26305-83-9

Usage

Class

Organosilicon compounds

Functional groups

Bromide group, Trimethylsilyloxy group

Structure

Contains an undecyl chain with the functional groups attached

Application

Used as a reagent in organic synthesis

Specific use

Preparation of bioactive molecules and pharmaceutical intermediates

Reactivity

Unique structure and reactivity make it a valuable building block in chemical synthesis and drug development.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 2834-05-1 11-bromoundecanoic acid 
• 6287-90-7 11-bromo-undecanoic acid methyl ester 
• 2754-27-0 trimethylsilyl acetate 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 

Downstream Products

• 26305-84-0 11-iodo-1-(trimethylsilyloxy)undecane 
• 18202-11-4 tridec-12-yn-1-ol 
• 499138-68-0 tridec-12-ynyltrimethylsilyl ether 
• 1438243-38-9 C₂₆H₅₄B₁₀OSi 
• 268227-43-6 ethyl (4-nitrophenyl)[11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate 
• 83905-97-9 (11-hydroxyundecyl)phosphonic acid diethyl ester 
• 499138-70-4 4-{13-[4-(2-triisopropylsilylethynyl)phenyl]tridec-12-yn-1-yloxy}-1-iodobenzene 
• 499138-69-1 13-[4-(2-triisopropylsilylethynyl)phenyl]tridec-12-yn-1-ol 
• 91146-06-4 1,44-tetratetracontanediol 

Relevant academic research and scientific papers

A novel biotinylated suicide inhibitor for directed molecular evolution of lipolytic enzymes

A bifunctional activity label (8)Scheme 1Reagents and conditions: (i) Me3SiCl, Et3N, CH2Cl2/ether; (ii) (EtO)3P/reflux; (iii) H2SO4/acetone; (iv) 1. COCl2, 2. N-hydrox

Trimethylsilyl Esters as Novel Dual-Purpose Protecting Reagents

Trimethylsilyl esters, AcOTMS, BzOTMS, TCAOTMS, etc., are inexpensive and chemically stable reagents that pose a negligible environmental hazard. Such compounds prove to serve as efficient dualpurpose reagents to respectively achieve acylation and trimethylsilylation of alcohols under acidic or basic conditions. Herein, a detailed study on protection of various substrates and new methodological investigations is described.

Direct chlorination of alcohols with chlorodimethylsilane catalyzed by a gallium trichloride/tartrate system under neutral conditions

The reaction of secondary alcohols 1 with chlorodimethylsilane (HSiMe 2Cl) proceeded in the presence of a catalytic amount of GaCl 3/diethyl tartrate to give the corresponding organic chlorides 3. In the catalytic cycle, the reaction of diethyl tartrate 4a with HSiMe 2Cl 2 gives the chlorosilyl ether 5 with generation of H2. Alcohol-exchange between the formed chlorosilyl ether 5 and the substrate alcohol 1 affords alkoxychlorosilane 6, which reacts with catalytic GaCl 3 to give the chlorinated product 3. The moderate Lewis acidity of GaCl3 facilitates chlorination. Strong Lewis acids did not give product due to excessive affinity for the oxy-functionalities. Although tertiary alcohols were chlorinated by this system even in the absence of diethyl tartrate, certain alcohols that are less likely to give carbocationic species were effectively chlorinated using the GaCl3/diethyl tartrate system. The Royal Society of Chemistry.

SYNTHESIS OF 1,44-TETRATETRACONTANEDIOL

The synthesis of the long-chain aliphatic diol 1,44-tetratetracontanediol was realized by chain growth in the Wurtz reation.Twofold condensation of the bifunctional fragments led to 1,44-tetratetracontanediol.Halogen-containing alcohols with protecting tetrahydrofuranyl and trimethylsilyl groups were used as starting compounds for the Wurtz condensation.