1-(4-Bromothiazol-2-YL)ethanone

Base Information

• Chemical Name: 1-(4-Bromothiazol-2-YL)ethanone
• CAS No.: 208264-53-3
• Molecular Formula: C5H4BrNOS
• Molecular Weight: 206.063
• European Community (EC) Number: 836-942-1
• Nikkaji Number: J2.759.456E
• Mol file: 208264-53-3.mol

Synonyms:208264-53-3;1-(4-BROMOTHIAZOL-2-YL)ETHANONE;1-(4-bromo-1,3-thiazol-2-yl)ethanone;2-acetyl-4-bromothiazole;1-(4-bromo-1,3-thiazol-2-yl)ethan-1-one;Ethanone, 1-(4-bromo-2-thiazolyl)-;1-(4-bromo-thiazol-2-yl)-ethanone;SCHEMBL1706430;EX-A7845F;YQJROTDRGHSQNZ-UHFFFAOYSA-N;AMY42165;BCP30691;MFCD10697512;1-(4-Bromothiazol-2-yl)ethan-1-one;AB59795;AS-61684;CS-0103680;EN300-247704

Chemical Property of 1-(4-Bromothiazol-2-YL)ethanone

Chemical Property:

• Boiling Point: 279.2±32.0 °C(Predicted)
• PKA: -2.72±0.10(Predicted)
• PSA: 58.20000
• Density: 1.719±0.06 g/cm3(Predicted)
• LogP: 2.10820
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 204.91970
• Heavy Atom Count: 9
• Complexity: 130

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-Acetyl-4-bromothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=NC(=CS1)Br
• Uses: 2-Acetyl-4-bromothiazole is the derivative of 2,4-Dibromothiazole (D426050), which is an intermediate used in the preparation of various 2,4-disubstituted thiazole derivatives with biologically active properties such as survival motor neuron (SMN) protein modulators.

Technology Process of 1-(4-Bromothiazol-2-YL)ethanone

There total 1 articles about 1-(4-Bromothiazol-2-YL)ethanone 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: 86.0%

4-acetylmorpholine (1696-20-4) + 2,4-dibromo-1,3-thiazole (4175-77-3) → 1-(4-bromo-1,3-thiazol-2-yl)ethanone (208264-53-3)

Guidance literature:

2,4-dibromo-1,3-thiazole; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.5h;

4-acetylmorpholine; In diethyl ether; hexane; at -78 - 20 ℃; for 12h;

DOI:10.1039/c7ob02866k

Reference yield: 73.0%

(4-ethoxyphenyl)boronic acid (22237-13-4) + 1-(4-bromo-1,3-thiazol-2-yl)ethanone (208264-53-3) → C13H13NO2S

Guidance literature:

With palladium diacetate; sodium carbonate; XPhos; In propan-1-ol; water; at 80 ℃; for 0.166667h;

Reference yield:

1-(4-bromo-1,3-thiazol-2-yl)ethanone (208264-53-3) → 2’-phenyl-4-(pyridin-2-yl)-2,4’-bithiazole

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium hydrobromide perbromide / tetrahydrofuran / 14 h / 45 °C

2: calcium carbonate / ethanol / 6 h / Reflux

3: potassium acetate; palladium diacetate; C₃₆H₃₂FeP₂⁽²⁺⁾ / 1,4-dioxane / 12 h / 110 °C / Sealed tube; Inert atmosphere

4: palladium diacetate; C₃₆H₃₂FeP₂⁽²⁺⁾; potassium phosphate / 1,4-dioxane; water / 12 h / 110 °C / Inert atmosphere

With potassium phosphate; C₃₆H₃₂FeP₂⁽²⁺⁾; potassium acetate; palladium diacetate; pyridinium hydrobromide perbromide; calcium carbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; water; 4: |Suzuki-Miyaura Coupling;

DOI:10.1039/c7ob02866k

upstream raw materials:

4-acetylmorpholine

2,4-dibromo-1,3-thiazole

Refernces

• 1、 Lassalas, Pierrik,Berini, Christophe,Rouchet, Jean-Baptiste E. Y.,Hédouin, Jonathan,Marsais, Francis,Schneider, Cédric,Baudequin, Christine,Hoarau, Christophe. "Miyaura borylation/Suzuki-Miyaura coupling (MBSC) sequence of 4-bromo-2,4′-bithiazoles with halides: Straightforward access to a heterocylic cluster of d-series of thiopeptide GE2270". supporting information. p. 526 - 530. Retrieved 2018/02/07.
• 2、 -. "Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents". Page/Page column 299. . Retrieved 2015/11/16.