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Sigma-Aldrich

4,4′-Di-tert-butylbiphenyl

99%

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Synonym(s):
1-tert-Butyl-4-(4-tert-butylphenyl)benzene, 4,4′-Bis(1,1-dimethylethyl)-1,1′-biphenyl, 4,4′-Di-tert-butyl-1,1′-biphenyl, DBB, p,p′-Di-tert-butylbiphenyl
Linear Formula:
(CH3)3CC6H4C6H4C(CH3)3
CAS Number:
1625-91-8
Molecular Weight:
266.42
Beilstein:
2095855
EC Number:
216-615-4
MDL number:
MFCD00008834
PubChem Substance ID:
24851615
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid

bp

190-192 °C/13 mmHg (lit.)

mp

126-130 °C (lit.)

SMILES string

CC(C)(C)c1ccc(cc1)-c2ccc(cc2)C(C)(C)C

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

InChI key

CDKCEZNPAYWORX-UHFFFAOYSA-N

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General description

4,4′-Di-tert-butylbiphenyl along with lithium catalyzes:
  • reaction of chloromethyl ethyl ether and different carbonyl compounds to yield corresponding hydroxyethers
  • reductive opening of N-phenylazetidine

Application

4,4′-Di-tert-butylbiphenyl was used in production of homoallylic amine derivatives. It was also used in the preparation of lithium di-tert-butylbiphenylide, a radical anion, superior to sodium or lithium naphthalenides for metalation reactions.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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C E Neipp et al.
The Journal of organic chemistry, 66(2), 531-537 (2001-06-30)
Lithiation of the N-2,4,6-triisopropylbenzenesulfonyl-2-pyrroline (16) and treatment of the resulting cyclic vinyllithium reagent with R2CuCNLi2 produced an acyclic vinyl organometallic species that, when treated with an electrophile (H2O or RX), gave the homoallylic sulfonamides 18a-k in 37-93% yields and in
4, 4'-Di -tert -butylbiphenyl-catalysed reductive opening of azetidines with lithium: A direct preparation of 3, N-dilithioalkylamines.
Almena J, et al.
Tetrahedron, 50(19), 5775-5782 (1994)
The Journal of Organic Chemistry, 55, 1528-1528 (1990)
4, 4′-Di-tert-butylbiphenyl-catalysed lithiation of chloromethyl ethyl ether: A barbier-type new and easy alternative to ethyl lithiomethyl ether.
Guijarro A and Yus M.
Tetrahedron Letters, 34(21), 3487-3490 (1993)

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