Chemical Properties of Acetaminophen (CAS 103-90-2)

InChI

InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)

InChI Key

RZVAJINKPMORJF-UHFFFAOYSA-N

Formula

C8H9NO2

SMILES

CC(=O)Nc1ccc(O)cc1

Molecular Weight¹

151.16

CAS

103-90-2

Other Names

• 4'-hydroxyacetanilide
• 4-(Acetylamino)phenol
• 4-(N-Acetylamino)phenol
• 4-Acetaminophenol
• 4-Hydroxyanilid kyseliny octove
• 4-acetamidophenol
• 4-hydroxyacetanilide
• APAP
• Abensanil
• Acamol
• Accu-Tap
• Acenol
• Acetalgin
• Acetamide, N-(p-hydroxyphenyl)-
• Acetaminofen
• Algotropyl
• Alpiny
• Alpinyl
• Alvedon
• Amadil
• Anaflon
• Anapap
• Anelix
• Anhiba
• Apadon
• Apamid
• Apamide
• Banesin
• Ben-u-Ron
• Bickie-mol
• Biocetamol
• Calpol
• Captin
• Cetadol
• Citramon P
• Claratal
• Clixodyne
• Cyclopam
• Dafalgan
• Daga
• Daphalgan
• Datril
• Dial-a-gesic
• Dimindol
• Dirox
• Disprol
• Doliprane
• Dolprone
• Dularin
• Dymadon
• Dypap
• Elixodyne
• Enelfa
• Eneril
• Eu-Med
• Exdol
• Febridol
• Febrilix
• Febrinol
• Febro-Gesic
• Febrolin
• Fendon
• Finimal
• G 1
• Gelocatil
• Hedex
• Homoolan
• Injectapap
• Janupap
• Korum
• Lestemp
• Liquagesic
• Lonarid
• Lyteca
• Lyteca Syrup
• Minoset
• Momentum
• Multin
• N-(4-hydroxyphenyl)acetamide
• N-(4-hydroxyphenyl)ethanamide
• N-(p-Hydroxyphenyl) acetamide
• N-Acetyl-4-aminophenol
• N-Acetyl-4-hydroxyaniline
• N-acetyl-p-aminophenol
• NAPA
• NAPAP
• NCI-C55801
• Napafen
• Naprinol
• Nealgyl
• Nebs
• Neotrend
• Nobedon
• Ortensan
• Pacemo
• Pacemol
• Painex
• Paldesic
• Panaleve
• Panasorb
• Panets
• Panex
• Panodil
• Panofen
• Paracet
• Paracetamol DC
• Paracetamole
• Paracetamolo
• Paracetanol
• Parapan
• Paraspen
• Parelan
• Parmol
• Pasolind N
• Pedric
• Phenaphen
• Phendon
• Phenol, p-acetamido-
• Pinex
• Pyral
• Pyrinazine
• Resfenol
• Resprin
• Rivalgyl
• SK-Apap
• Salzone
• Servigesic
• St. Joseph Fever Reducer
• Tabalgin
• Tapar
• Temlo
• Tempanal
• Tralgon
• Tussapap
• Tylenol
• Valadol
• Valgesic
• Vermidon
• acetagesic
• acetamide, N-(4-hydroxyphenyl)-
• acetanilide, 4'-hydroxy-
• p-(Acetylamino)phenol
• p-Acetoaminophen
• p-Hydroxyphenolacetamide
• p-acetamidophenol
• p-hydroxyacetanilide
• panadol
• paracetamol
• tempra

