4344-55-2

Basic information

• Product Name: 4-BUTOXYANILINE
• Synonyms: p-aminophenoln-butylether;p-Aminophenyl-n-butyl ether;p-butoxy-anilin;p-Butyloxyaniline;n-But-O-C6H4-NH2;4-n-Butoxyaniline,97%;4-n-Butoxyaniline, 98+%;4-butoxyphenylamine
• CAS NO: 4344-55-2
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• EINECS: 224-402-2
• Product Categories: Alkylanilines;Anilines (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Amines;C9 to C10;Nitrogen Compounds
• Mol File: 4344-55-2.mol
• Article Data: 43

Chemical Properties

• Melting Point: 130-132 °C
• Boiling Point: 148-149 °C13 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear dark brown liquid
• Density: 0.992 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00436mmHg at 25°C
• Refractive Index: n20/D 1.538(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.23±0.10(Predicted)
• BRN: 2084421
• CAS DataBase Reference: 4-BUTOXYANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BUTOXYANILINE(4344-55-2)
• EPA Substance Registry System: 4-BUTOXYANILINE(4344-55-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-28-36/37/39-45
• RIDADR: 2810
• WGK Germany: 3
• RTECS: BW9420000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4344-55-2(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR DARK BROWN LIQUID

Uses

4-Butoxyaniline was used in the preparation of:bis-4-butoxyphenyl-4,4′-(2,2′-bipyridyl)carbamide1-(4-butoxyphenyl)-3-(6-methyl-3-oxo-2-phenyl-2,3-dihydropyridazin-4-yl)urea

General Description

4-Butoxyaniline undergoes low-pressure hydrogenation in the presence of rhodium on alumina to yield 4-butoxycyclohexylamine.

InChI:InChI=1/C10H15NO/c1-2-3-8-12-10-6-4-9(11)5-7-10/h4-7H,2-3,8,11H2,1H3

Synthetic route

1-butoxy-4-nitrobenzene (7244-78-2) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With hydrazine hydrate In methanol for 4h; Reflux;	99%
With tin(ll) chloride In ethanol at 80℃; for 2h;	65%
With hydrogenchloride; tin(II) chloride dihdyrate In ethanol	48%

n-Butyl chloride (109-69-3) + N,N-dimethyl acetamide (127-19-5) + 4-amino-phenol (123-30-8) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With sodium hydroxide	93%

4-n-butoxyacetanilide (23563-26-0) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With hydrogenchloride In methanol; water for 18h; Reflux;	86%
With sulfuric acid
With potassium hydroxide In ethanol for 12h; Heating;

4-bromo-aniline (106-40-1) + butan-1-ol (71-36-3) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With copper(l) iodide; N1, N2-diphenethyloxalamide; sodium t-butanolate In 1,4-dioxane for 24h; Schlenk technique; Inert atmosphere; Molecular sieve; Heating;	86%

1-bromo-butane (109-65-9) + 4-amino-phenol (123-30-8) → para-butoxyaniline (4344-55-2) + (4-Butoxy-phenyl)-butyl-amine (136540-19-7) + (4-Butoxy-phenyl)-dibutyl-amine (136540-20-0)

Conditions	Yield
With potassium hydroxide; Aliquat 336 at 60℃; for 7h;	A 29 % Chromat. B 28 % Chromat. C 82%
With potassium hydroxide; Aliquat 336 at 60℃; for 2h;	A 15 % Chromat. B 47 % Chromat. C 30 % Chromat.

1-bromo-butane (109-65-9) + 4-amino-phenol (123-30-8) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 24h;	79%
With sodium hydride In acetonitrile at 20℃; for 24h;

3,6,9-trioxaundecane (112-36-7) + n-Butyl chloride (109-69-3) + 4-amino-phenol (123-30-8) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With sodium methylate In methanol	73.6%

n-Butyl chloride (109-69-3) + 4-amino-phenol (123-30-8) → para-butoxyaniline (4344-55-2) + (4-Butoxy-phenyl)-butyl-amine (136540-19-7)

Conditions	Yield
With sodium hydroxide; Aliquat 336 at 60℃; for 15h;	A 67% B 11%

p-aminoiodobenzene (540-37-4) + butan-1-ol (71-36-3) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate at 110℃; for 23h;	40%

1,10-Phenanthroline (66-71-7) + p-aminoiodobenzene (540-37-4) + butan-1-ol (71-36-3) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With CuI; caesium carbonate	40%

trans-4-<3-Chlorbuten-(2)-yloxy>-nitrobenzol (23028-71-9) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With hydrogen; Lindlar's catalyst

cis-4-<3-Chlorbuten-(2)-yloxy>-nitrobenzol (23028-70-8) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With hydrogen; Lindlar's catalyst

para-methoxynitrobenzene (100-17-4) + butan-1-ol (71-36-3) → para-butoxyaniline (4344-55-2) + 4-amino-phenol (123-30-8) + 4-methoxy-aniline (104-94-9)

Conditions	Yield
With sulfuric acid; hydrogen; platinum on activated charcoal under 760 Torr; Ambient temperature;	A 12 % Chromat. B 23 % Chromat. C 46 % Chromat.

