1-tert-butyl-4-(4-tert-butylphenyl)benzene

• ChemBase ID: 150131
• Molecular Formular: C20H26
• Molecular Mass: 266.42044
• Monoisotopic Mass: 266.20345083
• SMILES: CC(C)(C)c1ccc(cc1)c1ccc(cc1)C(C)(C)C
• Canonical SMILES: CC(c1ccc(cc1)c1ccc(cc1)C(C)(C)C)(C)C
• InChI: InChI=1S/C20H26/c1-19(2,3)17-11-7-15(8-12-17)16-9-13-18(14-10-16)20(4,5)6/h7-14H,1-6H3
• InChIKey: CDKCEZNPAYWORX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-tert-butyl-4-(4-tert-butylphenyl)benzene
• IUPAC Traditional name: 1-tert-butyl-4-(4-tert-butylphenyl)benzene
• Synonyms: 4,4′-Di-tert-butylbiphenyl; 4,4'-Di-tert-butylbiphenyl; 4,4′-二叔丁基联苯; 4,4'-双叔丁基联苯

Database IDs

• CAS Number: 1625-91-8
• EC Number: 216-615-4
• MDL Number: MFCD00008834
• Beilstein Number: 2095855
• PubChem SID: 162244293; 24851615
• PubChem CID: 74195

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.7105837
• LogD (pH = 7.4): 6.7105837
• Log P: 6.7105837
• Molar Refractivity: 88.526 cm^3
• Polarizability: 36.104164 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: dioxane: soluble0.1 g/mL, clear
• Melting Point: 126-129°C; 126-130 °C; 126-130 °C(lit.)
• Boiling Point: 190-192 °C/13 mmHg(lit.); 190-192°C/13mm

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: ≥98.0% (GC); 99%
• Grade: purum
• Linear Formula: (CH3)3CC6H4C6H4C(CH3)3

DETAILS

Sigma Aldrich - 193801

Packaging
5, 25 g in glass bottle
Application
For the preparation of lithium di-tert-butylbiphenylide, a radical anion, superior to sodium or lithium naphthalenides for metalation reactions.1

Sigma Aldrich - 34626

Other Notes
Generation of the soluble radical anion LDBB used for the preparation of alkyl-lithiums from halides, DBB can be used catalytically1; Preparation of alkyl-lithiums from alkyl phenyl sulfides2,3,4; Reduction of epoxides to lithium β-lithio alkoxides, synthetic intermediates5

REFERENCES

• Accepts electrons from Li metal to give a radical anion which is highly effective in the conversion of alkyl halides to alkyllithiums: Tetrahedron Lett., 1849 (1976); J. Org. Chem., 45, 1924 (1980). For use in the reductive lithiation of epoxides, see: J. Org. Chem., 55, 1528 (1990); Org. Synth. Coll., 9, 306 (1998).
• For use in the generation of 1,2-di(lithiomethyl)benzene, see Phthalan, A10217.