| Identification | More | [Name]
Triphenylsilyl chloride | [CAS]
76-86-8 | [Synonyms]
TPSCL
TRIPHENYLCHLOROSILANE
TRIPHENYLSILICON CHLORIDE
TRIPHENYLSILYL CHLORIDE
chlorotriphenyl-silan
Silane, chlorotriphenyl-
silane,chlorotriphenyl-
Triphenylchlorsoilane
Triphenylchlorosilane,96%
Triphenylchlorosilane(Chlorotriphenylsilane)
Triphenylchlorosilane,97%
Triphenylchlorosilane (TPSCl)
TRIPHENLCHLOROSILANE
triphenylchlorosilicane
Triphenyltrichlorosilane
TPSCl, Triphenylchlorosilane | [EINECS(EC#)]
200-989-0 | [Molecular Formula]
C18H15ClSi | [MDL Number]
MFCD00000496 | [Molecular Weight]
294.85 | [MOL File]
76-86-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystal, pungent, with acrid ordor of hydrogen chloride. | [Melting point ]
91-94 °C(lit.) | [Boiling point ]
378 °C | [density ]
1.14 | [Fp ]
>200°C | [storage temp. ]
Refrigerator | [solubility ]
acetone: 0.1 g/mL, clear
| [form ]
crystal | [color ]
white | [Specific Gravity]
1.16 | [Water Solubility ]
Reacts with water. | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents | [Sensitive ]
Moisture Sensitive | [BRN ]
1820487 | [InChIKey]
MNKYQPOFRKPUAE-UHFFFAOYSA-N | [CAS DataBase Reference]
76-86-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Triphenylchlorosilane(76-86-8) | [EPA Substance Registry System]
76-86-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns.
R37:Irritating to the respiratory system. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
1
| [RTECS ]
VV2720000
| [F ]
10-21 | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29310095 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white crystal or powder with acrid ordor of hydrogen chloride, used for synthesis of pharmaceutical intermediates.
| [Description]
Triphenylsilyl chloride is a white to off-white crystal or powder with acrid ordor of hydrogen chloride, used for synthesis of pharmaceutical intermediates. | [Physical properties]
mp 92–94°C; bp 240–243°C/35 mmHg. | [Uses]
A wide variety of Grignard reagents and organolithium complexes
participate in reactions with Ph3SiCl to afford organosilanes.
Thus the reaction of allylmagnesium chloride with Ph3SiCl gives the allylsilane in high yield (eq 3).However, when hydrosilyl
Grignard reagents are employed, reduction to the silane
occurs (eq 4).Azaallyl anion6 and diazolithium salts can each
be silylated to give the anticipated silane adducts (eqs 5 and 6).
Similarly, arylsilanes8 and alkynylsilanes are produced upon
silylation of the appropriate metalated13 carbanions with Ph3SiCl
(eqs 7–11).
| [Uses]
Chlorotriphenylsilane is used as a silylating agent. It is also used as a pharmaceutical intermediate. | [Purification Methods]
Likely impurities are tetraphenylsilane, small amounts of hexaphenyldisiloxane and traces of triphenylsilanol. Purify it by distillation at 2mm, then crystallise it from EtOH-free CHCl3, and from pet ether (b 30-60o) or hexane by cooling in a Dry-ice/acetone bath. [Allen & Modena J Chem Soc 3671 1957, Curran et al. J Am Chem Soc 72 4471 1950, Speier & Zimmerman J Am Chem Soc 77 6395 1955, Thomas & Rochow J Am Chem Soc 79 1843 1957, Beilstein 16 IV 1484.] |
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