C16H22N3O2(1+)*BF4(1-) → para-butoxyaniline (4344-55-2)

Conditions	Yield
With hydrogenchloride In ethanol for 2h; Heating;

4-acetaminophenol (103-90-2) → para-butoxyaniline (4344-55-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / 16 h / Heating 2: hydrochloric acid / ethanol / 24 h / Heating View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / acetone 2: aq. HCl View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / acetone / Heating 2: aq. HCl / 100 °C View Scheme

1-[(4-hydroxyphenylcarbomoyl)methyl]-3-methylimidazolium tetrafluoroborate → para-butoxyaniline (4344-55-2) + resin-CH2NHCO(CH2)3C6H4-p-N=CH-C6H4-p-C(O)OH

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / ethanol / 3 h / Heating 2: conc. HCl / ethanol / 2 h / Heating View Scheme

4-nitro-phenol (100-02-7) + monoacylated Me-capped β-cyclodextrin → para-butoxyaniline (4344-55-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / cyclohexanone / 4 h / Heating 2: N2H4 / Raney Ni / ethanol / 3 h / Heating View Scheme

4-nitro-phenol (100-02-7) + MOC-L-Phe-albumin → para-butoxyaniline (4344-55-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide 2: Fe, HCl View Scheme

4-nitro-phenol (100-02-7) + KOH-solution → para-butoxyaniline (4344-55-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / K2CO3 / acetone / 24 h / Heating 2: H2 / PtO2 / ethanol View Scheme
Multi-step reaction with 2 steps 1: 98 percent / potassium carbonate / acetone / 40 h / Heating 2: 41 percent / sodium formate, monobasic potassium phosphate, 1-methyl-2-pyrrolidone / 15 h / Heating View Scheme

4-nitro-phenol (100-02-7) → para-butoxyaniline (4344-55-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: butyl alcohol; aqueous-alcoholic KOH-solution 2: tin (II)-chloride; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / acetone / 100 h / 60 - 62 °C 2: H2 / Pd/CaCO3 View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / acetone / 100 h / 60 - 62 °C 2: H2 / Pd/CaCO3 View Scheme

1-bromo-butane (109-65-9) + p-hydroxybenzamide (619-57-8) → para-butoxyaniline (4344-55-2)

Conditions	Yield
Stage #1: 1-bromo-butane; p-hydroxybenzamide With potassium carbonate; potassium iodide In N,N-dimethyl-formamide Stage #2: With hydrogenchloride In ethanol

4-[(E)-(4'-butoxyphenyl)diazenyl]phthalonitrile → para-butoxyaniline (4344-55-2) + 3,4-dicyanoaniline (56765-79-8)

Conditions	Yield
With tin(ll) chloride In ethanol at 20℃;

4-hydroxy-benzoic acid (99-96-7) → para-butoxyaniline (4344-55-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium nitrite / water / 0 °C / Acidic conditions 1.2: 10 °C 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 2 h / Heating 3.1: tin(ll) chloride / ethanol / 20 °C View Scheme

4-[(E)-(4'-hydroxyphenyl)diazenyl]phthalonitrile → para-butoxyaniline (4344-55-2) + 3,4-dicyanoaniline (56765-79-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide; water / 2 h / Heating 2: tin(ll) chloride / ethanol / 20 °C View Scheme

para-butoxyaniline (4344-55-2) + phenol (108-95-2) → 4-hydroxy phenyl azo 4'-butyloxy benzene (3021-36-1)

Conditions	Yield
Stage #1: para-butoxyaniline With hydrogenchloride; sodium nitrite In water Stage #2: phenol With potassium hydroxide In methanol	100%
With sulfuric acid; sodium nitrite
With hydrogenchloride; sodium nitrite Multistep reaction;

para-butoxyaniline (4344-55-2) → (4-butoxyphenyl)hydrazine hydrochloride

Conditions	Yield
Stage #1: para-butoxyaniline With barium nitrite In water at 25℃; Acidic conditions; Flow reactor; Stage #2: With sodium hydrogensulfite In water at 90 - 110℃; Stage #3: With hydrogenchloride In water at 120℃;	97.8%

para-butoxyaniline (4344-55-2) + 4-(4'-heptyloxybenzoyloxy)-3-methoxy benzaldehyde (314058-97-4) → 4-Heptyloxy-benzoic acid 4-{[(E)-4-butoxy-phenylimino]-methyl}-2-methoxy-phenyl ester (108532-30-5)

