(S,S)-Methyl-DUPHOS

Base Information

• Chemical Name: (S,S)-Methyl-DUPHOS
• CAS No.: 136735-95-0
• Molecular Formula: C₁₈H₂₈P₂
• Molecular Weight: 306.368
• European Community (EC) Number: 682-734-7
• UNII: HL745J99SB
• DSSTox Substance ID: DTXSID90159910
• Nikkaji Number: J749.123I
• Mol file: 136735-95-0.mol

Synonyms:136735-95-0;(S,S)-Methyl-DUPHOS;(S,S)-Me-DUPHOS;(+)-1,2-Bis[(2S,5S)-2,5-dimethylphospholano]benzene;Methyl-duphos, (S,S)-;(S,S)-Me-duphos [MI];UNII-HL745J99SB;1,2-Bis((2S,5S)-2,5-dimethylphospholan-1-yl)benzene;(2S,5S)-1-[2-[(2S,5S)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane;(S,S)-Methyl-duphos, (+)-;HL745J99SB;(S,S)-1,2-Bis(2,5-dimethylphospholano)benzene;Phospholane, 1,1'-(1,2-phenylene)bis(2,5-dimethyl-, (2S,2'S,5S,5'S)-;Phospholane, 1,1'-(1,2-phenylene)bis[2,5-dimethyl-, (2S,2'S,5S,5'S)-;MFCD00142322;SCHEMBL9913795;DTXSID90159910;AJNZWRKTWQLAJK-VGWMRTNUSA-N;AKOS015910254;CS-0086465;D83772;J-006899;Q27279984;(+)-1,2-Bis[(2S,5S)-2,5-dimethylphospholano]benzene, kanata purity

Chemical Property of (S,S)-Methyl-DUPHOS

Chemical Property:

• Vapor Pressure: 1.03E-06mmHg at 25°C
• Melting Point: 67-76 °C
• Boiling Point: 415°C at 760 mmHg
• Flash Point: 216.3°C
• PSA: 27.18000
• LogP: 5.04260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 306.16662489
• Heavy Atom Count: 20
• Complexity: 277

Purity/Quality:

99%, ^*data from raw suppliers

(+)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene, 98+% (S,S)-Me-DUPHOS ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(P1C2=CC=CC=C2P3C(CCC3C)C)C
• Isomeric SMILES: C[C@H]1CC[C@@H](P1C2=CC=CC=C2P3[C@H](CC[C@@H]3C)C)C
• Uses: It is a DuPhos and BPE ligands which are highly efficient privileged ligands.

Technology Process of (S,S)-Methyl-DUPHOS

There total 4 articles about (S,S)-Methyl-DUPHOS 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: 96.0%

(S,S)-Me-BozPHOS (1380079-15-1) → 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene (147253-67-6,136735-95-0)

Guidance literature:

With copper(II) trifluoromethanesulfonate; 1,1,3,3-Tetramethyldisiloxane; In toluene; at 100 ℃; Inert atmosphere;

DOI:10.1021/ja301764m

Reference yield:

(2R,5R)-2,5-hexanediol (17299-07-9) → 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene (147253-67-6,136735-95-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) SOCl₂, 2.) RuCl₃*3H₂O, NaIO₄ / 1.) CCl₄, reflux, 1.5 h, 2.) CCl₄, CH₃CN, H₂O, 25 deg C, 1 h

2: 1.) n-BuLi, 3.) n-BuLi

With ruthenium trichloride; sodium periodate; n-butyllithium; thionyl chloride;

Reference yield:

1,2-bis(phosphino)benzene (80510-04-9) + (4R,7R)-4,7-dimethyl-[1,3,2]dioxathiepane 2,2-dioxide (136779-29-8) → 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene (147253-67-6,136735-95-0)

Guidance literature:

Multistep reaction;

DOI:10.1021/ja00022a047

upstream raw materials:

1,2-bis(phosphino)benzene

(4R,7R)-4,7-dimethyl-[1,3,2]dioxathiepane 2,2-dioxide

(2R,5R)-2,5-hexanediol

(S,S)-Me-BozPHOS

Refernces

Z-Selective Hydrothiolation of Racemic 1,3-Disubstituted Allenes: An Atom-Economic Rhodium-Catalyzed Dynamic Kinetic Resolution

10.1002/anie.201507623

The research explores a novel rhodium-catalyzed hydrothiolation process for 1,3-disubstituted allenes, aiming to develop an atom-economic and highly selective method for synthesizing Z-allylic sulfones. The study utilizes bidentate ligands such as 1,4-bis(diphenylphosphino)butane (dppb) and (S,S)-Me-DuPhos to achieve high Z-selectivity and enantioselectivity in the presence of various aromatic and aliphatic thiols. The purpose is to create a versatile synthetic pathway for producing bioactive compounds containing α-stereogenic C–S bonds, which are important in pharmaceuticals. The method demonstrated excellent Z/E-selectivities up to >99:1 and enantioselectivities up to 96% ee, tolerating a wide range of functionalized thiols and allene substrates. The research concludes that this rhodium-catalyzed hydrothiolation is a powerful and efficient approach for the synthesis of Z-allylic sulfones, with potential applications in the synthesis of complex bioactive molecules.

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