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Triethylsilane

Product Name
Triethylsilane
CAS No.
617-86-7
Chemical Name
Triethylsilane
Synonyms
Et3SiH;Triethylsilyl;Triethylsilyl hydride;PDFF;Silane, triethyl-;Medetomidine Impurity 40;DK845;CT2523;NSC 93579;SILANE E3H
CBNumber
CB8495938
Molecular Formula
C6H16Si
Formula Weight
116.28
MOL File
617-86-7.mol
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Triethylsilane Property

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.
Hydrolytic Sensitivity
3: reacts with aqueous base
Sensitive 
Moisture Sensitive
BRN 
1098278
Stability:
Stable, but moisture sensitive. Highly flammable. Generates highly flammable gas (hydrogen) in contact with water, acids and bases.
LogP
3.6 at 20℃
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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.18806
Product name
Triethylsilane
Purity
for synthesis
Packaging
10ML
Price
$71.1
Updated
2024/03/01
Sigma-Aldrich
Product number
8.18806
Product name
Triethylsilane
Purity
for synthesis
Packaging
50ML
Price
$179
Updated
2024/03/01
Sigma-Aldrich
Product number
230197
Product name
Triethylsilane
Purity
99%
Packaging
5g
Price
$35.1
Updated
2024/03/01
Sigma-Aldrich
Product number
230197
Product name
Triethylsilane
Purity
99%
Packaging
25g
Price
$89.7
Updated
2024/03/01
TCI Chemical
Product number
T0662
Product name
Triethylsilane
Purity
>98.0%(GC)
Packaging
25mL
Price
$45
Updated
2024/03/01
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Triethylsilane Chemical Properties,Usage,Production

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.

Chemical Properties

Clear liquid

Uses

Triethylsilane is a trialkylsilicon hydride used in the synthesis of alkylsilanes via hydrosilation of olefins. It acts as a reducing agent in the reduction of 2-chromanols, since it has an active hydride. It acts as a catalyst for redox initiated cationic polymerization, regioselective reductive coupling of enones and allenes, and Beckmann rearrangement of cyclododecanone oxime. It is associated with trifluoroacetic acid and involved in the selective reduction of alkenes.

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

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

Definition

ChEBI: Triethylsilane is an organosilicon compound. It has a role as a reducing agent.

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).

Flammability and Explosibility

Flammable

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.]

Precautions

Triethylsilane is a flammable, but not pyrophoric, liquid. As with all organosilicon hydrides, it is capable of releasing hydrogen gas upon storage, particularly in the presence of acids, bases, or fluoride-releasing salts. Proper precautions should be taken to vent possible hydrogen buildup when opening vessels in which triethylsilane is stored.

References

R. Boukherroub,?,?, C. Chatgilialoglu,,§ and, and G. Manuel?. "PdCl2-Catalyzed Reduction of Organic Halides by Triethylsilane." Organometallics 15.5(1996):1508-1510.
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.
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.
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.

Triethylsilane Preparation Products And Raw materials

Raw materials

Preparation Products

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Triethylsilane Suppliers

SHANGHAI BANGCHENG CHEMICAL Co.,Ltd.
Tel
021-69106960 13701823733
Fax
021-69106780
Email
13701823733@163.com
Country
China
ProdList
4776
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60
ZHEJIANG HUTU PHARMCHEM CO., LTD.
Tel
0570-6121498
Email
13757057990@126.com
Country
China
ProdList
1
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58
Shanghai Zhuorui Chemical Co.,Ltd.
Tel
021-69180038
Fax
0086-21-39177059
Email
zhuoruichem@163.com
Country
China
ProdList
105
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58
Shanghai Worldyang Chemical Co.,Ltd.
Tel
021-021-56795766
Fax
+86-21-56795266
Email
sales@worldyachem.com
Country
China
ProdList
9353
Advantage
58
Henan yu Chen pharmaceutical co., LTD
Tel
0374-5699939 18864655557
Fax
+86-374-5699958
Email
yuchenchem@126.com
Country
China
ProdList
27
Advantage
58
Changzhou Zidong Lianhua import and Export Co., Ltd
Tel
13328193929
Email
735789510@qq.com
Country
China
ProdList
215
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58
Shandong Vantage Specialty Chemicals Biotechnology Co., Ltd.
Tel
133-96369453 18678026865
Fax
0536-2101172
Email
sdfantai@163.com
Country
China
ProdList
851
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58
Nantong Jiaxingtai Biotechnology Co., Ltd.
Tel
18795782766
Email
769011731@qq.com
Country
China
ProdList
29
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58
Weifang Runzhong Fine Chemical Co., LTD
Tel
18653686003
Email
sq@runzhongchem.com
Country
China
ProdList
69
Advantage
58
Shanghai Yanze Chemical Co., Ltd.
Tel
13773155751; 19962611955
Email
260924549@qq.com
Country
China
ProdList
8507
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58
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View Lastest Price from Triethylsilane manufacturers

Hebei Yime New Material Technology Co., Ltd.
Product
Triethylsilane 617-86-7
Price
US $200.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10kg/day
Release date
2023-07-27
Hubei Changfu Chemical Co., Ltd.
Product
Triethylsilane 617-86-7
Price
US $0.00/kg
Min. Order
1kg
Purity
99
Supply Ability
20 tons
Release date
2024-03-12
Hebei Duling International Trade Co. LTD
Product
Triethylsilane 617-86-7
Price
US $15.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2023-01-07

617-86-7, TriethylsilaneRelated Search:


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  • Silicon Compounds (for Synthesis)
  • Reduction
  • Si-H Compounds
  • Si (Classes of Silicon Compounds)
  • 1
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  • organosilicon compound
  • Other Reagents
  • Reduction
  • Si (Classes of Silicon Compounds)
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  • Silicon Compounds (for Synthesis)
  • Synthetic Organic Chemistry