Product Name

  • Name

    4-N-NONYLPHENOL

  • EINECS 203-199-4
  • CAS No. 104-40-5
  • Article Data14
  • CAS DataBase
  • Density 0.933 g/cm3
  • Solubility 6.35mg/L(25 oC)
  • Melting Point 43-44 °C
  • Formula C15H24O
  • Boiling Point 330.642 °C at 760 mmHg
  • Molecular Weight 220.355
  • Flash Point 184.211 °C
  • Transport Information UN 3145 8/PG 2
  • Appearance viscous colourless liquid with a phenol-like smell
  • Safety 26-36/37/39-45-61-60
  • Risk Codes 22-34-50/53
  • Molecular Structure Molecular Structure of 104-40-5 (4-N-NONYLPHENOL)
  • Hazard Symbols CorrosiveC, DangerousN
  • Synonyms Phenol,p-nonyl- (6CI,8CI);4-n-Nonyl phenol;p-NP;p-Nonylphenol;p-n-Nonylphenol;
  • PSA 20.23000
  • LogP 4.68530

Synthetic route

1-(4-methoxyphenyl)nonane
32588-84-4

1-(4-methoxyphenyl)nonane

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
With perhydrodibenzo-18-crown-6 In toluene for 3h; Product distribution; Ambient temperature; other solvents, addition of isopropanol, other anisole derivatives;100%
With perhydrodibenzo-18-crown-6; toluene for 3h; Ambient temperature;100%
With hydrogen iodide
4-nonanoylphenol
14392-69-9

4-nonanoylphenol

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
With hydrogenchloride; mercury; zinc In ethanol for 20h; Reduction; Heating;83%
With hydrogenchloride; mercury; zinc71%
With potassium hydroxide; hydrazine hydrate 1.) diethylene glycol, reflux, 1h; 2.) reflux, 1h; Yield given. Multistep reaction;
1-(4-Benzyloxy-phenyl)-nonan-1-ol

1-(4-Benzyloxy-phenyl)-nonan-1-ol

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
With sulfuric acid; hydrogen; palladium on activated charcoal In ethyl acetate Yield given;
2,6-dibromononylphenol
103526-64-3

2,6-dibromononylphenol

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
With tritium; palladium on activated charcoal Dehalogenation;
1-<4-hydroxy-phenyl>-nonanone-(1)

1-<4-hydroxy-phenyl>-nonanone-(1)

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc; acetic acid
Nonanoyl chloride
764-85-2

Nonanoyl chloride

A

4-Nonylphenol
104-40-5

4-Nonylphenol

B

guinea pig hepatic microsomal protein

guinea pig hepatic microsomal protein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 37 percent / AlCl3 / 1,1,2,2-tetrachloro-ethane / 6 h / 50 °C
2: 83 percent / Zn(Hg); aq. HCl / ethanol / 20 h / Heating
View Scheme
phenol
108-95-2

phenol

pentacarbonyl(1-ethyloxy-3-cyclopentenyl-2-propyn-1-ylidene)tungsten

pentacarbonyl(1-ethyloxy-3-cyclopentenyl-2-propyn-1-ylidene)tungsten

A

4-Nonylphenol
104-40-5

4-Nonylphenol

B

guinea pig hepatic microsomal protein

guinea pig hepatic microsomal protein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 37 percent / AlCl3 / 1,1,2,2-tetrachloro-ethane / 6 h / 50 °C
2: 83 percent / Zn(Hg); aq. HCl / ethanol / 20 h / Heating
View Scheme
...Expand
Nonanoyl chloride
764-85-2

Nonanoyl chloride

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / AlCl3 / nitrobenzene / 8 h / Ambient temperature
2: 71 percent / Zn(Hg), HCl
View Scheme
Multi-step reaction with 2 steps
1: AlCl3 / CH2Cl2 / 1.) 0 deg C, 30 min; 0 deg C, 30 min; 2.) room temperature, overnight
2: 1.) hydrazine hydrate, 2.) KOH / 1.) diethylene glycol, reflux, 1h; 2.) reflux, 1h
View Scheme
phenol
108-95-2

phenol

m-bromo-toluene

m-bromo-toluene

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / AlCl3 / nitrobenzene / 8 h / Ambient temperature
2: 71 percent / Zn(Hg), HCl
View Scheme
p-benzyloxybenzaldehyde
4397-53-9

p-benzyloxybenzaldehyde

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Mg / tetrahydrofuran / 3 h / Ambient temperature
2: H2, cc. sulfuric acid / 5percent Pd-C / ethyl acetate
View Scheme
1-bromo-octane
111-83-1

