| Identification | More | [Name]
Triethylsilane | [CAS]
617-86-7 | [Synonyms]
SILANE E3H
SILICONTRIETHYL
TRIETHYLSILANE
Triethylsilyl hydride
(C2H5)3SiH
CT2523
triethyl-silan
Triethylsilicon hydride
Triethylsilane (TES)
TRIETHYLSILANE, WACKER QUALITY
Triethylsilane,98+%
Triethylsilyl
Triethylsilane,99%
Silane, triethyl-
Triethylsilane, 98.5+%
Triethylsilicon | [EINECS(EC#)]
210-535-3 | [Molecular Formula]
C6H16Si | [MDL Number]
MFCD00009018 | [Molecular Weight]
116.28 | [MOL File]
617-86-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear liquid | [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.)
| [Fp ]
25 °F
| [storage temp. ]
2-8°C
| [solubility ]
insol H2O; sol hydrocarbons, halocarbons, ethers. | [form ]
liquid | [color ]
colorless | [Specific Gravity]
0.728 | [Stability:]
Stable, but moisture sensitive. Highly flammable. Generates highly flammable gas (hydrogen) in contact with water, acids and bases. | [Water Solubility ]
Miscible with water. | [Hydrolytic Sensitivity]
3: reacts with aqueous base | [Sensitive ]
Moisture Sensitive | [BRN ]
1098278 | [InChI]
1S/C6H16Si/c1-4-7(5-2)6-3/h7H,4-6H2,1-3H3 | [InChIKey]
AQRLNPVMDITEJU-UHFFFAOYSA-N | [SMILES]
CC[SiH](CC)CC | [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]
617-86-7(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS02,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H225-H315-H319-H335 | [Precautionary statements ]
P210-P233-P240-P241-P303+P361+P353-P305+P351+P338 | [Hazard Codes ]
F,Xi | [Risk Statements ]
R11:Highly Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S29:Do not empty into drains .
S33:Take precautionary measures against static discharges .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 1993 3/PG 2
| [WGK Germany ]
1
| [F ]
10-21 | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29310095 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Eye Irrit. 2
Flam. Liq. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 | [Physical properties]
mp ?156.9 °C; bp 107.7 °C; d 0.7309 g cm?3. | [Reactions]
Triethylsilane 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. | [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. | [Definition]
ChEBI: Triethylsilane is an organosilicon compound. It has a role as a reducing agent. | [Production Methods]
A synthetic method of triethylsilane comprises the following steps: reacting sodium hydride with trimethyl borate to prepare trimethoxy sodium borohydride; adding triethylchlorosilane to trimethoxy sodium monohydroborate to react to obtain triethylsilane.
To a 500ml reaction flask, 20g (0.5mol) of 60% sodium hydride and 80g of anhydrous tetrahydrofuran were added. Stirring and cooling to 0-10 ℃ under the protection of nitrogen, the mixture was then maintained under nitrogen protection, stirred, and the liquid temperature at 0-10 ℃, and dropwise added 57.2g (0.55mol) of trimethyl borate. After the dropwise addition, the temperature was kept at 0-10 ℃ and stirred for 1 hour.Maintaining the nitrogen protection, stirring and liquid temperature of the reaction liquid at 0-10 ℃, and then dropwise adding 67.7g (0.45mol) of triethylchlorosilane. After the dropwise addition, continuously keep the temperature at 0-10 ℃ and stir for 1 hour. The reaction solution was then filtered at room temperature. Rectifying the filtrate at normal pressure and collecting fractions with the boiling range of 109-110 ℃ as triethylsilane to obtain 46.1g of triethylsilane, which yields 88.2%. 45-64 ℃: a mixed solution of trimethyl borate and tetrahydrofuran; 64-109 ℃:a mixture of tetrahydrofuran and a small triethylsilane.
| [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 | [reaction suitability]
reagent type: reductant | [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. |
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