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

Reaction

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(tert-butylmethylphosphino)quinoxaline
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
pka: -0.54±0.59(Predicted)
form: Powder
color: orange
InChI: InChI=1/C18H28N2P2/c1-17(2,3)21(7)15-16(22(8)18(4,5)6)20-14-12-10-9-11-13(14)19-15/h9-12H,1-8H3/t21-,22-/s3
InChIKey: DRZBLHZZDMCPGX-UHFFFAOYSA-N
SMILES: N1=C2C(C=CC=C2)=NC([P@@](C(C)(C)C)C)=C1[P@@](C(C)(C)C)C |&1:9,16,r|

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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: $140.27
Updated: 2025/07/31

Sigma-Aldrich

Product number: 676403
Product name: (R,R)-(–)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
Purity: 97%
Packaging: 500mg
Price: $478
Updated: 2025/07/31

TCI Chemical

Product number: B5301
Product name: (R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
Purity: >98.0%(HPLC)
Packaging: 100mg
Price: $212
Updated: 2025/07/31

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

Ligand for the rhodium-catalyzed, asymmetric hydrogenation of dehydroamino acid esters and α-enamides.
Ligand for the rhodium-catalyzed, asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds.
Ligand for the rhodium-catalyzed, asymmetric alkylative ring opening reaction
Ligand for the palladium-catalyzed asymmetric allylic alkylation and amination of racemic substrates.
Ligand for the ruthenium-catalyzed asymmetric hydrogenation of ketones.
Ligand for the rhodium-catalyzed, asymmetric hydroacylation of 1,1-disubstituted alkenes with aldehydes.
Ligand for the silver-catalyzed asymmetric nitroso aldol reaction.
Cu-catalyzed enantioconvergent allyllic borylation.
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:

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

(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

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

866081-62-1

C18H28N2P2

organophosphine ligand