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58479-61-1 - tert-Butyldiphenylchlorosilane, 97% - tert-Butylchlorodiphenylsilane - tert-Butyldiphenylsilyl chloride - A12721 - Alfa Aesar

A12721 tert-Butyldiphenylchlorosilane, 97%

Numéro CAS
58479-61-1
Synonymes
tert-Butylchlorodiphenylsilane
tert-Butyldiphenylsilyl chloride

Dimensions Prix ($) Quantité Disponibilité
10g 38,09
50g 130,81
250g 489,60
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tert-Butyldiphenylchlorosilane, 97%

MDL
MFCD00000497
EINECS
261-282-0

Propriétés chimiques

Formule
C16H19ClSi
Poids formulaire
274.87
Point d'ébullition
90-92°/0.01mm
Point d'éclair
112°(233°F)
Densité
1.072
Indice de réfraction
1.5680
Sensibilité
Moisture Sensitive
Solubilité
Miscible with chloroform and ethyl acetate. Immiscible with water.

Applications

tert-Butyldiphenylchlorosilane acts as a silylating reagent used to protect alcohols and in the preparation of silyl ethers. It plays a major role as a raw material and a precursor in organic synthesis and pharmaceuticals. It is also used for the synthesis of interphenylene phenyloxazoles which can be used for the treatment of circulatory disorders, angina and stroke.

Notes

Moisture sensitive. Incompatible with strong oxidizing agents, water and bases.

Références bibliographiques

Silylating agent (see Appendix 4) for the formation, with e.g. imidazole, of t-butyldiphenylsilyl (TBDPS) ethers of alcohols: Can. J. Chem., 53, 2975 (1975); Org. Synth. Coll., 9, 139 (1998). Alternative to tert-Butyl­dimethyl­chlorosilane, A13064, allowing selective protection of primary alcohols in the presence of secondary, using DMAP/ pyridine: Helv. Chim. Acta, 69, 1273 (1986), or DMAP/ triethylamine: Tetrahedron Lett., 99 (1979); 26, 1185 (1985). TBDPS ethers tend to be more crystalline and are much more stable to acidic conditions than TBDMS. They can also survive acetal formation and cleavage, as well as the acidic conditions required for cleavage of trityl and THP ethers. Silylation rates of hindered alcohols have been increased in the presence of silver nitrate: J. Am. Chem. Soc., 116, 5050 (1994).

Cleavage occurs readily with TBAF in THF: Org. Synth. Coll., 9, 4 (1998). For use of K10 clay in aqueous MeOH, see: J. Org. Chem., 61, 9026 (1996). Cleavage with BBr3 leads directly to the corresponding alkyl bromides: J. Org. Chem., 53, 3111 (1988).

The silyl copper species derived from the lithio-derivative and CuCN adds to terminal alkynes, giving vinyl copper intermediates which react with electrophiles to give vinyl silanes. The presence of the hindered TBDPS group confers some useful differences in comparison with less hindered silyl groups: J .Chem. Soc., Perkin 1., 1525 (1995); compare Chlorodimethyl­phenyl­silane, A15638. The hindered TBDPS group has also been utilized in the Peterson olefination reaction to promote high (Z)-selectivity: Synthesis, 1223 (2000).

Clement, L. L.; Tsakos, M.; Schaffert, E. S.; Scavenius, C.; Enghild, J. J.; Poulsen, T. B. The amido-pentadienoate-functionality of the rakicidins is a thiol reactive electrophile-development of a general synthetic strategy. Chem. Commun. 2015, 51 (62), 12427-12430.

Liu, Y.; Wang, S. Q.; Zhao, B. X. A novel pyrazoline-based fluorescent probe for detecting fluoride ion in water and its application on real samples. RSC Adv. 2015, 5 (42), 32962-32966.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Mentions de prudence: P280-P303+P361+P353-P305+P351+P338-P310

Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician.

Autres références

Beilstein
644023
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2931.90
TSCA
Yes

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Catalyseurs

Analytique et matériel de laboratoire