Basic information Reaction Safety Supplier Related

(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE

Basic information Reaction Safety Supplier Related

(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE Basic information

Product Name:
(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE
Synonyms:
  • (R)-1-[(S)-2-(Diphenylphosphino)ferrocenyl]-ethyl-di-tert-butylphosphine, Manufactured by Solvias AG
  • (R)-1-[(SP)-2-(Diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine >=97%
  • -2-(Diphenylphosphino)
  • ferrocenyl]ethyldi-tert-butylphosphine
  • "Josiphos SL-J002-1/ (R)-1-[(SP)-2-(Diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine"
  • Josiphos SL-J002
  • Josiphos SL-J002-1 / (R)-1-[(S)-2-(Diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine
  • (R)1[(1S)2(diphenylphosphino)ferrocenyl] et-di-T-butylphosph
CAS:
155830-69-6
MF:
C32H40FeP2
MW:
542.45
Product Categories:
  • Chiral Phosphine
  • Ferrocene Series
  • Josiphos Series
  • organophosphine ligand
Mol File:
155830-69-6.mol
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(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE Chemical Properties

Melting point:
218-220°C (dec.)
alpha 
-412° ±15° (c 0.5, CHCl3)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Chloroform, Methanol
form 
Powder
color 
Orange
InChI
InChI=1/C27H35P2.C5H5.Fe/c1-21(29(26(2,3)4)27(5,6)7)24-19-14-20-25(24)28(22-15-10-8-11-16-22)23-17-12-9-13-18-23;1-2-4-5-3-1;/h8-21H,1-7H3;1-5H;/t21-;;/s3
InChIKey
STAGMXYQPGLLTD-MGIYCFTINA-N
SMILES
P(C1=CC=CC=C1)(C1=CC=CC=C1)[C]1[CH][CH][CH][C]1[C@@H](C)P(C(C)(C)C)C(C)(C)C.[CH]1[CH][CH][CH][CH]1.[Fe] |&1:18,r,^1:13,14,15,16,17,29,30,31,32,33|
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Safety Information

Risk Statements 
20/21/22-36/37/38
Safety Statements 
24/25
WGK Germany 
3
F 
10
HS Code 
29319090
Storage Class
11 - Combustible Solids

MSDS

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(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE Usage And Synthesis

Reaction

  1. Ligand for Palladium-catalyzed amination of aryl halides
  2. Ligand for Rhodium-catalyzed asymmetric alcoholysis and aminolysis of oxabenzonorbornadiene
  3. Ligand for Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with organoboronic acids
  4. Ligand for Copper-catalyzed asymmetric 1,4-hydrosilylations of α,β-unsaturated esters
  5. Ligand for Ruthenium-catalyzed asymmetric hydrogenation of N-sulfonated-α-dehydroamino acids
  6. Ligand for Rhodium-catalyzed asymmetric hydrogenation of enamines
  7. Ligand for Palladium-catalyzed Kumada coupling of aryl and vinyl tosylates
  8. Ligand for Palladium-catalyzed enantioselective synthesis of aryl sulfoxides
  9. Ligand for Rhodium-catalyzed enantioselective insertion of a carbenoid carbon into a C-C bond


Chemical Properties

Orange powder

Uses

It may be used as a ligand in the palladium-catalyzed alkoxycarbonylation of 6-bromo-1,4-benzodioxane with sodium tert-butoxide to form the corresponding tert-butyl ester.

General Description

(R)-1-[(SP)-2-(Diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine (PPF-tBu) is a chiral ferrocenyl diphosphine ligand.

Synthesis

(1) Synthesis of (R)-1-ferrocenyl ethyl di-tert-butylphosphine
Under argon protection, vinyl ferrocene (1 mol, 212 g), (R)-3,3'-bis(3,5-dimethylphenyl)-1,1'-binaphthol phosphonate (0.01 mol, 5.6g) and 1L of toluene, then add di-tert-butylphosphine (1 mol, 147g), heating to 60 ?? reaction for 12 hours, and then cool down and cool down, to the system dropwise addition of water, and then partitioning, the organic layer with anhydrous magnesium sulfate drying, filtration, distillation under reduced pressure to remove the solvent to get a yellow solid, dichloromethane and methanol recrystallization to get (R)-1 - ferrocenylethyl di-tert-butylphosphine 347g, yield 97%, e.e. value 99.5%.
(2) Synthesis of (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine
Under the protection of argon, (R)-1-ferrocenyl ethyldi-tert-butylphosphine (0.9 mol, 321 g) and 1 L of ethyl ether were added to a dry reactor, and then a 1 M diethylzinc hexane solution (0.9 mol, 0.9 L ), after the reaction at 0??C for 3 hours, diphenylphosphonium chloride (0.9 mol, 199 g) was added dropwise to the system, and after the dropwise addition was completed, it was heated and refluxed for 2 hours, and quenched by adding water to the system, and then partitioned, and the organic layer was dried with anhydrous magnesium sulfate, filtered, and the yellow solid was obtained after the solvent was removed by distillation under reduced pressure, and recrystallized from methylene chloride and methanol to obtain (R)-(-)-1-[(S)-2- diphenylphosphine Ferrocene ethyl-di-tert-butylphosphorus 468g, yield 96%, e.e. value 99.3%.

(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE Preparation Products And Raw materials

Raw materials

Hydrochloric acidEthyl acetateDichloromethaneAcetic acid glacialPotassium carbonateAcetic anhydriden-ButyllithiumLithium aluminium hydrideMagnesiumPhosphorus trichloride2-Chloro-2-methylpropaneChlorodiphenylphosphine(R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE

(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINESupplier

Xinxiang Runyu Material Co., Ltd. Gold
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166-166-37336996 15690792173
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chenxi.song@runvmat.com
Zhengzhou HQ Material Co., Ltd. Gold
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0371-0371-67759225 13526468238
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sales@hqmat.com
Beijing Tianyukanghong Chemical Technology Co., Ltd. Gold
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13552605092
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Zhengzhou Kingorgchem Chemical Technology Co., Ltd.gy Co., Ltd. Gold
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0371-65511006 18625597674
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sales@kingorgchem.com
Sinocompound Catalysts Co., Ltd. Gold
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0512-67216630 67216634
Email
sales@sinocompound.com
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(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE(155830-69-6)Related Product Information