492-88-6

Basic information

• Product Name: 3-ETHOXYSALICYLALDEHYDE
• Synonyms: Ethoxysalicylaldehyde;o-Ethylvanilline;ORTHO-ETHYLVANILLIN;3-Ethoxysalicylaldehyde 97%;3-ETHOXY-2-HYDROXYBENZALDEHYDE;3-ETHOXYSALICYLALDEHYDE;AKOS BBS-00003146;2-HYDROXY-3-ETHOXYBENZALDEHYDE
• CAS NO: 492-88-6
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 207-765-1
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Aldehydes;C9;Carbonyl Compounds
• Mol File: 492-88-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 66-68 °C(lit.)
• Boiling Point: 263-264 °C(lit.)
• Flash Point: 263-264°C
• Appearance: /
• Density: 1.1097 (rough estimate)
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.30±0.10(Predicted)
• Water Solubility: Soluble in cold water. Insoluble in methanol, ethanol, acetone and acetonitrile
• Sensitive: Air Sensitive
• CAS DataBase Reference: 3-ETHOXYSALICYLALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ETHOXYSALICYLALDEHYDE(492-88-6)
• EPA Substance Registry System: 3-ETHOXYSALICYLALDEHYDE(492-88-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CU6123000
• TSCA: Yes
• Hazardous Substances Data: 492-88-6(Hazardous Substances Data)

Usage

Uses

3-Ethoxysalicylaldehyde was used in the preparation of:Schiff base ligand via condensation with trans-1,2-diaminocyclohexanesubstituted salen-type Schiff base ligandsa new Schiff base, 2-ethoxy-6-[(3-methylaminopropylimino)methyl]phenol, via reaction with N-methylpropane-1,3-diamine

Safety Profile

A poison by intraperitoneal andintravenous routes. When heated to decomposition itemits acrid smoke and irritating vapors.

InChI:InChI=1/C9H10O3/c1-2-12-8-5-3-4-7(6-10)9(8)11/h3-6,11H,2H2,1H3

Upstream product

• 94-71-3 2-Ethoxyphenol 
• 1666-65-5 2-ethoxy-6-propenyl-phenol 
• 98-95-3 nitrobenzene 
• 1755-53-9 2-ethoxy-6-allyl-phenol 
• 1666-74-6 1-allyloxy-2-ethoxybenzene 
• 74-96-4 ethyl bromide 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 67-66-3 chloroform 
• 609-19-8 3,4,5-trichlorophenol 
• 15950-66-0 2,3,4-trichlorophenol 
• 548756-57-6 tert-butyl 3-(3-ethoxy-2-hydroxyphenyl)-3-hydroxy-2-methylenenpropanoate 
• 75792-34-6 3-ethoxy-2-methoxy-benzaldehyde 
• 50-00-0 formaldehyd 

Downstream Products

• 24454-82-8 2,3-diethoxy-benzaldehyde 
• 944069-87-8 N,N′-bis(3-ethoxysalicylidene)-1,2-ethanediamine 
• 74476-16-7 (E)-3-(3-Ethoxy-2-hydroxy-phenyl)-1-pyrazin-2-yl-propenone 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 20035-45-4 6-bromo-3-ethoxy-2-hydroxybenzaldehyde 
• 128720-07-0 (E)-2-Cyano-3-(3-ethoxy-2-hydroxy-phenyl)-acrylic acid methyl ester 
• 444566-29-4 6-ethoxy-2-iminiomethylphenoxide 
• 20035-44-3 5-bromo-3-ethoxy-2-hydroxybenzaldehyde 
• 150655-06-4 3-ethoxy-2-hydroxy-5-nitrobenzaldehyde 
• 548756-57-6 tert-butyl 3-(3-ethoxy-2-hydroxyphenyl)-3-hydroxy-2-methylenenpropanoate 

Relevant articles and documents

Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles

A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.

Design, syntheses, structure - Activity relationships and docking studies of coumarin derivatives as novel selective ligands for the CB2 receptor

The CB2 receptor has been considered as an inspiring drug target for the treatment of pain and immune-related diseases. In the current manuscript, a novel series of coumarin derivatives is reported to be designed and synthesized by combining the structural features of some known ligands for the cannabinoid receptors based on the CoMFA model of the lead compounds. The compounds were evaluated to be highly selective ligands for the CB2 receptor over the CB1 receptor by calcium mobilization assays. Furthermore, SAR results Therefore, molecular docking simulations were performed to calculate the receptor-ligand interactions of our synthesized compounds binding to the CB2 receptor. The understanding of the binding modes could be advantageous for further development of selective ligands for the CB2 receptor.

Does the DABCO-catalysed reaction of 2-hydroxybenzaldehydes with methyl acrylate follow a Baylis-Hillman pathway?

Evidence is presented which supports the intermediacy of dipolar Baylis-Hillman-type adducts in the synthesis of coumarin and chromene derivatives from the reaction of 2-hydroxybenzaldehydes with methyl acrylate in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO).