Triphenylsilyl chloride
Synonym(s):TPSCl;Triphenylchlorosilane
- CAS NO.:76-86-8
- Empirical Formula: C18H15ClSi
- Molecular Weight: 294.85
- MDL number: MFCD00000496
- EINECS: 200-989-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-12-18 13:37:16
What is Triphenylsilyl chloride?
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.
The Uses of Triphenylsilyl chloride
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).
The Uses of Triphenylsilyl chloride
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.]
Properties of Triphenylsilyl chloride
Melting point: | 91-94 °C(lit.) |
Boiling point: | 378 °C |
Density | 1.14 |
Flash point: | >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. |
Sensitive | Moisture Sensitive |
Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
BRN | 1820487 |
CAS DataBase Reference | 76-86-8(CAS DataBase Reference) |
NIST Chemistry Reference | Triphenylchlorosilane(76-86-8) |
EPA Substance Registry System | Silane, chlorotriphenyl- (76-86-8) |
Safety information for Triphenylsilyl chloride
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 |
GHS Hazard Statements |
H314:Skin corrosion/irritation |
Precautionary Statement Codes |
P260:Do not breathe dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P363:Wash contaminated clothing before reuse. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Triphenylsilyl chloride
InChIKey | MNKYQPOFRKPUAE-UHFFFAOYSA-N |
New Products
(S)-3-Aminobutanenitrile hydrochloride 4-Methylphenylacetic acid N-Boc-D-alaninol N-BOC-D/L-ALANINOL Tert-butyl bis(2-chloroethyl)carbamate 3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin- 2(1H)-one Furan-2,5-Dicarboxylic Acid Tropic acid 1-Bromo-3,5-Di-Tert-Butylbenzene S-2-CHLORO PROPIONIC ACID ETHYL ISOCYANOACETATE 2-Bromo-1,3-Bis(Dimethylamino)Trimethinium Hexafluorophosphate 4-IODO BENZOIC ACID 3-NITRO-2-METHYL ANILINE 1-(2,4-DICHLOROPHENYL) ETHANAMINE (2-Hydroxyphenyl)acetonitrile 4-Bromopyrazole 2-(Cyanocyclohexyl)acetic acid 4-methoxy-3,5-dinitropyridine 1-(4-(aminomethyl)benzyl)urea hydrochloride 2-aminopropyl benzoate hydrochloride diethyl 2-(2-((tertbutoxycarbonyl)amino) ethyl)malonate tert-butyl 4- (ureidomethyl)benzylcarbamate Ethyl-2-chloro((4-methoxyphenyl)hydrazono)acetateRelated products of tetrahydrofuran
You may like
-
Triphenylchlorosilane CAS 76-86-8View Details
76-86-8 -
Triphenylchlorosilane 95% CAS 76-86-8View Details
76-86-8 -
Triphenylsilyl Chloride CAS 76-86-8View Details
76-86-8 -
Chlorotriphenylsilane CAS 76-86-8View Details
76-86-8 -
1975-50-4 98%View Details
1975-50-4 -
2-HYDROXY BENZYL ALCOHOL 98%View Details
90-01-7 -
14714-50-2 (2-Hydroxyphenyl)acetonitrile 98+View Details
14714-50-2 -
118753-70-1 98+View Details
118753-70-1