1-bromo-octane

dipotassium-salt of <1,3,4>thiadiazolidine-2,5-dithione

dipotassium-salt of <1,3,4>thiadiazolidine-2,5-dithione

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Mg / tetrahydrofuran / 3 h / Ambient temperature
2: H2, cc. sulfuric acid / 5percent Pd-C / ethyl acetate
View Scheme
phenol
108-95-2

phenol

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3 / CH2Cl2 / 1.) 0 deg C, 30 min; 0 deg C, 30 min; 2.) room temperature, overnight
2: 1.) hydrazine hydrate, 2.) KOH / 1.) diethylene glycol, reflux, 1h; 2.) reflux, 1h
View Scheme
4-nonylphenyl acetate
32604-44-7

4-nonylphenyl acetate

4-Nonylphenol
104-40-5

4-Nonylphenol

Conditions
ConditionsYield
Stage #1: 4-nonylphenyl acetate With aluminum (III) chloride In toluene for 10h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 50℃; for 1h; Purification / work up;
3,5-di-tert-butyl-4-hydroxybenzyl acetate
14387-17-8

3,5-di-tert-butyl-4-hydroxybenzyl acetate

4-Nonylphenol
104-40-5

4-Nonylphenol

4-nonyl-2,6-di-(3,5-di-tert-butyl-4-hydroxybenzyl)phenol

4-nonyl-2,6-di-(3,5-di-tert-butyl-4-hydroxybenzyl)phenol

Conditions
ConditionsYield
With perchloric acid In benzene for 24h; Ambient temperature;100%
With perchloric acid In acetone for 24h; Ambient temperature;100%
With acid at 50℃;
4-Nonylphenol
104-40-5

4-Nonylphenol

acetic acid
64-19-7

acetic acid

C17H26O

C17H26O

Conditions
ConditionsYield
With sodium hydrogen sulfate for 3h; Reflux;100%
formaldehyd
50-00-0

formaldehyd

4-Nonylphenol
104-40-5

4-Nonylphenol

5-nonyl-2-hydroxyl phenylaldehyde
63753-10-6

5-nonyl-2-hydroxyl phenylaldehyde

Conditions
ConditionsYield
With triethylamine; magnesium chloride In toluene for 4.5h;99%
With (C4H9)3N; tin(IV) chloride In toluene at 100℃;89%
Stage #1: 4-Nonylphenol With ethylmagnesium bromide In diethyl ether at 20℃;
Stage #2: formaldehyd With N,N,N,N,N,N-hexamethylphosphoric triamide In benzene Heating;		82.7%
4-Nonylphenol
104-40-5

4-Nonylphenol

acetic anhydride
108-24-7

acetic anhydride

4-nonylphenyl acetate
32604-44-7

4-nonylphenyl acetate

Conditions
ConditionsYield
montmorillonite acid clay for 0.166667h; microwave irradiation;94%
4-Nonylphenol
104-40-5

4-Nonylphenol

4-bromo-5-nitrophthalonitrile
206268-72-6

4-bromo-5-nitrophthalonitrile

4-nitro-5-(4-nonylphenoxy)phthalonitrile

4-nitro-5-(4-nonylphenoxy)phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In water; N,N-dimethyl-formamide at 25℃; for 0.5h;94%
4,4'-methylenebis(cyclohexyl urea)

4,4'-methylenebis(cyclohexyl urea)

4-Nonylphenol
104-40-5

4-Nonylphenol

4,4'-(4,4'-carbonylbis(azanediyl)bis(cyclohexane-4,1-diyl)bis(methylene))bis(cyclohexane-4,1-diyl)di(carbamic acid(4-nonylphenyl)ester)

4,4'-(4,4'-carbonylbis(azanediyl)bis(cyclohexane-4,1-diyl)bis(methylene))bis(cyclohexane-4,1-diyl)di(carbamic acid(4-nonylphenyl)ester)

