16245-79-7

Basic information

• Product Name: 4-N-OCTYLANILINE
• Synonyms: Benzenamine, 4-octyl-;4-OCTYLANILINE;4-N-OCTYLANILINE;P-OCTYLANILINE;TIMTEC-BB SBB008315;Octylaniline;4-N-OCTYLANILINE 95+%;4-Octylphenylamine
• CAS NO: 16245-79-7
• Molecular Formula: C₁₄H₂₃N
• Molecular Weight: 205.34
• EINECS: 240-358-7
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Alkyl;Alkylanilines;Anilines (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Amines;C11 to C38;Nitrogen Compounds
• Mol File: 16245-79-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 17°C
• Boiling Point: 175 °C13 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Light yellow to tan-brown liquid, aromatic amine odor
• Density: 0.898 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000598mmHg at 25°C
• Refractive Index: n20/D 1.516(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.96±0.10(Predicted)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: 4-N-OCTYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-N-OCTYLANILINE(16245-79-7)
• EPA Substance Registry System: 4-N-OCTYLANILINE(16245-79-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 16245-79-7(Hazardous Substances Data)

Usage

Chemical Properties

Orange liquid

Uses

Different sources of media describe the Uses of 16245-79-7 differently. You can refer to the following data:
1. 4-Octylaniline can be been used as an extractant during the extraction of microgram level concentrations of ruthenium(IV) from halide medium. It can also been used in the synthesis of selective benzimidazole based analogs of sphingosine-1-phosphate.
2. 4-Octylaniline has been used as an extractant during the extraction of microgram level concentrations of ruthenium(IV) from halide medium. It has also been used in the synthesis of selective benzimidazole based analogs of sphingosine-1-phosphate.

General Description

Micrometer-sized oil droplet of 4-octylaniline containing 5 mol% of an amphiphilic catalyst exhibits a self-propelled motion, producing tiny oil droplets. Kinetics of proton transfer facilitated by 4-octylaniline across the water/1,2-dichloroethane interface has been investigated by cyclic voltammetry and ac impedance.

Synthetic route

C8H17ZnBr*LiCl + 4-bromo-aniline (106-40-1) → 4-octylaniline (16245-79-7)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran at 25℃; for 2h; Inert atmosphere;	92%

(E)-1-nitro-4-(oct-1-en-1-yl)benzene → 4-octylaniline (16245-79-7)

Conditions	Yield
1% Pd/C In methanol at 20℃; for 2h; Inert atmosphere;	85%
With Pd-C In methanol	85%

1-nitro-4-(oct-1-yn-1-yl)benzene (326487-53-0) → 4-octylaniline (16245-79-7)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate under 3750.38 Torr; for 3h;	66%

octanol (111-87-5) + aniline (62-53-3) → 4-octylaniline (16245-79-7)

Conditions	Yield
With zinc(II) chloride at 255 - 258℃; for 21h;	48.7%
(i)CoCl2, (ii) aq. NH3; Multistep reaction;

9-octyl-9-bora-bicyclo[3.3.1]nonane (30089-00-0) + para-nitrophenyl triflate (17763-80-3) → 4-octylaniline (16245-79-7) + 1-(4-nitro-phenyl)-octane (78723-40-7)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 85℃; for 5h;	A 30% B 48%

N-octylaniline (3007-71-4) → 4-octylaniline (16245-79-7) + 4,N-dioctyl-aniline

Conditions	Yield
With cobalt(II) chloride at 212℃;

4'-aminooctanoylphenone (63884-78-6) → 4-octylaniline (16245-79-7)

Conditions	Yield
With hydrogenchloride; amalgamated zinc

Octylbenzene (2189-60-8) → 4-octylaniline (16245-79-7) + 2-octylaniline (37413-50-6)

Conditions	Yield
With hydrogen; nitric acid; nickel 1) 96 percent H2SO4, 35 deg C to 45 deg C, 1.5 h, 2) 120 deg C, 100 atm, 2 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

Octylbenzene (2189-60-8) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multistep reaction;
Stage #1: Octylbenzene With aluminum (III) chloride; acetyl chloride Stage #2: Schmidt reaction;

N-octylaniline (3007-71-4) + cobalt (II)-chloride → 4-octylaniline (16245-79-7) + 4,N-dioctyl-aniline + aniline (62-53-3)

