tert-Butyldimethylsilane Chemical Properties

Melting point:

13°C

Boiling point:

81-83 °C (lit.)

Density 

0.701 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4(lit.)

Flash point:

−9 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

0.701

Hydrolytic Sensitivity

3: reacts with aqueous base

BRN 

2231162

InChI

InChI=1S/C6H16Si/c1-6(2,3)7(4)5/h7H,1-5H3

InChIKey

QCIWZIYBBNEPKB-UHFFFAOYSA-N

SMILES

[SiH](C(C)(C)C)(C)C

CAS DataBase Reference

29681-57-0

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36-16/26/36

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

F 

10-21

TSCA 

Yes

HazardClass 

3.1

PackingGroup 

I

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

tert-Butyldimethylsilane Usage And Synthesis

Uses

Tert-Butyldimethylsilane (t-BuMe2SiH) is widely used for the protection of hydroxy groups in sugars. Its oxidation product, tert-butyldimethylsilyl hydroperoxide (t-BuMe2SiOOH), is used for preparing luminiscent sources and prostanoids, specifically clavulons[1].

Reactions

The iridium complex [Ir(COD)(PPh3)2]+SbF6- reacts with tert-butyldimethylsilane in DMA to form [IrH2(Sol)2(PPh3)2]+SbF6-, which is an active catalyst for the regioselective di- and trisilylation of a series of representative methyl hexopyranosides, β-1,6-anhydrohexopyranosides and 1,3,5-O-methylidene inositol.The silylcarbobicyclization of 4,4-disubstituted 1,6-heptadiynes with tert-butyldimethylsilane catalyzed by Rh(acac)(CO)2, Co2Rh2(CO)12, or (t-BuNC)4RhCo(CO)4 under 50 atm of carbon monoxide gives the corresponding novel 7,7-disubstituted 2-silylbicyclo[3.3.0]octa-1,5-dien-3-ones in good yields[2-3].

References

[1] Iwao Ojima, Jiawang Zhu, Dora Fracchiolla Kass. “New and Efficient Catalytic Route to Bicyclo[3.3.0]octa-1,5-dien-3-ones.” Organometallics 15 24 (1996): 5191–5195.
[2] Mee-Kyung Chung, Marcel Schlaf. “Regioselectively Trisilylated Hexopyranosides through Homogeneously Catalyzed Silane Alcoholysis.” Journal of the American Chemical Society 127 51 (2005): 18085–18092.
[3] Iwao Ojima, Jiawang Zhu, Dora Fracchiolla Kass. “New and Efficient Catalytic Route to Bicyclo[3.3.0]octa-1,5-dien-3-ones.” Organometallics 15 24 (1996): 5191–5195.

tert-Butyldimethylsilane(29681-57-0)Related Product Information

• TERT-BUTYLDIMETHYLSILANOL
• Chloro-tert-butyldimethylsilan
• t-Butyl methyl fumarate
• ALLYLOXY-T-BUTYLDIMETHYLSILANE
• t-butyldimethylIsopropoxylsilane
• tert-butyl-methoxy-dimethylsilane
• TERT-BUTYLDIMETHYLSILYL (R)-(-)-GLYCIDY&
• Tert-butyl-dimethyl-(tributylstannylmethoxy)silane
• tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)silane
• N-(tert-Butyldimethylsilyl)-N-methyl-trifluoroacetamide
• AMINOXY-TERT-BUTYLDIMETHYLSILANE
• DIMETHYLTHEXYLSILYL CHLORIDE
• N-BUTYLDIMETHYLSILANE
• 3-BROMOPROPOXY-T-BUTYLDIMETHYLSILANE,(3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE
• 5-O-(tert-Butyldimethylsilyl)-2,3-O-isoproylidene-D-ribofuranose
• (2-BROMOETHOXY)-TERT-BUTYLDIMETHYLSILANE
• ethynyl-t-butyldimethylsilane,ETHYNYL-TERT-BUTYLDIMETHYLSILANE
• DIMETHYLSILANE