4-Bromo-2-(2-methylbut-3-en-2-yl)thiazole

Base Information

• Chemical Name: 4-Bromo-2-(2-methylbut-3-en-2-yl)thiazole
• CAS No.: 845659-97-4
• Molecular Formula: C8H10BrNS
• Molecular Weight: 232.14100
• Hs Code.: 2934100090
• DSSTox Substance ID: DTXSID40458001
• Mol file: 845659-97-4.mol

Synonyms:4-Bromo-2-(2-methylbut-3-en-2-yl)thiazole;845659-97-4;4-bromo-2-(2-methylbut-3-en-2-yl)-1,3-thiazole;DTXSID40458001

Chemical Property of 4-Bromo-2-(2-methylbut-3-en-2-yl)thiazole

Chemical Property:

• PSA: 41.13000
• LogP: 3.36920
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 230.97173
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

≥99% ^*data from raw suppliers

4-Bromo-2-(2-methylbut-3-en-2-yl)thiazole 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C=C)C1=NC(=CS1)Br

Technology Process of 4-Bromo-2-(2-methylbut-3-en-2-yl)thiazole

There total 2 articles about 4-Bromo-2-(2-methylbut-3-en-2-yl)thiazole 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: 87.0%

3-methyl-2-butenylmagnesium chloride (35189-96-9) + 2,4-dibromo-1,3-thiazole (4175-77-3) → 4-bromo-2-(1,1-dimethylallyl)thiazole (845659-97-4)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ol047603q

Reference yield:

3,3-dimethyl-allyl chloride (503-60-6) → 4-bromo-2-(1,1-dimethylallyl)thiazole (845659-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: magnesium / tetrahydrofuran / 0.5 h / 20 °C

2: 4.98 g / tetrahydrofuran / 1 h / 0 °C

With magnesium; In tetrahydrofuran;

DOI:10.1016/j.tet.2006.07.010

Reference yield:

4-bromo-2-(1,1-dimethylallyl)thiazole (845659-97-4) → mycothiazole (114582-75-1)

Guidance literature:

Multi-step reaction with 18 steps

1.1: OsO₄; NMO / 2-methyl-propan-2-ol; H₂O / 20 °C

2.1: 3.37 g / NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

3.1: 87 percent / tetrahydrofuran; diethyl ether / 1 h / 20 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

5.1: t-BuLi / pentane; diethyl ether / 0.08 h / -78 °C

5.2: 85 percent / pentane; diethyl ether / 0.5 h / -78 °C

6.1: DIBAL-H / diethyl ether; hexane / 0.5 h / -78 °C

7.1: 97 percent / 2,6-lutidine; PPh₃; CBr₄ / acetonitrile / 0.5 h / 20 °C

8.1: 95 percent / N-methylpyrrolidinone / PdCl₂(CH₃CN)2 / 0.5 h / 20 °C

9.1: 94 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / 50 °C

10.1: DMAP / tetrahydrofuran / 1 h / 20 °C

11.1: 98 mg / second generation Grubbs' catalyst / benzene / 1 h / 70 °C

12.1: 76 percent / HMPA; LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

13.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

13.2: 60 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

14.1: PPTS / tetrahydrofuran; H₂O / 18 h / 50 °C

15.1: NaClO₂; NaH₂PO₄*H₂O; 2-methyl-but-2-ene / 2-methyl-propan-2-ol; H₂O / 1 h / 0 °C

16.1: diphenylphosphoryl azide; Et₃N / toluene / 1 h / 20 °C

17.1: 10 mg / 1 h / 110 °C

18.1: 33 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 2-methyl-but-2-ene; carbon tetrabromide; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; pentane; benzene; 8.1: Stille coupling reaction / 17.1: Curtius rearrangement;

DOI:10.1016/j.tet.2006.07.010

upstream raw materials:

3-methyl-2-butenylmagnesium chloride

2,4-dibromo-1,3-thiazole

3,3-dimethyl-allyl chloride

Downstream raw materials:

mycothiazole

Refernces

• 1、 Le Flohic, Alexandre,Meyer, Christophe,Cossy, Janine. "Reactivity of unsaturated sultones synthesized from unsaturated alcohols by ring-closing metathesis. Application to the racemic synthesis of the originally proposed structure of mycothiazole". . p. 9017 - 9037. Retrieved 2007/10/03.