526-75-0

Basic information

• Product Name: 2,3-Xylenol
• Synonyms: 2,3-Xylenol(8CI);1,2-Dimethyl-3-hydroxybenzene;1-Hydroxy-2,3-dimethylbenzene;2,3-DMP;NSC 62011;o-Xylenol;Dimethyl phenol
• CAS NO: 526-75-0
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.18
• EINECS: 208-395-3
• Mol File: 526-75-0.mol
• Article Data: 62

Chemical Properties

• Melting Point: 72-74℃
• Boiling Point: 216.9 °C at 760 mmHg
• Flash Point: 90.7 °C
• Appearance: brown crystalline solid
• Density: 1.014 g/cm³
• Vapor Pressure: 0.093mmHg at 25°C
• Refractive Index: 1.54
• PKA: 10.42±0.10(Predicted)
• Water Solubility: slightly soluble
• CAS DataBase Reference: 2,3-Xylenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Xylenol(526-75-0)
• EPA Substance Registry System: 2,3-Xylenol(526-75-0)

Safety Data

• Hazard Codes: T:Toxic;;
• Statements: R24/25:; R34:; R51/53:
• Safety Statements: S26:; S36/37/39:; S45:; S61:
• Hazardous Substances Data: 526-75-0(Hazardous Substances Data)

Usage

General Description

2,3-Xylenol is a chemical compound that belongs to the family of xylenols, which are aromatic organic compounds. It is also known as 2,3-dimethylphenol and is produced by the methylation of phenol. 2,3-Xylenol is commonly used as a precursor for the synthesis of various chemicals and pharmaceuticals. It is also used as an intermediate in the production of dyes, resins, and antioxidants. In addition, 2,3-Xylenol is used as a disinfectant and antiseptic in various industrial and healthcare settings. It is a colorless to pale yellow liquid with a characteristic phenolic odor, and it is soluble in organic solvents such as alcohol and ether. Due to its potential health hazards and environmental impact, proper handling and disposal of 2,3-Xylenol are essential to prevent harm to human health and the environment.

InChI:InChI: 1S/C8H10O/c1-6-4-3-5-8(9)7(6)2/h3-5,9H,1-2H3

Upstream product

• 1122-20-9 2,3-dimethylcyclohex-2-en-1-one 
• 105-67-9 2,4-Xylenol 
• 87-59-2 2,3-Dimethylaniline 
• 503-17-3 dimethylacetylene 
• 1470-91-3 but-3-enoyl chloride 
• 95-47-6 o-xylene 
• 526-73-8 1,2,3-trimethylbenzene 
• 103576-49-4 4,5-dimethyl-4-hexen-1-in-3-one 
• 77815-17-9 5,6-dimethyl-6-nitrocyclohexa-2,4-dienone 
• 75-11-6 diiodomethane 
• 108-39-4 3-methyl-phenol 
• 71913-02-5 3,4-Dimethylbicyclo<3.1.0>hex-3-en-2-on 
• 7446-70-0 aluminium trichloride 
• 100-84-5 1-methoxy-3-methyl-benzene 

Downstream Products

• 68097-86-9 2,3-dimethyl-6-piperidin-1-ylmethyl-phenol 
• 412019-02-4 succinic acid mono-(2,3-dimethyl-phenyl ester) 
• 115291-59-3 4-(4,4'-dihydroxy-2,3,2',3'-tetramethyl-benzhydrylidene)-2,3-dimethyl-cyclohexa-2,5-dienone 
• 526-86-3 2,3-dimethyl-1,4-benzoquinone 
• 7218-20-4 (RS)-6-Acetoxy-5,6-dimethyl-2,4-cyclohexadien-1-on 
• 91497-83-5 6,6-diacetoxy-2,3-dimethyl-cyclohexa-2,4-dienone 
• 55169-04-5 rac-3-(2,3-dimethylphenoxy)propane-1,2-diol 
• 1020846-48-3 1-(2,2-diethoxyethoxy)-2,3-dimethylbenzene 
• 55719-55-6 2,3-dimethyl-6-(1,1,3,3-tetramethylbutyl)phenol 
• 72569-14-3 1-(2-Hydroxy-3,4-dimethyl-phenyl)-2,2-dimethyl-propan-1-one 
• 63588-60-3 2,3-dimethylphenyl pivalate 
• 46170-85-8 2,3-dimethyl-6-tert-butyl phenol 
• 2944-49-2 2,3-dimethylanisole 
• 1526-92-7 2-(2,3-Dimethylphenoxy)-chinolin 

Relevant articles and documents

Active Site Dynamics of Xylene Hydroxylation by Cytochrome P-450 As Revealed by Kinetic Deuterium Isotope Effects

The cytochrome P-450 catalyzed hydroxylation of o- and p-xylene and five deuterated derivatives of each has been investigated using phenobarbital-induced rat liver microsomes.All possible monohydroxylation products were observed but benzylic hydroxylation predominated strongly (88-96percent).H/D discrimination was strongest when both isotopes were located on the same methyl gorup, less when they were located in different methyl groups on the same xylene molecule, and least when they were located in methyl groups on different molecules.Benzylic hydroxylation is subject to a large intrinsic (intramolecular) deuterium isotope effect (CH3/CD3=7.5-9.5), comprised of a large primary component (5.3-7.8) and a large normal α-secondary component (1.09-1.19).These isotope effects suggest a transition state for benzylic H-abstraction that is linear and symmetrical with substantial rehybridization toward planarity at the benzylic carbon and little residual C-H bond order remaining.In contrast aromatic hydroxylation of o- and p-xylene shows a small inverse α-secondary isotope effect (0.83-0.94).The D(V/K) isotope effect observed for benzylic hydroxylation in intermolecular competitions (ca. 1.9-2.3 for d0/d6 substrate mixtures) is substantially reduced by commitment to catalysis, with Cf=(kH+kr)k-1=3.6 for p-xylene and 5.9 for o-xylene.These results suggest a dynamic picture of catalysis with the following relative rates: methyl group rotation > substrate-orientation within the Michaelis complex (i.e. isotopically sensitive branching to different products) > product formation (i.e. commitment to catalysis) > substrate dissociation prior to hydroxylation.

Me3SI-promoted chemoselective deacetylation: a general and mild protocol

A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.

A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK

A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2andtBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.