Chemical Properties of Benzoin (CAS 119-53-9)

InChI

InChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H

InChI Key

ISAOCJYIOMOJEB-UHFFFAOYSA-N

Formula

C14H12O2

SMILES

O=C(c1ccccc1)C(O)c1ccccc1

Molecular Weight¹

212.24

CAS

119-53-9

Other Names

• (.+/-.)-Benzoin
• .alpha.-hydroxy-.alpha.-phenylacetophenone
• 1,2-diphenyl-2-hydroxyethanone
• 2-Hydroxy-1,2-diphenylethan-1-one
• 2-hydroxy-1,2-diphenylethanone
• 2-hydroxy-2-phenylacetophenone
• Acetophenone, 2-hydroxy-2-phenyl-
• Benzoylphenylcarbinol
• Bitter almond oil camphor
• Ethanone, 2-hydroxy-1,2-diphenyl-
• Fenyl-«alpha»-hydroxybenzylketon
• Ketone, «alpha»-hydroxybenzyl phenyl
• NCI-C50011
• NSC 8082
• Phenyl-«alpha»-hydroxybenzyl ketone
• Wy 42956
• ethanone, 2-hydroxyl-1,2-diphenyl-
• «alpha»-Hydroxy-«alpha»-phenylacetophenone
• «alpha»-Hydroxybenzyl phenyl ketone

• ω : Acentric Factor.
• Δ_cH°_solid : Standard solid enthalpy of combustion (kJ/mol).
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• η : Dynamic viscosity (Pa×s).
• Δ_fG° : Standard Gibbs free energy of formation (kJ/mol).
• Δ_fH°_gas : Enthalpy of formation at standard conditions (kJ/mol).
• Δ_fH°_solid : Solid phase enthalpy of formation at standard conditions (kJ/mol).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_vapH° : Enthalpy of vaporization at standard conditions (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).
• P_vap : Vapor pressure (kPa).
• T_boil : Normal Boiling Point Temperature (K).
• T_boilr : Boiling point at reduced pressure (K).
• T_c : Critical Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• T_triple : Triple Point Temperature (K).
• V_c : Critical Volume (m³/kmol).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ω	0.6689		Relay (1.0) Calculated Property
ΔcH°solid	-6976.00 ± 3.00	kJ/mol	NIST
ΔfG°	23.64	kJ/mol	Joback Calculated Property
ΔfH°gas	-139.47	kJ/mol	Relay (1.0) Calculated Property
ΔfH°solid	-247.90	kJ/mol	NIST
ΔfusH°	35.85	kJ/mol	Solubility of Benzoin in Six Monosolvents and in Some Binary Solvent Mixtures at Various Temperatures
ΔvapH°	91.91	kJ/mol	Relay (1.0) Calculated Property
IE	8.73	eV	Relay (1.0) Calculated Property
log10WS	[-3.23; -2.85]
log10WS	-3.23		Aq. Solubility Prediction
log10WS	-2.85		Estimated Solubility
logPoct/wat	2.603		Crippen Calculated Property
McVol	168.040	ml/mol	McGowan Calculated Property
Pc	3314.37	kPa	Joback Calculated Property
Tboil	579.67	K	Relay (1.0) Calculated Property
Tc	891.71	K	Relay (1.0) Calculated Property
Tfus	[406.00; 409.15]	K
Tfus	409.15	K	Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) Compiled value
Tfus	408.75	K	Aq. Solubility Prediction
Tfus	406.50 ± 0.50	K	NIST
Tfus	408.00 ± 2.00	K	NIST
Tfus	406.00 ± 3.00	K	NIST
Tfus	407.00 ± 3.00	K	NIST
Ttriple	410.90	K	Solubility Modeling and Mixing Properties for Benzoin in Different Monosolvents and Solvent Mixtures at the Temperature Range from 273.15 to 313.15 K
Vc	0.605	m3/kmol	Relay (1.0) Calculated Property

Pressure Dependent Properties

Property	Value	Unit	Pressure (kPa)	Source
Tboilr	[467.00; 617.00]	K	[1.60; 102.00]
Tboilr	467.00	K	1.60	NIST
Tboilr	617.00	K	102.00	NIST

