(4S)-4-tert-butyl-2-{[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]methyl}-4,5-dihydro-1,3-oxazole

• ChemBase ID: 146289
• Molecular Formular: C15H26N2O2
• Molecular Mass: 266.37914
• Monoisotopic Mass: 266.19942808
• SMILES: CC(C)(C)[C@H]1COC(=N1)CC1=N[C@H](CO1)C(C)(C)C
• Canonical SMILES: CC([C@H]1COC(=N1)CC1=N[C@H](CO1)C(C)(C)C)(C)C
• InChI: InChI=1S/C15H26N2O2/c1-14(2,3)10-8-18-12(16-10)7-13-17-11(9-19-13)15(4,5)6/h10-11H,7-9H2,1-6H3/t10-,11-/m1/s1
• InChIKey: WCCCBUXURHZPQL-GHMZBOCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-tert-butyl-2-{[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]methyl}-4,5-dihydro-1,3-oxazole
• IUPAC Traditional name: (4S)-4-tert-butyl-2-{[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]methyl}-4,5-dihydro-1,3-oxazole
• Synonyms: (S,S)-2,2′-Methylenebis(4-tert-butyl-2-oxazoline); (S,S)-2,2′-Methylenebis(4-tert-butyl-2-oxazoline); 2,2′-Methylenebis[(4S)-4-tert-butyl-2-oxazoline]; (S,S)-2,2′-亚甲基双(4-叔丁基-2-噁唑啉); (S,S)-2,2′-亚甲基双(4-叔丁基-2-噁唑啉); 2,2′-亚甲基双[(4S)-4-叔丁基-2-噁唑啉]

Database IDs

• CAS Number: 132098-54-5
• MDL Number: MFCD00192290
• Beilstein Number: 4190673
• PubChem SID: 162240487; 24865343
• PubChem CID: 688205

CALCULATED PROPERTIES

• Acid pKa: 19.575476
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.3815138
• LogD (pH = 7.4): 3.388219
• Log P: 3.388305
• Molar Refractivity: 74.6584 cm^3
• Polarizability: 29.738052 Å^3
• Polar Surface Area: 43.18 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 50-53 °C; 50-53 °C(lit.); 51-53 °C(lit.)
• Optical Rotation: [α]20/D -114±3°, c = 0.5% in chloroform stab. with amylenes; [α]20/D -118°, c = 0.5 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (sum of enantiomers, GC); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C15H26N2O2

DETAILS

Sigma Aldrich - 405965

Packaging
500 mg in glass bottle
Application
C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.1,2,3

Sigma Aldrich - 66680

Other Notes
Catalyst for the enantioselective cyclopropanation of olefins with diazoesters1,2