67562-19-0

Basic information

• Product Name: n-Propyl boronic acid pinacol
• Synonyms: n-Propyl boronic acid pinacol;1-Propylboronic acid pinacol ester, 98%
• CAS NO: 67562-19-0
• Molecular Formula: C₉H₁₉BO₂
• Molecular Weight: 170.058
• Mol File: 67562-19-0.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 166-168℃
• Flash Point: 47°(117°F)
• Appearance: /
• Density: 0.87±0.1 g/cm3(Predicted)
• Refractive Index: 1.4140
• Water Solubility: Not miscible or difficult to mix with water.
• CAS DataBase Reference: n-Propyl boronic acid pinacol(CAS DataBase Reference)
• NIST Chemistry Reference: n-Propyl boronic acid pinacol(67562-19-0)
• EPA Substance Registry System: n-Propyl boronic acid pinacol(67562-19-0)

Safety Data

• HazardClass: 3
• Hazardous Substances Data: 67562-19-0(Hazardous Substances Data)

Usage

General Description

n-Propyl boronic acid pinacol, also known as 1-propylboronic acid pinacol ester, is a chemical compound with the molecular formula C9H19BO2. It is a boronic acid derivative that is often used as a building block in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. It is commonly employed in Suzuki-Miyaura cross-coupling reactions to introduce the n-propyl group into organic molecules. The pinacol functionality in the molecule provides stability and solubility, making it a useful reagent in various synthetic applications. It is a colorless to pale yellow liquid with a characteristic boronic acid odor and should be handled and stored with care due to its potential reactivity and toxicity.

Upstream product

• 347389-75-7 4,4,5,5-tetramethyl-2-(prop-1-yn-1-yl)-1,3,2-dioxaborolane 
• 1584694-23-4 2-(1-bromoprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 108-86-1 bromobenzene 
• 124215-44-7 2-(3-Bromopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1360649-09-7 2-(1-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1333-74-0 hydrogen 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 590-13-6 (Z)-1-propenyl bromide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1116-61-6 tripropylborane 
• 67-64-1 acetone 
• 67-63-0 isopropyl alcohol 
• 133165-98-7 1-methyl-2-n-propyl-1H-indole 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 105-30-6 (S)-2-methyl-1-pentanol 

Relevant articles and documents

Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation

Selective carbon-carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2-Csp3 and Csp2-Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C-C bond activation to afford two C-B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C-B bond formation and C-C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C-C bond activation. This journal is

Photo-induced radical borylation of hemiacetals via C–C bond cleavage

In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal derivatives, were effectively transformed to the borylation product in moderate to good yields. Finally, the mechanism was studied in detail by DFT calculations, suggesting insight of the radical borylation process.

Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes

The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.