(+)-B-Chlorodiisopinocampheylborane

Base Information

• Chemical Name: (+)-B-Chlorodiisopinocampheylborane
• CAS No.: 85116-37-6
• Molecular Formula: C20H34BCl
• Molecular Weight: 320.754
• Hs Code.: 29319090
• European Community (EC) Number: 601-177-2,617-675-8
• Nikkaji Number: J734.744H
• Mol file: 85116-37-6.mol

Synonyms:112246-73-8;(+)-B-Chlorodiisopinocampheylborane;(+)-Ipc2BCl;(+)-DIP-Chloride;Borane, chlorobis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]-;(+)-Diisopinocampheyl chloroborane;(+)-b-chlorodiisopinocamphenylborane;(-)-B-Chlorodiisopinocampheylborane;(+)-Diisopinocampheylchloroborane;(+)-Chlorodiisopinocampheylborane;(+)-DIP-Cl;(+)-DIP-chloride;SCHEMBL4864880;PSEHHVRCDVOTID-NAVXHOJHSA-N;(+)-b-chlorodiisopinocampheyl-borane;AKOS016015001;AC-22730;CS-0008304;(+)-DIP-Chloride(TM), 90-105% (approx.);chlorobis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]borane

Chemical Property of (+)-B-Chlorodiisopinocampheylborane

Chemical Property:

• Vapor Pressure: 2.63E-06mmHg at 25°C
• Melting Point: 52-56 °C(lit.)
• Refractive Index: -51 ° (C=neat)
• Boiling Point: 369.6 °C at 760 mmHg
• Flash Point: 177.3 °C
• PSA: 0.00000
• Density: 0.99 g/cm³
• LogP: 6.36130
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 320.2442089
• Heavy Atom Count: 22
• Complexity: 428

Purity/Quality:

99% ^*data from raw suppliers

(-)-DIP-chloride(~60%inHeptane) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F+,
• Hazard Codes: C,F+,N,F
• Statements: 34-20/22-12-10-67-65-62-51/53-48/20-50/53-11-37
• Safety Statements: 9-16-29-33-36/37-61-62-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1CC2CC(C1C)C2(C)C)(C3CC4CC(C3C)C4(C)C)Cl
• Isomeric SMILES: B([C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C)([C@H]3C[C@H]4C[C@@H]([C@@H]3C)C4(C)C)Cl

Technology Process of (+)-B-Chlorodiisopinocampheylborane

There total 4 articles about (+)-B-Chlorodiisopinocampheylborane 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: 75.0%

diisopinocampheylborane (21932-54-7) → (-)-diisopinocamphenylborane chloride (85116-37-6)

Guidance literature:

With HCl; In diethyl ether; dry HCl in ether added to Ipc2BH-THF suspension at -78°C, stirring 15 min, warming to 0°C with stirring for complete soln. and gas evoln. ceased (2 h); solvent removal, cooling, prod. solidified, crystn. from pentane;

DOI:10.1021/ja00213a030

Reference yield:

(+)-α-pinene (7785-70-8,25766-18-1) → (-)-diisopinocamphenylborane chloride (85116-37-6)

Guidance literature:

With sodium tetrahydroborate; boron trichloride; In 1,2-dimethoxyethane; at 10 ℃; 1.) 10 deg C, 15 min; 2.) RT, 1 h; 3.) 40 deg C, 1 h;

DOI:10.1016/S0040-4039(97)00440-1

Reference yield:

Pinene (80-56-8,177698-18-9,25766-18-1) → (-)-diisopinocamphenylborane chloride (85116-37-6)

Guidance literature:

With monochloroborane dimethyl sulfide complex; In tetrahydrofuran; at -10 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo301182f

upstream raw materials:

(+)-α-pinene

diisopinocampheylborane

Pinene

hydrogenchloride

Downstream raw materials:

(1S,2R,3S,6R,8R)-2,9,9-Trimethyl-3-(1-phenyl-vinyl)-5-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-4-oxa-5-bora-tricyclo[6.1.1.0^2,6]decane

(1S,2R,3R,6R,8R)-2,9,9-Trimethyl-3-((E)-styryl)-5-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-4-oxa-5-bora-tricyclo[6.1.1.0^2,6]decane

(1R,2R)-2-chlorocyclohexanol

(1R,2R)-(-)-2-chlorocyclo-4-hexen-1-ol

Refernces

• 1、 Moeder, Charles W.,Whitener, Mark A.,Sowa Jr., John R.. "Quantitative stereochemical analysis of a reagent that exhibits asymmetric amplification, B-chlorodiisopinocampheylborane (Dip-Cl)". . p. 7218 - 7225. Retrieved 2000.
• 2、 Faber, Jonathan M.,Eger, Wilhelm A.,Williams, Craig M.. "Enantioselective total synthesis of the mexicanolides: Khayasin, proceranolide, and mexicanolide". . p. 8913 - 8921. Retrieved 2013/01/15.