Conditions	Yield
	93%

para-butoxyaniline (4344-55-2) → 1-azido-4-butoxybenzene (85862-66-4)

Conditions	Yield
Stage #1: para-butoxyaniline With hydrogenchloride; sodium nitrate; acetic acid In water at 0℃; for 0.0833333h; Stage #2: With sodium azide In water at 0℃; for 1.5h;	93%
Stage #1: para-butoxyaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Stage #2: With sodium azide In water at 0℃; for 2h; Further stages.;	39%
Stage #1: para-butoxyaniline With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: With sodium azide; sodium acetate In water at 0℃;	12%
Stage #1: para-butoxyaniline With hydrogenchloride; sodium nitrite Stage #2: With sodium azide; sodium acetate

para-butoxyaniline (4344-55-2) + C29H20O6 (1097203-22-9) → C49H46N2O6 (1097203-23-0)

Conditions	Yield
In chloroform for 3h; Reflux;	93%

para-butoxyaniline (4344-55-2) + 2,6-dibromo-1,5-naphthalenediol (84-59-3) → 2,6-dibromo-4-(4-butoxy-phenylimino)-5-hydroxy-4H-naphthalen-1-one

Conditions	Yield
With iodic acid In ethanol; water at 20℃; for 2h;	92%

para-butoxyaniline (4344-55-2) + ortho-toluoyl chloride (933-88-0) → N-(4-butoxyphenyl)-2-methylbenzamide (446850-08-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere;	92%

isonicotinic acid 4-formylphenyl ester + para-butoxyaniline (4344-55-2) → 4-((4'-butoxyphenylimino)methyl)phenylisonicotinate

Conditions	Yield
With acetic acid In ethanol at 75℃;	92%

para-butoxyaniline (4344-55-2) + dichloroglyoxime (2038-44-0) → N1,N2-bis(4-butoxyphenyl)-N1’,N2’-dihydroxyoxalamidine

Conditions	Yield
With triethylamine In ethanol at -10 - 20℃;	91%

2-chloronicotinic acid (2942-59-8) + para-butoxyaniline (4344-55-2) → 2-(4-Butoxy-phenylamino)-nicotinic acid (115891-04-8)

Conditions	Yield
	90%

para-butoxyaniline (4344-55-2) + dimethyl 2-(phenylimino)malonate (20815-42-3) → 2-(4-Butoxy-phenylimino)-malonic acid dimethyl ester (95359-86-7)

Conditions	Yield
With acetic acid Heating; under vacuum;	90%

succinic acid anhydride (108-30-5) + para-butoxyaniline (4344-55-2) → N-(4-butoxy-phenyl)-succinamic acid

Conditions	Yield
In acetone for 4h; Ring cleavage; Heating;	90%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;

2,6-bis((trimethylsilyl)ethynyl)-9,10-anthraquinone (906803-65-4) + para-butoxyaniline (4344-55-2) → N,N'-bis(4-n-butoxybenzene)(2,6-bis(trimethylsilylethynyl))anthraquinone diimine

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; titanium tetrachloride In chlorobenzene at 90 - 115℃; for 12h;	90%

para-butoxyaniline (4344-55-2) + 4-(4'-heptyloxybenzoyloxy)benzaldehyde (56800-32-9) → 4-Heptyloxy-benzoic acid 4-{[(E)-4-butoxy-phenylimino]-methyl}-phenyl ester (108532-21-4)

Conditions	Yield
	89%

1,5-dihydroxynaphthalene (83-56-7) + para-butoxyaniline (4344-55-2) → 4-(4-butoxy-phenylimino)-5-hydroxy-4H-naphthalen-1-one

Conditions	Yield
With iodic acid In ethanol; water at 20℃; for 2h;	88%

para-butoxyaniline (4344-55-2) + zinc(II) chloride (7646-85-7) + acenaphthene quinone (82-86-0) → 4-butoxyphenyl-BIAN zinc chloride

Conditions	Yield
Stage #1: zinc(II) chloride; acenaphthene quinone With acetic acid In neat (no solvent) at 60℃; Stage #2: para-butoxyaniline In neat (no solvent) for 1h; Reflux;	88%

propan-2-one O-acetyl oxime (18312-45-3) + para-butoxyaniline (4344-55-2) → 4-n-butoxyacetanilide (23563-26-0)

Conditions	Yield
In tert-butyl methyl ether at 20℃; for 4h; Molecular sieve;	86%

3-formyl-10-methylphenothiazine (4997-36-8) + para-butoxyaniline (4344-55-2) → C24H24N2OS (1417424-37-3)

