18278-34-7

Basic information

• Product Name: 4-Hydroxy-2-methoxybenzaldehyde
• Synonyms: TIMTEC-BB SBB008607;Benzaldehyde, 4-hydroxy-2-methoxy-;4-HYDROXY-2-METHOXYBENZALDEHYDE;4-FORMYL-3-METHOXY-PHENOL;4-HYDROXY-O-ANISALDEHYDE;4-HYDROXYL-2-METHOXYL BENZALDEHYDE;3-METHOXY-4-FORMYLPHENOL;2-METHOXY-4-HYDROXY BENZALDEHYDE
• CAS NO: 18278-34-7
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);pharmacetical;Benzaldehyde;API intermediates;aldehydes;Aromatics
• Mol File: 18278-34-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 158-161 °C
• Boiling Point: 234.6°C (rough estimate)
• Flash Point: 132.3 °C
• Appearance: Off-white to light brown/Powder
• Density: 1.2143 (rough estimate)
• Vapor Pressure: 0.000279mmHg at 25°C
• Refractive Index: 1.4447 (estimate)
• Storage Temp.: Store at 0°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.40±0.18(Predicted)
• Water Solubility: practically insoluble
• Sensitive: Air Sensitive
• BRN: 2045122
• CAS DataBase Reference: 4-Hydroxy-2-methoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-2-methoxybenzaldehyde(18278-34-7)
• EPA Substance Registry System: 4-Hydroxy-2-methoxybenzaldehyde(18278-34-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-6-36/37/39-27
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 18278-34-7(Hazardous Substances Data)

Usage

Chemical Properties

4-Hydroxy-2-methoxybenzaldehyde is off-white to greenish or light brown cryst. powder

Uses

Different sources of media describe the Uses of 18278-34-7 differently. You can refer to the following data:
1. A useful intermediate in the sythesis of solid phase supports for the preparation of fully protected peptide fragments.
2. 4-Hydroxy-2-methoxybenzaldehyde is a useful intermediate in the sythesis of solid phase supports for the preparation of fully protected peptide fragments

InChI:InChI=1/C8H8O3/c1-11-8-4-7(10)3-2-6(8)5-9/h2-5,10H,1H3

Upstream product

• 150-19-6 O-methylresorcine 
• 74-90-8 hydrogen cyanide 
• 67-66-3 chloroform 
• 1196-65-2 4-amino-2-methoxybenzaldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 71-43-2 benzene 
• 1233362-23-6 C₁₄H₁₁NO₇S 
• 4885-02-3 Dichloromethyl methyl ether 
• 114628-32-9 2-methoxy-4-(methoxylmethoxy)benzaldehyde 
• 95332-26-6 2-hydroxy-4-(methoxymethyloxy)benzaldehyde 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 73569-44-5 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde 

Downstream Products

• 67395-05-5 4-acetoxy-2-methoxy-benzaldehyde 
• 155912-31-5 4-hydroxy-2-methoxy-benzaldehyde-oxime 
• 860553-67-9 3,5-dibromo-4-hydroxy-2-methoxybenzaldehyde 
• 20511-02-8 4t-(4-hydroxy-2-methoxy-phenyl)-but-3-en-2-one 
• 58026-14-5 4-(benzyloxy)-2-methoxybenzaldehyde 
• 149428-72-8 2-methoxy-4-(2-phenylethoxy)benzaldehyde 
• 457628-23-8 2-hydroxy-4-(trifluoromethanesulfonyloxy)benzaldehyde 
• 635679-16-2 4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde 
• 635679-10-6 4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-triisopropylsilanyloxy-benzaldehyde 
• 635679-15-1 2-hydroxy-4-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-benzaldehyde 
• 84224-29-3 4-hydroxy-2-methoxybenzonitrile 
• 163041-68-7 2-methoxy-4-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde 
• 42924-32-3 4-ethoxy-2-methoxyphenyl formate 
• 156001-73-9 trifluoromethanesulfonic acid 4-formyl-3-methoxyphenyl ester 

Relevant articles and documents

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Design, synthesis and docking study of 5-(substituted benzylidene) thiazolidine-2,4-dione derivatives as inhibitors of protein tyrosine phosphatase 1B

A series of novel 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives was designed, and synthesized based on our previous studies. Also their activities were evaluated as competitive inhibitors of protein tyrosine phosphatase 1B (PTP1B). Compounds 6d-6g, 7b, 7c, 7e, 7j, 7k, 7m, 14b and 14e-14f showed potent inhibitory effects against PTP1B, and compound 7e, the most potent among the series, had an IC50 of 4.6 μM. Also a Surflex-Dock docking model of 7e was studied. Compound 7e showed a negative binding energy of -7.35 kcal/mol and a high affinity to PTP1B residues (Gly220, Ala217, Arg221, Asp181, Ser216, Cys215, Phe182, Gln262 and Ile219) in the active sites, indicating that it may stabilize the open form and generate tighter binding to the catalytic sites of PTP1B.

Concise synthesis of licochalcone a through water-accelerated [3,3]-sigmatropic rearrangement of an aryl prenyl ether

Claisen-Schmidt condensation of 4-(tetrahydropyran-2-yloxy)acetophenone with 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde gave a THP-protected chalcone ether. Removal of the THP group under mild acidic conditions gave the corresponding chalcone ether, which underwent a water-accelerated Claisen rearrangement under microwave irradiation or heating in a sealed tube in aqueous ethanol to give a good yield of licochalcone A, which has diverse biological activities; no product of deprenylation or abnormal Claisen rearrangement was formed. The abnormal Claisen rearrangement of -substituted allyl aryl ethers is known to be a problem in [3,3]-sigmatropic rearrangement reaction; this, however, was not detected in our water-accelerated system.