16882-23-8

Basic information

• Product Name: 4-METHOXY-3-METHYLPHENYLACETONE
• Synonyms: 4-METHOXY-3-METHYLPHENYLACETONE;1-(4-Methoxy-3-methylphenyl)-2-propanone
• CAS NO: 16882-23-8
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• Product Categories: Aromatic Ketones (substituted)
• Mol File: 16882-23-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 164-166 °C(Press: 10 Torr)
• Appearance: /
• Density: 1.011±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-METHOXY-3-METHYLPHENYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-3-METHYLPHENYLACETONE(16882-23-8)
• EPA Substance Registry System: 4-METHOXY-3-METHYLPHENYLACETONE(16882-23-8)

Safety Data

• Hazardous Substances Data: 16882-23-8(Hazardous Substances Data)

Usage

General Description

4-METHOXY-3-METHYLPHENYLACETONE, also known as piperonal, is a chemical compound commonly used in the production of perfumes and flavorings. It is used as a precursor in the synthesis of pharmaceuticals and is also employed in the manufacturing of insecticides and fungicides. Piperonal has a sweet, floral odor and is used as a fragrance ingredient in a variety of products. It is also utilized in the preparation of illicit drugs such as MDMA (ecstasy) and methamphetamine. Additionally, piperonal has been studied for its potential antimicrobial and anti-inflammatory properties. However, it is important to note that piperonal is a controlled substance in many countries due to its association with illegal drug production.

Synthetic route

2-(4-methoxy-3-methyl-phenyl)-acetoacetonitrile (714258-55-6) → (4-methoxy-3-methyl-phenyl)-acetone (16882-23-8)

Conditions	Yield
With sulfuric acid

(4-methoxy-3-methylphenyl)magnesium bromide (117896-10-3) + chloroacetone (78-95-5) → (4-methoxy-3-methyl-phenyl)-acetone (16882-23-8)

Conditions	Yield

2-methylmethoxybenzene (578-58-5) → (4-methoxy-3-methyl-phenyl)-acetone (16882-23-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: aqueous formaldehyde; aqueous HCl; petroleum ether 3: ethanolic sodium ethylate 4: aqueous H2SO4 View Scheme

3-methyl-4-methoxybenzyl chloride (60736-71-2) → (4-methoxy-3-methyl-phenyl)-acetone (16882-23-8)

Conditions	Yield
Multi-step reaction with 3 steps 2: ethanolic sodium ethylate 3: aqueous H2SO4 View Scheme

2-(4-methoxy-3-methylphenyl)acetonitrile (75391-57-0) → (4-methoxy-3-methyl-phenyl)-acetone (16882-23-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanolic sodium ethylate 2: aqueous H2SO4 View Scheme

1-(4-methoxy-3-methylphenyl)-2-nitroprop-1-ene + iron (7439-89-6) → (4-methoxy-3-methyl-phenyl)-acetone (16882-23-8)

Conditions	Yield
With acetic acid In methanol; dichloromethane; water

(4-methoxy-3-methyl-phenyl)-acetone (16882-23-8) → 2-(4-methoxy-3-methyl-phenyl)-1-methyl-ethylamine (114963-00-7)

Conditions	Yield
With methanol; ammonia; nickel at 80 - 90℃; under 25742.8 Torr; Hydrogenation;

(4-methoxy-3-methyl-phenyl)-acetone (16882-23-8) + methylamine (74-89-5) → [2-(4-methoxy-3-methyl-phenyl)-1-methyl-ethyl]-methyl-amine (827611-22-3)

Conditions	Yield
With methanol; nickel at 90 - 100℃; under 51485.6 Torr; Hydrogenation;

(4-methoxy-3-methyl-phenyl)-acetone (16882-23-8) → 4-(2-Amino-propyl)-2-methyl-phenol

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; methanol; NH3 / 80 - 90 °C / 25742.8 Torr / Hydrogenation 2: aqueous HBr View Scheme

(4-methoxy-3-methyl-phenyl)-acetone (16882-23-8) → 2-Methyl-4-(2-methylamino-propyl)-phenol (6036-83-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; methanol / 90 - 100 °C / 51485.6 Torr / Hydrogenation 2: aqueous HBr View Scheme

(4-methoxy-3-methyl-phenyl)-acetone (16882-23-8) → 2-[(aminocarbonyl)amino]-4-methyl-5-(3-methyl-4-methoxyphenyl)-3-thiophenecarboxamide

Conditions	Yield

(4-methoxy-3-methyl-phenyl)-acetone (16882-23-8) + 2-amino-1-(3-chloro-phenyl)-ethanol (53360-89-7) → N-[2-(4-methoxy-3-methylphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine

Conditions	Yield

Upstream product

• 117896-10-3 (4-methoxy-3-methylphenyl)magnesium bromide 
• 78-95-5 chloroacetone 
• 7439-89-6 iron 
• 75391-57-0 2-(4-methoxy-3-methylphenyl)acetonitrile 
• 60736-71-2 3-methyl-4-methoxybenzyl chloride 
• 578-58-5 2-methylmethoxybenzene 
• 714258-55-6 2-(4-methoxy-3-methyl-phenyl)-acetoacetonitrile 

Downstream Products

• 6036-83-5 2-Methyl-4-(2-methylamino-propyl)-phenol 
• 827611-22-3 [2-(4-methoxy-3-methyl-phenyl)-1-methyl-ethyl]-methyl-amine 
• 114963-00-7 2-(4-methoxy-3-methyl-phenyl)-1-methyl-ethylamine 

Relevant articles and documents

Process for producing phenylacetones

A phenylacetone or its derivative having the general formula (I): STR1 wherein X, Y, and Z are independently a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, an amino group, a lower alkyl group having 1 to 6 carbon atoms, a lower alkoxy group having 1 to 6 carbon atoms, or a benzyloxy group and any two substituents of X, Y, and Z may form, together with the benzene ring, a heterocycling ring having 5 to 7 members including 1 or 2 oxygen atoms is produced at a high yield and a high selectivity by reacting a 3-phenylpropylene or its derivative having the general formula (II): STR2 wherein X, Y, and Z are as defined above, with an alkyl nitrite having the general formula (III): wherein R is an aliphatic, aromatic, or alicyclic saturated or unsaturated hydrocarbon group in the presence of (a) water, (b) an alcohol, (c) a palladium catalyst, and (d) an optional amine or copper compound, or by reacting the above-mentioned 3-phenylpropylene or its derivative with the above-mentioned alkyl nitrite in the presence of (a) an alcohol, (b) a palladium catalyst and (c) an optional amine or copper compound to form 1-phenyl-2,2-dialkoxypropane or it derivative having the general formula (IV): STR3 wherein X, Y, Z and R are as defined above, followed by hydrolyzing the reaction product.

Tyrosine hydroxylase inhibitors. Synthesis and activity of substituted aromatic amino acids.

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