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Triethylsilane structure
Triethylsilane structure

Triethylsilane

Iupac Name:triethylsilicon
CAS No.: 617-86-7
Molecular Weight:116.28
Modify Date.: 2022-12-06 14:52
Introduction: Triethylsilane is a trialkylsilicon hydride used in the synthesis of alkylsilanes via hydrosilation of olefins. Triethylsilane is also used as an effective reducing agent. View more+
1. Names and Identifiers
1.1 Name
Triethylsilane
1.2 Synonyms

Co-Formula CFS-867 EINECS 210-535-3 MFCD00009018 Silane, triethyl- Triethylsilane,Triethylsilyl hydride Triethylsilicon Triethylsilyl Triethylsilyl hydride UNII:0F9429873L

1.3 CAS No.
617-86-7
1.4 EINECS(EC#)
210-535-3
1.5 Molecular Formula
C6H16Si (isomer)
1.6 Inchi
InChI=1S/C6H15Si/c1-4-7(5-2)6-3/h4-6H2,1-3H3
1.7 InChkey
QXTIBZLKQPJVII-UHFFFAOYSA-N
1.8 Canonical Smiles
CC[Si](CC)CC
1.9 Isomers Smiles
CC[Si](CC)CC
2. Properties
2.1 Density
0.728 g/mL at 25 °C (lit.)
2.1 Melting point
-157°C
2.1 Boiling point
107-108 °C (lit.)
2.1 Refractive index
1.41-1.412
2.1 Flash Point
25?°F
2.1 Precise Quality
116.10200
2.1 PSA
0.00000
2.1 logP
2.27320
2.1 Appearance
colorless liquid
2.2 Storage
Moisture Sensitive. Ambient temperatures.
2.3 Chemical Properties
Clear liquid
2.4 Color/Form
colorless
2.5 Water Solubility
Miscible with water.
2.6 Stability
Stable, but moisture sensitive. Highly flammable. Generates highly flammable gas (hydrogen) in contact with water, acids and bases.
2.7 StorageTemp
Store below +30°C.
3. Use and Manufacturing
3.1 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
3.2 Usage
Triethylsilane is a trialkylsilicon hydride used in the synthesis of alkylsilanes via hydrosilation of olefins. Triethylsilane is also used as an effective reducing agent.
4. Safety and Handling
4.1 Symbol
GHS02
4.1 Hazard Codes
F,Xi
4.1 Signal Word
Danger
4.1 Risk Statements
11-36/37/38-52/53
4.1 Safety Statements
9-16-29-33-37/39-26-61
4.1 Packing Group
II
4.1 Hazard Class
3
4.1 Hazard Declaration
H225-H412
4.1 RIDADR
UN 1993 3/PG 2
4.1 Caution Statement
P210-P273
4.1 WGK Germany
1
4.1 Safety

Safety Information of Triethylsilane (CAS NO.617-86-7):
Hazard Codes: FFlammable,XiIrritant
Risk Statements: 11-36/37/38
11:? Highly Flammable
36:? Irritating to the eyes?
37:? Irritating to the respiratory system?
38:? Irritating to the skin?
Safety Statements: 9-16-29-33-37/39-26
9:? Keep container in a well-ventilated place?
16:? Keep away from sources of ignition - No smoking?
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
29:? Do not empty into drains?
33:? Take precautionary measures against static discharges?
37:? Wear suitable gloves?
39:? Wear eye/face protection?

4.2 Sensitive
Moisture Sensitive
4.3 Specification

?Triethylsilane ,its CAS NO. is 617-86-7,the synonyms is EINECS 210-535-3 ; NSC 93579 ; Triethylsilicon hydride ; Silane, triethyl- .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 2

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H225 Highly flammable liquid and vapour

H412 Harmful to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.

P233 Keep container tightly closed.

P240 Ground and bond container and receiving equipment.

P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment.

P242 Use non-sparking tools.

P243 Take action to prevent static discharges.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P273 Avoid release to the environment.

Response

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P370+P378 In case of fire: Use ... to extinguish.

Storage

P403+P235 Store in a well-ventilated place. Keep cool.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Usage
Triethylsilane is used for the hydrosilation of olefins to prepare alkyl silanes. 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.
9.1 BRN
1098278
9.2 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.
9.3 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.
9.4 Chemical Properties
Clear liquid
9.5 Physical properties
mp ?156.9 °C; bp 107.7 °C; d 0.7309 g cm?3.
9.6 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.
9.7 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.
9.8 Uses
Triethylsilane is used as a reducing agent inmany organic synthetic reactions.
9.9 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).
9.10 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.]
10. Question & Answer
  • 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 ef...
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