141550-13-2

Basic information

• Product Name: 3,3-Dimethylallylboronic acid pinacol ester, 2-(3-Methyl-but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 3,3-Dimethylallylboronic acid pinacol ester, 2-(3-Methyl-but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-Methyl-2-butenylboronic acid pinacol ester;2-(3-Methyl-but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-Methylbut-2-enylboronic acid, pinacol ester;4,4,5,5-Tetramethyl-2-(3-methyl-2-buten-1-yl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(3-methylbut-2-en-1-yl)-1,3,2-dioxaborolane;4,4,5,5-tetraMethyl-2-(3-Methylbut-2-enyl)-1,3,2-dioxaborolane;3-Methyl-2-butenylboronic acid pinacol ester 96%
• CAS NO: 141550-13-2
• Molecular Formula: C₁₁H₂₁BO₂
• Molecular Weight: 196.1
• Mol File: 141550-13-2.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 42-45 °C/0.6 mmHg
• Flash Point: 77 °C
• Appearance: /
• Density: 0.885 g/mL at 25 °C
• Refractive Index: n20/D 1.4395
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,3-Dimethylallylboronic acid pinacol ester, 2-(3-Methyl-but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-Dimethylallylboronic acid pinacol ester, 2-(3-Methyl-but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(141550-13-2)
• EPA Substance Registry System: 3,3-Dimethylallylboronic acid pinacol ester, 2-(3-Methyl-but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(141550-13-2)

Safety Data

• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 141550-13-2(Hazardous Substances Data)

Usage

General Description

3,3-Dimethylallylboronic acid pinacol ester, also known as 2-(3-Methyl-but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, is a chemical compound typically used in organic synthesis. This ester contains elements such as Carbon, Hydrogen, Oxygen and Boron. As an allylboronic acid ester, its functionality is often utilized in transition-metal-catalyzed synthetic tactics, including Suzuki-Miyaura cross-coupling reactions. Its pinacol ester structure contributes to its stability, and the relatively high molecular weight signifies its utility in more complex synthetic processes. Like most chemicals, it should be handled with caution, stored properly, and used in a controlled environment.

Upstream product

• 598-25-4 Dimethylallene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 115-18-4 2-methyl-3-buten-2-ol 
• 73183-34-3 bis(pinacol)diborane 
• 870-63-3 prenyl bromide 
• 78-79-5 isoprene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 24509-88-4 2-methyl-3-buten-2-yl acetate 
• 1187817-21-5 4,4,5,5-tetramethyl-2-(3-methylbut-3-en-1-yl)-1,3,2-dioxaborolane 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 563-45-1 3-Methyl-1-butene 

Downstream Products

• 3558-31-4 2-amino-5-methylhex-4-enoic acid 
• 4489-84-3 3-methyl-1-phenylbut-2-ene 
• 4957-17-9 1-methoxy-2-(3-methylbut-2-en-1-yl)benzene 
• 4957-18-0 1-methoxy-4-(3-methyl-but-2-enyl)benzene 
• 1239020-84-8 S-cyclohexyl 5-hydroxy-6,6-dimethyloct-7-enethioate 
• 1239020-81-5 S-cyclohexyl 5-hydroxy-2,6,6-trimethyloct-7-enethioate 
• 27644-02-6 2,2-dimethyl-1-phenylbut-3-en-1-ol 
• 1401912-21-7 (R)-3-methyl-3-(2-methylbut-3-en-2-yl)-4-phenyl-2,3-dihydro-[1,2,5]thiadiazole-1,1-dioxide 
• 18272-88-3 1-methoxy-4-(2-methylbut-3-en-2-yl)benzene 
• 1146120-93-5 1,3-dimethyl-2-(3-methylbut-2-en-1-yl)benzene 
• 634-36-6 1,2,3-trimethoxybenzene 
• 93930-23-5 1,2,3-trimethoxy-5-(3-methylbut-2-en-1-yl)benzene 
• 18272-91-8 1-methoxy-3-(3-methylbut-2-en-1-yl)benzene 
• 73318-85-1 1-(4-(3-methylbut-2-en-1-yl)phenyl)ethanone 

Relevant articles and documents

Direct synthesis of functionalized allylic boronic esters from allylic alcohols and inexpensive reagents and catalysts

A remarkably simple and effective system for the direct conversion of allylic alcohols into high value allylic boronic esters using commercially available reagents and catalysts is described. Georg Thieme Verlag Stuttgart.

Regio- and stereoselective synthesis of allylboranes via platinum(0)- catalyzed borylation of allyl halides with pinacolborane

Various allyl halides were borylated with pinacolboranes in the presence of NEt3 and a catalytic amount of Pt(dba)2 and AsPh3 to afford regio- and stereodefined allylboranes in good yields. (C) 2000 Elsevier Science Ltd.

Practical Synthesis of Allyl, Allenyl, and Benzyl Boronates through SN1′-Type Borylation under Heterogeneous Gold Catalysis

Efficient borylation of sp3 C-O bonds by supported Au catalysts is described. Au nanoparticles supported on TiO2 showed high activity under mild conditions employing low catalyst loading conditions without the aid of any additives, such as phosphine and bases. A variety of allyl, propargyl, and benzyl substrates participated in the heterogeneously catalyzed reactions to furnish the corresponding allyl, allenyl, and benzyl boronates in high yields. Besides, Au/TiO2 was also effective for the direct borylation of allylic and benzylic alcohols. A mechanistic investigation based on a Hammett study and control experiments revealed that sp3 C-O bond borylation over supported Au catalysts proceeded through SN1′-type mechanism involving the formation of a carbocationic intermediate. The high activity, reusability, and environmental compatibility of the supported Au catalysts as well as the scalability of the reaction system enable the practical synthesis of valuable organoboron compounds.

Nickel-Catalysed Allylboration of Aldehydes

A nickel catalyst for the allylboration of aldehydes is reported, facilitating the preparation of homoallylic alcohols in high diastereoselectivity. The observed diastereoselectivities and NMR experiments suggest that allylation occurs through a well-defined six-membered transition state, with nickel acting as a Lewis acid.