132098-54-5

Basic information

• Product Name: (S,S)-2,2'-METHYLENEBIS(4-TERT-BUTYL-2-OXAZOLINE)
• Synonyms: (S,S)-2,2'-METHYLENEBIS(4-TERT-BUTYL-2-OXAZOLINE);2,2'-Methylenebis[(4S)-4-tert-butyl-4,5-dihydro-2-oxazole];Bis((4S)-4-tert-butyl-4,5-dihydrooxazol-2-yl)methane;bis((S)-4-(tert-butyl)-4,5-dihydrooxazol-2-yl)methane;(4S,4'S)-2,2'-methylenebis[4-(1,1-dimethylethyl)-4,5-dihydro-Oxazole
• CAS NO: 132098-54-5
• Molecular Formula: C₁₅H₂₆N₂O₂
• Molecular Weight: 266.38
• Mol File: 132098-54-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 51-53 °C(lit.)
• Boiling Point: 328.8°Cat760mmHg
• Flash Point: 124.8°C
• Appearance: /
• Density: 1.08g/cm³
• Storage Temp.: 2-8°C
• PKA: 5.39±0.70(Predicted)
• BRN: 4190673
• CAS DataBase Reference: (S,S)-2,2'-METHYLENEBIS(4-TERT-BUTYL-2-OXAZOLINE)(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-2,2'-METHYLENEBIS(4-TERT-BUTYL-2-OXAZOLINE)(132098-54-5)
• EPA Substance Registry System: (S,S)-2,2'-METHYLENEBIS(4-TERT-BUTYL-2-OXAZOLINE)(132098-54-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 132098-54-5(Hazardous Substances Data)

Usage

Description

(S,S)-2,2'-METHYLENEBIS(4-TERT-BUTYL-2-OXAZOLINE) is a C2 symmetric ligand that is widely utilized in the field of enantioselective catalysis. It is characterized by its ability to easily form bidentate coordination complexes with various metals, thanks to the strong affinity of the oxazoline nitrogen. This unique property makes it a valuable compound in the development of novel catalysts and chemical reactions.

Uses

Used in Chemical Industry:
(S,S)-2,2'-METHYLENEBIS(4-TERT-BUTYL-2-OXAZOLINE) is used as a chiral ligand for enantioselective catalysis to facilitate the synthesis of enantiomerically pure compounds. Its ability to form bidentate coordination complexes with metals enhances the efficiency and selectivity of the catalyzed reactions, leading to improved yields and reduced waste.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S,S)-2,2'-METHYLENEBIS(4-TERT-BUTYL-2-OXAZOLINE) is used as a key component in the development of novel drugs and drug candidates. Its role in enantioselective catalysis allows for the production of chiral drugs with desired stereochemistry, which is crucial for their efficacy and safety.
Used in Research and Development:
(S,S)-2,2'-METHYLENEBIS(4-TERT-BUTYL-2-OXAZOLINE) is also used in research and development as a tool to study the mechanisms of enantioselective catalysis and to develop new catalysts with improved performance. Its versatility and unique properties make it an essential compound in the advancement of chemical research and innovation.

Upstream product

• 10344-69-1 diethyl malonoimidate dihydrochloride 
• 3907-02-6 (2R)-2-amino-3,3-dimethylbutan-1-ol 
• 878766-81-5 malonodiimidic acid diethyl ester dihydrochloride 
• 112245-13-3 (S)-tert-leucinol 
• 133463-95-3 N,N'-Bis-((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-malonamide 
• 105-53-3 diethyl malonate 
• 133464-00-3 N,N'-Bis-((S)-1-chloromethyl-2,2-dimethyl-propyl)-malonamide 

Downstream Products

• 131833-93-7 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] 
• 1350771-49-1 5,5-bis[(S)-4-tert-butyl-4,5-dihydrooxazol-2-yl]pentyl-1-tosylate 
• 1350771-60-6 5,5-bis[(S)-4-tert-butyl-4,5-dihydrooxazol-2-yl]nonane-1,9-ditosylate 
• 572909-71-8 2,2-bis[(4S)-4-(1,1-dimethylethyl)-1,3-oxazolin-2-yl]-1,3-bis(4-hydroxyphenyl)propane 
• 345269-80-9 2,2-bis{2-[(4S)-4-(1,1-dimethylethyl)-1,3-oxazolin-2-yl]-1-(4-hydroxyphenyl)}propane 
• 345269-78-5 2,2-bis[(4S)-4-(1,1-dimethylethyl)-1,3-oxazolin-2-yl]-1-[4-(2-propenyl)oxyphenyl]propane 
• 319489-95-7 2,2'-[2-(4-vinylphenyl)-1-(4-vinylbenzyl)ethylidene]bis[(4S)-4-tert-butyl-4,5-dihydro-2-oxazole] 
• 195379-09-0 (4S,4'S)-2,2'-(cyclopropane-1,1-diyl)bis(4-(tert-butyl)-4,5-dihydrooxazole) 
• 2634687-78-6 2,2'-(1-benzyl-2-phenylethylidene)bis[(4S)-4-tert-butyl-4,5-dihydro-2-oxazole] 
• 2757082-26-9 1,1'-bis[2-((4S)-(1,1-dimethylethyl)-1,3-oxazolinyl)]cyclohexane 
• 298693-03-5 (4S,4'S)-2,2'-(cyclopentane-1,1-diyl)bis(4-(tert-butyl)-4,5-dihydrooxazole) 

Relevant articles and documents

Preparation of new bis(oxazoline) ligand bearing non-covalent interaction sites and an application in the highly asymmetric Diels-Alder reaction

New asymmetric bis(oxazoline) (Box) ligand bearing amide group at the oxazoline 4-position, (S,S)-2,2′-methylenebis(4-tert-butylcarbamoyl-2- oxazoline) (1S), was designed and synthesized for selective catalytic reaction. The crystal structure of the terna

Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds

Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, the first synthesis is reported for the corresponding ethynylbenziodazolone (EBZ) reagents, in which the oxygen atom in the iodoheterocycle is replaced by a nitrogen atom. The substituent on the nitrogen enables further fine-tuning of the reagent structure and reactivity. EBZ reagents are obtained easily from the corresponding benzamides by using a one-step procedure, and display reactivity comparable to that of EBX reagents. In particular, they are applied in an asymmetric copper-catalyzed oxyalkynylation of diazo compounds, which proceeds in high yield and enantioselectivity for a broad range of substituents on the diazo compounds and the alkyne.

Quest for Efficient Catalysts based on Zinc tert-Butyl Peroxides for Asymmetric Epoxidation of Enones: C2- vs C1-Symmetric Auxiliaries

Zinc tert-butyl peroxide-based catalysts for the asymmetric epoxidation of enones using tert-butyl hydroperoxide as an oxidant have been developed. A comparative study of chiral monoanioninc N,N′-bidentate ligands, C2-symmetric bisoxazolinates and C1-symmetric enaminooxazolinates, revealed excellent performance of C1-symmetric auxiliary ligands on catalytic asymmetric epoxidation of enones (up to 96% yield, 91% ee).