1504-74-1

Basic information

• Product Name: 2'-Methoxycinnamaldehyde
• Synonyms: (2E)-3-(2-Methoxyphenyl)-2-propenal;2-methoxycimnamaldehyde;2-Methoxycinnamic aldehyde;2-propenal,3-(2-methoxyphenyl)-;3-(2-methoxyphenyl)-2-propena;3-(2-methoxyphenyl)-2-Propenal;beta-(o-Methoxyphenyl)acrolein;Cinnamaldehyde, o-methoxy-
• CAS NO: 1504-74-1
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 216-131-3
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Alphabetical Listings;Flavors and Fragrances;M-N;Aldehydes;Building Blocks;C10-C12;Carbonyl Compounds;Chemical Synthesis;Nutrition Research;Ocimum basilicum (Basil);Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb)
• Mol File: 1504-74-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: 44-48 °C(lit.)
• Boiling Point: 160-161 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless crystal
• Density: 1.0281 (rough estimate)
• Vapor Pressure: 0.000125mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Sparingly)
• CAS DataBase Reference: 2'-Methoxycinnamaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Methoxycinnamaldehyde(1504-74-1)
• EPA Substance Registry System: 2'-Methoxycinnamaldehyde(1504-74-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• RTECS: GD6590000
• Hazardous Substances Data: 1504-74-1(Hazardous Substances Data)

Usage

Description

2'-Methoxycinnamaldehyde is a yellow crystalline compound with a sweet, warm, spicy-floral odor and fruity undertones. It has a sweet, spicy, and warm flavor, which becomes somewhat pungent at concentrations above 200-300 ppm. It is formed through various chemical reactions, such as the condensation of salicylaldehyde methylether with acetaldehyde under alkaline conditions or from the corresponding oxime.

Uses

Used in Flavor and Fragrance Industry:
2'-Methoxycinnamaldehyde is used as a flavoring agent for its sweet, spicy, and warm taste, making it suitable for the creation of various food and beverage products. Its warm, spicy, and floral odor with fruity undertones also makes it an ideal component for the fragrance industry, where it can be used to create a wide range of scent profiles.
Used in the Cosmetic Industry:
Due to its pleasant odor and flavor, 2'-Methoxycinnamaldehyde can be used in the cosmetic industry as an additive to enhance the sensory experience of products such as perfumes, lotions, and other personal care items.
Used in the Pharmaceutical Industry:
2'-Methoxycinnamaldehyde may have potential applications in the pharmaceutical industry, particularly in the development of drugs that require a sweet, spicy, or warm taste or odor. Its chemical properties could also be exploited for the synthesis of other bioactive compounds with potential therapeutic uses.

Preparation

It is formed after a long contact period between salicylaldehyde and acetaldehyde in diluted alkaline solution; it may also be formed by condensation of salicylaldehyde methylether with acetaldehyde under alkaline conditions; from the corresponding oxime. It may be isolated and purified from powdered cinnamon.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Aldehydes, such as 2'-Methoxycinnamaldehyde, are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Fire Hazard

2'-Methoxycinnamaldehyde is flammable.

InChI:InChI=1/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4+

Upstream product

• 86657-75-2 1-Methoxy-2-(1,3,3-triethoxy-propyl)-benzene 
• 109-92-2 ethyl vinyl ether 
• 135-02-4 ortho-anisaldehyde 
• 75-07-0 acetaldehyde 
• 1504-61-6 2-methoxycinnamyl alcohol 
• 6099-03-2 3-(2'-methoxyphenyl)propenoic acid 
• 98288-15-4 methyl 2-methoxycinnamate 
• 86657-70-7 1-(2-Methoxy-phenyl)-2-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-ethanol 
• 33538-83-9 3-(2-methoxyphenyl)propanal 
• 3698-28-0 2-allylanisole 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 624-67-9 Propargylic aldehyde 
• 100-66-3 methoxybenzene 
• 75-27-4 bromodichloromethane 

