ChemicalBook--->CAS DataBase List--->79265-30-8

79265-30-8

79265-30-8 Structure

79265-30-8 Structure
IdentificationMore
[Name]

2-(Trimethylsilyl)thiazole
[CAS]

79265-30-8
[Synonyms]

2-THIAZOLYTRIMETHYLSILANE
2-TRIMETHYLSILANYL-THIAZOLE
2-(TRIMETHYLSILYL)-1,3-THIAZOLE
2-(TRIMETHYLSILYL)THIAZOLE
2-TST
2-Thiazolyltrimethylsilane
Thiazole, 2-(trimethylsilyl)-
2-(trimethyl)thiazole
2-TRIMETHYLSILYTHIAZOLE
Dondoni
2-Thiazolyltrimethylsilane, 2-TST
[Molecular Formula]

C6H11NSSi
[MDL Number]

MFCD00066274
[Molecular Weight]

157.31
[MOL File]

79265-30-8.mol
Chemical PropertiesBack Directory
[Appearance]

Colorless to light yellow liqui
[Boiling point ]

56-57 °C10 mm Hg(lit.)
[density ]

0.985 g/mL at 25 °C(lit.)
[refractive index ]

n20/D 1.497(lit.)
[Fp ]

135 °F
[storage temp. ]

2-8°C
[solubility ]

THF: very soluble(lit.)
[form ]

Liquid
[pka]

2.91±0.10(Predicted)
[color ]

Clear colorless to slightly yellow
[Specific Gravity]

0.99
[Water Solubility ]

IMMISCIBLE
[Hydrolytic Sensitivity]

7: reacts slowly with moisture/water
[BRN ]

3538017
[CAS DataBase Reference]

79265-30-8(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[RIDADR ]

1993
[WGK Germany ]

3
[F ]

10-21
[HazardClass ]

3
[PackingGroup ]

III
[HS Code ]

29341000
Hazard InformationBack Directory
[Chemical Properties]

Colorless to light yellow liqui
[Physical properties]

bp 51–53 °C/10 mmHg; d 0.992 g mL?1; nD 1.4980.
[Uses]

2-(Trimethylsilyl)thiazole is used as formyl anion equivalent; effective one-carbon homologating reagent of alkoxy aldehydes, amino aldehydes, and dialdoses.It takes part in the reactions of Homologation of Aldehydes, Metalation and Reactivity with Electrophiles, Cross-coupling Reactions, etc.
[Preparation]

Although 2-(trimethylsilyl)thiazole (1) is commercially available, it can be easily prepared on a multigram scale from 2-bromothiazole, n-butyllithium, and chlorotrimethylsilane as shown in eq 1.

79265-30-8 synthesis

[Synthesis]

Thiazole

288-47-1

Chlorotrimethylsilane

75-77-4

2-(Trimethylsilyl)thiazole

79265-30-8

A solution of thiazole (5.03 g) dissolved in ether (59 mL) was slowly added dropwise to a mixture of n-butyllithium (2.5 M hexane solution, 24 mL) and ether (18 mL) at -78 °C. After completion of the dropwise addition, the reaction was kept at -78°C for 30 min. Subsequently, a solution of trimethylchlorosilane (TMSCl, 6.41 g) dissolved in ether (59 mL) was added at the same temperature. The reaction mixture was continued to be stirred at -78 °C for 1 h, followed by slow warming to room temperature. After completion of the reaction, the reaction mixture was washed with saturated sodium bicarbonate (NaHCO3) solution and the organic phase was dried with anhydrous sodium sulfate (Na2SO4). After removal of the solvent by decompression evaporation, the residue was subjected to decompression distillation (80 °C/14 mmHg) to afford the target product 2-(trimethylsilyl)thiazole (I-54) in 90% yield. The product was analyzed by GC-MS and showed the molecular ion peak (M+H)+ with m/z of 157.10.

