104-42-7

Basic information

• Product Name: 4-Dodecylaniline
• Synonyms: 4-DODECYLANILINE;P-DODECYLANILINE;4-dodecyl-benzenamin;4-dodecyl-Benzenamine;4-n-Dodecylamine;Benzenamine, 4-dodecyl-;Benzenamine,4-dodecyl-;4-dodecylibenzenamine
• CAS NO: 104-42-7
• Molecular Formula: C₁₈H₃₁N
• Molecular Weight: 261.45
• EINECS: 203-201-3
• Product Categories: Intermediates of Dyes and Pigments;Alkyl;Alkylanilines;Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 104-42-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 35-39 °C(lit.)
• Boiling Point: 220-221 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /Solid
• Density: 0.8907 (estimate)
• Vapor Pressure: 1.74E-05mmHg at 25°C
• Refractive Index: 1.5080 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.95±0.10(Predicted)
• BRN: 2646305
• CAS DataBase Reference: 4-Dodecylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Dodecylaniline(104-42-7)
• EPA Substance Registry System: 4-Dodecylaniline(104-42-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 9
• Hazardous Substances Data: 104-42-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 104-42-7 differently. You can refer to the following data:
1. 4-Dodecylaniline has been used: in the synthesis of sodium 4-dodecylphenylazosulfonate, to investigate the water solubilization of single-walled carbon nanotubes (SWNTs), in proton transfer step during molecular oxygen (O2) reduction by decamethylferrocene (DMFc).
2. 4-Dodecylaniline has been used:in the synthesis of sodium 4-dodecylphenylazosulfonateto investigate the water solubilization of single-walled carbon nanotubes (SWNTs)in proton transfer step during molecular oxygen (O2) reduction by decamethylferrocene (DMFc)

InChI:InChI=1/C18H31N/c1-2-3-4-5-6-7-8-9-10-11-12-17-13-15-18(19)16-14-17/h13-16H,2-12,19H2,1H3

Synthetic route

1-dodecyl alcohol (112-53-8) + aniline (62-53-3) → 4-dodecylaniline (104-42-7)

Conditions	Yield
With zinc(II) chloride at 255 - 258℃; for 21h;	45%

1-(dodec-1-yn-1-yl)-4-nitrobenzene (1022975-57-0) → 4-dodecylaniline (104-42-7)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol; ethyl acetate at 20℃; under 15001.5 Torr; for 24h; Autoclave;	41%

N-dodecylaniline (3007-74-7) + aniline hydrochloride (142-04-1) → 4-dodecylaniline (104-42-7)

Conditions	Yield
With zinc(II) chloride at 240℃;

N-dodecylaniline (3007-74-7) → 4-dodecylaniline (104-42-7) + 4,N-didodecyl-aniline (854306-07-3)

Conditions	Yield
With cobalt(II) chloride at 247℃;

1-chloro-4-dodecylbenzene (101874-34-4) → 4-dodecylaniline (104-42-7)

Conditions	Yield
With ammonia; water; copper(l) chloride

4'-aminododecanoylphenone (101778-21-6) → 4-dodecylaniline (104-42-7)

Conditions	Yield
With hydrogenchloride; amalgamated zinc
With potassium hydroxide; hydrazine hydrate; diethylene glycol

p'-(ω-(trimethylammonio)butyloxy)-p-(dodecylbenzylidene)aniline (72617-54-0) → 4-dodecylaniline (104-42-7) + 4-(p-formylphenyloxy)butyltrimethylammonium bromide (72617-53-9)

Conditions	Yield
With phosphate buffer In water at 30℃; Rate constant; Kinetics; ΔE(excit.); influence of pH and concentration of azometine on velocity constant;

[10-(4-{[(E)-4-Dodecyl-phenylimino]-methyl}-phenoxy)-decyl]-trimethyl-ammonium; bromide (72621-04-6) → 4-dodecylaniline (104-42-7) + 10-(p-formylphenyloxy)decyltrimethylammonium bromide (73000-51-8)

Conditions	Yield
With phosphate buffer In water at 30℃; Rate constant; Kinetics; ΔE(excit.); influence of pH and concentration of azometine on velocity constant, var. solvents;