Downstream Products

• 1011-54-7 2-methoxycinnamic acid 
• 1504-61-6 2-methoxycinnamyl alcohol 
• 130786-85-5 [(E)-3-(2-Methoxy-phenyl)-prop-2-en-(E)-ylidene]-(5-methyl-isoxazol-3-yl)-amine 
• 148119-36-2 DD⁽¹⁷⁵⁾D₀₀₈₃₂ 
• 117069-11-1 2-[(E)-3-(2-Methoxy-phenyl)-prop-2-en-(Z)-ylidene]-8-[(E)-3-(2-methoxy-phenyl)-prop-2-en-(E)-ylidene]-cyclooctanone 
• 130786-83-3 [(E)-3-(2-Methoxy-phenyl)-prop-2-en-(E)-ylidene]-[3-methyl-5-((E)-styryl)-isoxazol-4-yl]-amine 
• 117069-07-5 2-[(E)-3-(2-Methoxy-phenyl)-prop-2-en-(Z)-ylidene]-6-[(E)-3-(2-methoxy-phenyl)-prop-2-en-(E)-ylidene]-cyclohexanone 
• 117069-09-7 2-[(E)-3-(2-Methoxy-phenyl)-prop-2-en-(E)-ylidene]-6-[(E)-3-(2-methoxy-phenyl)-prop-2-en-(Z)-ylidene]-4-methyl-cyclohexanone 
• 120991-80-2 N-<3-(2-methoxyphenyl)propyl>-1,4-diaminobutane 
• 117069-05-3 2-[(E)-3-(2-Methoxy-phenyl)-prop-2-en-(Z)-ylidene]-5-[(E)-3-(2-methoxy-phenyl)-prop-2-en-(E)-ylidene]-cyclopentanone 
• 117069-10-0 2-[(E)-3-(2-Methoxy-phenyl)-prop-2-en-(Z)-ylidene]-7-[(E)-3-(2-methoxy-phenyl)-prop-2-en-(E)-ylidene]-cycloheptanone 
• 264598-04-1 <3-(2-Methoxy-phenyl)-allyliden>-malonsaeure 
• 4720-36-9 3-[3-(2-methoxy-phenyl)-allylamino]-propan-1-ol 
• 10493-37-5 3-(2-methoxyphenyl)propan-1-ol 

Relevant articles and documents

Stabilization and activation of unstable propynal in the zeolite nanospace and its application to addition reactions

Propynal (HC≡C-CHO), having both a C≡C triple bond and a formyl group in a molecule, is a promising building block but its labile property to easily polymerize often narrows its application for organic synthesis. In a similar way to unstable molecules, such as formaldehyde and acrolein, propynal is also stabilized and remains unchanged in supercages of Na-Y zeolite for over 30 days at ambient temperature. There, the carbonyl oxygen atoms of propynal coordinate to sodium ions in Na-Y which was proved by a 13C-DD/MAS-NMR analysis. In addition, propynal adsorbed in zeolite is sufficiently activated to allow unprecedented reactions; i.e., (1) a 1,3-dipolar cycloaddition with electron-deficient α-diazocarbonyl compounds, (2) a 1,4-addition with mono-, di-, and trimethoxy-substituted benzenes, and (3) a [2 + 2] cycloaddition of unactivated cycloalkenes. The nanospace of the zeolites keeps the products from dimerization during reaction (1) and from successive side-reactions in reaction (2). Quantum chemical calculations demonstrated that reaction (3) proceeds via a one-step-like non-concerted mechanism to afford the corresponding [2 + 2] cycloadducts. These three reactions can produce valuable synthetic intermediates retaining both a formyl group and a C=C double bond.

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.

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (?)-Paroxetine

A simple yet highly effective approach toward enantioselective synthesis of trans-3,4-disubstituted glutarimides from readily available starting materials is developed using oxidative N-heterocyclic carbene catalysis. The catalytic reaction involves a formal [3 + 3] annulation between enals and substituted malonamides enabling the production of glutarimide derivatives in a single chemical operation via concomitant formation of C-C and C-N bonds. The reaction offers easy access to a broad range of functionalized glutarimides with excellent enantioselectivity and good yield. Synthetic application of the method is demonstrated via formal synthesis of (?)-paroxetine and other bioactive molecules.