154820-95-8

Basic information

• Product Name: (E)-5-CHLORO-1-PENTENEBORONICACIDPIN
• Synonyms: (E)-5-CHLORO-1-PENTENEBORONICACIDPIN;TRANS-5-CHLORO-1-PENTEN-1-YLBORONIC ACID PINACOL ESTER, 97%;(E)-5-Chloro-1-penteneboronic acid pinacol ester, trans-5-Chloro-1-penteneboronic acid pinacol ester, trans-2-(5-Chloro-pent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, E-2-(5-Chloro-pent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 154820-95-8
• Molecular Formula: C₁₁H₂₀BClO₂
• Molecular Weight: 230.54
• Mol File: 154820-95-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 248.52°C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.004 g/mL at 25 °C
• Vapor Pressure: 0.038mmHg at 25°C
• Refractive Index: n20/D 1.4630
• CAS DataBase Reference: (E)-5-CHLORO-1-PENTENEBORONICACIDPIN(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-5-CHLORO-1-PENTENEBORONICACIDPIN(154820-95-8)
• EPA Substance Registry System: (E)-5-CHLORO-1-PENTENEBORONICACIDPIN(154820-95-8)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 154820-95-8(Hazardous Substances Data)

Usage

General Description

(E)-5-Chloro-1-penteneboronic acid pin is a chemical compound that is used in organic synthesis and pharmaceutical research. It is a boronic acid derivative, which are widely used in Suzuki-Miyaura cross-coupling reactions to create carbon-carbon bonds. (E)-5-CHLORO-1-PENTENEBORONICACIDPIN contains a boron atom, which can serve as a handle for attaching other functional groups to the molecule. Additionally, the chlorine substitution on the pentene chain can provide a site for further chemical modification. Overall, (E)-5-chloro-1-penteneboronic acid pin is a versatile building block in organic chemistry, with potential applications in the development of new drugs and materials.

InChI:InChI=1/C11H20BClO2/c1-10(2)11(3,4)15-12(14-10)8-6-5-7-9-13/h6,8H,5,7,9H2,1-4H3/b8-6+

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 14267-92-6 1-chloro-4-pentyne 
• 13292-87-0 dimethylsulfide borane complex 
• 159087-42-0 2-(5-chloropent-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 126726-63-4 2-[2-(3-chloropropyl)cyclopropyl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane 
• 1350619-77-0 (1R,2R)-2-(pent-4-yn-1-yl)cyclopropan-1-ol 
• 1425038-19-2 (S)-3,3-dimethyl-2-(((1R,2R)-2-(pent-4-ynyl)cyclopropoxy)carbonylamino)butanoic acid 
• 1425038-18-1 acetic acid (1S,2S)-2-pent-4-ynylcyclopropyl ester 

Relevant articles and documents

Chemoselective Cross-Coupling of gem-Borazirconocene Alkanes with Aryl Halides

The direct and chemoselective conversion of the carbon-metal bond of gem-dimetallic reagents enables rapid and sequential formation of multiple carbon-carbon and carbon-heteroatom bonds, thus representing a powerful method for efficiently increasing structural complexity. Herein, we report a visible-light-induced, nickel-catalyzed, chemoselective cross-coupling reaction between gem-borazirconocene alkanes and diverse aryl halides, affording a wide range of alkyl Bpin derivatives in high yields with excellent regioselectivity. This practical method features attractively simple reaction conditions and a broad substrate scope. Additionally, we systematically investigated a Bpin-directed chain walking process underlying the regioselectivity of alkylzirconocenes, thus uncovering the mechanism of the remote functionalization of internal olefins achieved with our method. Finally, DFT calculations indicate that the high regioselectivity of this reaction originates from the directing effect of the Bpin group.

Multikilogram-scale synthesis of a chiral cyclopropanol and an investigation of the safe use of lithium acetylide-ethylene diamine complex

A six-step route starting from a readily available vinyl boronate was identified to produce an enantioenriched cyclopropanol in an overall 16% yield. Key steps involve the use of lithium acetylide-ethylene diamine complex 5 and an enzymatic resolution of a racemic cyclopropanol acetate. Process safety considerations surrounding the use of 5 were examined, and an improved procedure is described which was safely demonstrated at multikilogram scale.

Vicinal diboronates in high enantiomeric purity through tandem site-selective NHC-Cu-catalyzed boron-copper additions to terminal alkynes

(Chemical Equation Presented) A Cu-catalyzed protocol for conversion of terminal alkynes to enantiomerically enriched diboronates is reported. In a single vessel, a site-selective hydroboration of an alkyne leads to the corresponding terminal vinylboronat