chlorotrimethylsilane

• ChemBase ID: 74408
• Molecular Formular: C3H9ClSi
• Molecular Mass: 108.64206
• Monoisotopic Mass: 108.0162045
• SMILES: [Si](C)(C)(C)Cl
• Canonical SMILES: C[Si](Cl)(C)C
• InChI: InChI=1S/C3H9ClSi/c1-5(2,3)4/h1-3H3
• InChIKey: IJOOHPMOJXWVHK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chlorotrimethylsilane
• IUPAC Traditional name: chlorotrimethylsilane
• Synonyms: Chlorotrimethylsilane solution; Dow Corning® Z-1224; Chlorotrimethylsilane; Chlorotrimethylsilane solution; Trimethylchlorosilane/o-Xylene 1/24 (v/v); Silanization solution IV; Trimethylsilyl chloride; TMCS; Chlorotrimethylsilane 99%; Chlorotrimethylsilane; TMSCl; Trimethylchlorosilane; Trimethylsilyl chloride; Silane M3; Chlorotrimethylsilane; TMS chloride; 三甲基氯硅烷 溶液; 三甲基硅基氯; 三甲基氯硅烷; 三甲基氯硅烷 溶液; 三甲基氯硅烷/邻二甲苯 1/24 (v/v); 硅烷化溶液 IV; 硅烷 M3

Database IDs

• CAS Number: 75-77-4
• EC Number: 200-900-5
• MDL Number: MFCD00000502
• Beilstein Number: 1209232
• PubChem SID: 24892952; 24890169; 24889641; 162039327; 24888307; 24863995; 24864026; 24864097
• PubChem CID: 6397
• Chemspider ID: 6157
• Wikipedia Title: Trimethylsilyl_chloride

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.0128
• LogD (pH = 7.4): 2.0128
• Log P: 2.0128
• Molar Refractivity: 23.4766 cm^3
• Polarizability: 11.012379 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: reacts in water
• Apperance: Colorless liquid, fumes in moist air
• Melting Point: -40 °C (233.2 K); -40 °C(lit.); -58°C; ca -58°C
• Boiling Point: 56-58°C; 56-58°C; 57 °C (330.2 K); 57 °C(lit.)
• Flash Point: -.4 °F; 104 °F; -18 °C; -18°C; -20 °C; -27°C(-16°F); -28 °C; 39.2 °F; 4 °C; -4 °F; 40 °C
• Auto Ignition Point: 400 °C; 752 °F
• Density: 0.856; 0.856 g/cm^3, liquid; 0.856 g/mL at 25 °C(lit.); 0.88 g/mL at 25 °C; 1.257 g/mL at 25 °C
• Refractive Index: 1.387; 1.3887; n20/D 1.387(lit.); n20/D 1.500
• Vapor Pressure: 100 mmHg ( 25 °C)
• Vapor Density: 3.7 (vs air)

Safety Information

• Storage Warning: Highly Flammable/Corrosive/Harmful/Moisture Sensitive/Store under Argon/Keep Cold; Moisture Sensitive
• RTECS: VV2710000
• European Hazard Symbols: Corrosive (C); Corrosive (C); Flammable (F); Flammable (F); X; Harmful (Xn)
• UN Number: 1298; 1993; 2920; 2924; UN1298
• German water hazard class: 1; 2
• Hazard Class: 3; 8
• Packing Group: 2; II
• Risk Statements: 10-14-34-40; 11-14-19-35-37; 11-14-20/21-35-37; 11-14-21-34; 11-20/21-36/38; R11, R14, R20, R21, R35, R37
• Safety Statements: 16-26-36/37; 16-26-36/37/39-45; 26-36/37/39-45; 7/9-16-26-36/37/39-45; 8-16-26-30-36/37/39-45-60; S16, S26, S36, S37, S39, S45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• NFPA704:
  

  3

  3
• Explode Limits: 6.4 %
• GHS Hazard statements: H225-H311-H314-H318; H225-H312-H314-H331-H335; H225-H312-H315-H318-H332; H225-H314-H335; H226-H314-H351
• GHS Precautionary statements: P210-P261-P280-P305 + P351 + P338-P310; P210-P280-P305 + P351 + P338; P210-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US); Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1298 3/PG 2; UN 1993 3/PG 2; UN 2920 8/PG 2; UN 2924 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides., Reacts violently with water.; Reacts violently with water.

