| DIISOPROPYLCHLOROSILANE Basic information |
| Product Name: | DIISOPROPYLCHLOROSILANE |
| Synonyms: | chloro(2,3-dimethylbutan-2-yl)silicon;Silane, chlorobis(1-methylethyl)-;CHLORODIISOPROPYLSILANE;DIISOPROPYLCHLOROSILANE;Diisopropylsilyl chloride;chloro-di(propan-2-yl)silicon;Chlorodiisopropylsilane >chlorobis(propan-2-yl)silane |
| CAS: | 2227-29-4 |
| MF: | C6H15ClSi |
| MW: | 150.72 |
| EINECS: | |
| Product Categories: | Pharmaceutical Intermediates;Monochlorosilanes;Reduction;Si (Classes of Silicon Compounds);Si-Cl Compounds;Si-H Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry |
| Mol File: | 2227-29-4.mol |
| DIISOPROPYLCHLOROSILANE Chemical Properties |
| Boiling point | 58-60 °C50 mm Hg(lit.) |
| density | 0.883 g/mL at 25 °C(lit.) |
| refractive index | n |
| Fp | 72 °F |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | generally sol organic solvents; reacts with alcohols, ammonia,and water. |
| form | clear liquid |
| color | Colorless to Almost colorless |
| Specific Gravity | 0.883 |
| Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
| BRN | 2231355 |
| CAS DataBase Reference | 2227-29-4(CAS DataBase Reference) |
| EPA Substance Registry System | Silane, chlorobis(1-methylethyl)- (2227-29-4) |
| Safety Information |
| Hazard Codes | C |
| Risk Statements | 10-34 |
| Safety Statements | 26-36/37/39-45 |
| RIDADR | UN 2986 8/PG 2 |
| WGK Germany | 3 |
| F | 10-21 |
| TSCA | Yes |
| HazardClass | 3.1 |
| PackingGroup | II |
| HS Code | 29319090 |
| MSDS Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| DIISOPROPYLCHLOROSILANE Usage And Synthesis |
| Physical properties | bp 150–153°C,bp 54–55°C/45 mmHg; d 0.872 gmL?1 |
| Uses | Intramolecular hydrosilylation is also possible within β-diisopropylsilyloxy esters (13), constituting an exceptionally mild method for reducing ester groups to the aldehyde oxidation level (eq 4).The derivatives (13) may be synthesized from β-hydroxy esters (12) as described above for the analogous ketones. Treatment with fluoride ions (but not Lewis acids) induces hydride transfer to give alkoxysiladioxanes (14) in excellent yields (≥95%). Although usually performed in dichloromethane, the hydrosilylation may also be accomplished with ethyl acetate as solvent, providing strong evidence for intramolecularity. |
| Application | Used in a silylation-reduction-allylation sequence of β-hydroxy esters to homoallylic-substituted 1,3-diols. Used in the silylation-hydrosilation-oxidation of allyl alcohols to 1,3-diols. Reaction carried out in diastereoselective manner. Reduces β-hydroxy ketones to anti-1,3 diols. |
| Preparation | obtained by reaction of trichlorosilane with isopropylmagnesium chloride;the original yield of 45% may be raised to 70–80% by employing conc hydrochloric acid to quench the reaction. |
| Purification Methods | Impurities can be readily detected by 1H NMR. Purify it by fractional distillation [Gilman & Clark J Am Chem Soc 69 1499 1947, Allen et al. J Chem Soc 3668 1957]. |
| DIISOPROPYLCHLOROSILANE Preparation Products And Raw materials |
| Raw materials | DIISOPROPYLSILANE-->ISOPROPYLMAGNESIUM BROMIDE-->2-Chloropropane-->ISOPROPYLMAGNESIUM CHLORIDE |
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