131826-11-4

Basic information

• Product Name: 3-Isobutylaniline
• Synonyms: 3-Isobutylaniline
• CAS NO: 131826-11-4
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.2328
• Mol File: 131826-11-4.mol

Chemical Properties

• Boiling Point: 245.7±9.0 °C(Predicted)
• Appearance: /
• Density: 0.944±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.60±0.10(Predicted)
• CAS DataBase Reference: 3-Isobutylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isobutylaniline(131826-11-4)
• EPA Substance Registry System: 3-Isobutylaniline(131826-11-4)

Safety Data

• Hazardous Substances Data: 131826-11-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Isobutylaniline is used as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications.
Used in Industrial Applications:
3-Isobutylaniline is used as a solvent in different industries, facilitating the manufacturing process and improving the efficiency of various chemical reactions. Its high miscibility with other organic solvents makes it a valuable component in industrial processes.
Safety Measures:
Due to its toxicity, 3-Isobutylaniline requires proper safety measures during handling, such as wearing protective clothing and using appropriate ventilation to minimize the risk of exposure. It is categorized as a hazardous substance under environmental regulations, emphasizing the need for careful handling and disposal.

Synthetic route

1-(2-methyl-1-propenyl)-3-nitrobenzene (6026-73-9) → 3-isobutylaniline (131826-11-4)

Conditions	Yield
With sodium hypophosphite monohydrate; palladium on activated charcoal; sodium carbonate In acetic acid butyl ester; water for 3h; Reagent/catalyst; Reflux;	93%
With hydrogenchloride; palladium on activated carbon In methanol; sodium hydrogencarbonate; ethyl acetate

C16H31NSi2 → 3-isobutylaniline (131826-11-4)

Conditions	Yield
Inert atmosphere;

3-Chloronitrobenzene (121-73-3) → 3-isobutylaniline (131826-11-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: (η3-allyl)(N,N'-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)chloropalladium(II); sodium carbonate / acetic acid butyl ester / 5 h / 160 °C / Autoclave 2: sodium hypophosphite monohydrate; palladium on activated charcoal; sodium carbonate / acetic acid butyl ester; water / 3 h / Reflux View Scheme

3-Bromonitrobenzene (585-79-5) → 3-isobutylaniline (131826-11-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; sodium carbonate / acetic acid butyl ester / 10 h / 140 °C / Autoclave 2: sodium hypophosphite monohydrate; palladium on activated charcoal; sodium carbonate / acetic acid butyl ester; water / 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; sodium carbonate / acetic acid butyl ester / 5 h / 140 °C / Autoclave 2: sodium hypophosphite monohydrate; palladium on activated charcoal; sodium carbonate / acetic acid butyl ester; water / 3 h / Reflux View Scheme

m-amino isobutyrophenone (42528-67-6) → 3-isobutylaniline (131826-11-4)

Conditions	Yield
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 105 - 180℃; for 8h; Temperature;

3-bromoaniline (591-19-5) → 3-isobutylaniline (131826-11-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / 1 h / 25 °C / 2585.81 Torr View Scheme

3-(2-methylprop-1-en-1-yl)aniline (153624-73-8) → 3-isobutylaniline (131826-11-4)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen at 25℃; under 2585.81 Torr; for 1h;

perfluoroisopropyl iodide (677-69-0) + 3-isobutylaniline (131826-11-4) → 3-isobutyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (870786-82-6)

Conditions	Yield
With sodium dithionite; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In tert-butyl methyl ether; water at 20℃;	60%
With sodium dithionite; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In tert-butyl methyl ether; water at 20℃;	47%

aqueous sodium nitrite + 3-isobutylaniline (131826-11-4) → 1-bromo-3-isobutylbenzene (139155-55-8)

Conditions	Yield
With copper(I) bromide In hydrogen bromide

3-isobutylaniline (131826-11-4) → 3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (870786-83-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; sodium dithionite / water; tert-butyl methyl ether / 20 °C 2: methanol / 5 h / Reflux View Scheme

3-isobutylaniline (131826-11-4) → N-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide

Conditions	Yield
Multi-step reaction with 3 steps 1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; sodium dithionite / water; tert-butyl methyl ether / 20 °C 2: methanol / 5 h / Reflux 3: triethylamine / tetrahydrofuran / 5 h / Reflux View Scheme

Upstream product

• 6026-73-9 1-(2-methyl-1-propenyl)-3-nitrobenzene 
• 153624-73-8 3-(2-methylprop-1-en-1-yl)aniline 
• 591-19-5 m-Bromoaniline 
• 42528-67-6 m-amino isobutyrophenone 
• 585-79-5 m-nitrobromobenzene 
• 121-73-3 3-Nitrochlorobenzene 

Downstream Products

• 870786-82-6 3-isobutyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline 
• 139155-55-8 1-bromo-3-isobutylbenzene 

Relevant articles and documents

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Process for synthesizing m-isobutylaniline

The invention relates to a process for synthesizing m-isobutylaniline. According to the invention, isobutyraldehyde and morpholine are used as starting materials and p-toluenesulfonic acid is used as a catalyst to synthesize 2-methyl-1-m-morpholinylpropylene; then 2-methyl-1-m-morpholinylpropylene and nitrobenzoyl chloride are subjected to condensation and hydrolysis, and then an aldehyde group is removed under the action of hydrochloric acid, so m-nitrophenylisobutyl ketone is synthesized; then m-aminophenylisobutyl ketone is synthesized through selective hydrogenation; and finally, m-isobutylaniline is synthesized through a Huang Minglong reaction.

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