1-(trimethylsilyl)-1H-imidazole

• ChemBase ID: 8470
• Molecular Formular: C6H12N2Si
• Molecular Mass: 140.25838
• Monoisotopic Mass: 140.07697493
• SMILES: n1(ccnc1)[Si](C)(C)C
• Canonical SMILES: C[Si](n1cncc1)(C)C
• InChI: InChI=1S/C6H12N2Si/c1-9(2,3)8-5-4-7-6-8/h4-6H,1-3H3
• InChIKey: YKFRUJSEPGHZFJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(trimethylsilyl)-1H-imidazole
• IUPAC Traditional name: 1-(trimethylsilyl)imidazole
• Synonyms: TSIM; N-Trimethylsilylimidazole; 1-(Trimethylsilyl)imidazole; 1-(Trimethylsilyl)imidazole; 1-(Trimethylsilyl)Imidazole; TMSI; N-TRIMETHYLSILYLIMIDAZOLE; n-(trimethylsilyl)imidazole; TMSIM; 1-(Trimethylsilyl)-1H-imidazole; N-(Trimethylsilyl)-1H-imidazole; N-(Trimethylsilyl)imidazol; N-(Trimethylsilyl)imidazole; NSC 139860; Trimethylimidazosilane; N-三甲基硅基咪唑; 1-(三甲基硅基)咪唑

Database IDs

• CAS Number: 18156-74-6
• EC Number: 242-040-3
• MDL Number: MFCD00005280
• Beilstein Number: 606148
• PubChem SID: 24849355; 24889712; 24864623; 160971777
• PubChem CID: 28925

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.1262809
• LogD (pH = 7.4): 0.77336043
• Log P: 0.9264
• Molar Refractivity: 36.9638 cm^3
• Polarizability: 15.598138 Å^3
• Polar Surface Area: 17.82 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -42°C
• Boiling Point: 212°C; 93-94 °C/14 mmHg(lit.); 93-94°C @ 14mm; 93-94°C/14mm
• Flash Point: 18°C(64°F); 42.8 °F; 6 °C; 6.1°C
• Density: 0.956; 0.956 g/ml; 0.956 g/mL at 25 °C(lit.); 0.957 g/mL at 20 °C
• Refractive Index: 1.4750; 1.4765; n20/D 1.475(lit.)

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Moisture Sensitive; MOISTURE SENSITIVE, FLAMMABLE
• RTECS: NI8700000
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Australian Hazchem: 3YE
• Risk Statements: 11-36/37/38; R:11
• Safety Statements: 16-26-33; 16-26-33-37; S:9-16-29
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 128
• TSCA Listed: true; 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0%; ≥98.0% (T); 96%; 97%
• Grade: for GC derivatization; synthesis grade
• Empirical Formula (Hill Notation): C6H12N2Si

DETAILS

MP Biomedicals - 02152172

For preparation of volatile derivatives for gas chromotography analysis.
1 ml = approx. 0.96 g

Sigma Aldrich - 153583

Packaging
5, 25, 100 mL in glass bottle
Application
Silylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.1

Sigma Aldrich - 92751

Other Notes
Powerful silylating agent, particularly for alcohols1,2,3; Synthesis of acyl imidazolides4

Sigma Aldrich - 394874

General description
Powerful silylating agent, particularly for alcohols1,2,3; Synthesis of acyl imidazolides4
Packaging
10×1 mL in ampule
5, 25 mL in glass bottle

Toronto Research Chemicals - T796830

A general silylating agent, particularly for alcohols. An intermediate for the synthesis of imidazole derivatives.

REFERENCES

• Shin, H. et al.: Chromatographia, 63, 77 (2006)
• Birkemeyer, C. et al.: J. Chrom., 993, 89 (2006)
• Powerful silylating agent (see Appendix 4) for a wide range of functional groups. O-Silylation in the presence of TBAF (0.02 equiv.) occurs under very mild conditions: Tetrahedron Lett., 35, 8409 (1994).