Dicyclohexylamine Borane

Base Information

• Chemical Name: Dicyclohexylamine Borane
• CAS No.: 131765-96-3
• Molecular Formula: C₁₂H₂₆BN
• Molecular Weight: 195.156
• European Community (EC) Number: 834-351-3
• Mol file: 131765-96-3.mol

Synonyms:Dicyclohexylamine Borane;131765-96-3;CID 20277598;dicha borane;SCHEMBL5395753;MFCD30343648;B5545;D89144

Chemical Property of Dicyclohexylamine Borane

Chemical Property:

• Melting Point: 118.2°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 192.1923549
• Heavy Atom Count: 14
• Complexity: 116

Purity/Quality:

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

Dicyclohexylamine borane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: [B].C1CCC(CC1)NC2CCCCC2
• Uses: Dicyclohexylamine borane complex applied by the Pucheault Group at the Universite de Bordeaux as a cost effective and easy to handle alternative to current borylation reagents. In one pot, aryl and vinyl halides can be converted to the boronic acid derivative of your choice (BF3K, Bpin, MIDA, and others) depending on quench and workup.

Technology Process of Dicyclohexylamine Borane

There total 6 articles about Dicyclohexylamine Borane 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%

→ dicyclohexylamine borane complex (131765-96-3)

Guidance literature:

Reference yield: 91.0%

sodium tetrahydroborate (16940-66-2) + N-cyclohexyl-cyclohexanamine (101-83-7) → dicyclohexylamine borane complex (131765-96-3)

Guidance literature:

sodium tetrahydroborate; With sulfuric acid; In tetrahydrofuran; at -5 ℃; for 1.5h;

N-cyclohexyl-cyclohexanamine; In tetrahydrofuran; at 0 - 20 ℃; for 23.5h;

DOI:10.1016/j.tet.2018.11.036

Reference yield: 63.0%

sodium tetrahydroborate (16940-66-2) + dicyclohexylamine hydrochloride (4693-92-9) → dicyclohexylamine borane complex (131765-96-3)

Guidance literature:

In 1,2-dimethoxyethane; NaBH4 added in portions to suspn. of (C6H11)2NH2Cl in DME at 20°Cunder stirring, mixt. stirred for 1 h; ppt. filtered off, washed with hexane, filtrate evapd. to dryness under vac., recrystd. from hexane; elem. anal.;

DOI:10.1023/B:RUCB.0000035660.32775.ab

upstream raw materials:

borane-THF

N-cyclohexyl-cyclohexanamine

sodium tetrahydroborate

dicyclohexylamine hydrochloride

Downstream raw materials:

4-butylphenylboronic acid

4-methoxyphenylboronic acid

naphthalene-2-boronic acid

1-Naphthylboronic acid

Refernces

• 1、 Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu. "Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids". . p. 164 - 171. Retrieved 2018/12/05.
• 2、 Kawano, Yasuro,Uruichi, Mikio,Shimoi, Mamoru,Taki, Seitaro,Kawaguchi, Takayuki,Kakizawa, Taeko,Ogino, Hiroshi. "Dehydrocoupling reactions of borane-secondary and -primary amine adducts catalyzed by group-6 carbonyl complexes: Formation of aminoboranes and borazines". . p. 14946 - 14957. Retrieved 2010/01/16.