Basic information description Referrence Safety Supplier Related
ChemicalBook >  Product Catalog >  Chemical Reagents >  Organic reagents >  Silane >  Triethylsilane

Triethylsilane

Basic information description Referrence Safety Supplier Related

Triethylsilane Basic information

Product Name:
Triethylsilane
Synonyms:
  • Co-Formula CFS-867
  • TRIETHYLSILANE, 97%TRIETHYLSILANE, 97%TRIETHYLSILANE, 97%
  • Triethylsilyl
  • Triethylsilane,99%
  • Silane, triethyl-
  • Triethylsilicon
  • Triethylsilane, 98.5+%
  • Triethylsilane,Triethylsilyl hydride
CAS:
617-86-7
MF:
C6H16Si
MW:
116.28
EINECS:
210-535-3
Product Categories:
  • 1
  • Silanes
  • Other Reagents
  • Reduction
  • Synthetic Reagents
  • organosilicon compound
  • Si (Classes of Silicon Compounds)
  • Si-H Compounds
  • Silicon Compounds (for Synthesis)
  • Synthetic Organic Chemistry
  • Alkyl Silanes
  • Hydrogensilanes Hydrogensiloxanes
  • Reducing Agents
  • Chemistry
  • Organics
Mol File:
617-86-7.mol
More
Less

Triethylsilane Chemical Properties

Melting point:
-157°C
Boiling point:
107-108 °C (lit.)
Density 
0.728 g/mL at 25 °C (lit.)
vapor pressure 
>1 hPa (20 °C)
refractive index 
n20/D 1.412(lit.)
Flash point:
25 °F
storage temp. 
Store below +30°C.
solubility 
insol H2O; sol hydrocarbons, halocarbons, ethers.
form 
liquid
color 
colorless
Specific Gravity
0.728
Water Solubility 
Miscible with water.
Sensitive 
Moisture Sensitive
Hydrolytic Sensitivity
3: reacts with aqueous base
BRN 
1098278
Stability:
Stable, but moisture sensitive. Highly flammable. Generates highly flammable gas (hydrogen) in contact with water, acids and bases.
CAS DataBase Reference
617-86-7(CAS DataBase Reference)
NIST Chemistry Reference
Silane, triethyl-(617-86-7)
EPA Substance Registry System
Triethylsilane (617-86-7)
More
Less

Safety Information

Hazard Codes 
F,Xi
Risk Statements 
11-36/37/38-52/53
Safety Statements 
9-16-29-33-37/39-26-61
RIDADR 
UN 1993 3/PG 2
WGK Germany 
1
10-21
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29310095

MSDS

More
Less

Triethylsilane Usage And Synthesis

description

Triethylsilane is a useful versatile reductant since it has a active hydride. It can be used for mediated the palladium-catalyzed dehalogenation reaction of alkyl or aryl halides, the reduction of primary, secondary, and tertiary chlorides, bromides, and iodides catalyzed by iridium, as well as efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection. It is also specifically for the hydrosilation of olefins to give alkyl silanes. It is also the catalyst for synthesis of a spiro-oxindole blocker of Nav1.7 for the treatment of pain, redox initiated cationic polymerization and Beckmann rearrangement of cyclododecanone oxime as well as regioselective reductive coupling of enones and allenes.

Referrence

  1. R. Boukherroub,†,‡, C. Chatgilialoglu,,§ and, and G. Manuel†. "PdCl2-Catalyzed Reduction of Organic Halides by Triethylsilane." Organometallics 15.5(1996):1508-1510.
  2. Jian Yang and, and M. Brookhart. "Iridium-Catalyzed Reduction of Alkyl Halides by Triethylsilane." Journal of the American Chemical Society 129.42(2007):12656-7.
  3. And, Pijus K. Mandal, and J. S. Mcmurray. "Pd−C-Induced Catalytic Transfer Hydrogenation with Triethylsilane." Journal of Organic Chemistry 72.17(2007):6599-6601.
  4. Chen, Bang Chi, et al. "Novel triethylsilane mediated reductive N -alkylation of amines: improved synthesis of 1-(4-imidazolyl)methyl-4-sulfonylbenzodiazepines, new farnesyltransferase inhibitors." Tetrahedron Letters 42.7(2001):1245-1246.

Chemical Properties

Clear liquid

Uses

Triethylsilane is a trialkylsilicon hydride used in the synthesis of alkylsilanes via hydrosilation of olefins. Triethylsilane is also used as an effective reducing agent.

Uses

Triethylsilane is used as a reducing agent inmany organic synthetic reactions.

Uses

Triethylsilane serves as an exemplar for organosilicon hydride behavior as a mild reducing agent. It is frequently chosen as a synthetic reagent because of its availability, convenient physical properties, and economy relative to other organosilicon hydrides which might otherwise be suitable for effecting specific chemical transformations.
This reagent is generally used in these reactions: Hydrosilylations, Silane Alcoholysis, Formation of Singlet Oxygen, Reduction of Acyl Derivatives to Aldehydes, Radical Chain Reductions, Ionic Hydrogenations and Reductive Substitutions(The polar nature of the Si–H bond enables triethylsilane to act as a hydride donor to electron-deficient centers.), Reductive Etherifications and Acetal Reductions, Ether Cleavages, Reductive Couplings and Cyclizations, Aromatic Silylations, Generation of Other Triethylsilyl Reagents, etc.
Related Reagents: Phenylsilane–cesium fluoride; tri-n-butylstannane; tricarbonylchloroiridium–diethyl(methyl) silane–carbon monoxide; triethylsilane–trifluoroacetic acid.

Application

Used to reduce metal salts. Enhances deprotection of t-butoxycarbonyl-protected amines and tert-butylesters. Used in the reductive amidation of oxazolidinones with amino acids to provide dipeptides. Converts aldehydes to symmetrical and unsymmetrical ethers.  Used in the ‘in-situ’ preparation of diborane and haloboranes.

Fire Hazard

Highly flammable; flash point -4°C (25°F) (Aldrich 1996).
It does not ignite spontaneously in air, but it can explode on heating. The ease of oxidation of this compound is relatively lower than mono- and dialkylsilanes. Reaction with oxidizing substances, however, can be violent. Reaction with boron trichloride could be explosive at room temperature. Even at 78°C ( 108°F), mixing these reagents caused pressure buildup and combustion (Matteson 1990).

Purification Methods

Reflux triethylsilane over molecular sieves, then distil it. It is passed through neutral alumina before use [Randolph & Wrighton J Am Chem Soc 108 3366 1986]. [Beilstein 4 IV 3895.]

Triethylsilane Preparation Products And Raw materials

Preparation Products

TriethylsilaneSupplier

ZHEJIANG HUTU PHARMCHEM CO., LTD. Gold
Tel
0570-6121498
Email
13757057990@126.com
Shanghai Zhuorui Chemical Co.,Ltd. Gold
Tel
021-69180038
Email
zhuoruichem@163.com
Shanghai Worldyang Chemical Co.,Ltd. Gold
Tel
021-56795766
Email
sales@worldyachem.com
Henan yu Chen pharmaceutical co., LTD Gold
Tel
0374-5699939 18864655557
Email
yuchenchem@126.com
Changzhou Zidong Lianhua import and Export Co., Ltd Gold
Tel
13328193929
Email
735789510@qq.com