1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID

Base Information

• Chemical Name: 1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID
• CAS No.: 850567-90-7
• Molecular Formula: C8H13BO4
• Molecular Weight: 184
• Hs Code.: 2932990090
• Mol file: 850567-90-7.mol

Synonyms:Boronicacid, 1,4-dioxaspiro[4.5]dec-7-en-8-yl- (9CI);[1,4-Dioxaspiro[4.5]dec-7-en-8-yl]boronic acid;

Chemical Property of 1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID

Chemical Property:

• Vapor Pressure: 8.07E-07mmHg at 25°C
• Melting Point: 154-158 °C
• Refractive Index: 1.52
• Boiling Point: 365.4 °C at 760 mmHg
• PKA: 9.18±0.20(Predicted)
• Flash Point: 174.8 °C
• PSA: 58.92000
• Density: 1.25 g/cm³
• LogP: -0.14820
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

98%min ^*data from raw suppliers

4-Borono-3-cyclohexen-1-one,ethyleneglycolketal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID

There total 3 articles about 1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC 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:

4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane (680596-79-6) → 1,4-dioxaspiro[4.5]dec-7-en-8-ylboronic acid (850567-90-7)

Guidance literature:

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

DOI:10.1002/anie.201202704

Reference yield:

1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (170011-47-9) → 1,4-dioxaspiro[4.5]dec-7-en-8-ylboronic acid (850567-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere

2: ammonium acetate; sodium periodate / water; acetone / 6 h / 25 °C

With sodium periodate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonium acetate; potassium acetate; In 1,4-dioxane; water; acetone;

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 1,4-dioxaspiro[4.5]dec-7-en-8-ylboronic acid (850567-90-7)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium hexamethyldisilazane / tetrahydrofuran / 3.5 h / -78 - 25 °C / Inert atmosphere

2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere

3: ammonium acetate; sodium periodate / water; acetone / 6 h / 25 °C

With sodium periodate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonium acetate; potassium acetate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; water; acetone;

upstream raw materials:

4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane

1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate

cyclohexanedione monoethylene ketal

Downstream raw materials:

4-(2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

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.