104-40-5

Basic information

• Product Name: 4-N-NONYLPHENOL
• Synonyms: 4-nonyl-pheno;Phenol, 4-nonyl-;Phenol, p-nonyl-;p-nonyl-pheno;4-N-NONYLPHENOL;4-N-NONYLPHENOL-D4;4-NONYLPHENOL;P-N-NONYLPHENOL
• CAS NO: 104-40-5
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.35
• EINECS: 203-199-4
• Product Categories: Phenol;Phenoles and thiophenoles;N-PAlphabetic;Pesticides&Metabolites;NJ - NZ;N-OAlphabetic;Alpha Sort;N;Volatiles/ Semivolatiles;Aromatics
• Mol File: 104-40-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 43-44°C
• Boiling Point: 293-297 °C
• Flash Point: >230 °F
• Appearance: viscous colourless liquid with a phenol-like smell
• Density: 0.937 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00016mmHg at 25°C
• Refractive Index: n20/D 1.511(lit.)
• Storage Temp.: APPROX 20°C
• Solubility: Sparingly Soluble (0.020 g/L) at 25°C.
• PKA: 10.15±0.15(Predicted)
• Water Solubility: 6.35mg/L(25 oC)
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 2047450
• CAS DataBase Reference: 4-N-NONYLPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-N-NONYLPHENOL(104-40-5)
• EPA Substance Registry System: 4-N-NONYLPHENOL(104-40-5)

Safety Data

• Hazard Codes: C,N
• Statements: 22-34-50/53-62-63
• Safety Statements: 26-36/37/39-45-61-60
• RIDADR: UN 3145 8/PG 2
• WGK Germany: 3
• RTECS: SM5650000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 104-40-5(Hazardous Substances Data)

Usage

Chemical Properties

viscous colourless liquid with a phenol-like smell

Uses

Different sources of media describe the Uses of 104-40-5 differently. You can refer to the following data:
1. 4-nonylphenol is used in the process for the manufacture of 5-nonyl salicylaldoxime, which is used for the selective purification and concentration of copper ions.
2. weevil pheromone, shows estrogenic activity
3. Principal use as an intermediate in the production of nonionic ethoxylated surfactants; as an intermediate in the manufacture of phosphite antioxidants used for the plastics and rubber industries

Definition

ChEBI: A member of the class of phenols that is phenol which is para-substituted with a nonyl group.

Health Hazard

Nonylphenol is a severe irritant of the eyes and skin.

Carcinogenicity

Nonylphenol has recently been shown to have estrogenic properties, triggering mitotic activity in rat endometrium and cell proliferation in estrogen-sensitive tumor cells.9 Potential toxicity to humans who may be exposed to nonylphenol through leaching of plastics has not been determined.

InChI:InChI=1/C15H24O/c1-2-3-4-5-6-7-8-11-14-12-9-10-13-15(14)16/h9-10,12-13,16H,2-8,11H2,1H3

Synthetic route

1-(4-methoxyphenyl)nonane (32588-84-4) → 4-Nonylphenol (104-40-5)

Conditions	Yield
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-Nonylphenol (104-40-5)

Conditions	Yield
With hydrogenchloride; mercury; zinc In ethanol for 20h; Reduction; Heating;	83%
With hydrogenchloride; mercury; zinc	71%
With potassium hydroxide; hydrazine hydrate 1.) diethylene glycol, reflux, 1h; 2.) reflux, 1h; Yield given. Multistep reaction;

1-(4-Benzyloxy-phenyl)-nonan-1-ol → 4-Nonylphenol (104-40-5)

Conditions	Yield
With sulfuric acid; hydrogen; palladium on activated charcoal In ethyl acetate Yield given;

2,6-dibromononylphenol (103526-64-3) → 4-Nonylphenol (104-40-5)

Conditions	Yield
With tritium; palladium on activated charcoal Dehalogenation;

1-<4-hydroxy-phenyl>-nonanone-(1) → 4-Nonylphenol (104-40-5)

Conditions	Yield
With hydrogenchloride; amalgamated zinc; acetic acid

Nonanoyl chloride (764-85-2) → 4-Nonylphenol (104-40-5) + guinea pig hepatic microsomal protein

Conditions	Yield
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) + pentacarbonyl(1-ethyloxy-3-cyclopentenyl-2-propyn-1-ylidene)tungsten → 4-Nonylphenol (104-40-5) + guinea pig hepatic microsomal protein

Conditions	Yield
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

Nonanoyl chloride (764-85-2) → 4-Nonylphenol (104-40-5)

Conditions	Yield
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) + m-bromo-toluene → 4-Nonylphenol (104-40-5)