(4-{[(E)-4-Dodecyl-phenylimino]-methyl}-phenyl)-trimethyl-ammonium; bromide (70987-23-4) → 4-dodecylaniline (104-42-7) + 4-formyl-N,N,N-trimethyl-benzenaminium bromide (72621-22-8)

Conditions	Yield
With phosphate buffer In water at 30℃; Rate constant; Kinetics; ΔE(excit.); influence of pH and concetration of azometine on velocity constant;

N-dodecylaniline (3007-74-7) + cobalt (II)-chloride → 4-dodecylaniline (104-42-7) + 4,N-didodecyl-aniline (854306-07-3) + aniline (62-53-3)

Conditions	Yield
at 250℃;

n-dodecanoyl chloride (112-16-3) → 4-dodecylaniline (104-42-7)

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: AlCl3; CS2 2: ethanolic NaOH 3: N2H4+H2O; KOH; diethylene glycol View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride 2: hydrazine 3: aluminum (III) chloride; acetyl chloride View Scheme

1-Iodododecane (4292-19-7) → 4-dodecylaniline (104-42-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: cobalt (II)-chloride / 247 °C View Scheme

1-(4-chloro-phenyl)-dodecan-1-one (408333-43-7) → 4-dodecylaniline (104-42-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuCl; aqueous NH3 / 250 - 270 °C 2: amalgamated zinc; aqueous HCl View Scheme
Multi-step reaction with 4 steps 1: aluminium isopropylate; isopropyl alcohol 2: KHSO4 / 200 °C / 10 Torr 3: Raney nickel; ethanol / Hydrogenation 4: water; CuCl; NH3 View Scheme

acetic acid-(4-lauroyl-anilide) (112508-20-0) → 4-dodecylaniline (104-42-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanolic NaOH 2: N2H4+H2O; KOH; diethylene glycol View Scheme

aniline (62-53-3) → 4-dodecylaniline (104-42-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: cobalt (II)-chloride / 247 °C View Scheme

chlorobenzene (108-90-7) → 4-dodecylaniline (104-42-7)

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

Acetanilid (103-84-4) → 4-dodecylaniline (104-42-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: AlCl3; CS2 2: ethanolic NaOH 3: N2H4+H2O; KOH; diethylene glycol View Scheme

1ξ-(4-chloro-phenyl)-dodec-1-ene (101887-54-1) → 4-dodecylaniline (104-42-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; ethanol / Hydrogenation 2: water; CuCl; NH3 View Scheme

1-(4-chloro-phenyl)-dodecan-1-ol (101874-35-5) → 4-dodecylaniline (104-42-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: KHSO4 / 200 °C / 10 Torr 2: Raney nickel; ethanol / Hydrogenation 3: water; CuCl; NH3 View Scheme

1-dodecene (112-41-4) + aniline (62-53-3) → 4-dodecylaniline (104-42-7)

Conditions	Yield
With aluminum (III) chloride; methyl tributylammonium chloride at 46 - 160℃; for 27.8h;

1-dodecylbenzene (123-01-3) → 4-dodecylaniline (104-42-7)

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

dodecanophenone (1674-38-0) → 4-dodecylaniline (104-42-7)

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

benzene (71-43-2) → 4-dodecylaniline (104-42-7)

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

p-nitrobenzene iodide (636-98-6) → 4-dodecylaniline (104-42-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / 2 h / 80 °C / Inert atmosphere 2: 5%-palladium/activated carbon; hydrogen / ethanol; ethyl acetate / 24 h / 20 °C / 15001.5 Torr / Autoclave View Scheme

1-dodecyne (765-03-7) → 4-dodecylaniline (104-42-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / 2 h / 80 °C / Inert atmosphere 2: 5%-palladium/activated carbon; hydrogen / ethanol; ethyl acetate / 24 h / 20 °C / 15001.5 Torr / Autoclave View Scheme

2-dodecylaniline (40938-30-5) → 4-dodecylaniline (104-42-7)

Conditions	Yield
With hydrogen sulfide

4-dodecylaniline (104-42-7) + 5,11,17,23-tetraformyl-25,26,27,28-tetrakis(methoxy)calix[4]arene (148402-69-1) → C108H148N4O4 (143519-67-9)

