19126-15-9

Basic information

• Product Name: 2,6-di-tert-Butylphenol
• Synonyms: Fluorene,9-methoxy- (6CI,8CI); 9-Methoxyfluorene
• CAS NO: 19126-15-9
• Molecular Formula: C₁₄H₁₂O
• Molecular Weight: 0
• EINECS: 204-884-0
• Mol File: 19126-15-9.mol

Chemical Properties

• Melting Point: 35-38℃
• Boiling Point: 251.4°C at 760 mmHg
• Flash Point: 118.3°C
• Appearance: /
• Vapor Pressure: 0.0129mmHg at 25°C
• Water Solubility: insoluble
• CAS DataBase Reference: 2,6-di-tert-Butylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-di-tert-Butylphenol(19126-15-9)
• EPA Substance Registry System: 2,6-di-tert-Butylphenol(19126-15-9)

Safety Data

• Hazard Codes: Xn:Harmful;;
• Statements: R22:; R51/53:
• Safety Statements: S29:; S61:
• Hazardous Substances Data: 19126-15-9(Hazardous Substances Data)

Usage

Class

Phenols, which are aromatic compounds containing a hydroxyl group attached to a benzene ring

Characterized by

Two tert-butyl groups attached to the phenol ring

Usage

Antioxidant and stabilizer in various industrial processes (e.g. production of polymers, plastics, rubber, adhesives, coatings, and sealants)

Potential

Anti-microbial and anti-fungal agent, role in inhibiting the production of inflammatory mediators

Precautions

Can be harmful if ingested or inhaled, can cause skin and eye irritation

InChI:InChI=1/C14H22O.K/c1-13(2,3)10-8-7-9-11(12(10)15)14(4,5)6;/h7-9,15H,1-6H3;/q;+1/p-1

Upstream product

• 67-56-1 methanol 
• 1689-64-1 9-Fluorenol 
• 832-80-4 9-diazofluorenone 
• 24225-40-9 9,9'‐dicyano‐9,9'-bifluorenyl 
• 1529-40-4 9H-fluorene-9-carbonitrile 
• 109-72-8 n-butyllithium 
• 132869-79-5 benzhydryl 9-fluorenyl ether 
• 74-88-4 methyl iodide 

Downstream Products

• 1460-02-2 1,3,5-Tri-tert-butylbenzene 
• 50616-99-4 9,9'-dimethoxy-9,9'-bifluorene 
• 106470-71-7 3,5-di-tert-butyl-1-isobutylbenzene 
• 86-73-7 9H-fluorene 
• 486-25-9 9-fluorenone 
• 1530-12-7 9,9'-bifluorenyl 
• 6311-22-4 9-methyl-9H-fluoren-9-ol 
• 275822-22-5 9-methoxy-9H-fluoren-9-yl hydroperoxide 
• 1603-73-2 fluoren-9-yl-phenyl ketone 
• 4535-09-5 N-phenyl-fluorenoneimine-N-oxide 
• 60930-70-3 C₁₉H₁₁Cl₂NO 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 599-94-0 1,2-bis(phenylsulfonyl)ethane 
• 592-13-2 2,5-dimethylhexane 

Relevant articles and documents

Photochemical generation of 9-Fluorenyl radicals

A series of 9H-fluorenols and 9H, 9′H-bifluorenyls were irradiated in less polar solvents giving photoproducts derived from their corresponding 9H-fluorenyl radicals. These transient species were directly observed by laser flash photolysis and their UV/visible spectra compared with those of their corresponding cations. Theoretical calculations (density functional theory [DFT]) of these intermediates indicate their destabilizing nature in similar fashion to the antiaromatic character of the corresponding cations.

Influence of Solvent and Cation on the Properties of Oxygen-containing Organic Anions. Part 4. Mechanism and Reactivity of Tetraaryloxirane Cleavage with Alkali Metals

Six tetraaryloxiranes 1a-f (Scheme 4) were reduced (Schemes 1-3) with alkali metals (M = Li, Na, K, Cs) in eight polar aprotic solvents under an inert atmosphere.The organometallic solutions thus obtained were hydrolysed and the reaction products analysed.Similar experiments were carried out where the same solutions were quenched with D2O or MeI.In some cases the same solutions were studied by NMR and ESR spectroscopy before quenching.A stepwise reduction mechanism was established where the transfer of a first electron produces CO-bond scission in the oxirane ring, yielding a short-lived radical anion 4 or 5 (Scheme 1), i. e., a tetraalkyl-β-oxidoethyl radical.This intermediate can either eliminate oxygen as metal oxide (MO) to produce a tetraarylethylene 24 (Scheme 2) or be further reduced to a dianion 8 or 9 (Scheme 1).This anion yields, upon hydrolysis, low yields,if any, of the corresponding tetraphenylethanol 15 or 16 (Z = H).The larger proportion of the dianion, after the first protonation step, yielding anion 11 or 22, undergoes CC-bond scission which leads eventually to the corresponding ketone and diarylmethane 19 + 20 or 21 + 23 (Z = H) (Scheme 2).Other possible pathways were excluded through experiments where other possible intermediates were generated.These led to different end products.A triparametric linear correlation as a function of solvent parameters ETN and DN, as well as the cationic radius, was established for the influence of the nature of the solvent and counter-ion on the ratio between the rates of formation of products stemming from metal oxide (MO) elimination by the ring-opened radical anion 4 or 5 (Schemes 1 and 2) and rates of formation of products stemming from further reduction of the same radical anion to the dianion 8 or 9, thus confirming the mechanism established.

