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34750

Sigma-Aldrich

2,6-Di-tert-butyl-4-methylphenol

purum, ≥99.0% (GC)

Synonym(s):

2,6-Di-tert-butyl-p-cresol, BHT, Butylated hydroxytoluene, Butylhydroxytoluene, DBPC

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About This Item

Linear Formula:
[(CH3)3C]2C6H2(CH3)OH
CAS Number:
128-37-0
Molecular Weight:
220.35
Beilstein:
1911640
EC Number:
204-881-4
MDL number:
MFCD00011644
UNSPSC Code:
12352100
PubChem Substance ID:
329755054
NACRES:
NA.22

vapor density

7.6 (vs air)

Quality Level

200

vapor pressure

<0.01 mmHg ( 20 °C)

grade

purum

Assay

≥99.0% (GC)

autoignition temp.

878 °F

bp

265 °C (lit.)

mp

68-72 °C
69-73 °C (lit.)

solubility

methanol: 0.1 g/mL, clear, colorless
methanol: soluble 100 mg/mL, clear, colorless

SMILES string

Cc1cc(c(O)c(c1)C(C)(C)C)C(C)(C)C

InChI

1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

InChI key

NLZUEZXRPGMBCV-UHFFFAOYSA-N

Gene Information

human ... CAPN1(823)
rat ... Capn1(29153) , Nos1(24598)

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General description

2,6-Di-tert-butyl-4-methylphenol is an 4-alkylphenol. It is an antioxidant and exhibit toxicities mediated by oxidative metabolism to electrophilic quinone methides. It acts as Michael acceptor and its reaction with simple nucleophiles and proteins have been reported. Reaction of 2,6-di-tert-butyl-4-methylphenol with ytterbium(II)-benzophenone dianion complex has been reported. 2,6-Di-tert-butyl-4-methylphenol, a food additive, promotes acute pulmonary toxicity and tumor growth in mice.

Application

2,6-Di-tert-butyl-4-methylphenol may be used in the preparation of an organoaluminum compound, methylaluminum bis(2,6-di-tert-butyl-4-alkylphenoxide).

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

260.6 °F - open cup

Flash Point(C)

127 °C - open cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0958
STBL3629
STBL0486
STBK9236
STBK9235

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Novel crystal structure of ytterbium (II)-benzophenone dianion complex and its reaction with 2, 6-di-tert-butyl-4-methylphenol.
Hou Z, et al.
Journal of the Chemical Society. Chemical Communications, 9, 722-724 (1999)
Methylaluminum bis (2, 6-di-tert-butyl-4-alkylphenoxide). A new reagent for obtaining unusual equatorial and anti-Cram selectivity in carbonyl alkylation.
Maruoka K, et al.
Journal of the American Chemical Society, 107(15), 4573-4576 (1985)
Rene Kupfer et al.
Chemical research in toxicology, 15(8), 1106-1112 (2002-08-20)
Acute pulmonary toxicity and tumor promotion by the food additive 2,6-di-tert-butyl-4-methylphenol (BHT) in mice are well documented. These effects have been attributed to either of two quinone methides, 2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dienone (BHT-QM) formed through direct oxidation of BHT by pulmonary cytochrome P450
M A Lewis et al.
Chemical research in toxicology, 9(8), 1368-1374 (1996-12-01)
4-Alkylphenols, such as the antioxidant 2, 6-di-tert-butyl-4-methylphenol (BHT), exhibit toxicities that appear to be mediated by their oxidative metabolism to electrophilic quinone methides. Reactions of these Michael acceptors with simple nucleophiles and proteins have been reported, but little information is
Xiao-Juan Duan et al.
Journal of natural products, 70(7), 1210-1213 (2007-07-03)
Four new highly brominated and fully substituted mono- and bis-phenols, 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)pyrrolidin-2-one (1), 1,2-bis(2,3,6-tribromo-4,5-dihydroxyphenyl)ethane (2), 6-(2,3,6-tribromo-4,5-dihydroxybenzyl)-2,5-dibromo-3,4-dihydroxybenzyl methyl ether (3), and 2,3,6-tribromo-4,5-dihydroxybenzyl methyl sulfone (4), were characterized from the marine red alga Symphyocladia latiuscula. In addition, five known bromophenols, bis(2,3,6-tribromo-4,5-dihydroxyphenyl)methane (5), bis(2,3,6-tribromo-4,5-dihydroxybenzyl)
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