1-(tert-butyldimethylsilyl)-1H-imidazole

• ChemBase ID: 139854
• Molecular Formular: C9H18N2Si
• Molecular Mass: 182.33812
• Monoisotopic Mass: 182.12392512
• SMILES: CC(C)(C)[Si](C)(C)n1ccnc1
• Canonical SMILES: CC([Si](n1cncc1)(C)C)(C)C
• InChI: InChI=1S/C9H18N2Si/c1-9(2,3)12(4,5)11-7-6-10-8-11/h6-8H,1-5H3
• InChIKey: VUENSYJCBOSTCS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(tert-butyldimethylsilyl)-1H-imidazole
• IUPAC Traditional name: 1-(tert-butyldimethylsilyl)imidazole
• Synonyms: TBDMSIM; 1-(tert-Butyldimethylsilyl)imidazole; 1-(tert-butyldimethylsilyl)imidazole; TBSIM; 1-(叔丁基二甲基甲硅烷基)咪唑; 叔丁基二甲基硅烷基咪唑

Database IDs

• CAS Number: 54925-64-3
• EC Number: 259-398-1
• MDL Number: MFCD00011682
• Beilstein Number: 606695
• PubChem SID: 24855044; 162234102
• PubChem CID: 171385

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.85517734
• LogD (pH = 7.4): 1.5030992
• Log P: 1.6546
• Molar Refractivity: 50.686 cm^3
• Polarizability: 21.125452 Å^3
• Polar Surface Area: 17.82 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Liquid
• Boiling Point: 247-250°C; 53 °C/0.2 mmHg(lit.)
• Flash Point: 210.2 °F; 99 °C; 99°C(210°F)
• Density: 0.939 g/mL at 25 °C(lit.); 0.94
• Refractive Index: 1.4805; n20/D 1.481; n20/D 1.481(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥95.0% (GC); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C9H18N2Si

DETAILS

Sigma Aldrich - 250236

Packaging
1 g in glass bottle

Sigma Aldrich - 19920

Other Notes
Convenient reagent for introducing the sterically crowded tert-butyldimethylsilyl group in unhindered hydroxy groups.; It is mostly used for derivatizations of steroid hormones and nucleosides to allow GC and MS measurements 1,2,3; Reagent of choice for the preparation of very moisture sensitive tert-butyldimethylsilyl derivatives of hydroxy-compounds as no aqueous work-up is necessary4

REFERENCES

• Reagent for the formation of the tert-butyldimethylsilyl (TBDMS, TBS) derivatives of hydroxyl groups under mild conditions: Anal. Chem., 50, 59 (1978); J. Chromat. Sci., 16, 201 (1978). Particularly recommended for silylation of steroids and nucleosides.