185427-48-9

Basic information

• Product Name: (E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER
• Synonyms: 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)HEXENE;(E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER;(E)-1-Hexene-1,2-diboronicacid;cisHex-1-ene-1,2-diyldiboronic acid,pinacol ester;(1E)-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-ene;(1E)-Hex-1-ene-1,2-diboronic acid, pinacol diester;4,4,5,5-tetramethyl-2-[(E)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-1,3,2-dioxaborolane
• CAS NO: 185427-48-9
• Molecular Formula: C₁₈H₃₄B₂O₄
• Molecular Weight: 336.08
• Mol File: 185427-48-9.mol

Chemical Properties

• Boiling Point: 292 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.954 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00064mmHg at 25°C
• Refractive Index: n20/D 1.455(lit.)
• BRN: 7768251
• CAS DataBase Reference: (E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER(185427-48-9)
• EPA Substance Registry System: (E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER(185427-48-9)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 185427-48-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, facilitating the synthesis of a wide range of organic molecules.
Used in Pharmaceutical Preparation:
In the pharmaceutical industry, (E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Chemical Research:
(E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER is employed as a research tool in the field of organic chemistry, aiding in the exploration of new synthetic methodologies and the production of complex organic molecules.
Used in Material Science:
In material science, (E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER is used as a component in the development of new materials with specific properties, such as those with enhanced stability or reactivity.
Used in Chemical Process Development:
(E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER is utilized in the optimization and development of chemical processes, where its stability and reactivity are crucial for achieving desired outcomes in various industrial applications.

InChI:InChI=1/C18H34B2O4/c1-10-11-12-14(20-23-17(6,7)18(8,9)24-20)13-19-21-15(2,3)16(4,5)22-19/h13H,10-12H2,1-9H3/b14-13-

Upstream product

• 693-02-7 hex-1-yne 
• 73183-34-3 bis(pinacol)diborane 
• 159087-40-8 2-hex-1-ynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 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

• 21541-97-9 1-(4-methylphenyl)-2-hexanone 
• 1519954-08-5 methyl 4-(4-methylphenyl)-2-(morpholino)oct-3-enoate 

Relevant articles and documents

Dehydrogenative Diboration of Alkynes Catalyzed by Ir/CO/tBuNC System

Catalytic dehydrogenative diboration (DHDB) of alkyne with HBpin was achieved using [Ir(COD)Cl]2 and other related Ir precursors under CO atmosphere. The selectivity for DHDB over hydroboration was higher in less polar solvents and under higher

Base-catalyzed diborylation of alkynes: synthesis and applications of cis-1,2-bis(boryl)alkenes

An efficient, transition-metal free, and practical approach to cis-bis(boryl)alkenes from various alkynes was disclosed in the presence of a catalytic amount of K2CO3 under mild conditions. Meanwhile, tetrasubstituted alkenes and phenanthrene derivatives were readily constructed from the target diborylalkenes via Suzuki-Miyaura cross coupling.

Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence

An efficient and straightforward synthesis of isoquinolines is reported from internal alkenyl boronic esters, easily prepared from the corresponding 1,2-bis(boronates), via a sequential copper-catalyzed azidation/aza-Wittig condensation. This synthetic method has been used to synthesize quinisocaine, a topical anesthetic used for the treatment of pain and pruritus, and further extended to thieno[2,3-c]pyridines by using 2-thiophenecarboxaldehyde as coupling partner in the first step.

Synthesis of 1-Amino-1H-Indenes via a Sequential Suzuki-Miyaura Coupling/Petasis Condensation Sequence

An efficient and straightforward synthesis of 1-amino-1H-indenes is reported from 1,2-bis(boronates) via a sequential Suzuki-Miyaura coupling/Petasis cyclization reaction. Starting from the same monoboronic ester intermediates, an intermolecular version of this approach also afforded (Z)-α,β-unsaturated amino esters in moderate to good yields.

Convenient synthesis of α,α-difluorinated carbonyl compounds from alkynes through a fluoro-deboronation process

Catalytic diboration of alkynes towards alkenyl diboronates provides suitable intermediates that can be converted into α-fluorinated and α,α-difluorinated carbonyl compounds via electrophilic fluorination with Selectfluor. Georg Thieme Verlag Stuttgart.

Platinum(0)-catalyzed diboration of alkynylboronates and alkynylphosphonates with bis(pinacolato)diborane(4) (see abstract)

The platinum(0)-catalyzed diboration addition reaction of bis(pinacolato)diborane(4) [(Me4C2O2)BB(O2C2Me4 ), 1] with various 1-alkynylphosphonates and 1-alkynylboronates 3a-d gave the desired novel cis-1,2-diboronated vinylphosphonate and trisboronated alkene products 5a, 5b and 5c, 5d respectively, in high yields. No detectable amount of the desired trisboronated alkene products 5c and 5d were isolated when the alkynylboronate was immediately added to a toluene solution of the catalyst and bis(pinacolato)diborane(4) followed by stirring overnight at 80 °C. Under these conditions, cis-1,2-diboronated alkenes 6c and 6d were obtained in 100% conversion yields. Only after changing the reaction conditions were 5c and 5d obtained in high yields. The structure and configuration of the new compounds have been fully characterized by 1H, 13C, 31P, and 11B NMR, GCMS, elemental analysis, and single-crystal X-ray structure determination. The structure of 5d was found to be fully isomorphous to that of 5c, with the C6H5 ring located in place (and similarly disordered about the 2-fold symmetry axis) of the C4H9 residue; therefore the results of the diffraction analysis, crystal data, and details of the structure determination of 5d are not included.