Conditions	Yield
With 4 A molecular sieve In chloroform for 29h; Heating;	100%

cobalt(II) perchlorate hydrate + 4-dodecylaniline (104-42-7) → Co(NC5H4NNC6H4NC6H4(CH2)11CH3)2(1+)*ClO4(1-)=(Co(NC5H4NNC6H4NC6H4(CH2)11CH3)2)ClO4

Conditions	Yield
In not given ligand reacted with Co salt instaneously;	99%

cycl-isopropylidene malonate (2033-24-1) + 4-dodecylaniline (104-42-7) + trimethyl orthoformate (149-73-5) → C25H37NO4

Conditions	Yield
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate for 1h; Reflux; Stage #2: 4-dodecylaniline for 2h; Reflux;	98%

4-dodecylaniline (104-42-7) + acryloyl chloride (814-68-6) → N-(para(dodecyl)phenyl)acrylamide (372941-32-7)

Conditions	Yield
Stage #1: 4-dodecylaniline With 1H-imidazole; triethylamine In tetrahydrofuran for 0.166667h; Stage #2: acryloyl chloride In tetrahydrofuran at 0 - 25℃; for 15.33h; Inert atmosphere;	95%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 15.16h; Inert atmosphere;	95%

4-dodecylaniline (104-42-7) → 4-dodecyl-2-iodoaniline

Conditions	Yield
With iodine; sodium hydrogencarbonate In water; toluene at 20℃; Inert atmosphere; Schlenk technique;	94%

4-dodecylaniline (104-42-7) + epichlorohydrin (106-89-8) → N,N-bis(2-hydroxy-3-chloropropyl)dodecylaniline

Conditions	Yield
In ethanol at 20℃; for 18h;	91.5%

4-dodecylaniline (104-42-7) + 2,2'-bipyridine-6,6'-dicarbaldehyde (49669-26-3) → C48H66N4

Conditions	Yield
With acid	90%

4-dodecylaniline (104-42-7) + ortho-chlorobenzoic acid (118-91-2) → 2-((4-dodecylphenyl)amino)benzoic acid (1373551-67-7)

Conditions	Yield
With copper diacetate; potassium carbonate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Reflux;	90%

4-dodecylaniline (104-42-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N'-(4-dodecylphenyl)-N,N-dimethylethanimidamide

Conditions	Yield
In acetonitrile at 80℃; under 760.051 Torr; for 0.25h;	90%

4-dodecylaniline (104-42-7) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(4-dodecylphenyl)acetamide

Conditions	Yield
Stage #1: 4-dodecylaniline With potassium carbonate In dichloromethane at 20℃; for 0.5h; Stage #2: chloroacetyl chloride In dichloromethane for 4h; Reflux;	89%
Stage #1: chloroacetyl chloride With potassium carbonate In dichloromethane at 20℃; for 0.5h; Stage #2: 4-dodecylaniline In dichloromethane for 4h; Reflux;	89%

3,5-dihydroxyphenol (108-73-6) + 4-dodecylaniline (104-42-7) → 1,3,5-tris(4-n-dodecylanilino)benzene (1198578-78-7)

Conditions	Yield
iodine In toluene at 130℃; for 2h;	87.8%

4-dodecylaniline (104-42-7) + 2-hydroxy-4-n-dodecyloxybenzaldehyde (111772-62-4) → 4-(dodecyloxy)-N-(4-dodecyl)-phenyl-2-hydroxybenzaldimine

Conditions	Yield
With acetic acid In ethanol for 18h; Reflux;	86%

trans-(2,6-diformyl-3,5-bis(2,5,8,11-tetraoxadecyl)phenyl)chlorobis(triphenylphosphine)palladium (1333471-38-7) + 4-dodecylaniline (104-42-7) → (3,5-bis(2,5,8,11-tetraoxadecyl)-2,6-bis(N-4-dodecylphenylimino)phenyl)chloropalladium (1333471-36-5)

Conditions	Yield
With (H2N)2CO*H2O2 In acetonitrile (N2); refluxing soln. of palladium compd. and aniline deriv. in anhyd. CH3CN for 72 h, cooling to 25°C, addn. of urea hydrogen peroxide, stirring at 50°C for 11 h; evapn., chromy. (silica gel, 0-5% methanol/ethyl acetate), gel permeating chromy. (CHCl3), elem. anal.;	85%

