conditions, including the choice of catalyst, acylating reagent, solvent, and reaction temperature, to maximize enantioselectivity and reaction efficiency. The chemicals used served specific purposes: (R)-benzotetramisole as the catalyst to facilitate the reaction, isobutyric anhydride as the acylating reagent to promote acylation, and diisopropyl ether as the solvent providing the appropriate polarity for the reaction. The study demonstrated that certain aryl groups, particularly phenyl and naphthyl groups, could yield high s values, indicating effective kinetic resolution. The research also provided preparative kinetic resolution examples to showcase the method's applicability in preparing enantiomerically pure 2,2,2-trifluoro-1-aryl ethanol derivatives.