Conditions
ConditionsYield
Reflux; Large scale;92%
4-Nonylphenol
104-40-5

4-Nonylphenol

2,4-tolylene diurea
10097-06-0

2,4-tolylene diurea

5,5'-carbonylbis(azanediyl)bis(2-methyl-5,1-phenylene)di(carbamic acid(4-nonylphenyl)ester)

5,5'-carbonylbis(azanediyl)bis(2-methyl-5,1-phenylene)di(carbamic acid(4-nonylphenyl)ester)

Conditions
ConditionsYield
Reflux; Large scale;89%
4-Nonylphenol
104-40-5

4-Nonylphenol

2,6-dibromononylphenol
103526-64-3

2,6-dibromononylphenol

Conditions
ConditionsYield
With bromine In water at 20 - 30℃; for 0.5h;87%
With bromine In acetic acid at 20℃; for 24h; Bromination;
With bromine
4-Nitrophthalonitrile
31643-49-9

4-Nitrophthalonitrile

4-Nonylphenol
104-40-5

4-Nonylphenol

C23H26N2O

C23H26N2O

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 14h; Inert atmosphere;85%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 14h; Inert atmosphere;85%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 14h; Inert atmosphere;85%
chloroform
67-66-3

chloroform

4-Nonylphenol
104-40-5

4-Nonylphenol

5-nonyl-2-hydroxybenzaldehyde oxime
50849-47-3

5-nonyl-2-hydroxybenzaldehyde oxime

Conditions
ConditionsYield
Stage #1: chloroform; 4-Nonylphenol With hydroxylamine; sodium hydroxide In water; isopropyl alcohol at 40 - 68℃; for 2h; Reimer-Tiemann Phenol Formylation;
Stage #2: With sulfuric acid In water; isopropyl alcohol at 20℃; pH=< 7; Reagent/catalyst; Reimer-Tiemann Phenol Formylation;		82.9%
nitromethane
75-52-5

nitromethane

4-Nonylphenol
104-40-5

4-Nonylphenol

5-nonylsalicylaldoxime
50849-47-3

5-nonylsalicylaldoxime

Conditions
ConditionsYield
With aluminium trichloride at 80℃; for 5h;80%
4-Nonylphenol
104-40-5

4-Nonylphenol

ethyl iodide
75-03-6

ethyl iodide

4-nonylphenol monoethoxylate

4-nonylphenol monoethoxylate

Conditions
ConditionsYield
Stage #1: 4-Nonylphenol With potassium hydroxide In tetrahydrofuran at 20 - 80℃;
Stage #2: ethyl iodide In tetrahydrofuran at 80℃; for 2h;		80%
4-Nonylphenol
104-40-5

4-Nonylphenol

acetic anhydride
108-24-7

acetic anhydride

acetic acid
64-19-7

acetic acid

2-hydroxy-5-nonylacetophenone
115851-77-9

2-hydroxy-5-nonylacetophenone

Conditions
ConditionsYield
With zinc(II) chloride at 100℃; for 10h; Temperature; Reagent/catalyst;80%
...Expand
4-Nonylphenol
104-40-5

4-Nonylphenol

2-Nitro-4-nonyl-phenol
62529-25-3

2-Nitro-4-nonyl-phenol

Conditions
ConditionsYield
With nitric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; acetic acid78%
With nitric acid; acetic acid
With nitric acid In water; acetic acid; benzene
4-Nonylphenol
104-40-5

4-Nonylphenol

C42H42Cl4N2O5

C42H42Cl4N2O5

C102H134N2O9

C102H134N2O9

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; Inert atmosphere;78%
4-Nonylphenol
104-40-5

4-Nonylphenol

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

5-nonyl-2-hydroxyl phenylaldehyde
63753-10-6

5-nonyl-2-hydroxyl phenylaldehyde

Conditions
ConditionsYield
With sulfuric acid; triethylamine; paraformaldehyde In diethyl ether; water; toluene76%
With sulfuric acid; paraformaldehyde In methanol; diethyl ether; water; toluene
4-Nonylphenol
104-40-5

4-Nonylphenol

C114H168Cl4N4O12

C114H168Cl4N4O12

C174H260N4O16

C174H260N4O16

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 8h; Inert atmosphere;74%
4-Nonylphenol
104-40-5

