36436-65-4

Basic information

• Product Name: 2'-HYDROXY-4',5'-DIMETHYLACETOPHENONE
• Synonyms: 2'-Hydroxy-4',5'-dimethylacetophenone,98%;2-Acetyl-4,5-diMethylphenol;1-(2-hydroxy-4,5-dimethylphenyl)ethan-1-one;OTAVA-BB BB7018930016;4'5'-DIMETHYL-2'-HYDROXYACETOPHENONE;1-(2-HYDROXY-4,5-DIMETHYLPHENYL)ETHANONE;2'-HYDROXY-4',5'-DIMETHYLACETOPHENONE;2-HYDROXY-4,5-DIMETHYLACETOPHENONE
• CAS NO: 36436-65-4
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 253-035-0
• Product Categories: Aromatics;Intermediates;Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 36436-65-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 69-73 °C
• Boiling Point: 144°C/18mmHg(lit.)
• Flash Point: 114.6 °C
• Appearance: White to light yellow/Crystalline Powder
• Density: 1.0326 (rough estimate)
• Refractive Index: 1.5290 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 10.59±0.23(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2'-HYDROXY-4',5'-DIMETHYLACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-4',5'-DIMETHYLACETOPHENONE(36436-65-4)
• EPA Substance Registry System: 2'-HYDROXY-4',5'-DIMETHYLACETOPHENONE(36436-65-4)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26
• Hazardous Substances Data: 36436-65-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystalline powder

Uses

Different sources of media describe the Uses of 36436-65-4 differently. You can refer to the following data:
1. 2'-Hydroxy-4',5'-dimethylacetophenone is a hydroxyacetophenone derivative used in the preparation of herbicides as well as chalcone derivatives with antibacterial activity.
2. 2'-Hydroxy-4',5'-dimethylacetophenone is used in the preparation of chalcone derivatives with antibacterial activity.

Preparation

Preparation by Fries rearrangement of 3,4-dimethylphenyl acetate with aluminium chloride without solvent between 110° and 150°.

Upstream product

• 22618-23-1 3,4-dimethylphenyl acetate 
• 877-82-7 5-acetoxy-m-xylene 
• 95-65-8 3,4-Dimethylphenol 
• 108-24-7 acetic anhydride 
• 496-78-6 2,4,5-trimethylphenol 
• 4685-47-6 3,4-dimethylanisole 
• 75-36-5 acetyl chloride 
• 3637-01-2 3,4-dimethylacetophenone 
• 57803-24-4 1-acetyl-2-difluoroboryloxy-4,5-dimethylbenzene 
• 90925-62-5 6-Acetyl-3,4-dimethyl-cyclohex-2-en-1-on 
• 64-19-7 acetic acid 
• 91969-74-3 2'-methoxy-4',5'-dimethylacetophenone 
• 69305-42-6 2,4,5-trimethyl-1-acetoxybenzene 
• 78347-89-4 methyl thymol 

Downstream Products

• 90922-67-1 1-(2-hydroxy-4,5-dimethyl-3-nitro-phenyl)-ethanone 
• 80378-10-5 1-(4,5-Dimethyl-2-hydroxyphenyl)-3-(2-phenyl-4-thiazolyl)propenone 
• 77635-54-2 2-{1-[(2,4-Dichloro-phenyl)-hydrazono]-ethyl}-4,5-dimethyl-phenol 
• 77635-55-3 2-{1-[(3,5-Dichloro-phenyl)-hydrazono]-ethyl}-4,5-dimethyl-phenol 
• 77635-56-4 2-{1-[(2,6-Dichloro-phenyl)-hydrazono]-ethyl}-4,5-dimethyl-phenol 
• 96755-10-1 1-(2-hydroxy-4,5-dimethylphenyl)-3-(6-benzodioxan-1,4-yl)propenone 
• 134130-03-3 Acetic acid 4,5-dimethyl-2-((E)-3-p-tolyl-acryloyl)-phenyl ester 
• 134130-01-1 Acetic acid 2-[(E)-3-(4-chloro-phenyl)-acryloyl]-4,5-dimethyl-phenyl ester 
• 134130-00-0 Acetic acid 2-[(E)-3-(2-chloro-phenyl)-acryloyl]-4,5-dimethyl-phenyl ester 
• 134150-92-8 2,3-Dibromo-1-(2-hydroxy-4,5-dimethyl-phenyl)-3-p-tolyl-propan-1-one 
• 134130-04-4 Acetic acid 2-[(E)-3-(2-methoxy-phenyl)-acryloyl]-4,5-dimethyl-phenyl ester 
• 134129-95-6 2,3-Dibromo-3-(4-chloro-phenyl)-1-(2-hydroxy-4,5-dimethyl-phenyl)-propan-1-one 
• 134130-02-2 Acetic acid 2-[(E)-3-(2,4-dichloro-phenyl)-acryloyl]-4,5-dimethyl-phenyl ester 
• 134129-94-5 2,3-Dibromo-3-(2-chloro-phenyl)-1-(2-hydroxy-4,5-dimethyl-phenyl)-propan-1-one 

Relevant articles and documents

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.

Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates

Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.

Synthesis of natural product inulavosin via Ga(OTf)3-Catalyzed Hetero Diels–Alder Dimerization of salicyl alcohol derivative

Inulavosin, a natural melanogenesis inhibitor, has been synthesized smoothly from readily available and inexpensive starting materials by using a Ga(OTf)3-catalyzed room temperature hetero Diels–Alder dimerization of salicyl alcohol derivative and a regioselective phenol monobromination as the key steps.