• C_p,gas : Ideal gas heat capacity (J/mol×K).
• C_sat : Molar heat capacity at saturation pressure (J/mol×K).
• Δ_fH°_gas : Enthalpy of formation at standard conditions (kJ/mol).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_fusH : Enthalpy of fusion at a given temperature (kJ/mol).
• Δ_subH° : Enthalpy of sublimation at standard conditions (kJ/mol).
• Δ_vapH° : Enthalpy of vaporization at standard conditions (kJ/mol).
• Δ_vapH : Enthalpy of vaporization at a given temperature (kJ/mol).
• IE : Ionization energy (eV).
• log₁₀WS : Log10 of Water solubility in mol/l.
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• I_np : Non-polar retention indices.
• T_boil : Normal Boiling Point Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• T_triple : Triple Point Temperature (K).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ΔfH°gas	-292.34	kJ/mol	Relay (1.0) Calculated Property
ΔfusH°	24.90	kJ/mol	Study of Glass Transition Phenomena in the Supercooled Liquid Phase of Methocarbamol, Acetaminophen and Mephensin
ΔsubH°	138.00 ± 3.00	kJ/mol	NIST
ΔvapH°	85.03	kJ/mol	Relay (1.0) Calculated Property
IE	7.57 ± 0.02	eV	NIST
log10WS	[-1.14; -1.03]
log10WS	-1.14		Aq. Solubility Prediction
log10WS	-1.06		Aq. Solubility Prediction
log10WS	-1.03		Estimated Solubility
log10WS	-1.07		Rytting (2005)
logPoct/wat	1.351		Crippen Calculated Property
McVol	117.240	ml/mol	McGowan Calculated Property
Inp	[1631.00; 1703.00]
Inp	1697.00		NIST
Inp	1632.00		NIST
Inp	1643.00		NIST
Inp	1650.00		NIST
Inp	1664.00		NIST
Inp	1678.00		NIST
Inp	1668.00		NIST
Inp	1631.00		NIST
Inp	1694.00		NIST
Inp	1631.00		NIST
Inp	1636.00		NIST
Inp	1703.00		NIST
Inp	1631.00		NIST
Inp	1636.00		NIST
Inp	1687.00		NIST
Inp	1636.00		NIST
Inp	1668.00		NIST
Tboil	579.82	K	Relay (1.0) Calculated Property
Tfus	[441.00; 445.60]	K
Tfus	Outlier 445.60	K	Vapor pressures and standard molar enthalpies, entropies and Gibbs energies of sublimation of three 4-substituted acetanilide derivatives
Tfus	442.35	K	Determination and prediction of solubilities of active pharmaceutical ingredients in selected organic solvents
Tfus	442.15	K	Liquid pharmaceuticals formulation by eutectic formation
Tfus	441.85	K	DSC study and phase diagrams calculation of binary systems of paracetamol
Tfus	443.15	K	Solubility of Anti-Inflammatory, Anti-Cancer, and Anti-HIV Drugs in Supercritical Carbon Dioxide
Tfus	442.37	K	Aq. Solubility Prediction
Tfus	441.20 ± 0.50	K	NIST
Tfus	441.00 ± 2.00	K	NIST
Ttriple	297.00	K	Endothermic features on heating of glasses show that the second glass to liquid transition of water was phenomenologically-mistaken

Cheméo can also estimate Critical Temperature, Critical Pressure, Critical Volume, Standard Gibbs free energy of formation, Acentric Factor for this compound, but they fall outside the models' validated range, so they are not shown here. Open the prediction tool to compute them on demand.

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
Csat	[346.60; 370.50]	J/mol×K	[463.15; 510.15]
Csat	346.60	J/mol×K	463.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	350.60	J/mol×K	468.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	353.60	J/mol×K	473.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	356.40	J/mol×K	478.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	359.00	J/mol×K	483.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	361.50	J/mol×K	488.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	363.40	J/mol×K	493.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	365.70	J/mol×K	498.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	367.70	J/mol×K	503.15	Interpretation of the global heat of melting in eutectic binary systems
Csat	370.50	J/mol×K	510.15	Interpretation of the global heat of melting in eutectic binary systems
ΔfusH	[26.02; 27.60]	kJ/mol	[440.30; 443.20]
ΔfusH	27.00	kJ/mol	440.30	NIST
ΔfusH	26.02	kJ/mol	441.20	NIST
ΔfusH	26.49	kJ/mol	441.90	NIST
ΔfusH	26.20	kJ/mol	443.00	NIST
ΔfusH	27.60	kJ/mol	443.20	NIST
ΔvapH	[99.00; 103.00]	kJ/mol	[494.00; 521.00]
ΔvapH	99.00 ± 1.00	kJ/mol	494.00	NIST
ΔvapH	103.00 ± 3.00	kJ/mol	521.00	NIST

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[151.93; 361.86]	J/mol×K	[273.00; 1000.00]	Joback Predicted correlation
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is Cp,gas in J/mol×K, T in K
Coefficient A			-4.10600e+01
Coefficient B			8.87720e-01
Coefficient C			-7.28860e-04
Coefficient D			2.44060e-07
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	151.93	J/mol×K	273.00	Calculated Property
Cp,gas	192.58	J/mol×K	353.78	Calculated Property
Cp,gas	227.09	J/mol×K	434.56	Calculated Property
Cp,gas	256.25	J/mol×K	515.33	Calculated Property
Cp,gas	280.82	J/mol×K	596.11	Calculated Property
Cp,gas	301.57	J/mol×K	676.89	Calculated Property
Cp,gas	319.28	J/mol×K	757.67	Calculated Property
Cp,gas	334.72	J/mol×K	838.44	Calculated Property
Cp,gas	348.65	J/mol×K	919.22	Calculated Property
Cp,gas	361.86	J/mol×K	1000.00	Calculated Property

Similar Compounds

Find more compounds similar to Acetaminophen.