Contrasting Photosolvolytic Reactivities of 9-Fluorenol vs 5-Suberenol Derivatives. Enhanced Rate of Formation of Cyclically Conjugated Four ? Carbocations in the Excited State

The photosolvolysis of 9-fluorenol (1) and several of its derivatives, as well as related systems, has been studied in aqueous methanol and acetonitrile solutions.The primary aim of this study was to examine the effect of the internal cyclic array (ICA) of these compounds in promoting photosolvolysis with respect to the number of ? electrons available in the ICA.It was observed that 9-fluorenol derivatives photosolvolyze much more efficiently than any of the related systems studied in this work.In contrast, ground-state 9-fluorenol derivatives are the least reactive systems with respect to solvolysis.Quantum yields for methyl ether formation for photosolvolysis in 50percent MeOH-H2O are reported for 1-3.Rate constants for solvent-assisted photodehydroxylation (ks) are calculated on the basis of the proposed mechanism of heterolytic C-OH bond rupture in the primary photochemical step and are in the range (1.3-1.6)x1E10 s-1 for 1-3.

Investigation of the 2,7-Dihalofluorenylidenes: Search for Heavy Atom Effects in the Reactions of Triplet Carbenes

The properties of the 2,7-dihalofluorenylidenes (Cl, Br, I) were examined by laser and EPR spectroscopy and by conventional chemical analyses.Their reactions with alcohols and olefins were studied.No evidence was found for the operation of a heavy atom effect in their reaction with methyl alcohol.Analysis of the kinetic and product results indicates an energy gap between the triplet (ground state) and the singlet for the three dihalofluorenylidenes of 4.2 +/- 0.5 kcal/mol, ca. twice the value of fluorenylidene itself.

On the Importance of Indiscriminate Insertion for Photoactivable Reagents - Photolysis of Diazofluorene in Mixed Organic Solvents

Photolysis of diazofluorene (I), a new fluorescent photoactivable reagent, in cyclohexane, cyclohexene, methanol and in mixtures of the solvents is reported.Quantitative analysis of products formed has been carried out.In bulk hydrophobic milieu diazofluorene does show some indiscriminateness in its insertion reactions.The importance of indiscriminate insertion in photoaffinity labeling studies has been dicussed.A simple method has thus been developed to test the indiscriminate properties of a photoactivable reagent by photolysing it first in simple organic solvents.Such studies should prove useful and photoactivable reagents can be tested before applying them directly to biological systems.

CHEMISTRY AND KINETICS OF ARYL CARBENES IN METHANOL AT LOW TEMPERATURES.

The chemistry and kinetics of six aryl carbenes in polycrystalline methanol are reported. The kinetics were monitored by triplet ESR spectroscopy. Isotope effects were used heavily to probe reaction mechanisms. Several analogues to solution chemistry and kinetics were found. It is concluded that the singlet-triplet energy separation decreases as DBS greater than DPC greater than DBT greater than NC greater than Fl greater than DMA.

Irradiation of Diazofluorene in Alcohols: Unusual Behaviour of Fluorenyl Ethers

Fluorenyl ethers formed in the reaction of singlet fluorenylidene with alcohols undergo photocleavage to give fluorene and fluorenone, which formally arise from triplet fluorenylidene.

Reactivity of Carbonyl Oxides. Characteristic Nucleophilic Oxygen Atom Transfer from R2COO beside Electrophilic and Radical Reactions

According to a MINDO/3 calculation, carbonyl oxide H2COO has a large contribution of zwitterionic structure 1a, which is not altered by phenyl substituent.The dye-sensitized photooxidation of diazomethanes in CH2Cl2 - MeOH afforded ca. 30percent yield of α-methoxy hydroperoxides as product from 1a and MeOH.Relative reactivities of various types of substrates toward the carbonyl oxide from diazofluorene and 1O2 have been determined.While benzene gave phenol in a low yield, substituted benzenes such as toluene or anisole yielded products by hydrogen atom abstraction on the side chain as a major reaction.Olefins gave a rather minor amount of epoxides; the predominant reaction was C-C cleavage or allylic hydrogen abstraction.The realtive reactivity with carbonyl oxide is in the order Ph2SO >> Ph2S > C = C > benzene, where C = C means α-methylstyrene.This order is in sharp contrast to the case of peroxy acid, Ph2S >> Ph2SO >> C = C, or to the order with acylperoxy radical, C = C >> Ph2S, Ph2SO.The above order with carbonyl oxide indicates a nucleophilic oxygen atom transfer as a characteristic reaction; this was clearly shown by the positive ρ value of +0.26 for substituted diphenyl sulfoxides.The reactivities of various substrates revealed that another characteristic reaction is hydrogen atom abstraction as a radical, and carbonyl oxides could be regarded as a rather poor electrophilic O-transfer agent.These features may be understood by representing carbonyl oxides as a resonance hybrid of R2C=O+-O- (1a) and R2C*-O-O* (1c).