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

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane
• CAS No.: 680596-79-6
• Molecular Formula: C14H23 B O4
• Molecular Weight: 266.145
• Hs Code.: 2932990090
• European Community (EC) Number: 689-678-2
• DSSTox Substance ID: DTXSID60395186
• Wikidata: Q72472731
• Mol file: 680596-79-6.mol

Synonyms:680596-79-6;4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane;1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID, PINACOL ESTER;1,4-Dioxa-spiro[4,5]dec-7-en-8-boronic acid pinacol ester;1,4-Dioxaspiro[4,5]dec-7-en-8-boronic acid pinacol ester;2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD04115656;2-{1,4-dioxaspiro[4.5]dec-7-en-8-yl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;8-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,4-DIOXASPIRO[4.5]DEC-7-ENE;1,4-Dioxaspiro[4.5]dec-7-en-8-boronic acid pinacol ester;2-[1,4-DIOXASPIRO[4.5]DEC-7-EN-8-YL]-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-(1,4-dioxaspiro[4.5]dec-8-en-8-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,4-Dioxaspiro[4.5]-7-decene-8-boronic Acid Pinacol Ester;SCHEMBL309717;DTXSID60395186;JCHWHOHZZYWUMP-UHFFFAOYSA-N;BCP15383;(1,4-DIOXASPIRO[4.5]DEC-7-EN-8-YL)BORONIC ACID PINACOL ESTER;BBL103064;STL556873;AKOS005258672;AB20340;CS-W009082;AC-24256;DS-11766;SY009515;AM20100630;FT-0644844;T3566;EN300-261433;A835997;J-504001;Z1741975343;1,4-dioxaspiro[4,5]dec-7-ene-8-boronic acid pinacol ester;1,4-Dioxaspiro[4.5]dec-7-en-8-boronic acid pinacol ester, 97%;4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro-[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane;8-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,4-dioxa-spiro[4.5]dec-7-ene;4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane

Chemical Property of 4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.000888mmHg at 25°C
• Melting Point: 60-62°C
• Boiling Point: 313.9°C at 760 mmHg
• Flash Point: 143.7°C
• PSA: 36.92000
• Density: 1.08g/cm³
• LogP: 2.47120
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 266.1689394
• Heavy Atom Count: 19
• Complexity: 380

Purity/Quality:

98% ^*data from raw suppliers

1,4-Dioxa-spiro[4,5]dec-7-en-8-boronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCC3(CC2)OCCO3

Technology Process of 4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane

There total 3 articles about 4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-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: 99.0%

bis(pinacol)diborane (73183-34-3) + 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (170011-47-9) → 4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane (680596-79-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110 ℃; for 10h; Inert atmosphere;

Reference yield:

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (170011-47-9) → 4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane (680596-79-6)

Guidance literature:

With triphenyl-arsane; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In toluene; at 80 ℃; for 2h;

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane (680596-79-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.42 h / -78 - -40 °C

1.2: 20 °C

2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane;

upstream raw materials:

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

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

bis(pinacol)diborane

cyclohexanedione monoethylene ketal

Downstream raw materials:

4-((S)-4-tert-butoxycarbonyl-2-{[6-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-2-phenyl-pyridine-4-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester

1,4-dioxaspiro[4.5]dec-7-en-8-ylboronic acid

4-(2-methylphenyl)cyclohexan-1-one

4-(3-methylphenyl)cyclohexan-1-one

Refernces

• 1、 Arunachalam, Pirama Nayagam,Balog, Aaron,Borzilleri, Robert M.,Cherney, Emily C.,Gupta, Anuradha,Hong, Zhenqiu,Kempson, James,Krishnamoorthy, Suresh,Kuppusamy, Prakasam,Manoharan, Haridhas,Mathur, Arvind,Nimje, Roshan Y.,Ramasamy, Duraisamy,Rampulla, Richard R.,Shanmugam, Yoganand,Zhang, Liping. "Development of a Stereoselective and Scalable Synthesis for the Potent Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor, BMT-297376; N-((R)-1-((cis)-4-(3-(Difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propyl)-6-methoxynicotinamide". . p. 1680 - 1689. Retrieved 2021/07/28.
• 2、 -. "SPIRO COMPOUND AS INDOLEAMINE-2,3-DIOXYGENASE INHIBITOR". Paragraph 0158; 0159; 0160. . Retrieved 2020/12/29.