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

Base Information

• Chemical Name: (R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
• CAS No.: 866081-62-1
• Molecular Formula: C₁₈H₂₈N₂P₂
• Molecular Weight: 334.381
• European Community (EC) Number: 634-522-0
• Nikkaji Number: J2.201.227D
• Wikidata: Q76421872
• Mol file: 866081-62-1.mol

Synonyms:(R,R)-QuinoxP*;2,3-Bis((R)-tert-butyl(methyl)phosphino)quinoxaline;(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline;(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline;SCHEMBL3174167;(R)-tert-butyl-[3-[tert-butyl(methyl)phosphanyl]quinoxalin-2-yl]-methylphosphane;(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline, 97%;B5301;CS-0086008;F17929;(r,r)-2,3-bis(tert-butylmethylphosphino)quinoxaline;(R,R)-()-2,3-Bis(tert-butylmethylphosphino)quinoxaline

Chemical Property of (R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline

Chemical Property:

• Vapor Pressure: 8.77E-08mmHg at 25°C
• Melting Point: 100-104 °C
• Boiling Point: 447.6°C at 760 mmHg
• PKA: -0.54±0.59(Predicted)
• Flash Point: 224.5°C
• PSA: 52.96000
• LogP: 4.70080
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 334.17277290
• Heavy Atom Count: 22
• Complexity: 336

Purity/Quality:

97% ^*data from raw suppliers

2,3-Bis((R)-tert-butyl(methyl)phosphino)quinoxaline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)P(C)C1=NC2=CC=CC=C2N=C1P(C)C(C)(C)C
• Isomeric SMILES: CC(C)(C)[P@@](C)C1=NC2=CC=CC=C2N=C1[P@](C)C(C)(C)C
• 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.
• Uses: Air-Stable and Highly Efficient Chiral Ligands

Technology Process of (R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline

There total 21 articles about (R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline 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: 80.0%

C18H34B2N2P2 (1338825-24-3,1416911-62-0,920505-31-3) → (R,R)-(?)-2,3-bis(t-butylmethylphosphino)quinoxaline (866081-62-1,959705-18-1,1107608-80-9)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at 20 ℃; for 2h;

Reference yield: 80.0%

2,3-dichloroquinoxaline (2213-63-0) + (S)-(tert-butyl)(methyl)phosphine-borane (263563-97-9,360787-11-7,263768-77-0) → (R,R)-(?)-2,3-bis(t-butylmethylphosphino)quinoxaline (866081-62-1,959705-18-1,1107608-80-9)

Guidance literature:

(S)-(tert-butyl)(methyl)phosphine-borane; With n-butyllithium; at -80 ℃; Inert atmosphere;

2,3-dichloroquinoxaline; at -80 - 20 ℃; Inert atmosphere;

With N,N,N,N,-tetramethylethylenediamine; at 20 ℃; Inert atmosphere;

DOI:10.1021/ja209700j

Reference yield: 80.0%

2,3-dichloroquinoxaline (2213-63-0) + (SP)-tert-butyl(methyl)phosphane-borane → (R,R)-(?)-2,3-bis(t-butylmethylphosphino)quinoxaline (866081-62-1,959705-18-1,1107608-80-9)

Guidance literature:

(S_P)-tert-butyl(methyl)phosphane-borane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

2,3-dichloroquinoxaline; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 4h;

With N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; for 2h;

DOI:10.1021/ja053458f

upstream raw materials:

2,3-dichloroquinoxaline

(R)-tert-butyl(hydroxymethyl)methylphosphine borane

C₁₈H₃₄B₂N₂P₂

(±)-tert-butylmethylphosphine borane

Downstream raw materials:

bis-[2,3-bis(tert-butylmethylphosphino)quinoxaline]gold(I) chloride

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