126689-01-8

Basic information

• Product Name: Cyclopropylboronic acid pinacol ester
• Synonyms: 3-hydroxy-2,3-diMethylbutan-2-yl hydrogen cyclopropylboronate;(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane Cyclopropylboronic Acid Pinacol Ester;cyclopropyl[(3-hydroxy-2,3-diMethylbutan-2-yl)peroxy]boranyl;Cyclopropylboronic acid pinacol ester 2-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Cyclopropylboronic acid picol ester;CYCLOPROPYLBORONIC ACID PINACOL ESTER;2-CYCLOPROPYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-CYCLOPROPYLBORONIC ACID, PINACOL ESTER
• CAS NO: 126689-01-8
• Molecular Formula: C₉H₁₇BO₂
• Molecular Weight: 168.04
• Product Categories: Boronic ester;Cyclopropyl;Organoborons;B (Classes of Boron Compounds);Boronic Acids Esters;Cyclopropanes;Simple 3-Membered Ring Compounds;CHIRAL CHEMICALS
• Mol File: 126689-01-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 146 °C
• Flash Point: 104 °F
• Appearance: /
• Density: 0.922 g/mL at 25 °C
• Vapor Pressure: 0.000776mmHg at 25°C
• Refractive Index: n20/D 1.433
• Storage Temp.: Refrigerator
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: Cyclopropylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropylboronic acid pinacol ester(126689-01-8)
• EPA Substance Registry System: Cyclopropylboronic acid pinacol ester(126689-01-8)

Safety Data

• Hazard Codes: Xi
• Statements: 10
• Safety Statements: 16
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• TSCA: No
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 126689-01-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 126689-01-8 differently. You can refer to the following data:
1. suzuki reaction
2. Cyclopropylboronic acid pinacol ester can be used:As a cyclopropylating reagent in the study of thiophenol S-cyclopropylation, catalyzed by copper(II) acetate.In one of the key synthetic steps for the preparation of 5-lipoxygenase activating protein (FLAP) inhibitor.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 4815, 1989 DOI: 10.1016/S0040-4039(01)80516-5

InChI:InChI=1/C9H19BO3/c1-8(2,11)9(3,4)13-10(12)7-5-6-7/h7,11-12H,5-6H2,1-4H3

Upstream product

• 7393-45-5 cyclopropyl chloride 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 4333-56-6 cyclopropyl bromide 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 411235-57-9 cyclopropylboronic acid 
• 76782-82-6 tert-Butyldimethyl(prop-2-ynyloxy)silane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 4039-82-1 Benzyl propargyl ether 
• 627-41-8 propargyl alcohol methyl ether 
• 1065010-87-8 potassium cyclopropyltrifluoroborate 

Downstream Products

• 1252036-41-1 3-(biphenyl-4-yl)-1-[(2S)-2-(4-cyclopropyl-1H-imidazol-2-yl)-pyrrolidin-1-yl]propan-1-one 
• 1236076-70-2 2-([1,1'-bi(cyclopropan)]-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1119088-63-9 2-cyclopropyl-5-nitro-3-phenylpyridine 
• 1119088-79-7 ethyl 2-chloro-5-cyclopropylbenzoate 
• 1065166-49-5 2-amino-4-(3-cyclopropylphenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one 
• 870220-93-2 4-cyclopropyl-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzeneamine 
• 2676863-29-7 5-cyclopropyl-7-fluoro-2,3-dihydro-1H-inden-4-amine 

Relevant articles and documents

Visible-light-driven graphene supported Cu/Pd alloy nanoparticle-catalyzed borylation of alkyl bromides and chlorides in air

A highly efficient photocatalytic protocol for borylation of alkyl bromides and chlorides with graphene supported Cu/Pd alloy nanoparticles as a heterogeneous catalyst is reported. This photocatalytic system operates with visible light in air, providing a wide range of primary and secondary alkyl halides with B2pin2 or B2neop2 in high yields at low temperatures, thereby demonstrating its broad utility and functional group tolerance. The high performance is attributed to a synergistic effect of localized surface plasmon resonance (LSPR) of Cu and charge transfer from Cu to Pd due to the alloy surface charge heterogeneity. Transfer of energetic electrons from Pd to electrophilic alkyl halides lead to the formation of the alkyl radicals, which quickly react with a nucleophilic adduct of a diboron compound with base adsorbed on the positively charged Cu sites to form the corresponding borylation product.

Hydrogen Atom Transfer Induced Boron Retaining Coupling of Organoboronic Esters and Organolithium Reagents

α-Functionalization of alkyl boronic esters and homologation of aryl boronic esters by regioselective radical C(sp3)-H activation in boron-ate complexes is reported. Reaction of commercial or readily accessed aryl boronic acid pinacol esters with alkyl lithium reagents provides boron-ate complexes. Selective α-C-H abstraction by in situ generated trifluoromethyl radicals leads to radical anions that undergo electron transfer oxidation followed by 1,2-aryl/alkyl migration from boron to carbon to give the α-arylated/alkylated alkyl boronic esters. The valuable boronic ester functionality remains in the products and the cheap trifluoromethyl iodide acts as the oxidant in these C-C couplings. The 1,2-alkyl migration from boron to carbon is highly stereospecific allowing access to stereoisomerically pure boronic esters.

One-Pot, Three-Step Synthesis of Cyclopropylboronic Acid Pinacol Esters from Synthetically Tractable Propargylic Silyl Ethers

Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient one-pot procedure. Terminal acetylenes undergo a Schwartz's reagent catalyzed hydroboration; subsequent addition of further Schwartz's reage