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

Uses

C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

Upstream product

• 112245-13-3 (S)-tert-leucinol 
• 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 
• 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

• 2757082-26-9 1,1'-bis[2-((4S)-(1,1-dimethylethyl)-1,3-oxazolinyl)]cyclohexane 
• 195379-09-0 (4S,4'S)-2,2'-(cyclopropane-1,1-diyl)bis(4-(tert-butyl)-4,5-dihydrooxazole) 
• 319489-95-7 2,2'-[2-(4-vinylphenyl)-1-(4-vinylbenzyl)ethylidene]bis[(4S)-4-tert-butyl-4,5-dihydro-2-oxazole] 
• 345269-78-5 2,2-bis[(4S)-4-(1,1-dimethylethyl)-1,3-oxazolin-2-yl]-1-[4-(2-propenyl)oxyphenyl]propane 
• 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 
• 131833-93-7 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] 
• 2634687-78-6 2,2'-(1-benzyl-2-phenylethylidene)bis[(4S)-4-tert-butyl-4,5-dihydro-2-oxazole] 
• 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).