Mixtures

• Acetaminophen + 1-Octanol
• Acetaminophen + Water
• Choline chloride + Acetaminophen
• Acetaminophen + Hydrochloric acid + Water
• sodium chloride + Acetaminophen + Water
• Acetaminophen + Ethanol
• 2-Propanol + Acetaminophen
• Acetaminophen + Methyl Alcohol
• Acetaminophen + caffeine
• Acetaminophen + Vitamin C
• Ethanol, 2-(2-ethoxyethoxy)- + Acetaminophen + Water
• Ethanol, 2-(2-ethoxyethoxy)- + Acetaminophen
• 1-Propanol + Acetaminophen
• Acetaminophen + 1-Butanol
• Acetaminophen + 1-Pentanol
• Acetaminophen + Acetone
• Carbon dioxide + Acetaminophen

Sources

• Cheméo Relay (1.0)
• Cheméo Relay (1.0, beta) Beta: served but experimental, data-limited and below our cross-validation release bar; the Joback value is recommended where available.
• Crippen Method
• Activity coefficients of the species in the methanol solutions of acetaminophen and two silylated derivatives at 298.15K
• Vapor pressures and standard molar enthalpies, entropies and Gibbs energies of sublimation of three 4-substituted acetanilide derivatives
• Determination and prediction of solubilities of active pharmaceutical ingredients in selected organic solvents
• Aqueous solubility of acetaminophen in the presence of 1-hexyl-3- methyl imidazolium bromide, ionic liquid as co-solvent
• Liquid pharmaceuticals formulation by eutectic formation
• Experimental determination and correlation of acetaminophen solubility in aqueous solutions of choline chloride based deep eutectic solvents at various temperatures
• Partial molar volume of paracetamol in water, 0.1 M HCl and 0.154 M NaCl at T = (298.15, 303.15, 308.15 and 310.65) K and at 101.325 kPa
• Partial molar volumes of some drug and pro-drug substances in 1-octanol at T = 298.15 K
• Diffusion coefficients of paracetamol in aqueous solutions
• Effect of paracetamol in aqueous sodium malonate solutions with reference to volumetric and viscometric measurements
• Enthalpies of solution of paracetamol and sodium diclofenac in phosphate buffer and in DMSO at 298.15K
• DSC study and phase diagrams calculation of binary systems of paracetamol
• Study of Glass Transition Phenomena in the Supercooled Liquid Phase of Methocarbamol, Acetaminophen and Mephensin
• Endothermic features on heating of glasses show that the second glass to liquid transition of water was phenomenologically-mistaken
• Sublimation enthalpies of 9 substituted acetanilides at 298 K estimated by solution calorimetry approach
• Interpretation of the global heat of melting in eutectic binary systems
• Pressurized-Synthetic Methodology for Solubility Determination at Elevated Temperatures with Application to Paracetamol in Pure Solvents
• Solid Liquid Phase Equilibrium of N,N'-Piperazinebis(neopentylglycol)phosphoramidate in Selected Solvents from T = (293.15 to 333.15) K
• Experimental and Modeling Studies on the Solubility of 2-Chloro-N-(4-methylphenyl)propanamide (S1) in Binary Ethyl Acetate + Hexane, Toluene + Hexane, Acetone + Hexane, and Butanone + Hexane Solvent Mixtures Using Polythermal Method
• Effect of Some Imidazolium-Based Ionic Liquids with Different Anions on the Thermodynamic Properties of Acetaminophen in Aqueous Media at T = 293.15 to 308.15 K
• Measurement and Correlation of Solubility of Resorcinol Bis(cyclic 2,2-dimethyl-1,3-propanediol phosphate) in Selected Solvents from T = 293.15 to 333.15 K
• Solubility Measurement and Thermodynamic Modeling of N-(4-Methylphenyl-Z-3-chloro-2-(phenylthio)propenamide in 12 Pure Solvents at Temperatures Ranging from 278.15 to 318.15 K
• Solubility of Anti-Inflammatory, Anti-Cancer, and Anti-HIV Drugs in Supercritical Carbon Dioxide
• Solubilities of Pharmaceutical Compounds in Ionic Liquids
• Solubilization Behavior of Paracetamol in Transcutol Water Mixtures at (298.15 to 333.15) K
• Dynamic and Static Characteristics of Drug Dissolution in Supercritical CO2 by Infrared Spectroscopy: Measurements of Acetaminophen Solubility in a Wide Range of State Parameters
• Joback Method
• Aqueous Solubility Prediction Method
• Estimated Solubility Method
• Aqueous and cosolvent solubility data for drug-like organic compounds
• McGowan Method
• NIST Webbook

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