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ChemicalBook > Product Catalog >Catalyst and Auxiliary >(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline

(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline

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Company Name: ATK CHEMICAL COMPANY LIMITED
Tel: +undefined-21-51877795
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Products Intro: CAS:866081-62-1
Purity:98% Package:10MG;50MG;100MG,1G,5G,10G.100G
Company Name: Hangzhou Cyanochem Co., Ltd.
Tel: +86 17788583750
Email: sales@cyanochem.com
Products Intro: Product Name:(R.R)-QuinoxP
CAS:866081-62-1
Purity:98% Package:100g;300g;1KG,5KG;25KG
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Products Intro: Product Name:(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline
CAS:866081-62-1
Purity:0.99 Package:5KG;1KG,25KG
Company Name: Jinan Honest Pharm Co., Ltd
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Products Intro: Product Name:(R,R)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
CAS:866081-62-1
Purity:99% Package:10g;50g;100g;
Company Name: Hubei Ipure Biology Co., Ltd
Tel: +8613367258412
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Products Intro: Product Name:(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
CAS:866081-62-1
Purity:0.99 Package:5KG;1KG
(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline Basic information
Reaction
Product Name:(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline
Synonyms:(R) QuinoxP;2,3-Bis((R)-tert-butyl(methyl)phosphino)quinoxaline;(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline 97%;(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline;(R,R)-QuinoxP*;(R) QuinoxP(R);(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline;(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline, min. 98% (R,R)-QuinoxP*
CAS:866081-62-1
MF:C18H28N2P2
MW:334.38
EINECS:
Product Categories:organophosphine ligand
Mol File:866081-62-1.mol
(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline Structure
(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline Chemical Properties
Melting point 100-104 °C
Boiling point 447.6±45.0 °C(Predicted)
alpha -54.3° (c 1.0, CHCl3)
storage temp. Inert atmosphere,Room Temperature
pka-0.54±0.59(Predicted)
form Powder
color orange
InChIKeyDRZBLHZZDMCPGX-UHFFFAOYSA-N
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38
Safety Statements 26
RIDADR UN2811 6.1/PG 3
WGK Germany 3
HS Code 2933.99.8290
MSDS Information
(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline Usage And Synthesis
Reaction
  1. Ligand for the rhodium-catalyzed, asymmetric hydrogenation of dehydroamino acid esters and α-enamides.
  2. Ligand for the rhodium-catalyzed, asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds.
  3. Ligand for the rhodium-catalyzed, asymmetric alkylative ring opening reaction
  4. Ligand for the palladium-catalyzed asymmetric allylic alkylation and amination of racemic substrates.
  5. Ligand for the ruthenium-catalyzed asymmetric hydrogenation of ketones.
  6. Ligand for the rhodium-catalyzed, asymmetric hydroacylation of 1,1-disubstituted alkenes with aldehydes.
  7. Ligand for the silver-catalyzed asymmetric nitroso aldol reaction.
  8. Cu-catalyzed enantioconvergent allyllic borylation.
  9. Cu-catalyzed enantioselective cyclopropylation.
Reactions of 866081-62-1_1
Reactions of 866081-62-1_2
Reactions of 866081-62-1_3
Description(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline is an efficient ligand exhibiting high levels of enantiocontrol in synthetic transformations ranging from metal-catalyzed 1,4-addition of arylboronic acids to asymmetric hydrogenation to alkylative ring opening.
UsesAir-Stable and Highly Efficient Chiral Ligands
ApplicationAir-Stable and Highly Efficient Chiral Ligands,Efficient ligand exhibiting high levels of enantiocontrol in synthetic transformations ranging from metal-catalyzed 1,4-addition of arylboronic acids to alkylative ring opening to asymmetric hydrogenation.
General Description(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline is an air-stable C2-symmetric P-stereogenic phosphine ligand.
Synthesis2.png
In 4 ml of tetrahydrofuran was dissolved 236 mg (2.0 mmol) of (R)-tert-butylmethylphosphine-borane (9), and the resulting solution was cooled to -78° C. with liquid nitrogen. To the cooled solution was added dropwise 1.25 ml of a 1.6 M hexane solution of n-butyllithium. Fifteen minutes later, a solution of 133 mg (0.67 mmol) of 2,3-dichloroquinoxaline (10) in 4 ml of tetrahydrofuran was added thereto dropwise while vigorously stirring to form a diphosphine-borane compound (11) as an intermediate. The liquid temperature was raised to room temperature over one hour, at which the mixture was stirred for 3 hours. One milliliter of TMEDA was added thereto, and the stirring was continued for an additional 2 hour period to complete deboranation. The reaction was ceased by addition of 1M hydrochloric acid. The reaction mixture was extracted with hexane. The extract was washed successively with 1M hydrochloric acid and a saturated sodium chloride aqueous solution and dried over sodium sulfate. The solvent was removed by evacuation, and the residue was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=30/1) to give (R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline (12) as an orange solid. Recrystallization from 1.7 ml of hot methanol gave orange crystals (>99% ee) in a yield of 80%.
(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline Preparation Products And Raw materials
Tag:(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline(866081-62-1) Related Product Information
(S) QuinoxP(R) (R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline

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