Conditions	Yield
at 212℃;

octanol (111-87-5) + chloro zinc aniline → 4-octylaniline (16245-79-7)

Conditions	Yield
at 270 - 280℃; ueber mehrere Stufen;

N-[4-[2-(trimethylammonio)ethoxy]benzylidene]-4-octylaniline bromide → 4-octylaniline (16245-79-7) + 2-(4-formylphenoxy)-N,N,N-trimethylethan-1-aminium bromide

Conditions	Yield
With water at 25℃; for 0.00833333h; pH=4.8 - 5.4; Product distribution; sonication;

1-Chlorooctane (111-85-3) + sodium → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / AlCl3 / 0.17 h / 60 °C 2: 1) 78 percent nitric acid, 2) H2 / 2) Raney nickel / 1) 96 percent H2SO4, 35 deg C to 45 deg C, 1.5 h, 2) 120 deg C, 100 atm, 2 h View Scheme

benzene (71-43-2) + dimethoxycarbonyl-β-resorcylic acid-chloride → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / AlCl3 / 0.17 h / 60 °C 2: 1) 78 percent nitric acid, 2) H2 / 2) Raney nickel / 1) 96 percent H2SO4, 35 deg C to 45 deg C, 1.5 h, 2) 120 deg C, 100 atm, 2 h View Scheme

1-Iodooctane (629-27-6) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: cobalt (II)-chloride / 212 °C View Scheme

1-(4-chlorophenyl)-5,5-dimethylhexan-1-one (7295-52-5) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuCl; aqueous NH3 / 250 - 270 °C 2: amalgamated zinc; aqueous HCl View Scheme

aniline (62-53-3) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: cobalt (II)-chloride / 212 °C View Scheme

chlorobenzene (108-90-7) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: AlCl3 2: CuCl; aqueous NH3 / 250 - 270 °C 3: amalgamated zinc; aqueous HCl View Scheme

n-octanoic acid chloride (111-64-8) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: AlCl3 2: CuCl; aqueous NH3 / 250 - 270 °C 3: amalgamated zinc; aqueous HCl View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride 2: hydrazine 3: aluminum (III) chloride; acetyl chloride View Scheme

N-(4-[2-[trimethylammonio]ethoxy]benzylidene)-4-n-octylaniline bromide (820976-33-8) → 4-octylaniline (16245-79-7) + 2-(4-formylphenoxy)-N,N,N-trimethylethan-1-aminium bromide

Conditions	Yield
With BF2(NC4H(CH3)2)2CO(CH2)10C3H4N2(1+)*Cl(1-)=BF2(NC4H(CH3)2)2CO(CH2)10C3H4N2Cl

n-octyne (629-05-0) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; N-ethyl-N,N-diisopropylamine / acetonitrile / 0.33 h / Inert atmosphere 1.2: 50 °C / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 3750.38 Torr View Scheme

n-octanophenone (1674-37-9) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine 2: aluminum (III) chloride; acetyl chloride View Scheme

benzene (71-43-2) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride 2: hydrazine 3: aluminum (III) chloride; acetyl chloride View Scheme

para-nitrophenyl bromide (586-78-7) → 4-octylaniline (16245-79-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate / water 2: Pd-C / methanol View Scheme

4-octylaniline (16245-79-7) + acetic anhydride (108-24-7) → N-(4-octylphenyl)acetamide (37593-11-6)

Conditions	Yield
at 20℃; for 1h;	100%
for 1h;	100%
sulfuric acid at 50℃; for 1h;	95%

di-tert-butyl dicarbonate (24424-99-5) + 4-octylaniline (16245-79-7) → p-octyl-N-t-butoxycarbonylaniline

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃; for 21h; Cooling with ether-dry ice;	100%
With triethylamine at 20 - 50℃; Inert atmosphere of N2;
With triethylamine In tetrahydrofuran at 25℃; for 21h; Inert atmosphere;

3,3',4,4'-biphenyltetracarboxylic anhydride (2420-87-3) + 4-octylaniline (16245-79-7) → 3,3′,4,4′‐biphenyltetracarboxy‐N,N′‐bis‐(4‐n‐octylphenyl)diimide

Conditions	Yield
In neat (no solvent) for 0.25h; Solvent; Time; Milling;	99%

2,4-dichloro-1,5-dinitrobenzene (3698-83-7) + 4-octylaniline (16245-79-7) → 4,6-dinitro-N,N'-bis(4-octylphenyl)-benzene-1,3-diamine (1000054-49-8)