4-dodecylaniline (104-42-7) + phenylpropyolic acid (637-44-5) → N-(p-dodecylphenyl)-3-phenylpropiolamide

Conditions	Yield
Stage #1: 4-dodecylaniline; phenylpropyolic acid With dmap In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;	80%

4-dodecylaniline (104-42-7) + 4'-formyl-2-diphenylphosphino-acetophenone (147622-34-2) → N-<4-(2-diphenylphosphinoacetyl)benzylidene>-4-(dodecyl)aniline

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 2h; Heating;	79%

4-dodecylaniline (104-42-7) + 1,2-epox-[60]fullerene (148347-18-6, 139141-81-4) → 1-(4-dodecylanilino)-2-hydroxy-1,2-dihydro[60]fullerene (1092060-75-7) + 5'-dodecylindolino[2',3':1,2][60]fullerene (1092060-70-2)

Conditions	Yield
With sepiolite In chlorobenzene at 100℃;	A n/a B 78%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4-dodecylaniline (104-42-7) → (4,6-Dichloro-[1,3,5]triazin-2-yl)-(4-dodecyl-phenyl)-amine (90850-59-2)

Conditions	Yield
With sodium hydroxide In water; acetone 1. 0 deg C, 1 h; 2. 20 deg C, 1 h;	76%

pyridine-4-carbaldehyde (872-85-5) + 4-dodecylaniline (104-42-7) → C24H34N2

Conditions	Yield
With acetic acid	76%

2-chloroethyl isothiocyanate (1943-83-5) + 4-dodecylaniline (104-42-7) → 4-dodecyl-1-[3-(2-chloroethyl)ureido]benzene

Conditions	Yield
at 20℃;	74%
for 6h; Ambient temperature;

4-dodecylaniline (104-42-7) → 2,6-dibromo-4-dodecylaniline

Conditions	Yield
With benzyltriethylammonium tribromide; calcium carbonate In methanol; dichloromethane at 20℃; for 1h;	74%
With hydrogenchloride; bromine In water for 3h;

4-dodecylaniline (104-42-7) + Propiolic acid (471-25-0) → N-(p-dodecylphenyl)propiolamide

Conditions	Yield
Stage #1: 4-dodecylaniline; Propiolic acid With dmap In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;	74%

4-dodecylaniline (104-42-7) + (S)-4-(3,7-dimethyloctyloxy)phenyl 4-formylbenzoate → (S)-4-(3,7-dimethyloctyloxy)phenyl 4-{[4-(dodecyl)phenylimino]methyl}benzoate

Conditions	Yield
With acetic acid In ethanol at 100℃; Inert atmosphere;	73%

4-dodecylaniline (104-42-7) + 2,3-bis(tert-butoxycarbonyl amino)propanoic acid (104010-92-6) → di-tert-butyl (3-((4-dodecylphenyl)amino)-3-oxopropane-1,2-diyl)dicarbamate

Conditions	Yield
Stage #1: 2,3-bis(tert-butoxycarbonyl amino)propanoic acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 2h; Inert atmosphere; Stage #2: 4-dodecylaniline With dmap In chloroform at 50℃; Inert atmosphere;	72%

4-dodecylaniline (104-42-7) + N-Boc-D-serine(Bzl)-OH (47173-80-8) → [2-benzyloxy-1-(4-decyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (448959-69-1)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine	71%

[Co(2-(phenylazo)pyridine)3](ClO4)2 + 4-dodecylaniline (104-42-7) → Co(NC5H4NNC6H4NC6H4(CH2)11CH3)2(1+)*ClO4(1-)=(Co(NC5H4NNC6H4NC6H4(CH2)11CH3)2)ClO4

Conditions	Yield
In neat (no solvent) Co complex mixed with ligand; heated on steam bath for 1 h; purified by preparative TLC (alumina, CHCl3); elem. anal.;	70%

1,4-bis(thiophen-2-yl)butane-1,4-dione (13669-05-1) + 4-dodecylaniline (104-42-7) → 1-(p-dodecylphenyl)-2,5-di(2-thienyl)pyrrole (499793-93-0)

