Chemical Properties of methyl 4-hydroxybenzoate (CAS 99-76-3)

InChI

InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3

InChI Key

LXCFILQKKLGQFO-UHFFFAOYSA-N

Formula

C8H8O3

SMILES

COC(=O)c1ccc(O)cc1

Molecular Weight¹

152.15

CAS

99-76-3

Other Names

• Benzoic acid, 4-hydroxy-, methyl ester
• methyl p-hydroxybenzoate
• methylparaben
• p-hydroxybenzoic acid methyl ester

• ω : Acentric Factor.
• PAff : Proton affinity (kJ/mol).
• BasG : Gas basicity (kJ/mol).
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• C_p,solid : Solid phase heat capacity (J/mol×K).
• η : Dynamic viscosity (Pa×s).
• 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).
• P_c : Critical Pressure (kPa).
• I_np : Non-polar retention indices.
• I_p : Polar retention indices.
• T_boil : Normal Boiling Point Temperature (K).
• T_c : Critical Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• V_c : Critical Volume (m³/kmol).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ω	0.6132		Relay (1.0) Calculated Property
PAff	863.40	kJ/mol	NIST
BasG	832.50	kJ/mol	NIST
ΔfH°gas	-452.97	kJ/mol	Relay (1.0) Calculated Property
ΔfusH°	26.40	kJ/mol	Thermodynamic properties of the methyl esters of p-hydroxy and p-methoxy benzoic acids
ΔsubH°	98.80 ± 0.80	kJ/mol	NIST
ΔvapH°	83.10	kJ/mol	NIST
IE	8.74	eV	Relay (1.0) Calculated Property
log10WS	[-1.83; -1.78]
log10WS	-1.78		Aq. Solubility Prediction
log10WS	-1.83		Estimated Solubility
logPoct/wat	1.179		Crippen Calculated Property
McVol	113.130	ml/mol	McGowan Calculated Property
Pc	4438.52	kPa	Joback Calculated Property
Inp	[1410.00; 1475.00]
Inp	1410.00		NIST
Inp	1419.00		NIST
Inp	1459.00		NIST
Inp	1465.00		NIST
Inp	1435.00		NIST
Inp	1452.00		NIST
Inp	1470.40		NIST
Inp	1460.00		NIST
Inp	1475.00		NIST
Inp	1420.00		NIST
Inp	1419.00		NIST
Inp	1435.00		NIST
Inp	1419.00		NIST
Inp	1419.00		NIST
Inp	1452.00		NIST
Inp	1459.00		NIST
Ip	[2911.00; 2932.00]
Ip	2932.00		NIST
Ip	2930.00		NIST
Ip	2932.00		NIST
Ip	2911.00		NIST
Ip	2925.00		NIST
Ip	2911.00		NIST
Tboil	540.67	K	Relay (1.0) Calculated Property
Tc	746.73	K	Relay (1.0) Calculated Property
Tfus	[398.40; 404.15]	K
Tfus	398.60	K	The standard molar enthalpy of the base catalysed hydrolysis of methyl paraben revisited
Tfus	398.90	K	Solubility and preferential solvation of some n-alkyl-parabens in methanol + water mixtures at 298.15 K
Tfus	399.00	K	Experimental and theoretical study of methyl n-hydroxybenzoates
Tfus	404.15	K	Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) Compiled value
Tfus	402.77	K	Aq. Solubility Prediction
Tfus	398.40 ± 0.50	K	NIST
Vc	0.393	m3/kmol	Relay (1.0) Calculated Property

Cheméo can also estimate Standard Gibbs free energy of formation for this compound, but it falls outside the models' validated range, so it is not shown here. Open the prediction tool to compute it on demand.

