4-tert-Butyl-1-cyclohexen-1-ylboronic acid

Base Information

• Chemical Name: 4-tert-Butyl-1-cyclohexen-1-ylboronic acid
• CAS No.: 850567-91-8
• Molecular Formula: C10H19BO2
• Molecular Weight: 182.071
• Hs Code.: 2931900090
• Mol file: 850567-91-8.mol

Synonyms:4-(tert-Butylcyclohexen-1-yl)boronic acid;4-tert-Butylcyclohexen-1-ylboronic acid;

Chemical Property of 4-tert-Butyl-1-cyclohexen-1-ylboronic acid

Chemical Property:

• Vapor Pressure: 0.000151mmHg at 25°C
• Melting Point: 166-170℃
• Refractive Index: 1.474
• Boiling Point: 296.101 °C at 760 mmHg
• Flash Point: 132.878 °C
• PSA: 40.46000
• Density: 0.976 g/cm³
• LogP: 1.77100
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Water Solubility.: Slightly soluble in water.

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-t-Butylcyclohexen-1-ylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-tert-Butyl-1-cyclohexen-1-ylboronic acid

There total 2 articles about 4-tert-Butyl-1-cyclohexen-1-ylboronic acid 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:

2-(4-(tert-butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (287944-06-3) → 4-tert-butylcyclohex-1-en-1-ylboronic acid (850567-91-8)

Guidance literature:

With sodium periodate; ammonium acetate; In water; acetone; for 48h;

DOI:10.1002/anie.201202704

Reference yield:

4-tert-butylcyclohexanone tosylhydrazone (41780-53-4) → 4-tert-butylcyclohex-1-en-1-ylboronic acid (850567-91-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / hexane / 3 h / -78 - 25 °C

1.2: -78 °C

2.1: water; sodium periodate; ammonium acetate / acetone

With sodium periodate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; ammonium acetate; water; In hexane; acetone;

DOI:10.1039/d0gc01514h

Reference yield: 91.0%

4-tert-butylcyclohex-1-en-1-ylboronic acid (850567-91-8) + (±)-trans-tert-butyl 3-(2-bromo-4-(methoxycarbonyl)phenoxy)-4-hydroxypyrrolidine-1-carboxylate → (±)-trans-tert-butyl 3-((4′-(tert-butyl)-5-(methoxycarbonyl)-2′,3′,4′,5′-tetrahydro[1,1′-biphenyl]-2-yl)oxy)-4-hydroxypyrrolidine-1-carboxylate

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; water; at 90 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c00596

upstream raw materials:

2-(4-(tert-butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-tert-butylcyclohexanone tosylhydrazone

Downstream raw materials:

[4-(4-tert-butylcyclohex-1-enyl)phenyl]acetic acid ethyl ester

C₂₇H₃₂O₄

4-{(R)-2-[4-(4-tert-butylcyclohex-1-enyl)phenyl]-2-carboxyethyl}benzoic acid tert-butyl ester

C₁₈H₂₁NO₃

Refernces

• 1、 Patil, Aditi S.,Mo, Dong-Liang,Wang, Heng-Yen,Mueller, Daniel S.,Anderson, Laura L.. "Preparation of α-oxygenated ketones by the dioxygenation of alkenyl boronic acids". supporting information; experimental part. p. 7799 - 7803. Retrieved 2012/09/08.