56038-89-2

Basic information

• Product Name: N-(1-Ethylpropyl)-3,4-dimethylaniline
• Synonyms: N-(1-ETHYLPROPYL)-3,4-DIMETHYLANILINE;Benzenamine, N-(1-ethylpropyl)-4,5-dimethyl-;N-(1-Ethylpropyl)-3,4-diMethylaniline, N-(1-Ethylpropyl)-3,4-xylidine;3,4-dimethyl-N-pentan-3-yl-aniline
• CAS NO: 56038-89-2
• Molecular Formula: C13H21N
• Molecular Weight: 191.31
• Mol File: 56038-89-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 290.2 °C at 760 mmHg
• Flash Point: 129 °C
• Appearance: Red-brown to brown liquid
• Density: 0.92 g/cm³
• Vapor Pressure: 0.0021mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• PKA: 6.11±0.33(Predicted)
• CAS DataBase Reference: N-(1-Ethylpropyl)-3,4-dimethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-Ethylpropyl)-3,4-dimethylaniline(56038-89-2)
• EPA Substance Registry System: N-(1-Ethylpropyl)-3,4-dimethylaniline(56038-89-2)

Safety Data

• Hazardous Substances Data: 56038-89-2(Hazardous Substances Data)

Usage

Uses

N-(1-Ethylpropyl)-3,4-xylidine is a useful compound in the synthesis of dinitro herbicides via one-step dinitration with nitric acid in continuous-flow microreactor.

InChI:InChI=1/C13H21N/c1-5-12(6-2)14-13-8-7-10(3)11(4)9-13/h7-9,12,14H,5-6H2,1-4H3

Synthetic route

3,4-dimethyliodobenzene (31599-61-8) + 3-aminopentane (616-24-0) → N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; sodium carbonate; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 90℃; for 6h; Reagent/catalyst; Temperature; Buchwald-Hartwig Coupling;	99.5%

4-chloro-1,2-dimethylbenzene (615-60-1) + 3-aminopentane (616-24-0) → N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; sodium carbonate; sodium t-butanolate In toluene at 80℃; for 6h; Temperature; Reagent/catalyst; Buchwald-Hartwig Coupling;	98.9%

3-aminopentane (616-24-0) + 3,4-dimethylphenyl trifluoromethanesulfonate (255837-23-1) → N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; sodium carbonate; sodium t-butanolate In toluene at 90℃; for 6h; Reagent/catalyst; Buchwald-Hartwig Coupling;	98.4%

4-amino-o-xylene (95-64-7) + pentan-3-one (96-22-0) → N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2)

Conditions	Yield
platinum	95.4%
With naphthalene-2-sulfonate; platinum on carbon; hydrogen at 60 - 70℃; under 3750.38 - 7500.75 Torr; for 1h; Autoclave; Inert atmosphere;

4-bromo-o-xylene (583-71-1) + 3-aminopentane (616-24-0) → N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; caesium carbonate In toluene at 80℃; for 6h; Reagent/catalyst; Buchwald-Hartwig Coupling;	93.7%

3,5-Dihydroxybenzoic acid (99-10-5) + 4-amino-o-xylene (95-64-7) + pentan-3-one (96-22-0) → N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2)

Conditions	Yield
platinum	75.1%

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) + acetic anhydride (108-24-7) → N-(1-ethylpropyl)-N-(3,4-dimethylphenyl)acetamide

Conditions	Yield
at 110℃; for 5h;	99.1%

4-bromoethylbutanoate (2969-81-5) + N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) → C19H31NO2

Conditions	Yield
With potassium hydroxide In acetone for 3h; Reflux;	94.97%

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) + chlorobenzene (108-90-7) → prowl (40487-42-1)

Conditions	Yield
With sulfuric acid; nitric acid In water; 1,2-dichloro-ethane

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) → N-(1-Ethylpropyl)-6-nitro-3,4-xylidin (56038-88-1) + N-(1-Ethylpropyl)-2-nitro-3,4-xylidin (56038-87-0)

Conditions	Yield
With nitric acid at 30℃;

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) → N-nitroso-N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethyl-benzenamine + N-(1-ethylpropyl)-N,2,6-trinitro-3,4-xylidine (73215-09-5) + prowl (40487-42-1)

Conditions	Yield
Stage #1: N-(1-ethylpropyl)-3,4-dimethyl-benzenamine With nitric acid at 30℃; Stage #2: at 30 - 60℃; Overall yield = 89 %;

