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ChemicalBook > CAS DataBase List > (R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline

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

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Product Name
(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline
CAS No.
866081-62-1
Chemical Name
(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline
Synonyms
(R) QuinoxP;(R,R)-QuinoxP*;(R) QuinoxP(R);2,3-Bis((R)-tert-butyl(methyl)phosphino)quinoxaline;(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline;2,3-bis((R)-tert-butyl(methyl)phosphaneyl)quinoxaline;(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline;(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline 97%;Quinoxaline, 2,3-bis[(R)-(1,1-dimethylethyl)methylphosphino]-;(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline, min. 98% (R,R)-QuinoxP*
CBNumber
CB42102445
Molecular Formula
C18H28N2P2
Formula Weight
334.38
MOL File
866081-62-1.mol
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(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline Property

Melting point:
100-104 °C
alpha 
-54.3° (c 1.0, CHCl3)
Boiling point:
447.6±45.0 °C(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
form 
Powder
pka
-0.54±0.59(Predicted)
color 
orange
InChIKey
DRZBLHZZDMCPGX-UHFFFAOYSA-N
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
676403
Product name
(R,R)-(–)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
Purity
97%
Packaging
100mg
Price
$102.6
Updated
2024/03/01
Sigma-Aldrich
Product number
676403
Product name
(R,R)-(–)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
Purity
97%
Packaging
500mg
Price
$278.4
Updated
2024/03/01
TCI Chemical
Product number
B5301
Product name
(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
Purity
>98.0%(HPLC)
Packaging
100mg
Price
$213
Updated
2024/03/01
Strem Chemicals
Product number
15-0126
Product name
(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline, min. 98% (R,R)-QuinoxP*
Packaging
100mg
Price
$116
Updated
2024/03/01
Strem Chemicals
Product number
15-0126
Product name
(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline, min. 98% (R,R)-QuinoxP*
Packaging
500mg
Price
$458
Updated
2024/03/01
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(R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline Chemical Properties,Usage,Production

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.


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

Application

Air-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.

Synthesis


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

Raw materials

Preparation Products

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

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866081-62-1, (R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxalineRelated Search:


  • (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*
  • Quinoxaline, 2,3-bis[(R)-(1,1-dimethylethyl)methylphosphino]-
  • 2,3-bis((R)-tert-butyl(methyl)phosphaneyl)quinoxaline
  • 866081-62-1
  • C18H28N2P2
  • organophosphine ligand