Triethylsilane

Iupac Name：triethylsilicon

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+

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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: F,Xi
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

View all

6. NMR Spectrum

ESR : PHOTOLYSIS WITH DIMETHYLBICYCLOHEPTANE/DTBPO

ESR : PHOTOLYSIS WITH METHANONAPHTHALENE/DTBPO

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : liquid film

SOLID (BETWEEN SALTS)

SOLUTION (11% CCl4 FOR 3800-1300, 2% CS2 FOR 1300-600, AND 11% CCl4 FOR 600-250)

Mass

7. Synthesis Route

617-86-7Total: 47 Synthesis Route

994-49-0 12 Suppliers

617-86-7 282 Suppliers

Literatures:
DE1009631 , ;
Yield: null

998-30-1 112 Suppliers

617-86-7 282 Suppliers

Literatures:
J. chem. Soc. Japan ind. Chem. Sect. (japan.), , vol. 54, p. 769 - 771 C. A., , p. 3889
Yield: null

631-36-7 24 Suppliers

617-86-7 282 Suppliers

Literatures:
Journal of the Chemical Society, , p. 3077 - 3089
Yield: null

View all

8. Precursor and Product

precursor:

557-20-0

7360-64-7

76358-43-5

78-10-4

299925-75-0

2117-17-1

101631-06-5

54509-73-8

631-36-7

1631-33-0

90414-09-8

4342-22-7

358-43-0

925-90-6

998-30-1

542-91-6

1112-48-7

1112-49-8

994-49-0

994-30-9

90414-10-1

2386-64-3

View all

product :

2117-18-2

79271-56-0

648955-87-7

2117-17-1

109-21-7

141-78-6

2290-36-0

1631-33-0

53201-16-4

597-67-1

358-43-0

597-52-4

2290-35-9

1112-48-7

57080-44-1

1112-49-8

994-49-0

994-30-9

89984-46-3

89984-49-6

57246-22-7

89984-47-4

17957-35-6

View all

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

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.

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

Applications of Triethylsilane Jan 29 2021
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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