2-[4-(1,1-Dimethylethyl)-1-cyclohexen-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-[4-(1,1-Dimethylethyl)-1-cyclohexen-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 287944-06-3
• Molecular Formula: C16H29BO2
• Molecular Weight: 264.216
• Hs Code.: 2934999090
• European Community (EC) Number: 868-071-8
• DSSTox Substance ID: DTXSID30573232
• Nikkaji Number: J1.414.668G
• Mol file: 287944-06-3.mol

Synonyms:287944-06-3;2-[4-(1,1-Dimethylethyl)-1-cyclohexen-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(4-TERT-BUTYLCYCLOHEX-1-ENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;4-TERT-BUTYL-1-CYCLOHEXEN-1-YLBORONIC ACID PINACOL ESTER;2-(4-tert-butylcyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-(4-tert-butyl-1-cyclohexen-1-yl)-1,3,2-dioxaborolane;2-(4-(tert-Butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(4-TERT-BUTYLCYCLOHEX-1-EN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;SCHEMBL2420982;AMY2488;DTXSID30573232;GTRURWFRLWPOBJ-UHFFFAOYSA-N;MFCD11520535;AKOS016005864;FS-6307;MB09929;C15496;EN300-263272;A819597;J-516000;4-tert-Butylcyclohex-1-ene-1-boronic Acid Pinacol Ester;Z2044755233;2-(4-tert-Butyl-cyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-(4-tert-Butylcyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Chemical Property of 2-[4-(1,1-Dimethylethyl)-1-cyclohexen-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.00354mmHg at 25°C
• Refractive Index: 1.465
• Boiling Point: 290.7 °C at 760 mmHg
• Flash Point: 129.6 °C
• PSA: 18.46000
• Density: 0.92 g/cm³
• LogP: 4.39040
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 264.2260603
• Heavy Atom Count: 19
• Complexity: 361

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-[4-(1,1-Dimethylethyl)-1-cyclohexen-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCC(CC2)C(C)(C)C

Technology Process of 2-[4-(1,1-Dimethylethyl)-1-cyclohexen-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 3 articles about 2-[4-(1,1-Dimethylethyl)-1-cyclohexen-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: 94.0%

1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene (77412-96-5) + bis(pinacol)diborane (73183-34-3) → 2-(4-(tert-butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (287944-06-3)

Guidance literature:

With triphenylphosphine; bis(triphenylphosphine)palladium(II) chloride; In toluene; mixt. in toluene stirred at 50°C for 3 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: 77.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 4-tert-butylcyclohexanone tosylhydrazone (41780-53-4) → 2-(4-(tert-butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (287944-06-3)

Guidance literature:

4-tert-butylcyclohexanone tosylhydrazone; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; at -78 - 20 ℃; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In hexane; at -78 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1080/00397910802245762

Reference yield:

1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene (77412-96-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-tert-butylcylohexene (2228-98-0) + 2-(4-tert-butyl-cyclohex-2-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane + 2-(4-(tert-butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (287944-06-3)

Guidance literature:

With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; In 1,4-dioxane; at 80 ℃; for 16h; Title compound not separated from byproducts;

DOI:10.1055/s-2000-6274

upstream raw materials:

1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene

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

bis(pinacol)diborane

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

Downstream raw materials:

(4R,5R)-4,5-bis(2-(4-tert-butylcyclohex-1-enyl)phenyl)-2,2-dimethyl-1,3-dioxolane

C₁₈H₂₁NO₃

4-tert-butylcyclohex-1-en-1-ylboronic acid

Refernces

• 1、 Rauniyar, Vivek,Zhai, Huimin,Hall, Dennis G.. "Convenient preparation of cycloalkenyl boronic acid pinacol esters". experimental part. p. 3984 - 3995. Retrieved 2009/04/11.
• 2、 -. "Vanilloid receptor ligands and their use in treatments". Page/Page column 33. . Retrieved 2008/06/13.