150639-34-2

Basic information

• Product Name: (R,R)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE)
• Synonyms: (R,R)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE);(4R,4'R)-2,2'-methylenebis[4,5-dihydro-4-phenyl-Oxazole;(4R)-4-phenyl-2-[[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]methyl]-4,5-dihydro-1,3-oxazole
• CAS NO: 150639-34-2
• Molecular Formula: C₁₉H₁₈N₂O₂
• Molecular Weight: 306.35842
• Product Categories: Chiral Reagent
• Mol File: 150639-34-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 458.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.54±0.70(Predicted)
• CAS DataBase Reference: (R,R)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE)(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE)(150639-34-2)
• EPA Substance Registry System: (R,R)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE)(150639-34-2)

Safety Data

• Hazardous Substances Data: 150639-34-2(Hazardous Substances Data)

Usage

General Description

(R,R)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE), also known as MBO, is a chiral derivative of 2-oxazoline. It is commonly used as a chiral ligand in asymmetric catalysis, particularly in the asymmetric addition of diethylzinc to aldehydes. MBO is also used as a resolving agent for racemic acids and esters, and as a chiral derivatizing agent for the analysis of amino acids and carboxylic acids in chromatography. (R,R)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE) has a wide range of applications in the pharmaceutical and chemical industries due to its ability to induce chirality in reactions and its high stability and solubility.

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 10344-69-1 diethyl malonoimidate dihydrochloride 
• 20989-17-7 (2S)-2-phenylglycinol 
• 2935-35-5 (S)-2-phenylglycine 

Downstream Products

• 784206-51-5 C₄₃H₇₀N₂O₄Si₂ 
• 848563-13-3 C₃₈H₃₄N₄O₄Zn 
• 573968-16-8 (4R,4'R)-2,2'-(cyclopropane-1,1-diyl)bis(4-phenyl-4,5-dihydrooxazole) 
• 1350771-46-8 1,1'-{5,5-bis[(R)-4,5-dihydro-4-phenyloxazol-2-yl]nonane-1,9}bis-(1H-imidazole) 
• 1350771-45-7 (S)-2-{1,9-dichloro-5-[(R)-4,5-dihydro-4-phenyloxazol-2-yl]nonan-5-yl}-4,5-dihydro-4-phenyloxazole 
• 1350771-59-3 5,5-bis[(R)-4,5-dihydro-4-phenyloxazol-2-yl]nonane-1,9-ditosylate 
• 1350771-56-0 5,5-bis[(R)-4,5-dihydro-4-phenyloxazol-2-yl]nonane-1,9-diol 
• 1350771-53-7 5,5-bis[(R)-4,5-dihydro-4-phenyloxazol-2-yl]nonane-1,9-di(tert-butyl)dimethylsilane 
• 1206767-98-7 (4R,4'R)-2,2'-(2,3-dihydro-1H-phenalene-2,2-diyl)bis(4-phenyl-4,5-dihydrooxazole) 

Relevant articles and documents

New chiral bis(oxazoline) Rh(I)-, Ir(I)- and Ru(II)-complexes for asymmetric transfer hydrogenations of ketones

Chiral bis(oxazoline)-based Rh(I)-, Ir(I)- and Ru(II)-complexes have been prepared and used for asymmetric transfer hydrogenation of prochiral ketones. The presence of a free hydroxyl group on the ligand is necessary for high enantioselectivity. With acetophenone, up to 50% conversion and 89% ee were achieved.

Nickel/bis(oxazoline)-catalyzed asymmetric Kumada reactions of alkyl electrophiles: Cross-couplings of racemic α-bromoketones

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Heterogeneous asymmetric nitro-Mannich reaction using a bis(oxazoline) ligand grafted on mesoporous silica

A chiral bis(oxazoline) ligand was immobilized on mesoporous silica (SBA-15) and examined in an asymmetric heterogeneous nitro-Mannich reaction. Depending upon the size of the alkyl chain in the nitroalkane substrates, enantioselectivities comparable to and higher diastereoselectivities (syn/anti ratio) than those obtained from homogeneous reactions were observed. In the case of the long chain substituted nitroalkane substrate (nitrohexane), the best selectivities (diastereoselectivity: syn/anti = 98/2, and enantioselectivity: 93% and 82% ee's for syn- and anti-isomers, respectively), were observed. Recycling of the catalyst in subsequent reactions was carried out and gradually diminishing levels of both diastereo and enantioselectivities were observed after each recycle.