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) → prowl (40487-42-1) + C13H17N3O4 (1417827-06-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / 1,2-dichloro-ethane; water / 1 h / 60 °C 2: 0.17 h / 180 °C View Scheme

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) → prowl (40487-42-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: nitric acid / 30 °C 1.2: 30 - 60 °C 2.1: iron(III) chloride; hydrogenchloride / 3 h / 75 °C View Scheme
Multi-step reaction with 2 steps 1: nitric acid / 1,2-dichloro-ethane; water / 1 h / 60 °C 2: iron(III) chloride; hydrogenchloride / 3 h / 75 °C View Scheme
Multi-step reaction with 3 steps 1: 5 h / 110 °C 2: nitric acid / 1,2-dichloro-ethane / 7 h / 40 °C 3: sulfuric acid / 1,2-dichloro-ethane; water / 4 h / 85 °C View Scheme

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) → N-nitroso-N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethyl-benzenamine + prowl (40487-42-1)

Conditions	Yield
With nitric acid In water; 1,2-dichloro-ethane at 60℃; for 1h; Temperature; Concentration; Reagent/catalyst; Overall yield = 97 %; Overall yield = 0.54 kg;
Stage #1: N-(1-ethylpropyl)-3,4-dimethyl-benzenamine With nitric acid at 30℃; Stage #2: at 30 - 60℃; for 4h; Overall yield = 89 %;

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) → N-(1-ethylpropyl)-2,6-dinitro-N-(3,4-dimethylphenyl)acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 h / 110 °C 2: nitric acid / 1,2-dichloro-ethane / 7 h / 40 °C View Scheme

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) → C17H25N3O6

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / acetone / 3 h / Reflux 2: sulfuric acid; nitric acid / 4 h / 20 °C 3: potassium hydroxide; water / 3 h / 60 °C View Scheme

4-bromoethylbutanoate (2969-81-5) + N-(1-ethylpropyl)-3,4-dimethyl-benzenamine (56038-89-2) → C19H29N3O6

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / acetone / 3 h / Reflux 2: sulfuric acid; nitric acid / 4 h / 20 °C View Scheme

Upstream product

• 31599-61-8 3,4-dimethyliodobenzene 
• 616-24-0 3-aminopentane 
• 255837-23-1 3,4-dimethylphenyl trifluoromethanesulfonate 
• 615-60-1 4-chloro-1,2-dimethylbenzene 
• 583-71-1 4-bromo-o-xylene 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 95-64-7 4-amino-o-xylene 
• 96-22-0 pentan-3-one 

Downstream Products

• 40487-42-1 prowl 
• 1417827-06-5 C₁₃H₁₇N₃O₄ 
• 73215-09-5 N-(1-ethylpropyl)-N,2,6-trinitro-3,4-xylidine 
• 56038-88-1 N-(1-Ethylpropyl)-6-nitro-3,4-xylidin 
• 56038-87-0 N-(1-Ethylpropyl)-2-nitro-3,4-xylidin 

Relevant articles and documents

Synthetic method of pendimethalin key intermediate N-(1-ethylpropyl)-3,4-dimethylaniline

The invention discloses a synthetic method of a pendimethalin key intermediate N-(1-ethylpropyl)-3,4-dimethylaniline. The synthetic method comprises the following steps: taking a compound as shown inthe formula (I) and 3-aminopentane as raw materials, and performing Buchwald-Hartwig cross-coupling reaction in the presence of a palladium catalyst to obtain the N-(1-ethylpropyl)-3,4-dimethylaniline. The invention provides a new idea for synthesis of the N-(1-ethylpropyl)-3,4-dimethylaniline. The method has the advantages that the path is short, the technology is simple, the path yield is stable, reaction conditions are mild, the raw material cost is lowered in synthetic processes, the conversion rate is high, few side reactions are caused, the yield is high, and the purity is high and can reach 97% or above. In addition, the palladium compound is taken as the catalyst which is easy to recycle, waste residues of the catalyst can not be generated, less waste water, waste gas and waste residues are generated, and the expansibility is strong. (The formula is shown in the description.).

Reductive alkylation of substituted anilines

N-alkylated aromatic amines are produced by reductively alkylating an aromatic amine with pressurized hydrogen in the presence of a ketone, a noble metal catalyst and a promoter acid having a pKa between 0.3 and 1.5.