159087-42-0

Basic information

• Product Name: 2-(5-CHLOROPENT-1-YNYL)-4,4,5,5-TETRAMETHYL-(1,3,2) DIOXABOROLANE
• Synonyms: 2-(5-CHLOROPENT-1-YNYL)-4,4,5,5-TETRAMETHYL-(1,3,2) DIOXABOROLANE;2-(5-CHLOROPENT-1-YNYL)BORONIC ACID PINACOL ESTER;2-(5-Chloropent-1-ynyl)boronic acid pinacol ester, 2-(5-Chloropent-1-ynyl)-4,4,5,5-tetramethyl-(1,3,2)dioxaborolane;5-Chloro-1-pentynyl-1-boronic acid pinacol ester;5-Chloropent-1-ynylboronic acid, pinacol ester;2-(5-Chloropent-1-yn-1-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;5-Chloro-1-pentynyl-1-boronic acid pinacol ester 97%
• CAS NO: 159087-42-0
• Molecular Formula: C11H18BClO2
• Molecular Weight: 228.52
• Mol File: 159087-42-0.mol
• Article Data: 8

Chemical Properties

• Flash Point: 110 °C
• Appearance: /
• Density: 1.0422 g/mL at 25 °C
• Refractive Index: n20/D 1.4719
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(5-CHLOROPENT-1-YNYL)-4,4,5,5-TETRAMETHYL-(1,3,2) DIOXABOROLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(5-CHLOROPENT-1-YNYL)-4,4,5,5-TETRAMETHYL-(1,3,2) DIOXABOROLANE(159087-42-0)
• EPA Substance Registry System: 2-(5-CHLOROPENT-1-YNYL)-4,4,5,5-TETRAMETHYL-(1,3,2) DIOXABOROLANE(159087-42-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 159087-42-0(Hazardous Substances Data)

Usage

General Description

2-(5-Chloropent-1-ynyl)-4,4,5,5-tetramethyl-(1,3,2) dioxaborolane is a chemical compound that belongs to the class of boron-containing compounds. It is commonly used as a building block in organic synthesis, particularly in the field of pharmaceuticals and agrochemicals. 2-(5-CHLOROPENT-1-YNYL)-4,4,5,5-TETRAMETHYL-(1,3,2) DIOXABOROLANE is known for its versatile reactivity and ability to participate in various chemical reactions, making it a valuable tool for synthetic chemists. Its unique structure and properties make it a valuable tool for the development of new molecules and materials with potential applications in various industries.

Upstream product

• 14267-92-6 1-chloro-4-pentyne 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 154820-95-8 2-(5-chloropent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

General Method for the Synthesis of Substituted Cyclopentenones via α-Borylzirconacyclopentene Intermediates

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Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides

A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.

Copper-catalyzed dehydrogenative borylation of terminal alkynes with pinacolborane

LCuOTf complexes [L = cyclic (alkyl)(amino)carbenes (CAACs) or N-heterocyclic carbenes (NHCs)] selectively promote the dehydrogenative borylation of C(sp)-H bonds at room temperature. It is shown that σ,π-bis(copper) acetylide and copper hydride complexes are the key catalytic species.