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

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

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-2-methoxybenzaldehyde is used as an intermediate in the synthesis of solid phase supports for the preparation of fully protected peptide fragments. This application is crucial in the development of new drugs and therapies, as peptide fragments are essential components in the creation of various pharmaceutical compounds.
Used in Chemical Synthesis:
4-Hydroxy-2-methoxybenzaldehyde serves as a valuable intermediate in the synthesis of various chemical compounds due to its unique structure and reactivity. Its ability to form meta-depside bonds and interact with biopolymers and macromolecules makes it a promising candidate for further research and development in the chemical industry.

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

Upstream product

• 50-00-0 formaldehyd 
• 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 
• 77-78-1 dimethyl sulfate 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 67-56-1 methanol 
• 74-83-9 methyl bromide 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 71-43-2 benzene 
• 60-29-7 diethyl ether 

Downstream Products

• 42924-32-3 4-ethoxy-2-methoxyphenyl formate 
• 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 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 79571-16-7 2-methoxy-4-(1,1-dimethyl-2-propynyloxy)benzaldehyde 
• 4230-92-6 3-Methoxy-4-(2nitrovinyl)phenol 
• 127444-22-8 2-{2-[(E)-2-(4-Hydroxy-2-methoxy-phenyl)-vinyl]-5-oxo-4-[1-phenyl-meth-(E)-ylidene]-4,5-dihydro-imidazol-1-yl}-benzoic acid 
• 146630-26-4 7-Ethoxy-2-(4-hydroxy-2-methoxy-phenyl)-4-oxo-9-phenyl-1,2,3,4-tetrahydro-pyrido[3',2':4,5]thieno[3,2-d]pyrimidine-8-carbonitrile 
• 119138-29-3 4-hydroxy-2-methoxy-benzyl alcohol 
• 110842-67-6 1-(2-methoxy-4-hydroxybenzylidene)-4-phenylthiosemicarbazone 
• 103981-29-9 2-hydroxy-4-((3-nitrobenzyl)oxy)benzaldehyde 
• 824-46-4 methoxyhydroquinone 

Relevant articles and documents

Formylation of electron-rich aromatic rings mediated by dichloromethyl methyl ether and TiCl4: Scope and limitations

Here the aromatic formylation mediated by TiCl4 and dichloromethyl methyl ether previously described by our group has been explored for a wide range of aromatic rings, including phenols, methoxy- and methylbenzenes, as an excellent way to produce aromatic aldehydes. Here we determine that the regioselectivity of this process is highly promoted by the coordination between the atoms present in the aromatic moiety and those in the metal core.

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.

Synthesis of banana-like 1,3-dihydroxybenzene and 2,7-dihydroxynaphthalene esters and luminescence of their terbium(III) complexes

New esters of 1,3-dihydroxybenzene and 2,7-dihydroxynaphthalene with 4-(4-alkoxybenzoyloxy)-2-(or 3-)methoxybenzoic acids were synthesized. The correlation between their structure and liquid crystal properties was examined, and the luminescence characteristics of terbium(III) complexes with these esters were studied.

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.

Selective deprotection of phenolic polysulfonates

Nosylates of phenols can be selectively deprotected by thiocresol anions in DMSO. Successful deprotection can be accomplished in molecules containing aryl-appended halides, ethers, aldehydes, alkanesulfonates or arylsulfonates. Nosylate deprotection is accomplished by the CS bond rupture which is believed to proceed by nucleophilic aromatic substitution.

Chromogenic substrates of sialidase and methods of making and using the same

The subject invention discloses materials and methods for the design, synthesis, and biochemical evaluation of chromogenic substrate compounds for sialidases of bacterial, viral, protozoa, and vertebrate (including humans) origin. In particular, this invention provides a novel class of effective compounds as chromogenic substrates of these sialidases which yield chromogenic products after reactions catalyzed by sialidase take place. Also provided are methods of making these substrate compounds, methods of diagnosis and prognosis of sialidase related diseases using these substrate compounds.

Influence of hydrogen bonding in the activation of nucleophiles: PhSH- (catalytic) KF in N-methyl-2-pyrrolidone as an efficient protocol for selective cleavage of alkyl/aryl esters and aryl alkyl ethers under nonhydrolytic and neutral conditions

The nucleophilicity of arenethiols can be augmented via hydrogen bonding with 'naked' halide anion. The activity of the halide anions follow the order F- ?Cl- ～ Br- ～ I- and is dependent on the countercation (Bu4N ～ Cs ～ K > Na ?Li). The solvent plays an important role in nucleophilic activation as well as regeneration of the effective nucleophile (e.g. ArS-) and those with high dielectric constant, high molecular polarizability, high donor number (DN), and low acceptor number (AN) are the most effective. Selective deprotection of alkyl/aryl esters and aryl alkyl ethers can be achieved under nonhydrolytic and neutral conditions by the treatment with thiophenol in 1-methyl-2-pyrrolidone (NMP) in the presence of a catalytic amount of KF. Aryl esters are selectively deprotected in the presence of alkyl esters and alkyl methyl ethers during intramolecular competitions.

A mild and chemoselective method for deprotection of aryl acetates and benzoates under non-hydrolytic condition

Chemoselective deprotection of aryl acetates and benzoates can be achieved under non-hydrolytic condition by treatment with K2CO3 in N-methyl-2-pyrrolidone (NMP) at 100°C. Selective cleavage of aryl acetates and benzoates take place in the presence of alkyl carboxylates during intramolecular competitions.

Selective deprotection of propargyl ethers using tetrathiomolybdate

Benzyltriethylammonium tetrathiomolybdate, [PhCH2NEt3]2MoS4, 1 deprotects propargyl ethers of alcohols and phenols in a selective manner in high yields. Easily reducible groups like nitro, aldehyde, keto and allyl are not affected.