61676-62-8

Basic information

• Product Name: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-ISOPROPOXY-4,4,5,5-TETRAMETHYL-1,3,2-DIOABOROLANE;2-Isopropoxyboronic acid, pinacol cyclic ester;4,4,5,5-Tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane;Isopropyl pinacol borate;Isopropoxyboronic acid pinacol este;2-isopropxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;[(Prop-2-yl)oxy]boronic acid, pinacol ester, 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Isopropoxy-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(Isopropoxyboronic acid pinacol ester)
• CAS NO: 61676-62-8
• Molecular Formula: C₉H₁₉BO₃
• Molecular Weight: 186.06
• EINECS: -0
• Product Categories: Boronic ester;Organoborons;B (Classes of Boron Compounds);Boric Acid Esters;Boric Acid Triesters;Boronic Acids and Derivatives;Organoborates;Organometallic Reagents;Boric Acid| Boric Acid Ester| Potassium Trifluoroborate;Organic boronic acid
• Mol File: 61676-62-8.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 73 °C15 mm Hg(lit.)
• Flash Point: 109 °F
• Appearance: Colorless/Liquid
• Density: 0.912 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.924mmHg at 25°C
• Refractive Index: n20/D 1.409(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 1906370
• CAS DataBase Reference: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(61676-62-8)
• EPA Substance Registry System: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(61676-62-8)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 61676-62-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 61676-62-8 differently. You can refer to the following data:
1. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be used as a reagent to borylate arenes and to prepare fluorenylborolane.It can also be used in the synthesis of following intermediates for generating conjugated copolymers:9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl1,3,2-dioxaborolane-2-yl)dibenzosilole.3,9-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,11-di(1-decylundecyl)indolo[3,2-b]carbazole.2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene.2,7-Bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N-9′′-heptadecanylcarbazole.
2. suzuki reaction

InChI:InChI=1/C9H19BO3/c1-7(2)11-10-12-8(3,4)9(5,6)13-10/h7H,1-6H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 52732-22-6 isopropoxyboronic acid 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 75-56-9 methyloxirane 
• 108-21-4 Isopropyl acetate 
• 924-88-9 diisopropyl succinate 
• 97-62-1 Ethyl isobutyrate 
• 67-64-1 acetone 
• 5419-55-6 Triisopropyl borate 
• 129217-85-2 trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane 
• 67-63-0 isopropyl alcohol 
• 929887-20-7 2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 222549-37-3 diethyl (E)-2-(but-2-yn-1-yl)-2-(penta-2,4-dien-1-yl)malonate 

Downstream Products

• 250726-93-3 2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-4,4,5,5-tetramethyl-2-thiophen-2-yl-1,3,2-dioxaborolane 
• 306775-04-2 2-hept-6-en-1-ynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 796851-30-4 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran 
• 635305-48-5 4,4,5,5-tetramethyl-2-(4-methylthiophen-2-yl)[1,3,2]dioxaborolane 
• 313484-56-9 2-(3,4-dimethoxy-2-methoxymethoxyphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane 
• 881690-53-5 2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-8,8-di-p-tolyl-8H-3-thia-cyclopenta[a]indene 
• 254755-24-3 9,9-dihexyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)fluorene 
• 916486-98-1 2-(2-(1,3-dioxolan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 214360-66-4 2-(4-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 960116-25-0 C₁₆H₁₉BO₂S 
• 904873-75-2 N,N-bis-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-(p-trifluoromethyl)aniline 
• 865163-50-4 4,4'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-hexyldiphenylamine 
• 865163-48-0 3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(4-dodecyloxyphenyl)carbazole 
• 476360-83-5 N-(2-ethylhexyl)-2,7-bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaboralan-2′-yl)-9H-carbazole 

Relevant articles and documents

A study of the effect on nucleophilic hydrolytic activity of pancreatic elastase, trypsin, chymotrypsin, and leucine aminopeptidase by boronic acids in the presence of arabinogalactan: A subsequent study on the hydrolytic activity of chymotrypsin by boronic acids in the presence of mono-, di-, and trisaccharides

The hydrolytic activity of trypsin, chymotrypsin, elastase, and leucine aminopeptidase, is inhibited by different boronic acids. However, all the enzymes are inhibited by the compound CbzAla(boro)Gly(OH)2. Therefore, these additives can control the nucleophilic hydrolytic activity of these enzymes.

Hydroboration of nitriles, esters, and amides catalyzed by simple neosilyllithium

We present here an efficient method for the hydroboration of organic nitriles, carboxylic esters, and carboxamides with pinacolborane (HBpin) using an alkali metal catalyst, neosilyllithium (LiCH2SiMe3), in neat reaction conditions. The reactions were accomplished with efficient catalytic reactivity and demonstrated by neosilyllithium at room temperature, in solvent-free condition, to afford a high yield of the corresponding N-boryl amines, boryl ethers, and amine hydrochlorides. The protocol for the catalytic reaction presented in this paper is simple and efficient, with diverse substrate scope for nitriles, carboxylic esters, and carboxamides showing excellent functional group tolerance. DLPNO-CCSD(T) calculations were also performed, showing that the hydroboration of nitriles catalyzed by neosilyllithium occurs through the pre-coordination of the nitrile at Lewis acid lithium followed by hydride migration from the B–H entity.

Hydroboration of aldehydes, ketones and CO2under mild conditions mediated by iron(iii) salen complexes

The hydroboration of aldehydes, ketones and CO2is demonstrated using a cheap and air stable [Fe(salen)]2-μ-oxo pre-catalyst with pinacolborane (HBpin) as the reductant under mild conditions. This catalyst system chemoselectively hydroborates aldehydes over ketones and ketones over alkenes. In addition, the [Fe(salen)2]-μ-oxo pre-catalyst shows good efficacy at reducing “wet” CO2with HBpin at room temperature.

Construction of Silicon-Containing Seven-Membered Rings by Catalytic [4 + 2 + 1] Cycloaddition through Rhodium Silylenoid

A rhodium-catalyzed [4 + 2 + 1] cycloaddition involving 1,3-diene, alkyne, and silylene to afford silicon-containing seven-membered rings was established. In the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM), nona-1,3-dien-8-yne derivatives reacted efficiently at 80-110 °C with boryl(isopropoxy)silane or boryl(diethyamino)silane, which reacts as the synthetic equivalent of silylene, to afford 1-silacyclohepta-2,5-dienes (2,5-dihydro-1H-silepines). Regiodivergent and chemo- and stereoselective functionalization of the seven-membered nonconjugated diene was achieved by hydroboration mediated by Cs2CO3 or an iridium catalyst.