Conditions	Yield
In N,N-dimethyl-formamide for 20h; Reflux;	86%

2-Amino-4,6-dichloropyrimidine (56-05-3) + para-butoxyaniline (4344-55-2) → 6-chloro-N4-(4-butoxyphenyl)-2,4-pyrimidinediamine

Conditions	Yield
With triethylamine In neat (no solvent) Heating;	86%

para-butoxyaniline (4344-55-2) → Bis-(4-butoxy-phenyl)-diazene

Conditions	Yield
With pyridine; oxygen; copper(l) chloride for 24h;	85%

para-butoxyaniline (4344-55-2) + 1,1'-(3,4,4-trichloro-2-nitrobuta-1,3-diene-1,1-diyl)bis(1H-benzo[d][1,2,3]triazole) (153759-82-1) → 1-(1-benzotriazolyl)-1-(4-butoxyphenylamino)-3,3,4-trichloro-2-nitro-1,3-butadiene

Conditions	Yield
In diethyl ether at 20℃; for 4h;	85%

pentachloro-2-nitro-1,3-butadiene (61351-34-6) + para-butoxyaniline (4344-55-2) → N,N'-bis(4-butoxyphenyl)-3,4,4-trichloro-2-nitrobuta-1,3-diene-1,1-diamine (1585977-39-4)

Conditions	Yield
In methanol at -20 - 20℃; for 6h;	85%
In methanol Cooling;

2.6-dimethylphenol (576-26-1) + para-butoxyaniline (4344-55-2) → 4-((4-butoxyphenyl)diazenyl)-2,6-dimethylphenol

Conditions	Yield
Stage #1: para-butoxyaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: 2.6-dimethylphenol With sodium hydroxide In water at 12℃; for 0.5h; pH=9 - 10;	85%

para-butoxyaniline (4344-55-2) + p-butylphenyl isothiocyanate (23165-44-8) → N-(4-butoxy-phenyl)-N'-(4-butyl-phenyl)-thiourea

Conditions	Yield
In ethanol at 50℃; for 2h;	84%

para-butoxyaniline (4344-55-2) + propionyl chloride (79-03-8) → 4-Butoxy-propionanilid (27817-15-8)

Conditions	Yield
With pyridine In toluene	83.5%

para-butoxyaniline (4344-55-2) + 4-formylphenyl 4'-formylbenzoate (219595-78-5) → 4-{[(E)-4-Butoxy-phenylimino]-methyl}-benzoic acid 4-{[(E)-4-butoxy-phenylimino]-methyl}-phenyl ester

Conditions	Yield
With acetic acid In ethanol at 20℃; Condensation;	83%

Upstream product

• 109-65-9 1-bromo-butane 
• 123-30-8 4-amino-phenol 
• 109-69-3 n-Butyl chloride 
• 100-02-7 4-nitro-phenol 
• 106-40-1 4-bromo-aniline 
• 71-36-3 butan-1-ol 
• 99-96-7 4-hydroxy-benzoic acid 
• 619-57-8 p-hydroxybenzamide 
• 112-36-7 3,6,9-trioxaundecane 
• 127-19-5 N,N-dimethyl acetamide 
• 66-71-7 1,10-Phenanthroline 
• 540-37-4 p-aminoiodobenzene 
• 103-90-2 4-acetaminophenol 
• 100-17-4 para-methoxynitrobenzene 

Downstream Products

• 101288-68-0 thioisonicotinic acid-(4-butoxy-anilide) 
• 28439-86-3 4-butoxyphenyl isocyanate 
• 95131-06-9 N-(4-butoxy-phenyl)-N'-(4-[2]pyridyl-phenyl)-thiourea 
• 107524-91-4 N,N-diethyl-N'-(4-butoxy-phenyl)-ethylenediamine 
• 27817-15-8 4-Butoxy-propionanilid 
• 14921-46-1 <4-Methoxybenzal>-4-butoxy-anilin 
• 245442-77-7 C₅₈H₆₆N₄O₄ 
• 139328-26-0 4-n-butyloxy-2',4'-dihydroxyazobenzene 
• 183019-19-4 1-(4-butoxyphenyl)-1H-imidazole 
• 3021-36-1 4-hydroxy phenyl azo 4'-butyloxy benzene 
• 170622-07-8 Methyl 5-(((4-(1-butyloxy)phenyl)amino)carbonyl)-3-chloropyridine-2-carboxylate 
• 501673-61-6 1-(tert-Butoxycarbonyl)-4-[(4-butoxyphenyl)amino]piperidine 
• 110662-13-0 4,4'-di-n-butoxydiphenylamine 

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