Hydroxydip-tolylborane

Base Information

• Chemical Name: Hydroxydip-tolylborane
• CAS No.: 66117-64-4
• Molecular Formula: C14H15BO
• Molecular Weight: 210.084
• Hs Code.: 2931900090
• ChEMBL ID: CHEMBL2386008
• DSSTox Substance ID: DTXSID30521677
• Nikkaji Number: J3.111.713E
• Wikidata: Q82386287
• Mol file: 66117-64-4.mol

Synonyms:Hydroxydip-tolylborane;66117-64-4;Hydroxydi-p-tolylborane;bis(4-methylphenyl)borinic acid;CHEMBL2386008;Borinic acid, bis(4-methylphenyl)-;BIS(4-TOLYL)BORONIC ACID;di-p-tolylborinic acid;bis(p-tolyl)borinic acid;SCHEMBL2964428;DTXSID30521677;ZJHMSSYDWCPSFN-UHFFFAOYSA-N;BDBM50434554;MFCD09972117;AKOS015855907;Bis(4-methylphenyl)borinic AcidIaaEIaaE;BS-29361;CS-0179003;H11973

Chemical Property of Hydroxydip-tolylborane

Chemical Property:

• PSA: 20.23000
• LogP: 1.40140
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 210.1215953
• Heavy Atom Count: 16
• Complexity: 181

Purity/Quality:

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

Hydroxydi-p-tolylborane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C)(C2=CC=C(C=C2)C)O
• Uses: Hydroxydi-p-tolylborane is a building block used as a reactant in the nickel-catalyzed cross-coupling of diarylborinic acids with aryl chlorides.

Technology Process of Hydroxydip-tolylborane

There total 17 articles about Hydroxydip-tolylborane 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: 96.0%

para-bromotoluene (106-38-7) + diisopropopylaminoborane (22092-92-8) → di(p-tolyl)borinic acid (66117-64-4)

Guidance literature:

With magnesium; In tetrahydrofuran; at 70 ℃; for 20h; Solvent; Temperature;

DOI:10.1021/acs.orglett.5b01620

Reference yield: 67.0%

Triisopropyl borate (5419-55-6) + C7H7BrMg*ZnCl2*LiCl → 4-methylphenylboronic acid (5720-05-8) + di(p-tolyl)borinic acid (66117-64-4)

Guidance literature:

With copper(I) iodide-lithium chloride; In tetrahydrofuran; at 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/cctc.201800939

Reference yield: 64.0%

8-[(di-p-tolylboryl)oxy]quinolone → di(p-tolyl)borinic acid (66117-64-4)

Guidance literature:

With hydrogenchloride; In methanol; water; acetone; at 20 ℃; for 12h;

DOI:10.1246/CL.200213

upstream raw materials:

boric acid tributyl ester

para-methylphenylmagnesium bromide

cyclotriboric acid trimethyl ester

tris(isobutyloxy) boroxine

Downstream raw materials:

[(H₃C)Co((ONC(CH₃)C(CH₃)NOB(C₆H₄CH₃)2)2)(C₃H₃N₂CH₃)]

[(C₆H₅)Co((ONC(CH₃)C(CH₃)NOB(C₆H₄CH₃)2)2)(C₃H₃N₂CH₃)]

[(CH₃)Co((ONC(CH₃)C(CH₃)NOB(C₆H₄CH₃)2)2)(H₂O)]

2-Cyano-4'-methylbiphenyl

Refernces

• 1、 Fu, Ying,Gou, Bei-Lei,Shi, Chun-Zhao,Du, Zhengyin,Shen, Tong. "Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates". . p. 4253 - 4257. Retrieved 2018/09/18.
• 2、 Marciasini, Ludovic,Cacciuttolo, Bastien,Vaultier, Michel,Pucheault, Mathieu. "Synthesis of Borinic Acids and Borinate Adducts Using Diisopropylaminoborane". supporting information. p. 3532 - 3535. Retrieved 2015/07/28.