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Sigma-Aldrich

4-Bromo-2,6-di-tert-butylphenol

98%

Synonym(s):

2,6-Di-tert-butyl-4-bromophenol, 4-Bromo-2,6-bis(1,1-dimethylethyl)phenol, 4-Hydroxy-3,5-di(tert-butyl)bromobenzene

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About This Item

Linear Formula:
BrC6H2[C(CH3)3]2OH
CAS Number:
1139-52-2
Molecular Weight:
285.22
Beilstein/REAXYS Number:
2051052
EC Number:
214-521-8
MDL number:
MFCD00051598
UNSPSC Code:
12352100
PubChem Substance ID:
24864590
NACRES:
NA.22

assay

98%

form

solid

mp

78-83 °C (dec.) (lit.)

SMILES string

CC(C)(C)c1cc(Br)cc(c1O)C(C)(C)C

InChI

1S/C14H21BrO/c1-13(2,3)10-7-9(15)8-11(12(10)16)14(4,5)6/h7-8,16H,1-6H3

InChI key

SSQQUEKFNSJLKX-UHFFFAOYSA-N

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General description

4-Bromo-2,6-di-tert-butylphenol is a 4-substituted-2,6-di-tert-butylphenol. It is synthesized by the bromination of 2,6-di-tert-butylphenol. The structure was confirmed by 1H NMR. Its photolysis reaction in benzene solution has been investigated. The photochemical reaction of 4-bromo-2,6-di-tert-butylphenol single crystals doped with 2,6-di-tert-butyl-p-quinone has been studied by EPR spectroscopy.

Application

4-Bromo-2,6-di-tert-butylphenol may be used in the following studies:
  • As a terminating comonomer phenol in the phase transfer catalyzed (PTC) polymerization of 4-bromo-2,6-dimethylphenol.
  • Synthesis of 1,1-[1,10-decanediylbis(oxy)]bis[(2,6-ditertbutyl-4-bromo)benzene], a monomer, which forms poly(p-phenylenevinylene) derivatives by reaction with 1,10-dibromodecane.
  • As a reactant in the synthesis of 2,6-di-tert-butyl-phenolnorbornene (NArOH), a norbornene comonomer bearing an antioxidant hindered phenol.
  • As a catalyst with methyl aluminium to form methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR) which may be utilized for the transformation of various epoxides to carbonyl compounds.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Effect of donor and acceptor on the mechanism of a photochemical reaction in doped single crystals for radical pairs in 4-bromo-2, 6-di-tert-butylphenol single crystal doped with 2, 6-di-tert-butyl-p-quinone.
Tipikin DS, et al.
Kinetics and Catalysis, 42(2), 246-250 (2001)
An efficient, catalytic procedure for epoxide rearrangement.
Maruoka K, et al.
Tetrahedron Letters, 30(41), 5607-5610 (1989)
Blue light-emitting poly (p-phenylenevinylene) derivatives containing alternating conjugated segments and aliphatic spacers.
Mpallas JG, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 41(8), 1091-1098 (2003)
Phase transfer catalyzed polymerization of 4-bromo-2, 6-dimethylphenol in the presence of a terminating comonomer phenol: 2, 4, 6-tri-tert-butylphenol or 4-bromo-2, 6-di-tert-butylphenol.
Wang JH and Percec V.
Polym. Bull., 25(1), 33-40 (1991)
Photolysis of 4-bromo-2, 6-di-tert-butylphenol in benzene solution.
Lappin GR and Zannucci JS.
Tetrahedron Letters, 10(58), 5085-5087 (1969)
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