2785-75-3

Basic information

• Product Name: 3,5-Dimethylpyrocatechol
• Synonyms: 3,5-Dimethyl-1,2-benzenediol;3,5-Dimethylpyrocatechol
• CAS NO: 2785-75-3
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.1638
• Mol File: 2785-75-3.mol

Chemical Properties

• Melting Point: 64-66 °C
• Boiling Point: 258.2°Cat760mmHg
• Flash Point: 124.5°C
• Appearance: /
• Density: 1.162g/cm³
• Vapor Pressure: 0.00861mmHg at 25°C
• Refractive Index: 1.582
• PKA: 10.02±0.15(Predicted)
• CAS DataBase Reference: 3,5-Dimethylpyrocatechol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethylpyrocatechol(2785-75-3)
• EPA Substance Registry System: 3,5-Dimethylpyrocatechol(2785-75-3)

Safety Data

• Hazardous Substances Data: 2785-75-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 4873, 1983 DOI: 10.1021/jo00173a018

InChI:InChI=1/C8H10O2/c1-5-3-6(2)8(10)7(9)4-5/h3-4,9-10H,1-2H3

Upstream product

• 2785-85-5 2-methoxy-3,5-dimethylphenol 
• 7277-36-3 6-acetoxy-4,6-dimethyl-cyclohexa-2,4-dienone 
• 105-67-9 2,4-Xylenol 
• 1666-02-0 2-hydroxy-4,6-dimethylbenzaldehyde 
• 108-68-9 3,5-Dimethylphenol 
• 1446354-11-5 7-methyl-3,4-dihydro-2H-benzo[b]1,4-dioxepine 
• 35490-72-3 2-methoxy-3,5-dimethylaniline 
• 69051-75-8 4,6-dimethyl-2-nitroanisole 
• 14452-34-7 2,4-dimethyl-6-nitrophenol 
• 854037-93-7 2-(3,5-dimethyl-phenoxy)-5-nitro-benzophenone 
• 91061-56-2 2-Acetoxy-3,5-dimethyl-phenol 
• 15191-36-3 2-bromo-4,6-dimethylphenol 
• 2931-90-0 5-formylvanillin 
• 875845-99-1 2-(2-hydroxy-3,5-dimethyl-phenoxy)-5-nitro-benzophenone 

Downstream Products

• 4370-49-4 3,5-dimethyl-3,5-cyclohexadiene-1,2-dione 
• 859739-61-0 4-iodo-1,2-dimethoxy-3,5-dimethyl-benzene 
• 13312-36-2 1,2-dimethoxy-3,5-dimethyl-4-nitro-benzene 
• 87568-17-0 4-chloro-3,5-dimethyl-1,2-benzenediol 
• 87567-88-2 4-chloro-3,5-dimethyl-3,5-cyclohexadiene-1,2-dione 
• 1048383-07-8 4,6-dimethyl-2-[2-(phenylazo)phenyl]-1,3,2-benzodioxaborole 
• 91061-56-2 2-Acetoxy-3,5-dimethyl-phenol 
• 256428-74-7 3,5,4',6'-tetramethyl-2,2'-methanediyl-di-phenol 
• 30718-65-1 1,2-dimethoxy-3,5-dimethylbenzene 
• 49582-95-8 1,2-diacetoxy-3,5-dimethyl-benzene 

Relevant articles and documents

Catalytic Regioselective C-H Acetoxylation of Arenes Using 4,6-Dimethoxy-1,3,5-triazin-2-yloxy as a Removable/Modifiable Directing Group

One of the major current challenges in the field of C-H functionalization is the development of new removable/modifiable directing groups (DGs). We report here the 4,6-dimethoxy-1,3,5-triazin-2-yloxy group as a new readily removable/modifiable DG for the regioselective acetoxylation of 2-(aryloxy)-4,6-dimethoxy-1,3,5-triazine. This developed phenol-derived DG can be easily removed to offer synthetically versatile pyrocatechols or converted into a useful biphenyl skeleton. In addition, the acetoxylation of 2-(aryloxy)-4,6-dimethoxy-1,3,5-triazine offers a new avenue to synthesize polysubstituted s-triazine derivatives.

Inhibition of Urease, a Ni-Enzyme: The Reactivity of a Key Thiol With Mono- and Di-Substituted Catechols Elucidated by Kinetic, Structural, and Theoretical Studies

The inhibition of urease from Sporosarcina pasteurii (SPU) and Canavalia ensiformis (jack bean, JBU) by a class of six aromatic poly-hydroxylated molecules, namely mono- and dimethyl-substituted catechols, was investigated on the basis of the inhibitory efficiency of the catechol scaffold. The aim was to probe the key step of a mechanism proposed for the inhibition of SPU by catechol, namely the sulfanyl radical attack on the aromatic ring, as well as to obtain critical information on the effect of substituents of the catechol aromatic ring on the inhibition efficacy of its derivatives. The crystal structures of all six SPU-inhibitors complexes, determined at high resolution, as well as kinetic data obtained on JBU and theoretical studies of the reaction mechanism using quantum mechanical calculations, revealed the occurrence of an irreversible inactivation of urease by means of a radical-based autocatalytic multistep mechanism, and indicate that, among all tested catechols, the mono-substituted 3-methyl-catechol is the most efficient inhibitor for urease.

