Cyclohexylboronic acid

Base Information

• Chemical Name: Cyclohexylboronic acid
• CAS No.: 4441-56-9
• Molecular Formula: C6H13BO2
• Molecular Weight: 127.979
• Hs Code.: 29319090
• European Community (EC) Number: 672-297-0
• DSSTox Substance ID: DTXSID30196162
• Nikkaji Number: J48.536E
• Wikidata: Q72459869
• Mol file: 4441-56-9.mol

Synonyms:Cyclohexylboronic acid;4441-56-9;Cyclohexylboronicacid;Boronic acid, cyclohexyl-;Cyclohexaneboronic acid;MFCD01311824;BRN 1921820;C6H13BO2;Boronic acid, cyclohexyl- (9CI);4-16-00-01653 (Beilstein Handbook Reference);Cyclohexyl boronic acid;CYCLOHEXYLBORANEDIOL;SCHEMBL127115;DTXSID30196162;BCP22758;C6-H13-B-O2;BBL102850;STL556658;AKOS001013988;AB08478;AC-9537;BCP9000567;CS-W007574;GS-6574;LS-56500;SY008103;A7051;AM20070527;C2188;FT-0601791;EN300-103018;J-520170;Z56789446;F0001-1209

Chemical Property of Cyclohexylboronic acid

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 0.00302mmHg at 25°C
• Melting Point: 122-123 °C
• Refractive Index: 1.452
• Boiling Point: 252.4 °C at 760 mmHg
• PKA: 10.47±0.20(Predicted)
• Flash Point: 106.4 °C
• PSA: 40.46000
• Density: 1 g/cm³
• LogP: 0.79350
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: soluble in Methanol
• Water Solubility.: 25 g/L
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 128.1008598
• Heavy Atom Count: 9
• Complexity: 79.1

Purity/Quality:

99% ^*data from raw suppliers

Cyclohexylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1CCCCC1)(O)O
• Uses: Reactant involved in:? ;HF-free synthesis of tetrabutylammonium trifluoroborates1? ;Cross-coupling with aromatic amines2? ;Suzuki cross-coupling reactions3? ;Arylation and alkylation of diphenylisoxazole4 suzuki reaction Reactant involved in:HF-free synthesis of tetrabutylammonium trifluoroboratesCross-coupling with aromatic aminesSuzuki cross-coupling reactionsArylation and alkylation of diphenylisoxazole

Technology Process of Cyclohexylboronic acid

There total 34 articles about Cyclohexylboronic 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: 97.0%

diisopropopylaminoborane (22092-92-8) + water (7732-18-5) + cyclohexylmagnesium bromide (931-50-0) → cyclohexylboronic acid (4441-56-9)

Guidance literature:

diisopropopylaminoborane; cyclohexylmagnesium bromide; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

water; With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 0.583333h; Inert atmosphere;

DOI:10.3987/COM-12-S(N)14

Reference yield: 90.0%

cyclohexylboronic acid pinacol ester (87100-15-0) → cyclohexylboronic acid (4441-56-9)

Guidance literature:

With sodium periodate; ammonium acetate; In water; acetone; at 20 ℃; for 48h;

DOI:10.1002/anie.201811210

Reference yield: 85.0%

lithium cyclohexylborohydride → cyclohexylboronic acid (4441-56-9)

Guidance literature:

hydrolysis;

DOI:10.1016/0022-328X(88)87067-0

upstream raw materials:

cyclohexylboroxine

methyl boric acid

cyclohexylmagnesium bromide

cyclohexylmagnesiumchloride

Downstream raw materials:

(cyclohexyl)difluoroborane

2-cyclohexyl-1,3,2-dioxaborinane

bicyclohexyl-3,6-diene-2,5-dione

cyclohexylboroxine

Refernces

• 1、 Wollenburg, Marco,Moock, Daniel,Glorius, Frank. "Hydrogenation of Borylated Arenes". supporting information. p. 6549 - 6553. Retrieved 2019/01/04.
• 2、 Bojaryn, Kevin,Hoffmann, Chris,Struth, Felix R.,Hirschh?user, Christoph. "Ambient-Pressure Asymmetric Preparation of S,S -DICHED, a C 2 -Symmetrical Director for Matteson Reactions". supporting information. p. 1092 - 1094. Retrieved 2018/01/27.