2-(trimethylsilyl)-1,3-benzothiazole

• ChemBase ID: 141097
• Molecular Formular: C10H13NSSi
• Molecular Mass: 207.36742
• Monoisotopic Mass: 207.05379695
• SMILES: C[Si](C)(C)c1nc2ccccc2s1
• Canonical SMILES: C[Si](c1nc2c(s1)cccc2)(C)C
• InChI: InChI=1S/C10H13NSSi/c1-13(2,3)10-11-8-6-4-5-7-9(8)12-10/h4-7H,1-3H3
• InChIKey: MNXBVXVIRAIAEG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(trimethylsilyl)-1,3-benzothiazole
• IUPAC Traditional name: 2-(trimethylsilyl)-1,3-benzothiazole
• Synonyms: 2-(Trimethylsilyl)benzothiazole; 2-(TRIMETHYLSILYL)BENZOTHIAZOLE; 2-(三甲基硅基)苯并噻唑

Database IDs

• CAS Number: 32137-73-8
• EC Number: 000-000-0
• MDL Number: MFCD00068185
• Beilstein Number: 1073964
• PubChem SID: 162235332
• PubChem CID: 520560

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.366153
• LogD (pH = 7.4): 4.3664956
• Log P: 4.3665
• Molar Refractivity: 52.6656 cm^3
• Polarizability: 24.094158 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 128-130°C/2mm
• Density: 1.058 g/mL at 25 °C; 1.06
• Refractive Index: 1.5720; n20/D 1.573

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H227; H315-H319-H335-H413
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%; tech. 90%
• Empirical Formula (Hill Notation): C10H13NSSi

DETAILS

Sigma Aldrich - 691569

Packaging
1, 5 g in glass bottle

REFERENCES

• Reacts with electrophiles to give 2-substituted benzothiazoles: J. Heterocycl. Chem., 8, 257 (1971). Reactivity is increased by F^- catalysis; e.g. CsF with aldehydes: Tetrahedron Lett., 23, 5079 (1982). The thiazole ring can be cleaved, so that the reagent behaves as a formyl anion equivalent; see also Benzothiazole, A10380, and 2-(Trimethylsilyl)thiazole, B21903. Unlike 2-lithiobenzothiazole, reaction with a chiral aldehyde can be diastereoselective: Tetrahedron Lett., 26,5477 (1985).
• Reaction with PCl₃, PhPCl₂ or Ph₂PCl gives the corresponding benzothiazolylphosphine: J. Org. Chem., 47, 1489 (1982). With 2-lithiobenzothiazole, 2,2'-bibenzothiazole is formed: Heterocycles, 30, 347 (1990).