Catalytic activity of Fe-porphyrins grafted on multiwalled carbon nanotubes in the heterogeneous oxidation of sulfides and degradation of phenols in water

A biomimetic heterogeneous catalyst was prepared by immobilization of meso-tetrakis(4-carboxyphenyl)porphyrinatoiron(III) chloride (Fe(TCPP)Cl) on multiwalled carbon nanotubes (MWCNTs). The anchored catalyst was characterized by transmission electron microscopy, powder X-ray diffraction, ultraviolet–visible, and Fourier transform infrared spectroscopy. The amount of Fe-porphyrin loaded on the nanotubes was estimated by atomic absorption spectroscopy The thermogravimetric analysis demonstrated that the catalyst was thermally stable up to almost 350 °C, exhibiting high thermal stability. Oxidation of sulfides and phenols with urea hydrogen peroxide (UHP) in water was efficiently enhanced with excellent selectivity under the influence of [Fe(TCPP)Cl@MWCNT]. The title heterogeneous catalytic system facilitates a greener reaction because the reaction solvent is water and UHP is used as a safe oxidant.

Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides

A common approach to the synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations facilitate the dioxygenation of alkenylboronic acids for the synthesis of α-oxygenated ketones and the dioxygenation of arylboronic acids for the synthesis of catechols. The rearrangements of N-enoxyisoindolinones have also been shown to be diastereoselective.

A Catalyst-Controlled Aerobic Coupling of ortho-Quinones and Phenols Applied to the Synthesis of Aryl Ethers

ortho-Quinones are underutilized six-carbon-atom building blocks. We herein describe an approach for controlling their reactivity with copper that gives rise to a catalytic aerobic cross-coupling with phenols. The resulting aryl ethers are generated in high yield across a broad substrate scope under mild conditions. This method represents a unique example where the covalent modification of an ortho-quinone is catalyzed by a transition metal, creating new opportunities for their utilization in synthesis.

Catalytic ozonation with γ-Al2O3 to enhance the degradation of refractory organics in water

Nowadays, heterogeneous catalytic ozonation appears as a promising way to treat industrial wastewaters containing refractory pollutants, which resist to biological treatments. Several oxides and minerals have been used and their behavior is subject to controversy with particularly the role of Lewis acid sites and/or basic sites and the effect of salts. In this study, millimetric mesoporous γ-Al2O3 particles suitable for industrial processes were used for enhancing the ozonation efficiency of petrochemical effluents without pH adjustment. A phenol (2,4-dimethylphenol (2,4-DMP)) was first chosen as petrochemical refractory molecule to evaluate the influence of alumina in ozonation. Single ozonation and ozonation in presence of γ-Al2O3 led to the disappearance of 2,4-DMP in 25 min and a decrease in pH from 4.5 to 2.5. No adsorption of 2,4-DMP occurred on γ-Al2O3. Adding γ-Al2O3 in the process resulted in an increase of the 2,4-DMP oxidation level. Indeed, the total organic carbon (TOC) removal was 14% for a single ozonation and 46% for ozonation with γ-Al2O3. Similarly, chemical oxygen demand (COD) removal increases from 35 to 75%, respectively. Various oxidized by-products were produced during the degradation of 2,4-DMP, but after 5 h ozonation 90% of organic by-products were acetic acid > formic acid ?

An efficient strategy for protecting dihydroxyl groups of catechols

A novel strategy for protecting dihydroxyl groups of catechols has been developed. Base-mediated cyclizations of catechols with 1,3-dibromopropane provided the corresponding benzo[b]1,4-dioxepans, and herefrom the protecting group was easily cleaved by aluminum chloride. The preparation of the antibacterial and antifungal agent 4-(2-aminothiazol-4-yl)benzene-1,2-diol from catechol reliably verified its availability amenable to various harsh reaction conditions. Georg Thieme Verlag Stuttgart - New York.

Efficient ortho-oxidation of phenols with diacyl peroxides

A stable symmetric diacyl peroxide, m-chlorobenzoyl peroxide (mCBPO), and an asymmetric diacyl peroxide, chloroacetyl m-chlorobenzoyl peroxide (CAMCBPO), were synthesized from m-chloroperbenzoic acid. Both peroxides oxidized phenols selectively at the ortho position predoninantly. CAMCBPO gave para-oxidized compounds as minor products from some phenols. The improvement of the yield of ortho-oxidation of phenols with mCBPO was also reported.

Quassinoid Synthesis via o-Quinone Diels-Alder Reactions

The reaction of 3,5-disubstituted o-quinones (2a, 2c) and 4-chloro-3,5-disubstituted o-quinones (2b, 2d) with simple dienes was investigated as a potential route to the quassinoid skeleton.Quinones 2a and 2c reacted in high yield at the 3,4-position with only a small excess of diene.Attempted equilibration of cis-fused cycloadducts to the trans-fused system failed due to the intervention of a stable enol form, as in 20.Compound 2c with ethyl 3,5-hexadienoate gave 15a, which upon reduction and lactonization provided BCD-ring tricyclic quassinoid analogues 18a and 19a.Again isomerization to the BC trans-fused system was not possible.The chloroquinones showed some preference for Diels-Alder reaction at the 5,6-position, but the additions were characterized generelly by low yields, side reactions, and lessened stereoselectivity.

Process for preparing dihydric phenol derivatives

A process for preparing dihydric phenol derivatives by oxidizing monohydric phenol derivatives with hydrogen peroxide in the presence of a ketone. This reaction can be promoted in the presence of sulfuric acid or a salt thereof or a sulfonic acid or a salt thereof.