2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 141091-37-4
• Molecular Formula: C12H21BO2
• Molecular Weight: 208.109
• Hs Code.: 2931900090
• European Community (EC) Number: 640-223-6
• DSSTox Substance ID: DTXSID80448820
• Nikkaji Number: J994.245I
• Wikidata: Q72459746
• Mol file: 141091-37-4.mol

Synonyms:141091-37-4;2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Cyclohexene-1-boronic acid pinacol ester;1-Cyclohexen-yl-boronic acid pinacol ester;1-Cyclohexen-1-yl-boronic acid pinacol ester;Cyclohexen-1-ylboronic acid, pinacol ester;1-Cyclohexeneboronic Acid Pinacol Ester;1-cyclohexeneboronic acid;MFCD05663845;2-cyclohexenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(1-cyclohexenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(cyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(1-CYCLOHEXEN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;1,3,2-DIOXABOROLANE, 2-(1-CYCLOHEXEN-1-YL)-4,4,5,5-TETRAMETHYL-;1-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexene;1-cyclohexenylboronic acid pinacol ester;Cyclohexen-1-yl-boronic acid pinacol ester;1-(1-Cyclohexenyl)boronic Acid Pinacol Ester;SCHEMBL422542;C12H21BO2;DTXSID80448820;QNZFUMVTUFOLRT-UHFFFAOYSA-N;BCP12569;cyclohexenylboronic acid pinacol ester;AKOS000283810;AB21933;AM90050;CS-W007746;GS-6455;HY-W007746;1-cyclohexenyl boronic acid pinacol ester;SY007878;1-cyclohexen-1-ylboronic acid pinacol ester;A3046;BB 0261155;C2707;FT-0643321;EN300-98764;J-007459;J-520162;CYCLOHEX-1-EN-1-YLBORONIC ACID PINACOL ESTER;Z1318515141;2-cyclohex-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-cyclohexen-1-yl-4,4,5,5-tetramethyl-[1.3.2]dioxaborolane;2-cyclohex-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Cyclohexenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.092mmHg at 25°C
• Refractive Index: 1.464
• Boiling Point: 232.001 °C at 760 mmHg
• Flash Point: 94.111 °C
• PSA: 18.46000
• Density: 0.955 g/cm³
• LogP: 3.11820
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 208.1634601
• Heavy Atom Count: 15
• Complexity: 265

Purity/Quality:

98% ^*data from raw suppliers

Cyclohexen-1-ylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCCCC2
• Uses: Cyclohexen-1-ylboronic acid, pinacol ester

Technology Process of 2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 35 articles about 2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-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: 99.0%

1-bromocyclohex-1-ene (2044-08-8) + bis(pinacol)diborane (73183-34-3) → 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (141091-37-4)

Guidance literature:

With triphenylphosphine; bis(triphenylphosphine)palladium(II) chloride; In toluene; mixt. in toluene stirred at 50°C for 5 h; treated (H2O) at room temp.; extd. (benzene); washed with brine; dried (MgSO4); purified by chromy. on silica gel or by distn. (vac.);

DOI:10.1021/ja0202255

Reference yield: 94.0%

cyclohex-1-en-1-yl(mesityl)iodonium tetrafluoroborate + bis(pinacol)diborane (73183-34-3) → 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (141091-37-4)

Guidance literature:

With copper(l) iodide; triphenylphosphine; lithium tert-butoxide; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

DOI:10.1039/d0ob01121e

Reference yield: 90.0%

C14H25BO2 (212127-65-6) → 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (141091-37-4)

Guidance literature:

Grubbs catalyst first generation; In benzene; room temp., 12 h;

DOI:10.1021/ja980958i

upstream raw materials:

1-bromocyclohex-1-ene

bis(pinacol)diborane

1-iodo-1-cyclohexene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

4-cyclohex-1-enyl-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine

1-(1-cyclopentenyl)-1-cyclohexene

methyl 2-cyclohex-1-en-1-yl-3-cyclohexyl-1-{2-[4-(dimethylamino)piperidin-1-yl]-2-oxoethyl}-1H-indole-6-carboxylate

4-bromo-2-cyclohex-1-enyl-phenylamine

Refernces

• 1、 Murata, Miki,Oyama, Takashi,Watanabe, Shinji,Masuda, Yuzuru. "Synthesis of alkenylboronates via palladium-catalyzed borylation of alkenyl triflates (or Iodides) with pinacolborane". . p. 778 - 780. Retrieved 2000.
• 2、 Connor, Kieran P. E.,Horvath, Kelsey L.,Magann, Nicholas L.,Sherburn, Michael S.,Sowden, Madison J.,Westley, Erin. "Substituted Tetraethynylethylene–Tetravinylethylene Hybrids". . p. 977 - 986. Retrieved 2022/02/03.
• 3、 Tao, Lei,Guo, Xueying,Li, Jie,Li, Ruoling,Lin, Zhenyang,Zhao, Wanxiang. "Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation". supporting information. p. 18118 - 18127. Retrieved 2020/11/26.