Conditions	Yield
In acetic acid; toluene at 140 - 150℃;	69%

4-dodecylaniline (104-42-7) → 2-bromo-4-dodecylaniline (891780-19-1)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 20℃; for 20h;	66%
With sodium perborate; acetic acid; potassium bromide; sodium vanadate at 20℃; for 10h;	59%
With N-Bromosuccinimide; ammonium acetate In acetonitrile at 20℃; for 3h;

4-dodecylaniline (104-42-7) → 1-dodecyl-4-iodobenzene (170698-90-5)

Conditions	Yield
With C5H11NO2; potassium iodide	65%
Stage #1: 4-dodecylaniline With hydrogenchloride; sodium nitrite at 0℃; Stage #2: With potassium iodide at 40℃; for 0.333333h;	49%

4-dodecylaniline (104-42-7) + phenol (108-95-2) → 4-dodecyl-4’-hydroxyazobenzene (141510-15-8)

Conditions	Yield
Stage #1: 4-dodecylaniline With hydrogenchloride; sodium nitrite In tetrahydrofuran; water at 0℃; for 2h; Inert atmosphere; Stage #2: phenol With sodium carbonate; potassium carbonate In tetrahydrofuran; water at 20℃; for 12h;	65%
With hydrogenchloride; sodium carbonate; sodium nitrite In water
Stage #1: 4-dodecylaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: phenol With sodium carbonate In water at 0℃; for 1h;

Upstream product

• 3007-74-7 N-dodecylaniline 
• 142-04-1 aniline hydrochloride 
• 101874-34-4 1-chloro-4-dodecylbenzene 
• 101778-21-6 4'-aminododecanoylphenone 
• 112-53-8 1-dodecyl alcohol 
• 62-53-3 aniline 
• 72617-54-0 p'-(ω-(trimethylammonio)butyloxy)-p-(dodecylbenzylidene)aniline 
• 72621-04-6 [10-(4-{[(E)-4-Dodecyl-phenylimino]-methyl}-phenoxy)-decyl]-trimethyl-ammonium; bromide 
• 70987-23-4 (4-{[(E)-4-Dodecyl-phenylimino]-methyl}-phenyl)-trimethyl-ammonium; bromide 
• 112-16-3 n-dodecanoyl chloride 
• 4292-19-7 1-Iodododecane 
• 408333-43-7 1-(4-chloro-phenyl)-dodecan-1-one 
• 112508-20-0 acetic acid-(4-lauroyl-anilide) 
• 108-90-7 chlorobenzene 

Downstream Products

• 65833-03-6 N-(4-dodecyl-phenyl)-maleimide 
• 854306-07-3 4,N-didodecyl-aniline 
• 3663-30-7 N-acetyl-4-n-dodecylaniline 
• 56259-08-6 6-dodecyl-quinoline 
• 29246-97-7 3-hydroxy-[2]naphthoic acid-(4-dodecyl-anilide) 
• 23326-26-3 N-(4-Dodecyl-phenyl)-N'-(4-ethoxy-phenyl)-oxalamide 
• 50671-15-3 3-Nitro-4-methoxybenzolsulfo-4-dodecylanilid 
• 1627-52-7 3-methyl-isoxazole-4,5-dione 4-[(4-dodecyl-phenyl)-hydrazone] 
• 90850-59-2 (4,6-Dichloro-[1,3,5]triazin-2-yl)-(4-dodecyl-phenyl)-amine 
• 72621-09-1 [4-(3-{[(E)-4-Dodecyl-phenylimino]-methyl}-phenoxy)-butyl]-trimethyl-ammonium; bromide 
• 70987-23-4 (4-{[(E)-4-Dodecyl-phenylimino]-methyl}-phenyl)-trimethyl-ammonium; bromide 
• 72617-54-0 p'-(ω-(trimethylammonio)butyloxy)-p-(dodecylbenzylidene)aniline 
• 72621-04-6 [10-(4-{[(E)-4-Dodecyl-phenylimino]-methyl}-phenoxy)-decyl]-trimethyl-ammonium; bromide 
• 143519-67-9 C₁₀₈H₁₄₈N₄O₄ 

Relevant articles and documents

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