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
Cp,solid	214.41	J/mol×K	298.15	Evaluation of sublimation enthalpy by thermogravimetry: Analysis of the diffusion effects in the case of methyl and phenyl substituted hydantoins
ΔfusH	[24.31; 25.30]	kJ/mol	[398.50; 399.20]
ΔfusH	24.31	kJ/mol	398.50	NIST
ΔfusH	24.31	kJ/mol	398.50	NIST
ΔfusH	25.30	kJ/mol	399.20	NIST
ΔvapH	81.50	kJ/mol	481.50	NIST

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[151.16; 344.06]	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			-2.18000e+01
Coefficient B			7.84720e-01
Coefficient C			-6.04360e-04
Coefficient D			1.85500e-07
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	151.16	J/mol×K	273.00	Calculated Property
Cp,gas	188.39	J/mol×K	353.78	Calculated Property
Cp,gas	220.30	J/mol×K	434.56	Calculated Property
Cp,gas	247.48	J/mol×K	515.33	Calculated Property
Cp,gas	270.52	J/mol×K	596.11	Calculated Property
Cp,gas	289.99	J/mol×K	676.89	Calculated Property
Cp,gas	306.50	J/mol×K	757.67	Calculated Property
Cp,gas	320.62	J/mol×K	838.44	Calculated Property
Cp,gas	332.95	J/mol×K	919.22	Calculated Property
Cp,gas	344.06	J/mol×K	1000.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
η	[0.0007704; 0.0000546]	Pa×s	[400.30; 544.54]	Joback Predicted correlation
Equation			Y = exp(A + B/T + C·ln(T) + D·T^E) Y is η in Pa×s, T in K
Coefficient A			-1.71601e+01
Coefficient B			3.99964e+03
Coefficient C			0.00000e+00
Coefficient D			0.00000e+00
Coefficient E			0.00000e+00
Comment			Liquid phase. Joback/Reid (1987), valid from Tf to 0.7·Tc.
Temperature range, min.			400.30
Temperature range, max.			544.54
η	0.0007704	Pa×s	400.30	Calculated Property
η	0.0005244	Pa×s	416.33	Calculated Property
η	0.0003673	Pa×s	432.36	Calculated Property
η	0.0002639	Pa×s	448.38	Calculated Property
η	0.0001940	Pa×s	464.41	Calculated Property
η	0.0001455	Pa×s	480.44	Calculated Property
η	0.0001112	Pa×s	496.46	Calculated Property
η	0.0000865	Pa×s	512.49	Calculated Property
η	0.0000682	Pa×s	528.52	Calculated Property
η	0.0000546	Pa×s	544.54	Calculated Property

Similar Compounds

Find more compounds similar to methyl 4-hydroxybenzoate.

Mixtures

• methyl 4-hydroxybenzoate + Methyl Alcohol + Water
• methyl 4-hydroxybenzoate + Water
• methyl 4-hydroxybenzoate + Methyl Alcohol
• Carbon dioxide + methyl 4-hydroxybenzoate

Sources

• Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) ChEDL chemicals 1.5.2, from Bradley, J.-C.; Williams, A.; Lang, A. Jean-Claude Bradley Open Melting Point Dataset. Figshare, 2014 (CC0).
• Cheméo Relay (1.0)
• Crippen Method
• Thermodynamic properties of the methyl esters of p-hydroxy and p-methoxy benzoic acids
• The standard molar enthalpy of the base catalysed hydrolysis of methyl paraben revisited
• Relationships between fusion, solution, vaporization and sublimation enthalpies of substituted phenols
• Solubility and preferential solvation of some n-alkyl-parabens in methanol + water mixtures at 298.15 K
• Experimental and theoretical study of methyl n-hydroxybenzoates
• Evaluation of sublimation enthalpy by thermogravimetry: Analysis of the diffusion effects in the case of methyl and phenyl substituted hydantoins
• Analysis of solute-pyridine intermolecular interactions based on experimental enthalpies of solution and enthalpies of solvation of solutes dissolved in pyridine
• Solubility of the Drugs Bisacodyl, Methimazole, Methylparaben, and Iodoquinol in Supercritical Carbon Dioxide
• Solubility of Parabens in Subcritical Water
• Joback Method
• Aqueous Solubility Prediction Method
• Estimated Solubility Method
• McGowan Method
• NIST Webbook

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