• TCI B5301 866081-62-1 (R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
  • 866081-62-1 (R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline - AMI Scientific
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TCI

CAS 866081-62-1

(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline TCI B5301

(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline TCI B5301

Chemical Identity

CAS No.
866081-62-1
PubChem
CID 11695692·SID 354334700
Formula
C18H28N2P2
Molecular weight
334.4 g/mol
Purity
>98.0%(HPLC)
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
(R)-tert-butyl-[3-[tert-butyl(methyl)phosphanyl]quinoxalin-2-yl]-methylphosphane
SMILES
CC(C)(C)[P@@](C)C1=NC2=CC=CC=C2N=C1[P@](C)C(C)(C)C
InChIKey
DRZBLHZZDMCPGX-VXKWHMMOSA-N
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(TCI B5301) is a chiral ligand used in asymmetric synthesis to accelerate chemical reactions and produce products with specific spatial structures. This compound is commonly found in catalytic reactions requiring high stereochiral control, such as in the production of pharmaceuticals, organic chemicals, and pharmacological compounds. In the laboratory, this material functions as a catalyst or reagent that enhances the efficiency of complex chemical reactions. Its chiral nature allows for the selective formation of desired enantiomers, making it a valuable tool in synthetic chemistry. The compound is widely utilized in research settings where precision and control over reaction outcomes are critical.

The compound features a quinoxaline structure surrounded by tert-butylmethylphosphino groups, which contribute to its high reactivity and chemical stability. These properties make it a preferred choice for asymmetric reactions that demand accuracy and efficiency. The ligand's non-toxic nature and ease of processing further enhance its appeal in laboratory environments. Its ability to maintain stability under various reaction conditions ensures consistent performance, making it a reliable option for researchers working on complex chemical transformations.

In Indonesian laboratories, this compound is frequently used in pharmaceutical research and development, as well as in academic and industrial settings focused on synthetic chemistry. Its role in producing high-purity chiral compounds aligns with the growing demand for advanced chemical synthesis techniques in the region. The compound supports the development of new drugs and specialty chemicals, contributing to the advancement of scientific research in Indonesia.

Advantages (TCI brochure)

  • Relatively stable and easy-to-handle crystalline solid
  • Optically active phosphine with a chiral center at phosphorus
  • Can coordinate to transition metals
  • Applicable to asymmetric hydrogenation under mild conditions

TCI brochures (PDF)

Related TCI products

  • Asymmetric synthesis is a key application where this ligand enables the selective production of enantiomers, crucial for pharmaceutical development.
  • Catalytic reactions benefit from its high reactivity and stability, allowing for efficient and controlled chemical transformations.
  • Organic chemistry research utilizes this compound to achieve precise stereochemical control in complex molecule synthesis.
  • Pharmaceutical research leverages its chiral properties to develop new drugs with specific spatial configurations.
  • Industrial chemical synthesis relies on its reliability and performance in producing high-purity chiral compounds.

From the TCI brochure

  • Ruthenium-Catalyzed Asymmetric Hydrogenation of Malonic Acid Derivatives
  • Rhodium-Catalyzed Asymmetric Hydroacylation of Acrylic Amide Derivatives
  • Copper-Catalyzed Asymmetric Conjugate Addition

Brand TCI
CAS number 866081-62-1
Molecular formula —
Purity —
Category Chemistry > Asymmetric Synthesis > Chiral Catalysts, Chiral Ligands, Chiral Reagents
Pack sizes —
Physical form —
Storage Store in a cool, dry place away from light and moisture

Data from the TCI brochure

Kemasan100 mg
Yield (hidrogenasi asimetris Ru)73 - 99% yield (EtOH/CH2Cl2, 50 - 70 °C, 24 h)
ee (hidrogenasi asimetris Ru)97 - 99.9% ee (EtOH/CH2Cl2, 50 - 70 °C, 24 h)
Yield (hidroasilasi asimetris Rh)73 - 87% yield ((CH2Cl)2, 80 °C)
ee (hidroasilasi asimetris Rh)96 - 99% ee ((CH2Cl)2, 80 °C)
Yield (adisi konjugasi asimetris Cu)80 - 99% yield (DMSO, rt, 12 h, t-BuOLi)
ee (adisi konjugasi asimetris Cu)70 - 98% ee (DMSO, rt, 12 h, t-BuOLi)

Source: TCI brochure RR104 (2025-02-21)

This compound should be stored in a cool, dry place, away from light and moisture to maintain its chemical stability. It is recommended to use airtight containers to prevent exposure to air and humidity. General laboratory precautions include handling with care to avoid contamination and ensuring proper ventilation when working with the material. Since it is non-toxic, it is generally safe to handle, but standard laboratory safety practices should still be followed. The compound does not require special protective equipment beyond standard lab protocols, making it accessible for routine use in research settings.

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