Conditions	Yield
In ethanol at 80℃;	98%

4-octylaniline (16245-79-7) → 2-bromo-4-octylaniline

Conditions	Yield
With N-Bromosuccinimide; ammonium acetate In acetonitrile at 0 - 20℃; Inert atmosphere; Schlenk technique;	97%
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; Inert atmosphere;	92.5%

4-octylaniline (16245-79-7) + Boc-O-benzyl-D-threonine (69355-99-3) → [(1R,2S)-2-Benzyloxy-1-(4-octyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester (868553-64-4)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h;	96%

4-octylaniline (16245-79-7) → 2-iodo-4-n-octylaniline (876290-12-9)

Conditions	Yield
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; calcium carbonate In methanol; dichloromethane at 20℃; for 2h;	96%
With dihydrogen peroxide; iodine In methanol at 20℃;	86%
With dihydrogen peroxide; iodine In methanol at 20℃;	86%
With N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; dichloromethane at 20℃; for 4h;	82%
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; calcium carbonate In methanol; dichloromethane at 20℃; for 2.5h;	73%

2,4-dichloro-1,5-dinitrobenzene (3698-83-7) + 4-octylaniline (16245-79-7) → N-(5-chloro-2,4-dinitrophenyl)-4-octylaniline

Conditions	Yield
In ethanol at 20℃;	96%

bromobenzene (108-86-1) + 4-octylaniline (16245-79-7) → 4-octyl-N,N-diphenylaniline (850354-75-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene for 16h; Inert atmosphere; Reflux;	95%

4-octylaniline (16245-79-7) + 1-amino-naphthalene (134-32-7) → C24H29N3

Conditions	Yield
Stage #1: 4-octylaniline With hydrogenchloride; sodium nitrite In ethanol; water at 0 - 5℃; for 1h; Stage #2: 1-amino-naphthalene In ethanol at 0 - 5℃; for 4h;	95%

3,3'dibromo-2,2'-bithiophene (51751-44-1) + 4-octylaniline (16245-79-7) → N-[4-octylphenyl]dithieno[3,2-b:2',3'-d]pyrrole (1443677-01-7)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	92%
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux;	92%

4-octylaniline (16245-79-7) + 1,2-dichloro-ethane (107-06-2) → N-(p-octylphenyl)-2,4,6-trimethylpyridinium sulfoacetate

Conditions	Yield
In 2,4,6-trimethylpyrylium sulfoacetate	89%

4-octylaniline (16245-79-7) + phenol (108-95-2) → 4-((4-octylphenyl)diazenyl)phenol (104526-72-9)

Conditions	Yield
Stage #1: 4-octylaniline With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice; Stage #2: phenol With sodium hydroxide In ethanol; water at 0℃;	88%
With hydrogenchloride; sodium carbonate; sodium nitrite In water
Stage #1: 4-octylaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: phenol With sodium carbonate In water at 0℃; for 1h;

4-octylaniline (16245-79-7) + 2-(4-formylphenoxy)-N,N,N-trimethylethan-1-aminium bromide → N-(4-[2-[trimethylammonio]ethoxy]benzylidene)-4-n-octylaniline bromide (820976-33-8)

Conditions	Yield
With triethylamine In methanol at 85℃; for 50h;	88%

1-Bromo-2-iodobenzene (583-55-1) + 4-octylaniline (16245-79-7) → 2-bromo-N-(4-octylphenyl)aniline (1380244-71-2)

Conditions	Yield
With sodium t-butanolate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 100℃; for 24h; Inert atmosphere;	88%

4-octylaniline (16245-79-7) + 10-(p-formylphenyloxy)decyltrimethylammonium bromide (73000-51-8) → [10-[4'-(4''-octylphenylimino)phenoxy]decyl]trimethylammonium bromide

Conditions	Yield
With acetic acid In ethanol for 12h; Heating;	87%

ethyl 3-isocyanatopropanoate (5100-34-5) + 4-octylaniline (16245-79-7) → ethyl 3-(3-(4-octylphenyl)ureido)propanoate (1220972-29-1)

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Reflux;	87%

4-octylaniline (16245-79-7) → 2,6-diiodo-4-octylaniline (1313995-16-2)

