(-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE

Base Information

• Chemical Name: (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE
• CAS No.: 147253-67-6
• Molecular Formula: C18H28P2
• Molecular Weight: 306.368
• Hs Code.: 2934999090
• European Community (EC) Number: 604-579-6
• UNII: H5W03D1HAQ
• DSSTox Substance ID: DTXSID20163641
• Nikkaji Number: J922.960D
• Mol file: 147253-67-6.mol

Synonyms:Phospholane,1,1'-(1,2-phenylene)bis[2,5-dimethyl-, [2R-[1(2'R*,5'R*),2a,5b]]- (9CI);1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene;(-)-1,2-Bis(2R,5R-2,5-dimethylphospholano)benzene;(-)-1,2-Bis[(2R,5R)-dimethylphospholano]benzene;(2R,2'R,5R,5'R)-1,1'-(1,2-phenylene)bis[2,5-dimethylphospholane];(R,R)-1,2-Bis(2,5-dimethylphospholano)benzene;(R,R)-MeDuPHOS;(R,R)-Methyl-DuPhos;1,2-Bis((2R,5R)-2,5-dimethylphospholan-1-yl)benzene;

Chemical Property of (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE

Chemical Property:

• Appearance/Colour: 22-24/25
• Vapor Pressure: 1.03E-06mmHg at 25°C
• Melting Point: 66-76 °C
• Boiling Point: 414.958 °C at 760 mmHg
• Flash Point: 216.272 °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:

98%,99%, ^*data from raw suppliers

1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

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: 1,2-Bis[(2R,5R)-2,5-dimethyl-1-phospholanyl]benzene is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. It is used as highly efficient privileged ligands.

Technology Process of (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE

There total 6 articles about (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE 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

• 1、 Li, Yuehui,Das, Shoubhik,Zhou, Shaolin,Junge, Kathrin,Beller, Matthias. "General and selective copper-catalyzed reduction of tertiary and secondary phosphine oxides: Convenient synthesis of phosphines". scheme or table. p. 9727 - 9732. Retrieved 2012/07/14.
• 2、 -. "Method for Producing Polyhydroxyalkanoates". . . Retrieved 2009/05/28.