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[201.07; 512.78]	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			-6.66800e+01
Coefficient B			1.18790e+00
Coefficient C			-8.15100e-04
Coefficient D			2.06660e-07
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	201.07	J/mol×K	273.00	Calculated Property
Cp,gas	260.71	J/mol×K	353.78	Calculated Property
Cp,gas	312.56	J/mol×K	434.56	Calculated Property
Cp,gas	357.30	J/mol×K	515.33	Calculated Property
Cp,gas	395.57	J/mol×K	596.11	Calculated Property
Cp,gas	428.03	J/mol×K	676.89	Calculated Property
Cp,gas	455.32	J/mol×K	757.67	Calculated Property
Cp,gas	478.11	J/mol×K	838.44	Calculated Property
Cp,gas	497.05	J/mol×K	919.22	Calculated Property
Cp,gas	512.78	J/mol×K	1000.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
η	[0.0020619; 0.0000618]	Pa×s	[407.57; 664.27]	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			-1.52602e+01
Coefficient B			3.69912e+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.			407.57
Temperature range, max.			664.27
η	0.0020619	Pa×s	407.57	Calculated Property
η	0.0011388	Pa×s	436.09	Calculated Property
η	0.0006766	Pa×s	464.61	Calculated Property
η	0.0004269	Pa×s	493.13	Calculated Property
η	0.0002833	Pa×s	521.66	Calculated Property
η	0.0001961	Pa×s	550.18	Calculated Property
η	0.0001408	Pa×s	578.70	Calculated Property
η	0.0001043	Pa×s	607.22	Calculated Property
η	0.0000793	Pa×s	635.74	Calculated Property
η	0.0000618	Pa×s	664.27	Calculated Property

Property	Value	Unit	Temperature (K)	Source
Pvap	[0.13; 100.58]	kPa	[408.80; 616.00]	NIST
Equation			ln(Y) = A + B/(T + C) Y is Pvap in kPa, T in K
Coefficient A			1.63331e+01
Coefficient B			-6.73380e+03
Coefficient C			-4.15480e+01
Reference			Stull, 1947
Comment			Coefficents calculated by NIST from author's data.
Temperature range, min.			408.80
Temperature range, max.			616.00
Pvap	0.13	kPa	408.80	Calculated Property
Pvap	0.40	kPa	431.82	Calculated Property
Pvap	1.04	kPa	454.84	Calculated Property
Pvap	2.46	kPa	477.87	Calculated Property
Pvap	5.33	kPa	500.89	Calculated Property
Pvap	10.73	kPa	523.91	Calculated Property
Pvap	20.27	kPa	546.93	Calculated Property
Pvap	36.22	kPa	569.96	Calculated Property
Pvap	61.66	kPa	592.98	Calculated Property
Pvap	100.58	kPa	616.00	Calculated Property

Similar Compounds

Find more compounds similar to Benzoin.

Mixtures

• Benzoin + Methyl Alcohol
• Benzoin + Ethanol
• Benzoin + 2-Propanol
• Benzoin + 1-Butanol
• Benzoin + Acetone
• Benzoin + Ethyl Acetate
• Benzoin + Acetonitrile
• Benzoin + Toluene
• Benzoin + Cyclohexane
• Benzoin + Acetic acid, butyl ester
• Benzoin + 1-Propanol
• Benzoin + 1-Propanol, 2-methyl-
• Benzoin + Ethanol + Ethyl Acetate
• Benzoin + Carbon dioxide
• Benzoin + Ethyl Acetate + Methyl Alcohol

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
• Determining the Solubility of Organic Compounds in Supercritical Carbon Dioxide Using Supercritical Fluid Chromatography Directly Interfaced to Supercritical Fluid Solubility Apparatus
• Solubility of Benzoin in Six Monosolvents and in Some Binary Solvent Mixtures at Various Temperatures
• Solubility Modeling and Mixing Properties for Benzoin in Different Monosolvents and Solvent Mixtures at the Temperature Range from 273.15 to 313.15 K
• Joback Method
• Aqueous Solubility Prediction Method
• Estimated Solubility Method
• McGowan Method
• NIST Webbook

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