(R,R)-Chiraphos

Base Information

• Chemical Name: (R,R)-Chiraphos
• CAS No.: 74839-84-2
• Molecular Formula: C28H28P2
• Molecular Weight: 426.478
• Hs Code.: 29310099
• European Community (EC) Number: 633-296-0
• UNII: 1T086B9Q1J
• DSSTox Substance ID: DTXSID901336752
• Nikkaji Number: J849.432K
• Wikidata: Q27893135
• Mol file: 74839-84-2.mol

Synonyms:74839-84-2;(R,R)-Chiraphos;(2R,3R)-Butane-2,3-diylbis(diphenylphosphine);Cira;Chiraphos, (R,R)-;(2r,3r)-(+)-bis(diphenylphosphino)butane;(2R,3R)-Bis(diphenylphosphino)butane;(2R,3R)-(+)-2,3-Bis(diphenylphosphino)butane;UNII-1T086B9Q1J;[(2R,3R)-3-diphenylphosphanylbutan-2-yl]-diphenylphosphane;1T086B9Q1J;Phosphine, [(1R,2R)-1,2-dimethyl-1,2-ethanediyl]bis[diphenyl-;Phosphine, 1,1'-((1R,2R)-1,2-dimethyl-1,2-ethanediyl)bis(1,1-diphenyl-;(2R,3R)-Chiraphos;SCHEMBL29178;DTXSID901336752;ZCA83984;MFCD00075403;AKOS027327497;AS-66828;CS-0035254;D94676;(2R,3R)-(+)-2,3-Bis-(Diphenylphosphino)butane;((2R,3R)-butane-2,3- diyl)bis(diphenylphosphan e);Q27893135;[(2R,3R)-3-(DIPHENYLPHOSPHANYL)BUTAN-2-YL]DIPHENYLPHOSPHANE

Chemical Property of (R,R)-Chiraphos

Chemical Property:

• Vapor Pressure: 9.4E-11mmHg at 25°C
• Melting Point: 104-109 °C
• Boiling Point: 529.2 °C at 760 mmHg
• Flash Point: 291.2 °C
• PSA: 27.18000
• LogP: 6.02920
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 426.16662489
• Heavy Atom Count: 30
• Complexity: 387

Purity/Quality:

98% ^*data from raw suppliers

(2R,3R)-Bis(diphenylphosphino)butane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 36/37/39-26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C)P(C1=CC=CC=C1)C2=CC=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C[C@H]([C@@H](C)P(C1=CC=CC=C1)C2=CC=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4
• Uses: (2R,3R)-Bis(diphenylphosphino)butane is a reagent used in the synthesis of endothelin A receptor antagonists. Also used in the synthesis of (R)-Tolterodine and (S)-Tolterodine.

Technology Process of (R,R)-Chiraphos

There total 6 articles about (R,R)-Chiraphos 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: 95.0%

(R,R)-2,3-Bis(diphenylphosphinoyl)butane (192449-15-3) → (R,R)-chiraphos (74839-84-2)

Guidance literature:

With trichlorosilane; In xylene; 1.) from 0 deg C to RT, 2.) from 100 to 120 deg C, 2 h, 3.) reflux, 3 h;

DOI:10.1016/S0957-4166(97)00132-8

Reference yield: 32.0%

(2S,3S)-bis(4-methylbenzenesulfonyl)butane (74839-83-1) + lithium diphenylphosphide (65567-06-8,4541-02-0) → (R,R)-chiraphos (74839-84-2)

Guidance literature:

In tetrahydrofuran; 1.) -4 deg C, 20 min, 2.) room temp., 30 min;

Reference yield:

2,3-dibuta-1,3-diene (113017-77-9) → (R,R)-chiraphos (74839-84-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / NaBH₄ / tetrahydrofuran; H₂O; CH₂Cl₂ / 42 h / 20 °C

3: 95 percent / HSiCl₃ / xylene / 1.) from 0 deg C to RT, 2.) from 100 to 120 deg C, 2 h, 3.) reflux, 3 h

With sodium tetrahydroborate; trichlorosilane; In tetrahydrofuran; dichloromethane; water; xylene;

DOI:10.1016/S0957-4166(97)00132-8

upstream raw materials:

(2S,3S)-bis(4-methylbenzenesulfonyl)butane

lithium diphenylphosphide

(R,R)-2,3-Bis(diphenylphosphinoyl)butane

2,3-dibuta-1,3-diene

Refernces

• 1、 -. "Ethylene oligomerization catalyst systems having enhanced selectivity". Page/Page column 14. . Retrieved 2013/02/27.
• 2、 Koettner, Johann,Greber, Gerd. "A New Chiral Rhodium(I) Complex of (2R,3R)-2,3-Bis(diphenylphosphino)butane for Asymmetric Hydrogenations". . p. 2323 - 2325. Retrieved 2007/10/02.