Conditions	Yield
With pyridine iodine monochloride In methanol Reflux;	87%

p-n-octylbenzoyl chloride (50606-97-8) + 4-octylaniline (16245-79-7) → 4-octyl-N-(4-octylphenyl)benzamide (1375477-02-3)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 18h;	87%

1-Bromo-3-iodobenzene (591-18-4) + 4-octylaniline (16245-79-7) → 3-bromo-N-(3-bromophenyl)-N-(4-octylphenyl)aniline

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 120℃; for 4h; Inert atmosphere;	87%

5-bromoisophthalic acid (23351-91-9) + 4-octylaniline (16245-79-7) → C36H47BrN2O2

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 24h;	87%

1-bromo-4-octylbenzene (51554-93-9) + 4-octylaniline (16245-79-7) → 4,4'-dioctyldiphenylamine (101-67-7)

Conditions	Yield
With sodium t-butanolate; XPhos In toluene at 70℃; for 0.25h; Buchwald-Hartwig amination; Inert atmosphere;	86%
With η5‐cyclopentadienyl‐η3‐1‐phenylallylpalladium; sodium t-butanolate; XPhos In toluene at 90℃; Inert atmosphere;	86%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 1h; Inert atmosphere; Reflux;	78%

4-octylaniline (16245-79-7) → 4-octylbenzenediazonium tetrafluoroborate

Conditions	Yield
Stage #1: 4-octylaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h; Stage #2: With tetrafluoroboric acid In water	85%

4-octylaniline (16245-79-7) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N-(4-octylphenyl)acetamide

Conditions	Yield
In toluene at 110℃; for 4h;	83%

2,5-dibromo-1,4-benzoquinone (1633-14-3) + 4-octylaniline (16245-79-7) → 2,5-dibromo-N,N'-bis-(4-octyl-phenyl)-benzene-1,4-diamine (599575-85-6)

Conditions	Yield
With titanium tetrachloride In chlorobenzene at 135℃; for 48h;	82%

4-octylaniline (16245-79-7) + 1,1′-bis(2,4-dinitrophenyl)-[4,4′-bipyridine]-1,1′-diium chloride (41168-79-0) → 1,1'-bis(4-n-octylphenyl)-4,4'-bipyridilium dichloride

Conditions	Yield
In ethanol; water for 18h; Heating;	82%
With air In ethanol; water at 60℃; for 18h;	63%

2-chloroethyl isothiocyanate (1943-83-5) + 4-octylaniline (16245-79-7) → 1-(2-Chloro-ethyl)-3-(4-octyl-phenyl)-urea

Conditions	Yield
at 20℃;	81%
for 6h; Ambient temperature;

Upstream product

• 3007-71-4 N-octylaniline 
• 30089-00-0 9-octyl-9-bora-bicyclo[3.3.1]nonane 
• 17763-80-3 para-nitrophenyl triflate 
• 71-43-2 benzene 
• 108-90-7 chlorobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 1674-37-9 n-octanophenone 
• 326487-53-0 1-nitro-4-(oct-1-yn-1-yl)benzene 
• 629-05-0 n-octyne 
• 820976-33-8 N-(4-[2-[trimethylammonio]ethoxy]benzylidene)-4-n-octylaniline bromide 
• 106-40-1 4-bromo-aniline 
• 111-64-8 n-octanoic acid chloride 
• 62-53-3 aniline 
• 7295-52-5 1-(4-chlorophenyl)-5,5-dimethylhexan-1-one 

Downstream Products

• 1167-42-6 toluene-4-sulfonic acid-(4-octyl-anilide) 
• 97586-29-3 5-Ethoxy-2-{[(E)-4-octyl-phenylimino]-methyl}-phenol 
• 134098-62-7 N-<4-(4-octylphenylazo)phenyl>-monoaza-15-crown-5 
• 183662-85-3 1-{(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-[(4-octyl-phenylamino)-methyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 448959-68-0 [2-benzyloxy-1-(4-octyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 448959-80-6 [2-(di-tert-butoxy-phosphoryloxy)-1-(4-octyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 133826-41-2 4-n-octyliodobenzene 
• 876290-12-9 2-iodo-4-n-octylaniline 
• 400858-36-8 [(4-dimethylaminophenyl)methyl](4-octylphenyl)amine 

Relevant articles and documents

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Self-propelled oil droplets consuming "Fuel" surfactant

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