[References]

[1] Patent: WO2011/79114, 2011, A1. Location in patent: Page/Page column 125
[2] Patent: WO2012/48129, 2012, A2. Location in patent: Page/Page column 385
[3] Tetrahedron Letters, 2008, vol. 49, # 1, p. 66 - 69
[4] Journal of Organic Chemistry, 1988, vol. 53, # 8, p. 1748 - 1761
[5] Patent: WO2009/21992, 2009, A2. Location in patent: Page/Page column 84
Spectrum DetailBack Directory
[Spectrum Detail]

2-(Trimethylsilyl)thiazole(79265-30-8)MS
2-(Trimethylsilyl)thiazole(79265-30-8)1HNMR
2-(Trimethylsilyl)thiazole(79265-30-8)13CNMR
2-(Trimethylsilyl)thiazole(79265-30-8)IR1
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2-(Trimethylsilyl)thiazole, 96%(79265-30-8)
[Alfa Aesar]

2-(Trimethylsilyl)thiazole, 97%(79265-30-8)
[Sigma Aldrich]

79265-30-8(sigmaaldrich)
[TCI AMERICA]

2-Trimethylsilylthiazole,>95.0%(GC)(79265-30-8)
79265-30-8 suppliers list
Company Name: J & K SCIENTIFIC LTD.  
Telephone: 18210857532 18210857532
Website: https://www.jkchemical.com
Company Name: Meryer (Shanghai) Chemical Technology Co., Ltd.  
Telephone: 4006356688 18621169109
Website: www.x-labseek.com/
Company Name: New Energy Chemicals  
Telephone: 0515-82159099 13770142076
Website: http://www.njuchem.com/
Company Name: Alfa Aesar  
Telephone: 400-6106006
Website: http://chemicals.thermofisher.cn
Company Name: TCI (Shanghai) Development Co., Ltd.  
Telephone: 021-67121386
Website: https://www.tcichemicals.com/CN/zh/
Company Name: BeiJing Hwrk Chemicals Limted  
Telephone: 0757-86329057 18934348241
Website: www.hwrkchemical.com/
Company Name: Energy Chemical  
Telephone: 400-0056266
Website: www.energy-chemical.com
Company Name: Capot Chemical Co., Ltd  
Telephone: +86 (0) 571 85 58 67 18
Website: www.capotchem.com
Company Name: JinYan Chemicals(ShangHai) Co.,Ltd.  
Telephone: 13817811078
Website: www.jingyan-chemical.com
Company Name: Shanghai Longsheng chemical Co.,Ltd.  
Telephone: 58099637 13585536065
Website: www.shlshg.com
Company Name: Shanghai Hanhong Scientific Co.,Ltd.  
Telephone: 021-54306202 13764082696
Website: https://www.hanhongsci.com
Company Name: China DongFan Chemical Co.,LTD  
Telephone: 86-0571-85151182
Website: www.chemicalbook.com/ShowSupplierProductsList14819/0_EN.htm
Company Name: Shandong Xiya Chemical Co., Ltd  
Telephone: 13355009207 13355009207
Website: http://www.xiyashiji.com
Company Name: Sinopharm Chemical Reagent Co,Ltd.  
Telephone: 86-21-63210123
Website: www.reagent.com.cn
Company Name: Nanjing Kaitian Chemical Co., Ltd.  
Telephone: +86 (25) 5860-8846
Website: www.kt-chem.com
Company Name: Shanghai Sunway Pharmaceutical Technology Co., Ltd  
Telephone: 13761987713
Website: www.sunwaypharm.cn
Company Name: Nanjing Vital Chemical Co., Ltd.  
Telephone: Please Send Email 18652950785
Website: www.chemicalbook.com/ShowSupplierProductsList15337/0_EN.htm
Company Name: Maya High Purity Chemicals  
Telephone: +86 (573) 82222445 (0)18006601000 452520369
Website: www.chemicalbook.com/ShowSupplierProductsList15221/0_EN.htm
Tags:79265-30-8 Related Product Information
13435-12-6 2682-20-4 1066-54-2 4039-32-1 288-47-1 999-97-3 10200-59-6 32137-73-8 79265-30-8