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 
• 95-47-6 o-xylene 
• 526-73-8 1,2,3-trimethylbenzene 
• 38440-90-3 1,2-Dimethyl-7-oxa-bicyclo[4.1.0]hepta-2,4-diene 
• 90963-43-2 1-(2,3-dimethylphenoxy)silatrane 
• 102741-58-2 Benzoylamino-acetic acid 2,3-dimethyl-phenyl ester 
• 71913-02-5 3,4-Dimethylbicyclo<3.1.0>hex-3-en-2-on 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 7664-93-9 sulfuric acid 
• 70766-54-0 6-Hydroxy-1.2-dimethyl-3.5-di-tert.-butyl-benzol 
• 583-71-1 4-bromo-o-xylene 
• 576-23-8 2,3-dimethylbromobenzene 
• 67-56-1 methanol 

Downstream Products

• 5554-27-8 1-(benzoyloxy)-2,3-dimethylbenzene 
• 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 
• 46170-85-8 2,3-dimethyl-6-tert-butyl phenol 
• 68189-19-5 6-Hydroxy-1.2-dimethyl-3-tert.-butyl-benzol 
• 55719-55-6 2,3-dimethyl-6-(1,1,3,3-tetramethylbutyl)phenol 
• 25347-58-4 4,4'-Dihydroxy-2,2',3,3'-tetramethyl-stilben 
• 76893-54-4 2-[(2,3-dimethylphenyl)oxy]-5-nitropyridine 
• 102741-58-2 Benzoylamino-acetic acid 2,3-dimethyl-phenyl ester 
• 2196-36-3 (5E,11E)-6,12-Bis-(2,3-dimethyl-phenoxy)-dibenzo[b,f][1,5]diazocine 
• 149367-73-7 2,3-dimethylphenyl hexyl ether 
• 71321-28-3 2-Hydroxy-2-(2-hydroxy-3,4-dimethyl-phenyl)-indan-1,3-dione 
• 80767-62-0 dimethyl-2,3 (p-methene-3 yl-2)-6 phenol 

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.

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.

REARRANGEMENT OF DIMETHYLPHENYLACYLATES USING ZEOLITES

The present invention relates to a Fries rearrangement of specific dimethylphenylacylates to form the desired respective hydroxyaryl ketones having two methyl groups bound to the aromatic ring. It has been found that the process is surprisingly very specific in view of the number and position of the methyl group(s) bound to the aromatic ring.

Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment

Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.