Cyclohexylmethylboronic Acid

Base Information

• Chemical Name: Cyclohexylmethylboronic Acid
• CAS No.: 27762-64-7
• Molecular Formula: C7H15 B O2
• Molecular Weight: 142.006
• Hs Code.: 2931900090
• European Community (EC) Number: 818-217-1
• DSSTox Substance ID: DTXSID50449965
• Wikidata: Q82269514
• Mol file: 27762-64-7.mol

Synonyms:Cyclohexylmethylboronic Acid;27762-64-7;(Cyclohexylmethyl)boronic acid;Boronic acid, B-(cyclohexylmethyl)-;Boronic acid, (cyclohexylmethyl)-;(Cyclohexylmethyl)boronicacid;SCHEMBL2957845;DTXSID50449965;CBA76264;MFCD09878538;AKOS013014323;AB53934;CS-W000907;Cyclohexylmethylboronic acid, AldrichCPR;DS-18077;EN300-258457;W17229;J-016878

Chemical Property of Cyclohexylmethylboronic Acid

Chemical Property:

• Boiling Point: 268.9±23.0 °C(Predicted)
• PKA: 10.33±0.43(Predicted)
• PSA: 40.46000
• Density: 0.982±0.06 g/cm3(Predicted)
• LogP: 1.03950
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 142.1165099
• Heavy Atom Count: 10
• Complexity: 89.6

Purity/Quality:

98%Min ^*data from raw suppliers

Cyclohexylmethylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(CC1CCCCC1)(O)O

Technology Process of Cyclohexylmethylboronic Acid

There total 1 articles about Cyclohexylmethylboronic 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:

sodium tetrahydroborate (16940-66-2) + 4-(cyclohexylidenemethyl)morpholine (16963-29-4) + trifluoroborane diethyl ether (109-63-7) → 2-(cyclohexylmethyl)-boronic acid (27762-64-7)

Guidance literature:

In tetrahydrofuran; under N2, dropwise addn. of BF3*Et2O to a suspension of NaBH4 in THF at 25°C with stirring, addn. of morpholino derivate after 1h, stirred for additional 3h at 25°C; slowly quenched with MeOH, addn. of NaOH, solvent evapn. (25°C, 12 Torr), alkaline aq. layer cooled to 0°C and acidified (concd. HCl), boronic acid extd.(ether), washed (H2O), dried (MgSO4), evapn.;

Reference yield: 100.0%

(R)-N-((R)-7-bromo-1,2,3,4-tetrahydronaphthalen-1-yl)-2-methylpropane-2-sulfinamide + 2-(cyclohexylmethyl)-boronic acid (27762-64-7) → (R)-N-((R)-7-(cyclohexylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-2-methylpropane-2-sulfinamide

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; silver(l) oxide; In tetrahydrofuran; at 80 ℃; for 1h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/acs.jmedchem.5b01270

Reference yield: 95.0%

para-bromoacetophenone (99-90-1) + 2-(cyclohexylmethyl)-boronic acid (27762-64-7) → 4-(cyclohexylmethyl)acetophenone (68266-59-1)

Guidance literature:

With potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; In xylene; at 130 ℃; for 20h;

DOI:10.1016/j.tet.2004.03.009

upstream raw materials:

sodium tetrahydroborate

4-(cyclohexylidenemethyl)morpholine

trifluoroborane diethyl ether

Downstream raw materials:

4-(cyclohexylmethyl)benzonitrile

4-(cyclohexylmethyl)acetophenone

2-(cyclohexylmethyl)-5-[(2-methylpyrrolidin-1-yl)carbonyl]pyridine

2-(cyclohexylmethyl)-1,3,2-dioxaborinane

Refernces