2735-04-8

Basic information

• Product Name: 2,4-Dimethoxyaniline
• Synonyms: 4-Aminoresorcinol dimethyl ether;Aniline, 2,4-dimethoxy-;aniline,2,4-dimethoxy-[qr];2,4-DIMETHOXYANILINE;2,4-DIMETHOXY BENZAMINE;4-AMINORESORCINOL;AKOS BBS-00003627;2,4-dimethoxybenzenamine
• CAS NO: 2735-04-8
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.18
• EINECS: 220-355-7
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amines;C8;Nitrogen Compounds
• Mol File: 2735-04-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 33-36 °C(lit.)
• Boiling Point: 75-80 C
• Flash Point: >230 °F
• Appearance: Dark brown/Crystalline Solid
• Density: 1.075 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.4640 (estimate)
• Storage Temp.: Refrigerator
• PKA: 5.14±0.10(Predicted)
• Water Solubility: 7 g/L (20 ºC)
• Stability: Stability Stable, but sensitive to prolonged exposure to light. Incompatible with acids.
• BRN: 638704
• CAS DataBase Reference: 2,4-Dimethoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dimethoxyaniline(2735-04-8)
• EPA Substance Registry System: 2,4-Dimethoxyaniline(2735-04-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22
• RIDADR: 2811
• WGK Germany: 3
• RTECS: BX4200000
• F: 8-10-23
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 2735-04-8(Hazardous Substances Data)

Usage

Uses

Various 2,4-dimethoxyphenylsemicarbazones were synthesized starting from 2,4-dimethoxyaniline via a phenylcarbamate intermediate. The hydrochloride of 2,4-dimethoxyaniline was prepared by intro- ducing hydrogen chloride gas into an etheral solution and washing the precipitate with absolute diethyl ether.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 2441, 1993 DOI: 10.1016/S0040-4039(00)60436-7

General Description

Black crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2,4-Dimethoxyaniline neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: 2,4-Dimethoxyaniline is a local irritant.

InChI:InChI=1/C7H9NO2/c1-10-5-2-3-6(8)7(9)4-5/h2-4,9H,8H2,1H3

Upstream product

• 4920-84-7 2,4-dimethoxynitrobenzene 
• 29418-46-0 (2,4-dimethoxy-phenyl)-phenyl-diazene 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 151-10-0 1,3-Dimethoxybenzene 
• 29418-55-1 bis-(2,4-dimethoxy-phenyl)-diazene 
• 1137558-12-3 benzyl 2,4-dimethoxyphenylcarbamate 
• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 20629-90-7 1-(2-chlorophenyl)-3-methyl-5-pyrazolone 
• 5307-06-2 N-(4-hydroxy-2-methoxyphenyl)acetamide 
• 61638-01-5 4-Amino-3-methoxyphenol 
• 106063-48-3 4-benzenesulfonic acid 
• 150-19-6 O-methylresorcine 
• 592489-17-3 1,3-dimethyl-2-(2,4-dimethoxyphenylimino)imidazolidine 
• 67-56-1 methanol 

Downstream Products

• 156086-10-1 N-(2,4-dimethoxyphenyl)-4-methoxybenzamide 
• 2876-29-1 2-Methoxy-phenazin-10-oxid 
• 430454-31-2 methoxy-acetic acid-(2,4-dimethoxy-anilide) 
• 2672-77-7 3-hydroxy-[2]naphthoic acid-(2,4-dimethoxy-anilide) 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 39501-57-0 2,4-dimethoxy-1-nitrosobenzene 
• 1984-21-0 1-isocyano-2,4-dimethoxybenzene 
• 52872-77-2 5-nitro-thiazole-2-carboxylic acid 2,4-dimethoxy-anilide 
• 18906-37-1 2,4-dimethoxybenzenethiol 
• 152586-90-8 4-nitro-N-(2,4-dimethoxyphenyl)benzamide 
• 770743-66-3 2-[2-(2,4-dimethoxy-phenylamino)-2-methyl-propionylamino]-benzoic acid 
• 770743-62-9 3-{2-[1-(2,4-dimethoxy-phenylamino)-ethyl]-4-oxo-4H-quinazolin-3-yl}-propionic acid ethyl ester 
• 770743-63-0 3-benzyl-2-[1-(2,4-dimethoxy-phenylamino)-ethyl]-3H-quinazolin-4-one 
• 562836-26-4 2-[1-(2,4-dimethoxy-phenylamino)-ethyl]-3-(4-methyl-piperazin-1-yl)-3H-quinazolin-4-one 

Relevant articles and documents

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage

The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

A Ru(ii) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The practical applicability of this tandem process was revealed by preparative scale reactions with different organic azides and synthesis of an anti-vertigo drug betahistine. Several kinetic experiments and DFT studies were carried out to understand the mechanism of this transformation.