4,4,5,5-tetramethyl-2-[(Z)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-tetramethyl-2-[(Z)-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: C18H34 B2 O4
• Molecular Weight: 336.088
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID90421745
• Nikkaji Number: J1.814.373I
• Wikidata: Q82233372
• Mol file: 185427-48-9.mol

Synonyms:4,4,5,5-tetramethyl-2-[(Z)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-1,3,2-dioxaborolane;185427-48-9;cisHex-1-ene-1,2-diyldiboronic acid, pinacol ester;AC1O030K;DTXSID90421745;CID 6026893;(Z)-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1-hexene

Chemical Property of 4,4,5,5-tetramethyl-2-[(Z)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.00064mmHg at 25°C
• Refractive Index: n20/D 1.455(lit.)
• Boiling Point: 292℃(lit.)
• Flash Point: >230℉
• PSA: 36.92000
• Density: 0.954g/mLat25℃(lit.)
• LogP: 4.36580
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 336.2643199
• Heavy Atom Count: 24
• Complexity: 465

Purity/Quality:

99% ^*data from raw suppliers

(E)-1-Hexene-1,2-diboronic acid bis(pinacol) ester, 98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C=C(B2OC(C(O2)(C)C)(C)C)CCCC
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C(/B2OC(C(O2)(C)C)(C)C)\CCCC

Technology Process of 4,4,5,5-tetramethyl-2-[(Z)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-1,3,2-dioxaborolane

There total 5 articles about 4,4,5,5-tetramethyl-2-[(Z)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-1-en-2-yl]-1,3,2-dioxaborolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

hex-1-yne (693-02-7) + bis(pinacol)diborane (73183-34-3) → [(((CH3)4C2O2)B)(C4H9)CCH(B(O2C2(CH3)4))] (185427-48-9)

Guidance literature:

With methanol; potassium carbonate; In diethyl ether; at 40 ℃; for 12h; chemoselective reaction; Inert atmosphere;

DOI:10.1007/s11426-018-9344-4

Reference yield: 50.0%

hex-1-yne (693-02-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → [(((CH3)4C2O2)B)(C4H9)CCH(B(O2C2(CH3)4))] (185427-48-9)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; tert-butylisonitrile; carbon monoxide; at 50 ℃; under 760.051 Torr;

DOI:10.1016/j.jorganchem.2020.121614

Reference yield:

hex-1-yne (693-02-7) → [(((CH3)4C2O2)B)(C4H9)CCH(B(O2C2(CH3)4))] (185427-48-9) + 2,2',2''-(hex-1-ene-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl; (n-C₄H₉)Li / hexane; diethyl ether

2: tetrakis(triphenylphosphine)platinum / toluene

With HCl; (n-C₄H₉)Li; tetrakis(triphenylphosphine)platinum; In diethyl ether; hexane; toluene;

DOI:10.1021/om020334s

upstream raw materials:

hex-1-yne

bis(pinacol)diborane

2-hex-1-ynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces

• 1、 Kuang, Zhijie,Gao, Guoliang,Song, Qiuling. "Base-catalyzed diborylation of alkynes: synthesis and applications of cis-1,2-bis(boryl)alkenes". . p. 62 - 66. Retrieved 2018/09/27.
• 2、 Jayaram, Vankudoth,Sridhar, Tailor,Sharma, Gangavaram V. M.,Berrée, Fabienne,Carboni, Bertrand. "Synthesis of 1-Amino-1H-Indenes via a Sequential Suzuki-Miyaura Coupling/Petasis Condensation Sequence". . p. 1803 - 1811. Retrieved 2017/02/10.