135-02-4

Basic information

• Product Name: o-Anisaldehyde
• Synonyms: o-Anisaldehyde：2-Methoxybenzaldehyde;o-Anisaldehyde, 98% 100GR;o-Anisaldehyde, 98% 5GR;2-Methoxybenzaldehyde Salicylaldehyde Methyl Ether;Adjacent Methoxy benzene forMaldehyde;o-Anisaldehyde 〔o-Methoxybenzaldehyde〕;2-methoxy-benzaldehyd;2-Methoxybenzenecarboxaldehyde
• CAS NO: 135-02-4
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.15
• EINECS: 205-171-7
• Product Categories: aldehyde;Pyridines;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Fluorescent
• Mol File: 135-02-4.mol
• Article Data: 407

Chemical Properties

• Melting Point: 34-40 °C(lit.)
• Boiling Point: 238 °C(lit.)
• Flash Point: 244 °F
• Appearance: Light yellow to pale brown/Low Melting Crystalline Mass
• Density: 1.127 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00128mmHg at 25°C
• Refractive Index: 1.5608
• Storage Temp.: Store below +30°C.
• Solubility: Solubility Slightly soluble in water; soluble in ethanol
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 606301
• CAS DataBase Reference: o-Anisaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: o-Anisaldehyde(135-02-4)
• EPA Substance Registry System: o-Anisaldehyde(135-02-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• RTECS: BZ2610000
• F: 9-23
• TSCA: Yes
• Hazardous Substances Data: 135-02-4(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 135-02-4 differently. You can refer to the following data:
1. O-Anisaldehyde (also 2-methoxybenzaldehyde) is found in cassia oil, cinnamon bark, and cinnamon bark oil. It is a clear colorless liquid with a strong aroma. O-Anisaldehyde is used as a flavor agent in foods including nonalcoholic/alcoholic beverages, baked goods, chewing gum, confections, frozen dairy, fruit ices, hard/soft candy, instant coffee, tea, Jams, jellies, and milk products. O-Anisaldehyde has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus and to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.
2. o-Methoxybenzaldehyde has a faint, sweet, floral odor. It blends well with cassia. It has a spice-like flavor, quite bitter above 30 - 40 ppm. May be prepared from salicylaldehyde and dimethyl sulfate in weak alkaline solution.

References

[1] George A. Burdock (2016) Fenraoli’s Handbook of Flavor Ingredients, Sixth Edition. [2] https://www.alfa.com/en/catalog/A10770/

Chemical Properties

Different sources of media describe the Chemical Properties of 135-02-4 differently. You can refer to the following data:
1. Colorless to cream amber crystalline powder; sweet powdery hawthorn guaiacol vanilla acetophenone almond aroma.
2. light yellow to pale brown

Occurrence

Reported found in Cassia oil, cinnamon bark, and Cinnamon bark oil (Cinnamomum zeylanicum Blume), Sri Lanka (0.09–0.15%)

Uses

Different sources of media describe the Uses of 135-02-4 differently. You can refer to the following data:
1. 2-Methoxybenzaldehyde has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus. It has also been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.
2. Intermediate.
3. 2-Methoxybenzaldehyde has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.

Aroma threshold values

Medium strength odor; anisic type; recommend smelling in a 10.00% solution or less.

Taste threshold values

Sweet powdery guaiacol musty vanilla floral almond taste at 50 ppm in water.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 11, p. 943, 1974 DOI: 10.1002/jhet.5570110616Tetrahedron Letters, 25, p. 1843, 1984 DOI: 10.1016/S0040-4039(01)90056-5

Biochem/physiol Actions

Naturally-occurring aromatic aldehyde with acaricidal activity. May condense with L-tryptophan in foods to form the corresponding phenolic tetrahydro-β-carboline-3-carboxylic acid which is a potent antioxidant.

