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

• ChemBase ID: 82116
• Molecular Formular: C19H18N2O2
• Molecular Mass: 306.35842
• Monoisotopic Mass: 306.13682783
• SMILES: N1=C(CC2=N[C@@H](c3ccccc3)CO2)OC[C@@H]1c1ccccc1
• Canonical SMILES: C1OC(=N[C@H]1c1ccccc1)CC1=N[C@H](CO1)c1ccccc1
• InChI: InChI=1S/C19H18N2O2/c1-3-7-14(8-4-1)16-12-22-18(20-16)11-19-21-17(13-23-19)15-9-5-2-6-10-15/h1-10,16-17H,11-13H2/t16-,17-/m1/s1
• InChIKey: IUFHJPXOLHSJTC-IAGOWNOFSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 132098-59-0
• MDL Number: MFCD00192295; MFCD00978440
• Beilstein Number: 4202633
• PubChem SID: 24866074; 162069235
• PubChem CID: 736684

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.5921574
• LogD (pH = 7.4): 3.592637
• Log P: 3.5926433
• Molar Refractivity: 87.599 cm^3
• Polarizability: 34.18814 Å^3
• Polar Surface Area: 43.18 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 131-134 °C/0.01 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Density: 1.28 g/mL at 20 °C(lit.); 1.28 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.586(lit.); n20/D 1.587
• Optical Rotation: [α]20/D ~-90°, c = 1 in ethanol

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: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0% (sum of enantiomers, GC); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C19H18N2O2

DETAILS

Sigma Aldrich - 416428

Packaging
1 g in glass bottle
250 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 - 66705

Other Notes
Preparation of a cyanobisoxazoline; simultaneous use of this ligand and the starting material for cyanohydrin formation from aldehydes1