Conditions	Yield
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) → 4-Nonylphenol (104-40-5)

Conditions	Yield
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) + dipotassium-salt of <1,3,4>thiadiazolidine-2,5-dithione → 4-Nonylphenol (104-40-5)

Conditions	Yield
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) → 4-Nonylphenol (104-40-5)

Conditions	Yield
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-Nonylphenol (104-40-5)

Conditions	Yield
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) + 4-Nonylphenol (104-40-5) → 4-nonyl-2,6-di-(3,5-di-tert-butyl-4-hydroxybenzyl)phenol

Conditions	Yield
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) + acetic acid (64-19-7) → C17H26O

Conditions	Yield
With sodium hydrogen sulfate for 3h; Reflux;	100%

formaldehyd (50-00-0) + 4-Nonylphenol (104-40-5) → 5-nonyl-2-hydroxyl phenylaldehyde (63753-10-6)

Conditions	Yield
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) + acetic anhydride (108-24-7) → 4-nonylphenyl acetate (32604-44-7)

Conditions	Yield
montmorillonite acid clay for 0.166667h; microwave irradiation;	94%

4-Nonylphenol (104-40-5) + 4-bromo-5-nitrophthalonitrile (206268-72-6) → 4-nitro-5-(4-nonylphenoxy)phthalonitrile

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at 25℃; for 0.5h;	94%

4,4'-methylenebis(cyclohexyl urea) + 4-Nonylphenol (104-40-5) → 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	Yield
Reflux; Large scale;	92%

4-Nonylphenol (104-40-5) + 2,4-tolylene diurea (10097-06-0) → 5,5'-carbonylbis(azanediyl)bis(2-methyl-5,1-phenylene)di(carbamic acid(4-nonylphenyl)ester)

Conditions	Yield
Reflux; Large scale;	89%

4-Nonylphenol (104-40-5) → 2,6-dibromononylphenol (103526-64-3)

Conditions	Yield
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-Nonylphenol (104-40-5) → C23H26N2O

Conditions	Yield
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) + 4-Nonylphenol (104-40-5) → 5-nonyl-2-hydroxybenzaldehyde oxime (50849-47-3)

Conditions	Yield
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) + 4-Nonylphenol (104-40-5) → 5-nonylsalicylaldoxime (50849-47-3)

Conditions	Yield
With aluminium trichloride at 80℃; for 5h;	80%

4-Nonylphenol (104-40-5) + ethyl iodide (75-03-6) → 4-nonylphenol monoethoxylate

Conditions	Yield
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) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → 2-hydroxy-5-nonylacetophenone (115851-77-9)

Conditions	Yield
With zinc(II) chloride at 100℃; for 10h; Temperature; Reagent/catalyst;	80%

4-Nonylphenol (104-40-5) → 2-Nitro-4-nonyl-phenol (62529-25-3)

Conditions	Yield
With nitric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; acetic acid	78%
With nitric acid; acetic acid
With nitric acid In water; acetic acid; benzene

4-Nonylphenol (104-40-5) + C42H42Cl4N2O5 → C102H134N2O9

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; Inert atmosphere;	78%

4-Nonylphenol (104-40-5) + ethylmagnesium bromide (925-90-6) → 5-nonyl-2-hydroxyl phenylaldehyde (63753-10-6)

Conditions	Yield
With sulfuric acid; triethylamine; paraformaldehyde In diethyl ether; water; toluene	76%
With sulfuric acid; paraformaldehyde In methanol; diethyl ether; water; toluene

4-Nonylphenol (104-40-5) + C114H168Cl4N4O12 → C174H260N4O16

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 8h; Inert atmosphere;	74%

4-Nonylphenol (104-40-5) + C90H120Cl4N4O10 → C150H212N4O14

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 8h; Inert atmosphere;	70%

4-Nonylphenol (104-40-5) + C66H72Cl4N4O8 → C126H164N4O12

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 8h; Inert atmosphere;	68%

4-Nonylphenol (104-40-5) + acetyl chloride (75-36-5) → 2-hydroxy-5-nonylacetophenone (115851-77-9)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane at 110 - 120℃; for 8h;	63%

4-Nonylphenol (104-40-5) + allyl bromide (106-95-6) → 1-(allyloxy)-4-n-nonylbenzene (147044-32-4)

Conditions	Yield
With potassium carbonate In acetone Reflux;	61%

formaldehyd (50-00-0) + 1-aminopyrene (1606-67-3) + 4-Nonylphenol (104-40-5) → C33H35NO

