2,2-Dimethylpropanethioamide

Base Information

• Chemical Name: 2,2-Dimethylpropanethioamide
• CAS No.: 630-22-8
• Molecular Formula: C5H11 N S
• Molecular Weight: 117.215
• Hs Code.: 2930909899
• European Community (EC) Number: 677-829-5
• NSC Number: 381432
• DSSTox Substance ID: DTXSID00388714
• Nikkaji Number: J134.572I
• Mol file: 630-22-8.mol

Synonyms:2,2-dimethylpropanethioamide;630-22-8;2,2,2-Trimethylthioacetamide;2,2-Dimethylthiopropionamide;Propanethioamide, 2,2-dimethyl-;Neopentanethioamide;thiopivalamide;2,2-dimethyl-thiopropionamide;2,2-dimethylthio propionamide;SCHEMBL1026012;NIOSH/UE4523000;SCHEMBL12102191;DTXSID00388714;2-Methyl-2-methylthiopropionamide;FJZJUSOFGBXHCV-UHFFFAOYSA-N;MFCD09742834;NSC381432;AKOS000150524;Propionamide, 2-methyl-2-methylthio-;NSC-381432;AS-10697;AM20100553;CS-0044786;FT-0698711;UE45230000;EN300-36990;A846842;Z278180216

Chemical Property of 2,2-Dimethylpropanethioamide

Chemical Property:

• Vapor Pressure: 2.2mmHg at 25°C
• Melting Point: 117-119℃ (ethyl acetate hexane )
• Boiling Point: 162.1±23.0℃ (760 Torr)
• PKA: 13.33±0.29(Predicted)
• Flash Point: 51.9±22.6℃
• PSA: 58.11000
• Density: 0.978±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 2.01890
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Soluble in water (10 g/L) (25°C).
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 117.06122053
• Heavy Atom Count: 7
• Complexity: 80.6

Purity/Quality:

99.9% ^*data from raw suppliers

2,2-Dimethylthiopropionamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=S)N
• Uses: 2,2-Dimethylthiopropionamide is used as a reagent to synthesize Dabrafenib, an inhibitor of BRAF kinase that is used to treat BRAF V600-mutation positive carcinoma. BRAF is a gene that mediates cell growth and is activated by mutations caused by cancer. 2,2-Dimethylthiopropionamide is also used as a reagent to prepare sulfonyl-substituted 4,5-diarylthiazoles, compounds that act as cyclooxygenase-2 inhibitors (anti-inflammatory agents).

Technology Process of 2,2-Dimethylpropanethioamide

There total 2 articles about 2,2-Dimethylpropanethioamide 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: 49.0%

→ 2,2-dimethylpropanethioamide (630-22-8) + 2-(tert-butyl)-4-(4-fluorophenyl)-5-[(4-methylsulfonyl)phenyl]thiazole

Guidance literature:

Reference yield:

thiopivalamide S-oxide (107106-62-7) → 2,2-dimethylpropionamide (754-10-9) + 2,2-dimethylpropanethioamide (630-22-8)

Guidance literature:

In chloroform-d1; at 55 ℃; Yield given. Yields of byproduct given;

Reference yield: 86.0%

2,2-dimethylpropanethioamide (630-22-8) + tert-butyl (3-(2-(2-chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)carbamate → tert-butyl (3-(2-(tert-butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)carbamate

Guidance literature:

tert-butyl (3-(2-(2-chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)carbamate; With N-Bromosuccinimide; In N,N-dimethyl acetamide; at 20 ℃; for 1h;

2,2-dimethylpropanethioamide; In N,N-dimethyl acetamide; at 20 - 50 ℃;

upstream raw materials:

thiopivalamide S-oxide

Downstream raw materials:

2-tert-butyl-5,6-diphenyl-5,6-dihydro-[1,3]thiazin-4-one

2,2-Dimethyl-thiopropionimidic acid (Z)-3-oxo-3-phenyl-propenyl ester; compound with perchloric acid

2-(tert-butyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole

2,2-dimethylpropionamide

Refernces

• 1、 Hillhouse, John H.,Blair, Ian A.,Field, Lamar. "THIONO COMPOUNDS. 7. OXIDATION OF THIOAMIDES IN RELATION TO ADVERSE BIOLOGICAL EFFECTS". . p. 169 - 184. Retrieved 2007/10/02.