Dicyclohexylborane

Base Information

• Chemical Name: Dicyclohexylborane
• CAS No.: 1568-65-6
• Molecular Formula: C12H23 B
• Molecular Weight: 178.126
• Hs Code.: 2931900090
• European Community (EC) Number: 803-381-9
• DSSTox Substance ID: DTXSID50431825
• Wikidata: Q82245808
• Mol file: 1568-65-6.mol

Synonyms:dicyclohexylborane;1568-65-6;Dicyclohexylboron;Borane, dicyclohexyl-;dicylohexylborane;dicyclohexyl borane;dicyclohexyl-borane;Cy2BH;(Cy)2BH;DTXSID50431825;XNYOSXARXANYPB-UHFFFAOYSA-N;AKOS025296257;CS-0310588

Chemical Property of Dicyclohexylborane

Chemical Property:

• Boiling Point: 263.7±23.0 °C(Predicted)
• PSA: 0.00000
• LogP: 4.19580
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 177.1814559
• Heavy Atom Count: 13
• Complexity: 116

Purity/Quality:

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

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 17-34
• Safety Statements: 16-23-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [B](C1CCCCC1)C2CCCCC2
• Uses: Dicyclohexylborane is a reducing reagent such as in the synthesis of chlorosulfolipid products such as deschloromytilipin A.

Technology Process of Dicyclohexylborane

There total 11 articles about Dicyclohexylborane 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: 89.0%

cyclohexene (110-83-8) → bis(cyclohexanyl)borane (1568-65-6)

Guidance literature:

With borane N-ethyl-N-isopropylaniline complex; In 1,4-dioxane; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(99)00272-0

Reference yield: 80.0%

dimethylsulfide borane complex (13292-87-0) + cyclohexene (110-83-8) → bis(cyclohexanyl)borane (1568-65-6)

Guidance literature:

In diethyl ether; at 0 ℃; for 3h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.1c00008 DOI:10.1002/ejoc.202100681

Reference yield:

dimethylsulfide borane complex (13292-87-0) → bis(cyclohexanyl)borane (1568-65-6)

Guidance literature:

With cyclohexene; In diethyl ether; at 0 ℃; for 3h;

upstream raw materials:

tricyclohexylborane

cyclohexene

dimethylsulfide borane complex

dimethyl sulfide borane

Downstream raw materials:

Dicyclohexyl-((E)-1-trimethylsilanyl-propenyl)-borane

B-methoxydicyclohexylborane

(Z)-1-bromo-1-cyclohexyl-1-hexene

Dicyclohexyl-((Z)-hex-1-enyl)-borane

Refernces

[2,2]paracyclophane-based N,O-ligands in alkenylzinc additions to aldehydes

10.1021/ol016954r

The study explores the application of [2,2]paracyclophane-based N,O-ligands in the asymmetric addition of alkenylzinc reagents to aldehydes, leading to the formation of chiral allyl alcohols. These compounds are important intermediates in various organic reactions. The research details the development of a method to generate alkenylzinc species through transmetalation using different reagents, which allows for fine-tuning the steric bulk and selectivity of the reaction. The study reports high enantioselectivities, especially for challenging substrates such as α-branched aliphatic aldehydes, and demonstrates the significant impact of the transmetalation agent on catalytic efficiency.

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