4-Nonylphenol

C90H120Cl4N4O10

C90H120Cl4N4O10

C150H212N4O14

C150H212N4O14

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 8h; Inert atmosphere;70%
4-Nonylphenol
104-40-5

4-Nonylphenol

C66H72Cl4N4O8

C66H72Cl4N4O8

C126H164N4O12

C126H164N4O12

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 8h; Inert atmosphere;68%
4-Nonylphenol
104-40-5

4-Nonylphenol

acetyl chloride
75-36-5

acetyl chloride

2-hydroxy-5-nonylacetophenone
115851-77-9

2-hydroxy-5-nonylacetophenone

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane at 110 - 120℃; for 8h;63%
4-Nonylphenol
104-40-5

4-Nonylphenol

allyl bromide
106-95-6

allyl bromide

1-(allyloxy)-4-n-nonylbenzene
147044-32-4

1-(allyloxy)-4-n-nonylbenzene

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;61%
formaldehyd
50-00-0

formaldehyd

1-aminopyrene
1606-67-3

1-aminopyrene

4-Nonylphenol
104-40-5

4-Nonylphenol

C33H35NO

C33H35NO

Conditions
ConditionsYield
In ethanol at 75℃; for 5h;60.7%
...Expand
4-Nonylphenol
104-40-5

4-Nonylphenol

ketone

ketone

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide at 20℃; for 2h; Purification / work up;60%
4-Nonylphenol
104-40-5

4-Nonylphenol

di(2-hydroxy-5-n-nonylphenyl)sulphide
1258-75-9

di(2-hydroxy-5-n-nonylphenyl)sulphide

Conditions
ConditionsYield
With sulfur dichloride In chloroform at 0 - 20℃;59.1%
4,4'-methylenebis(cyclohexyl urea)

4,4'-methylenebis(cyclohexyl urea)

4-Nonylphenol
104-40-5

4-Nonylphenol

A

4,4′-methylenebis(cyclohexane-4,1-diyl)di(carbamic acid(4-nonylphenyl)ester)
1266554-96-4

4,4′-methylenebis(cyclohexane-4,1-diyl)di(carbamic acid(4-nonylphenyl)ester)

B

4,4'-(4,4'-carbonylbis(azanediyl)bis(cyclohexane-4,1-diyl)bis(methylene))bis(cyclohexane-4,1-diyl)di(carbamic acid(4-nonylphenyl)ester)

4,4'-(4,4'-carbonylbis(azanediyl)bis(cyclohexane-4,1-diyl)bis(methylene))bis(cyclohexane-4,1-diyl)di(carbamic acid(4-nonylphenyl)ester)

Conditions
ConditionsYield
Reflux; Large scale;A 52%
B n/a
...Expand
indan-1,2,3-trione hydrate
485-47-2

indan-1,2,3-trione hydrate

4-Nonylphenol
104-40-5

4-Nonylphenol

4b,9b-dihydroxy-8-nonyl-4bH-benzo[d]indeno[1,2-b]furan-10(9bH)-one
1416230-76-6

4b,9b-dihydroxy-8-nonyl-4bH-benzo[d]indeno[1,2-b]furan-10(9bH)-one

Conditions
ConditionsYield
With acetic acid for 20h; Reflux;47%
With acetic acid for 20h; Reflux;47%
4-Nonylphenol
104-40-5

4-Nonylphenol

Benzotrichlorid
98-07-7

Benzotrichlorid

2-hydroxy-5-nonylbenzophenone
58085-73-7

2-hydroxy-5-nonylbenzophenone

Conditions
ConditionsYield
With sodium hydroxide In water at 75 - 80℃; for 2.5h;42%
glutaric anhydride,
108-55-4

glutaric anhydride,

4-Nonylphenol
104-40-5

4-Nonylphenol

5-(2-hydroxy-5-nonyl-phenyl)-5-oxo-pentanoic acid

5-(2-hydroxy-5-nonyl-phenyl)-5-oxo-pentanoic acid

Conditions
ConditionsYield
With aluminium trichloride In nitrobenzene at 100℃; for 1.5h; Friedel-Crafts acylation;42%

4-N-Nonylphenol Toxicity Data With Reference

1.   

orl-rat LD50:1620 mg/kg

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) No. PB85-143766 .

4-N-Nonylphenol Consensus Reports

Reported in EPA TSCA Inventory.

4-N-Nonylphenol Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.

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