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193801

4,4′-Di-tert-butylbiphenyl

99%

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

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About This Item

Linear Formula:
(CH3)3CC6H4C6H4C(CH3)3
CAS Number:
1625-91-8
Molecular Weight:
266.42
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24851615
EC Number:
216-615-4
Beilstein/REAXYS Number:
2095855
MDL number:
MFCD00008834
Assay:
99%
Form:
solid
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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

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9672
BCBT1383
BCCL2037
BCBF9475V
BCBB1454V

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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)
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
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Global Trade Item Number

SKUGTIN
193801-5G04061833063477
193801-25G04061833063460