Product Information

• Purity: ≥97%; ≥98.0% (GC); ≥99%; ≥99.0% (GC); 97%; 98+%
• Concentration: ~1 M in THF; 1.0 M in methylene chloride; 1.0 M in THF
• Grade: produced by Wacker; puriss.; purum; Selectophore™
• Impurities: <0.1% dichlorodimethylsilane
• Purified By: glass distillation; redistillation
• Linear Formula: (CH3)3SiCl

DETAILS

Sigma Aldrich - 385433

Packaging
800 mL in Sure/Seal™

Sigma Aldrich - C72854

Application
For the preparation of volatile derivatives of a wide range of compounds for GC analysis.
Packaging
100, 500 mL in Sure/Seal™
5 mL in glass bottle
View returnable container options.

Sigma Aldrich - 92361

Application
Used in Fisher Glycosylation
Packaging
1 L in glass bottle
100, 250, 500 mL in glass bottle

Sigma Aldrich - 95541

Application
Used in Fisher Glycosylation
Other Notes
Silane M3
prices for bulk quantities on request
Packaging
5 kg in ss drum
500 g in Sure/Seal™

Sigma Aldrich - 384410

Packaging
100, 800 mL in Sure/Seal™

Sigma Aldrich - 92360

Other Notes
Silylating agent1,2

Sigma Aldrich - 386529

Application
Used in Fisher Glycosylation
Packaging
1 L in Sure/Seal™
25, 100 mL in Sure/Seal™

Sigma Aldrich - 85120

General description
Visit our Sensor Applications portal to learn more.
Other Notes
Ready-to-use solution for silanizing microelectrode pipettes by the dip-and-bake method1,2
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

REFERENCES

• For facile O-silylation of tertiary alcohols in the presence of Mg metal, see: Synlett, 1025 (2000).
• Carbonyl compounds can be converted to their silyl enol ethers, e.g. with triethylamine in DMF: Org. Synth. Coll., 6, 327 (1988); 7,424 (1990); 8, 460 (1993); or using catalysis with NaI: Org. Synth. Coll., 9, 573 (1998).
• Conjugated enones give trimethylsilyloxydienes. For examples, see: Org. Synth. Coll., 6, 445 (1988); 7, 282 (1990). TMS chloride, LiBr and trimethylamine in THF is a convenient system for silylation of enones: Acta Chem. Scand., 43, 188 (1989). The same combination converts ɑ- and ?-diketones to their bis silyl enol ethers: Acta Chem. Scand., 43, 304 (1989). See also Trimethylsilyl trifluoromethanesulfonate, A12535.
• The conversion of alcohols to alkyl chlorides requires catalysis, e.g. SeO₂: J. Org. Chem., 53, 3634 (1988), or by DMSO: J. Org. Chem., 60, 2638 (1995). The same system is also effective in opening epoxides.
• For cleavage of ethers, see Sodium iodide, A15480.
• Silylation at carbon atoms is usually carried out using organometallic reagents, e.g. vinylmagnesium bromide: Org. Synth. Coll., 6, 1033 (1988). In aromatic rings, silyl groups can be introduced by directed metallation, followed by silylation; see e.g.: J. Org. Chem., 49, 4657 (1989). The silyl substituents can readily be replaced by electrophiles, allowing "abnormal" patterns of substitution. See 1,3-Dimethoxybenzene, A13380.
• For further details and reviews, see Appendix 4.