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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:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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

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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