439693-30-8

Basic information

• Product Name: 1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2,2-dimethyl-
• CAS NO: 439693-30-8
• Molecular Formula: C22H32O2Si
• Molecular Weight: 356.58
• Mol File: 439693-30-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2,2-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2,2-dimethyl-(439693-30-8)
• EPA Substance Registry System: 1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2,2-dimethyl-(439693-30-8)

Safety Data

• Hazardous Substances Data: 439693-30-8(Hazardous Substances Data)

Usage

Physical properties

Clear, colorless liquid with a faint odor; insoluble in water; miscible with many organic solvents

Uses

Reagent in organic synthesis; protecting group for alcohols; solvent and intermediate in the production of pharmaceuticals and other fine chemicals

Safety precautions

Handle and use in accordance with proper safety precautions and guidelines due to its flammable and potentially hazardous properties.

Upstream product

• 597-43-3 2,2-dimethylsuccinic acid 
• 32812-23-0 2,2-dimethylbutane-1,4-diol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 187869-61-0 4-(tert-butyldiphenysilanyloxy)-2,2-dimethylbutyraldehyde 
• 1610010-43-9 C₂₃H₃₀Br₂OSi 
• 1610010-27-9 C₂₉H₃₉NO₅Si 
• 1610010-46-2 C₂₇H₃₅NO₃Si 
• 1610010-45-1 C₂₅H₃₄O₄SSi 
• 1610010-44-0 C₂₄H₃₂O₂Si 
• 1610010-11-1 C₂₇H₃₅NO₃Si 
• 1334541-61-5 2-(4-{[tert-butyl(diphenyl)silyl]oxy}-2,2-dimethylbutyl)-1H-isoindole-1,3(2H)-dione 
• 936724-65-1 (4Z)-tert-butyl-(3,3-dimethylhepta-4,6-dienyloxy)diphenylsilane 
• 936724-58-2 (E)-tert-butyl((3,3-dimethylhepta-4,6-dien-1-yl)oxy)diphenylsilane 
• 924898-75-9 4-(tert-butyldiphenylsilanyloxy)-2,2-dimethylbutyl ethenesulfonate 

Relevant articles and documents

A Palladium(II)-Catalyzed C-H Activation Cascade Sequence for Polyheterocycle Formation

Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)-catalyzed C-H activation strategy for the construction of such systems has been developed. Starting from simple 1,3-dienyl-substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step. Don't overdo it: A palladium(II)-catalyzed C-H activation cascade sequence for the synthesis of polyheterocycles is reported. Aromatization of the initially formed dihydro species occurred with a quinone oxidant. In some cases the use of one equivalent of the oxidant enabled isolation of the dihydro species as a single isomer (see scheme; X=NMe, O, S).

Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins

Lithium 2,2,6,6-tetramethylpiperidide (LTMP)-induced intramolecular cyclopropanation of unsaturated terminal epoxides provides an efficient and completely stereoselective entry to bicyclo[3.1.0]hexan-2-ols and bicyclo[4.1.0]heptan-2-ols. Further elaboration of C-5 and C-6 stannyl-substituted bicyclo[3.1.0]-hexan-2-ols via Sn-Li exchange/electrophile trapping or Stille coupling generates a range of substituted bicyclic cyclopropanes. An alternative straightforward cyclopropanation protocol using a catalytic amount of 2,2,6,6-tetramethylpiperidine (TMP) allows for a convenient (1 g-7.5 kg) synthesis of bicyclo[3.1.0]-hexan-2-ol and other bicyclic adducts. The synthetic utility of this chemistry has been demonstrated in a concise asymmetric synthesis of (+)-β-cuparenone. The related unsaturated chlorohydrins also undergo intramolecular cyclopropanation via in situ epoxide formation.