Safety Profile

Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C8H8O2/c1-10-8-5-3-2-4-7(8)6-9/h2-6H,1H3

Upstream product

• 91-22-5 quinoline 
• 74-90-8 hydrogen cyanide 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 7022-48-2 2-methoxy-N-methyl-N-phenyl-benzamide 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 90-02-8 salicylaldehyde 
• 80-48-8 methyl p-toluene sulfonate 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 3116-83-4 sodium salicylate 
• 6948-61-4 (E)-1-(2-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 3698-28-0 2-allylanisole 
• 6850-57-3 2-methoxybenzylamine 

Downstream Products

• 100797-66-8 2-((E)-2-methoxy-benzylidene)-pent-4-enoic acid 
• 111211-31-5 2-((E)-2-methoxy-benzylidene)-tridec-12-enoic acid 
• 6768-22-5 diethyl 2-methoxybenzylidenemalonate 
• 29175-53-9 N-(2-methoxybenzyl)piperidine 
• 103040-07-9 (2-methoxy-benzyl)-(1H-[1,2,4]triazol-3-yl)-amine 
• 111042-61-6 (E)-1-(furan-2-yl)-3 (2-methoxyphenyl)-2-propen-1-one 
• 74441-57-9 3t-(2-methoxy-phenyl)-1-[2]thienyl-propenone 
• 27652-91-1 α-(2-methoxyphenyl)-2-pyridinemethanol 
• 21730-69-8 5-(2-methoxybenzylidene)hydantoin 
• 119450-19-0 (5Z)-5-(2-methoxybenzylidene)-2-thioxoimidazolidin-4-one 
• 107455-95-8 1-(5-bromo-[2]thienyl)-3t-(2-methoxy-phenyl)-propenone 
• 97871-86-8 (Z)-2-(2-methoxybenzylidene)benzofuran-3(2H)-one 

Relevant articles and documents

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Oxidation of benzyl alcohols to benzaldehydes in water catalyzed by a Cu(II) complex with a zwitterionic calix[4]arene ligand

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α-MnO2 modified exfoliated porous g-C3N4 nanosheet (2D) for enhanced photocatalytic oxidation efficiency of aromatic alcohols

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SBA-15 Supported Silver Catalyst for the Efficient Aerobic Oxidation of Toluene Under Solvent-Free Conditions

The efficient SBA-15 supported silver catalysts(Ag/SBA-15) were prepared and characterized by ICP-OES, XRD, TEM, SEM, XPS and N2 adsorption–desorption techniques. The catalysts exhibited an excellent catalytic activity for the aerobic oxidation of toluene to benzaldehyde under solvent-free conditions. Conversion of toluene and selectivity of benzaldehyde were 50% and 89% respectively over catalyst with 9.1 wt% Ag loading (10Ag/SBA-15). A wide range of substrates were tolerated under the selected reaction conditions. The kinetic study shows that the oxidation of toluene over 10Ag/SBA-15 is pseudo-first-order reaction and the activation energy Ea is 45.1?kJ/mol. A plausible mechanism involving oxygen free radicals was proposed for the aerobic oxidation reaction. Compared with the traditional method, the newly designed heterogeneous catalytic system shows better economic applicability, environmental friendliness and broader application prospects. Graphical abstract: [Figure not available: see fulltext.]

Method for synthesizing 2 -methoxycinnamaldehyde

The invention provides a synthetic method of 2 -methoxycinnamaldehyde, and belongs to the technical field of organic synthesis. The synthesis method provided by the invention comprises the following steps: (1) methylation reaction of 2 - hydroxybenzaldehyde and a methylation reagent under the action of a quaternary ammonium salt catalyst to obtain 2 - methoxybenzaldehyde. (2) Under alkaline conditions, 2 - methoxybenzaldehyde is subjected to a condensation reaction with acetaldehyde to obtain 2 -methoxycinnamaldehyde. 2 - Hydroxybenzaldehyde is used as a starting material, and the method has the advantages of wide sources and low cost. The method has the advantages of short synthetic route and less side reaction, and the obtained 2 -methoxycinnamaldehyde has high yield and purity and is suitable for industrial popularization and application. The results show that the yield 2 - and the purity ≥ 90% of ≥ 95% -methoxycinnamaldehyde obtained by the synthesis method provided by the invention are high.