6-tert-butyl-2-(3-tert-butyl-2-hydroxy-5,6-dimethylphenyl)-3,4-dimethylphenol

• ChemBase ID: 140590
• Molecular Formular: C24H34O2
• Molecular Mass: 354.52556
• Monoisotopic Mass: 354.25588033
• SMILES: Cc1cc(c(c(c1C)c1c(c(cc(c1O)C(C)(C)C)C)C)O)C(C)(C)C
• Canonical SMILES: Cc1cc(c(c(c1C)c1c(C)c(C)cc(c1O)C(C)(C)C)O)C(C)(C)C
• InChI: InChI=1S/C24H34O2/c1-13-11-17(23(5,6)7)21(25)19(15(13)3)20-16(4)14(2)12-18(22(20)26)24(8,9)10/h11-12,25-26H,1-10H3
• InChIKey: NMVVBVMYPLMIOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-tert-butyl-2-(3-tert-butyl-2-hydroxy-5,6-dimethylphenyl)-3,4-dimethylphenol
• IUPAC Traditional name: 6-tert-butyl-2-(3-tert-butyl-2-hydroxy-5,6-dimethylphenyl)-3,4-dimethylphenol
• Synonyms: BIPHEN-H2; (+/-)-3,3'-Di-tert-butyl-2,2'-dihydroxy-5,5',6,6'-tetramethylbiphenyl; (±)-3,3'-Di-tert-butyl-5,5',6,6'-tetramethylbiphenyl-2,2'-diol; (S)-BIPHEN-H2; (S)-3,3'-Di-tert-butyl-2,2'-dihydroxy-5,5',6,6'-tetramethylbiphenyl; (S)-(-)-3,3'-Di-tert-butyl-5,5',6,6'-tetramethylbiphenyl-2,2'-diol; 5,5′,6,6′-Tetramethyl-3,3′-di-tert-butyl-1,1′-biphenyl-2,2′-diol; (S)-(-)-5,5′,6,6′-Tetramethyl-3,3′-di-tert-butyl-1,1′-biphenyl-2,2′-diol; (+/-)-3,3'-二-叔丁-5,5',6,6'-四甲基二联苯-2,2'-二醇; (S)-(-)-3,3'-二-叔丁-5,5',6,6'-四甲基联苯-2,2'-二醇; 5,5′,6,6′-四甲基-3,3′-二叔丁基-1,1′-联苯-2,2′-二醇; (S)-(-)-5,5′,6,6′-四甲基-3,3′-二叔丁基-1,1′-联苯-2,2′-二醇

Database IDs

• CAS Number: 101203-31-0; 205927-03-3
• MDL Number: MFCD01862439
• PubChem SID: 162234833; 24885270; 24880926
• PubChem CID: 3255344

CALCULATED PROPERTIES

• Acid pKa: 10.280254
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 8.157131
• LogD (pH = 7.4): 8.15657
• Log P: 8.157139
• Molar Refractivity: 112.6526 cm^3
• Polarizability: 44.211834 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 164-169 °C; 164-169°C; 170-174 °C; 171-173°C
• Optical Rotation: [α]20/D -83±3°, c = 0.4 in THF; -84 (c=0.35 in THF)

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 99%
• Empirical Formula (Hill Notation): C24H34O2

DETAILS

Sigma Aldrich - 578428

Packaging
100, 500 mg in glass bottle

Sigma Aldrich - 675229

Packaging
10 g in glass bottle
Application

• Cocatalyst in titanium-catalyzed intermolecular hydroamination1Reactant in preparation of:
• Sulfonate phenol ligands via sulfonylation2
• Catalysts for asymmetric olefin hydroamination/cyclization reactions3
• Single site catalyst precursors for catalysis of ring-opening reactions4
• Biphen-Mo complex used for catalysis of enantioselective ring-closing metathesis5