Conditions	Yield
In ethanol at 75℃; for 5h;	60.7%

4-Nonylphenol (104-40-5) → ketone

Conditions	Yield
With sulfuric acid; sulfur trioxide at 20℃; for 2h; Purification / work up;	60%

4-Nonylphenol (104-40-5) → di(2-hydroxy-5-n-nonylphenyl)sulphide (1258-75-9)

Conditions	Yield
With sulfur dichloride In chloroform at 0 - 20℃;	59.1%

4,4'-methylenebis(cyclohexyl urea) + 4-Nonylphenol (104-40-5) → 4,4′-methylenebis(cyclohexane-4,1-diyl)di(carbamic acid(4-nonylphenyl)ester) (1266554-96-4) + 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	Yield
Reflux; Large scale;	A 52% B n/a

indan-1,2,3-trione hydrate (485-47-2) + 4-Nonylphenol (104-40-5) → 4b,9b-dihydroxy-8-nonyl-4bH-benzo[d]indeno[1,2-b]furan-10(9bH)-one (1416230-76-6)

Conditions	Yield
With acetic acid for 20h; Reflux;	47%
With acetic acid for 20h; Reflux;	47%

4-Nonylphenol (104-40-5) + Benzotrichlorid (98-07-7) → 2-hydroxy-5-nonylbenzophenone (58085-73-7)

Conditions	Yield
With sodium hydroxide In water at 75 - 80℃; for 2.5h;	42%

glutaric anhydride, (108-55-4) + 4-Nonylphenol (104-40-5) → 5-(2-hydroxy-5-nonyl-phenyl)-5-oxo-pentanoic acid

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

Upstream product

• 14392-69-9 4-nonanoylphenol 
• 764-85-2 Nonanoyl chloride 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 32604-44-7 4-nonylphenyl acetate 
• 108-95-2 phenol 
• 111-83-1 1-bromo-octane 
• 103526-64-3 2,6-dibromononylphenol 
• 32588-84-4 1-(4-methoxyphenyl)nonane 

Downstream Products

• 62529-25-3 2-Nitro-4-nonyl-phenol 
• 55231-78-2 dichlorophosphoric acid-(4-nonyl-phenyl ester) 
• 6316-62-7 4-nonyllphenyl benzoate 
• 1149-66-2 4-Nonyl-phenylcyanat 
• 38444-39-2 4-Hexyloxy-benzoic acid 4-nonyl-phenyl ester 
• 133883-30-4 4-(5-Hexyl-pyrimidin-2-yl)-benzoic acid 4-nonyl-phenyl ester 
• 88108-22-9 4-(4-Bromo-benzoyloxy)-3-methoxy-benzoic acid 4-nonyl-phenyl ester 
• 38444-38-1 4-Butoxy-benzoic acid 4-nonyl-phenyl ester 
• 38444-37-0 4-Methoxy-benzoic acid 4-nonyl-phenyl ester 
• 33314-02-2 2-Methylthiomethyl-4n-nonylphenol 
• 33367-74-7 2,6-Bis-methylsulfanylmethyl-4-nonyl-phenol 
• 63753-10-6 5-nonyl-2-hydroxyl phenylaldehyde 
• 32604-44-7 4-nonylphenyl acetate 

Related news

Biodegradation and utilization of 4-N-NONYLPHENOL (cas 104-40-5) by Aspergillus versicolor as a sole carbon and energy source08/20/2019

4-n-Nonylphenol (4-n-NP) is an environmental pollutant with endocrine-disrupting activities that is formed during the degradation of nonylphenol polyethoxylates, which are widely used as surfactants. Utilization of 4-n-NP by the filamentous fungus Aspergillus versicolor as the sole carbon and en...detailed

Different pathways for 4-N-NONYLPHENOL (cas 104-40-5) biodegradation by two Aspergillus strains derived from estuary sediment: Evidence from metabolites determination and key-gene identification08/19/2019

Nonylphenols (NPs) are known as Endocrine Disputing Chemicals (ECDs) and Persistent Organic Pollutants (POPs) and have attracted continuous attention. Biodegradation is one of the effective ways for pollutant removal in aquatic, sedimentary and soil environments. In this study, two estuarine der...detailed

Effects of 4-N-NONYLPHENOL (cas 104-40-5) on aquatic hyphomycetes08/18/2019

We measured the removal of 4-n-nonylphenol (between 50 and 500 μg L−1) from an aqueous solution with or without linden and oak leaf disks. More 4-n-NP was removed when the leaves were first exposed for 3 weeks in a stream, which allowed colonization by aquatic hyphomycetes. The response of fung...detailed

