| Identification | More | [Name]
Triphenylsilane | [CAS]
789-25-3 | [Synonyms]
SILANE, TRIPHENYL-
TRIPHENYLSILANE
Triphenylhydrosilane
triphenyl-silan
Triphenylsilaneminoffwhitepowder
Triphenylsilane,min.97%
Triphenysilane
Tri(phenyl)silicon
Triphenylsilane ,98%
TRIPHENYLSILANE, 99+%
Triphenylsilane, min. 97% | [EINECS(EC#)]
212-333-0 | [Molecular Formula]
C18H16Si | [MDL Number]
MFCD00003003 | [Molecular Weight]
260.41 | [MOL File]
789-25-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white solid | [Melting point ]
43-45 °C (lit.) | [Boiling point ]
152 °C/2 mmHg (lit.) | [refractive index ]
1.6160 | [Fp ]
169 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
sol most organic solvents. | [form ]
Powder | [color ]
off-white | [Water Solubility ]
REACTS | [Hydrolytic Sensitivity]
3: reacts with aqueous base | [Sensitive ]
Air Sensitive | [Detection Methods]
GC,NMR | [BRN ]
978182 | [InChI]
1S/C18H16Si/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H | [InChIKey]
AKQNYQDSIDKVJZ-UHFFFAOYSA-N | [SMILES]
c1ccc(cc1)[SiH](c2ccccc2)c3ccccc3 | [CAS DataBase Reference]
789-25-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Silane, triphenyl-(789-25-3) | [EPA Substance Registry System]
789-25-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319 | [Precautionary statements ]
P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
1
| [TSCA ]
Yes | [HS Code ]
29310095 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
Triphenylsilane is an off-white solid that is soluble in most organic solvents. It is used in certain cases for the preparation of triphenylsilyl ethers, which serve as alcohol-protecting groups. The triphenylsilyl group is considerably more stable (about 400 times) than the TMS group toward acidic hydrolysis.
| [Uses]
Triphenylsilane acts as a reactant or reagent for catalytic hydrogen deuterium exchange reactions of silanes, to be oxidized by carbon nanotube-gold nanohybrids, for hydrolysis by ruthenium complexes, for hydrosilylation to produce enolsilanes, for synthesis of bromosilanes, for ozone oxidation of silyl-alkenes for synthesis of α-O-silylated acyloin derivatives. It is used to synthesize hydrido silyl and bis(silyl) bis(imidazolinylidene) nickel complexes. | [Uses]
Triphenylsilane(789-25-3) is reducing agent for esters, xanthates, and polychloroalkanes;
protecting group for alcohols. It takes part in the reactions of Deoxygenations, Hydrosilylations, Lewis Acid-assisted Hydrosilylations, Heteroatom Reductions, Multiple Bond Reductions, Alkene Hydrogenations, Silylations, etc.
| [Application]
More effective radical-based reagent for reduction of
organic halides than the trialkylsilanes. Compares
well with tri-n-butyltin hydride in reduction of enones to
ketones. Shows good selectivity in the reduction of cyclic
hemiacetals. Converts O-acetyl furanoses and pyranoses
to deoxy sugars. | [Preparation]
Triphenylsilane(789-25-3) can be synthesized by reducing phenylsilane (PhSiH3) with a reducing agent such as lithium aluminum hydride (LiAlH4). The overall reaction equation is as follows:
3 PhSiH3 + 2 LiAlH4 → C18H16Si + 2 LiH + 2 AlH3
This reaction is typically carried out in anhydrous conditions and under inert gas atmosphere.
| [reaction suitability]
reagent type: reductant | [storage]
This reagent is stable in the air. Because the toxicogical properties are unknown, it should be handled in a well-ventilated fume hood. Contact with the eyes and skin should be avoided. | [Purification Methods]
Purify it by recrystallisation from MeOH. [Gilman & Zuech J Am Chem Soc 81 5925 1959, Westermark Acta Chem Scand 9 947 1955, IR: Kaplan J Am Chem Soc 76 5880 1954, Beilstein 16 II 605, 16 III 1199, 16 IV 1369.] |
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