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58479-61-1 molecular structure
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tert-butyl(chloro)diphenylsilane

ChemBase ID: 90053
Molecular Formular: C16H19ClSi
Molecular Mass: 274.86056
Monoisotopic Mass: 274.09445482
SMILES and InChIs

SMILES:
[Si](c1ccccc1)(c1ccccc1)(Cl)C(C)(C)C
Canonical SMILES:
CC([Si](c1ccccc1)(c1ccccc1)Cl)(C)C
InChI:
InChI=1S/C16H19ClSi/c1-16(2,3)18(17,14-10-6-4-7-11-14)15-12-8-5-9-13-15/h4-13H,1-3H3
InChIKey:
MHYGQXWCZAYSLJ-UHFFFAOYSA-N

Cite this record

CBID:90053 http://www.chembase.cn/molecule-90053.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
tert-butyl(chloro)diphenylsilane
IUPAC Traditional name
tert-butyl(chloro)diphenylsilane
Synonyms
Tert-Butylchlorodiphenylsilane
TBDPSCl
tert-Butyldiphenylchlorosilane
tert-Butyl(chloro)diphenylsilane
tert-Butylchlorodiphenylsilane solution
(tert-Butyl)diphenylsilyl chloride
(tert-Butyl)(chloro)diphenylsilane
t-BUTYLCHLORODIPHENYL-SILANE
tert-Butylchlorodiphenylsilane
tert-Butyldiphenylsilyl chloride
tert-Butyldiphenylchlorosilane
叔丁基二苯基氯硅烷
叔丁基(氯)二苯基硅烷
叔丁基氯二苯基硅烷 溶液
叔丁基二苯基氯硅烷
CAS Number
58479-61-1
EC Number
261-282-0
MDL Number
MFCD00000497
Beilstein Number
644023
PubChem SID
24851697
24851910
162076908
PubChem CID
94078

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 5.8932  LogD (pH = 7.4) 5.8932 
Log P 5.8932  Molar Refractivity 76.5872 cm3
Polarizability 32.05464 Å3 Polar Surface Area 0.0 Å2
Rotatable Bonds Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Boiling Point
40 °C expand Show data source
90 °C/0.01 mmHg(lit.) expand Show data source
90°C expand Show data source
90-92°C/0.01mm expand Show data source
90-92°C/0.01mm expand Show data source
Flash Point
>110 °C expand Show data source
>230 °F expand Show data source
112 °C expand Show data source
112°C(233°F) expand Show data source
233.6 °F expand Show data source
Density
1.057 expand Show data source
1.057 g/mL at 25 °C(lit.) expand Show data source
1.068 g/ml expand Show data source
1.072 expand Show data source
1.249 g/mL at 25 °C expand Show data source
Refractive Index
1.568 expand Show data source
1.5680 expand Show data source
n20/D 1.567 expand Show data source
n20/D 1.568(lit.) expand Show data source
Storage Condition
2-8°C, Desiccate, Store Under Nitrogen expand Show data source
Storage Warning
Corrosive/Moisture Sensitive/Store under Argon expand Show data source
Moisture Sensitive expand Show data source
European Hazard Symbols
Corrosive Corrosive (C) expand Show data source
UN Number
2922 expand Show data source
2987 expand Show data source
UN2987 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
8 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Australian Hazchem
4WE expand Show data source
Risk Statements
34 expand Show data source
34-37 expand Show data source
34-37-40 expand Show data source
R:34 expand Show data source
Safety Statements
26-36/37/39-45 expand Show data source
S:26-27/28-36/37/39-46-64 expand Show data source
EU Classification
C3 expand Show data source
EU Hazard Identification Number
8B expand Show data source
Emergency Response Guidebook(ERG) Number
156 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H314 expand Show data source
H314-H318 expand Show data source
H314-H351 expand Show data source
GHS Precautionary statements
P280-P303+P361+P353-P305+P351+P338-P310 expand Show data source
P280-P305 + P351 + P338-P310 expand Show data source
Personal Protective Equipment
Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US) expand Show data source
Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 2922 8/PG 2 expand Show data source
UN 2987 8/PG 2 expand Show data source
Purity
≥97.0% (GC) expand Show data source
97% expand Show data source
98% expand Show data source
Concentration
1 M in methylene chloride expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Linear Formula
(CH3)3CSi(C6H5)2Cl expand Show data source
Empirical Formula (Hill Notation)
C16H19ClSi expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02154908 external link
1 ml = approx. 1.06 g
Sigma Aldrich - 195537 external link
Packaging
2, 10 g in glass bottle
50, 250 g in Sure/Seal™
Application
Silylating reagent used in the protection of alcohols1,2 and the preparation of silyl ethers.3
Sigma Aldrich - 702730 external link
Packaging
100, 500 mL in Sure/Seal™
Sigma Aldrich - 19938 external link
Other Notes
Silylating agent for the introduction of the selective TBDPS group1,2,3

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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