Determination of 4-n-octylphenol, 4-N-NONYLPHENOL (cas 104-40-5) and bisphenol A in fish samples from lake and rivers within Hunan Province, China08/16/2019

The presence of endocrine disrupting chemicals such as 4-n-octylphenol, 4-n-nonylphenol and bisphenol A in environmental samples and artificial products may cause health problems for human and organisms. This developed method was efficient for monitoring of those tracing emerging contaminates an...detailed

Synergistic effect of co-exposure to cadmium (II) and 4-N-NONYLPHENOL (cas 104-40-5) on growth inhibition and oxidative stress of Chlorella sorokiniana08/15/2019

Toxicological effect of freshwater algae co-exposure to Cd and 4-n-nonylphenol (4-n-NP) was seldom reported. In the present study, Chlorella sorokiniana was selected for testing the single and combined effect of Cd and 4-n-NP by detecting the growth inhibition and oxidative stress after exposure...detailed

4-N-NONYLPHENOL (cas 104-40-5) degradation by the genus Metarhizium with cytochrome P450 involvement08/13/2019

In this study, the ability of 4-n-nonylphenol (4-n-NP) elimination by fungal species belonging to the genus Metarhizium was investigated. The occurrence of 35 metabolites from 4-n-NP degradation was confirmed. For the first time, based on the obtained results, the 4-n-NP biodegradation pathway d...detailed

Adsorption kinetics of 4-N-NONYLPHENOL (cas 104-40-5) on hematite and goethite08/12/2019

The adsorption of 4-n-Nonylphenol (4-n-NP), a persistent emerging contaminant, onto the surface of hematite and goethite was studied using Attenuated Total Reflectance (ATR)-FTIR spectroscopy. The adsorption kinetics for hematite and goethite show that equilibrium was reached in less than 24 h, ...detailed

A comparison of endocrine disruption potential of nonylphenol ethoxylate, vanillin ethoxylate, 4-N-NONYLPHENOL (cas 104-40-5) and vanillin in vitro08/11/2019

The widely used surfactant nonylphenol ethoxylate (NPEO) and its raw material 4-n-nonylphenol (4-n-NP), as well as its degradation products, are recognized as endocrine disrupting chemicals. The USA Environmental Protection Agency (EPA) released an assessment that looked for safe alternatives to...detailed

Relevant articles and documents

Biodegradation of Nonionic Surfactants. I. Biotransformation of 4-(1-Nonyl)phenol by a Candida maltosa Isolate

Results are reported concerning biodegradation of 4-(1-nonyl)phenol by cultures of a Candida maltosa strain isolated from aerobic sludge samples collected at a depuration plant treating wastewaters from a textile industry. The yeast was able to utilize 4-(1-nonyl)phenol as a sole carbon and energy source. Preliminary attempts to draw the actual metabolic pathway evidenced microbial attack on the alkyl chain with the production of 4-acetylphenol. To the best of our knowledge this is the first report describing a microorganism capable of attacking nonylphenol in axenic culture and at the same time allowing for the identification of its degradation products.

Characterization of biliary metabolites of 4-n-nonylphenol in rainbow trout (Oncorhynchus mykiss)

1. [R-2,6-3H]-4-n-nonylphenol was synthesized and a single dose (5 mg, 1850 KBq) orally administered to rainbow trout. After 48 h, the radioactivity present in the bile amounted 5.5%. More than ten biliary metabolites were separated by hplc and collected for subsequent mass spectrometry analysis. The metabolic profile was totally modified by β-glucuronidase hydrolysis, showing that most of the metabolites were glucuronic acid conjugates. 2. Conjugated metabolites were identified by lc-ms analysis and their aglycones were analysed by gc-ms analysis as TMS and acetyl derivatives. 3. The major metabolite accounted for 52 ± 11% of the biliary radioactivity and was identified as nonylphenol-glucuronide. 4. Nonylphenol was hydroxylated at both ω and ω-1 positions of the alkyl chain, giving 9-hydroxynonylphenol and 8-hydroxynonylphenol. 5. 9-Hydroxynonylphenol was oxidized to the corresponding acid, and subsequently β-oxidized, yielding 7-(4-hydroxyphenyl)heptanoic acid, 5-(4-hydroxyphenyl)pentanoic acid, 3-(4-hydroxyphenyl)propionic acid and 3-(4-hydroxyphenyl)-2-propenoic acid.

Dissolving metal reduction with crown ether --- reductive demethylation of mono-, di- and trimethoxybenzene derivatives with toluene radical anion

Toluene radical anion generated from potassium metal and toluene with the assistance of crown ether has been proved effective for reductive demethylation of methoxybenzene derivatives.