Chemical Properties of Diphenylamine (CAS 122-39-4)

InChI

InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H

InChI Key

DMBHHRLKUKUOEG-UHFFFAOYSA-N

Formula

C12H11N

SMILES

c1ccc(Nc2ccccc2)cc1

Molecular Weight¹

169.22

CAS

122-39-4

Other Names

• Aniline, N-phenyl-
• Anilinobenzene
• Benzene, (phenylamino)-
• Benzene, anilino-
• Big Dipper
• C.I. 10355
• DFA
• DPA
• Deccoscald 282
• Difenylamin
• N,N-Diphenylamine
• N-Fenylanilin
• N-PHENYL-BENZENAMINE
• N-Phenylbenzeneamine
• N-phenylaniline
• N-phenylbenzenamine
• NSC 215210
• Naugalube 428L
• No-Scald
• No-Scald dpa 283
• Phenylaniline
• Scaldip
• benzenamine, N-phenyl-

• ω : Acentric Factor.
• Δ_cH°_liquid : Standard liquid enthalpy of combustion (kJ/mol).
• Δ_cH°_solid : Standard solid enthalpy of combustion (kJ/mol).
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• Δ_fG° : Standard Gibbs free energy of formation (kJ/mol).
• Δ_fH°_gas : Enthalpy of formation at standard conditions (kJ/mol).
• Δ_fH°_liquid : Liquid phase 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_fusH : Enthalpy of fusion at a given temperature (kJ/mol).
• Δ_subH° : Enthalpy of sublimation at standard conditions (kJ/mol).
• Δ_subH : Enthalpy of sublimation at a given temperature (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).
• NFPA Fire : NFPA Fire Rating.
• NFPA Health : NFPA Health Rating.
• P_c : Critical Pressure (kPa).
• P_sub : Sublimation pressure (kPa).
• P_vap : Vapor 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	0.3047		PSRK revision IV (2005), critical constants and acentric factors of 1000 components Compiled value
ΔcH°liquid	-6426.20	kJ/mol	NIST
ΔcH°solid	[-6436.71; -6409.50]	kJ/mol
ΔcH°solid	-6424.20 ± 1.40	kJ/mol	NIST
ΔcH°solid	-6436.71	kJ/mol	NIST
ΔcH°solid	-6411.10	kJ/mol	NIST
ΔcH°solid	-6409.50 ± 5.40	kJ/mol	NIST
ΔcH°solid	-6429.72	kJ/mol	NIST
ΔcH°solid	-6424.50	kJ/mol	NIST
ΔcH°solid	-6431.60	kJ/mol	NIST
ΔfG°	364.37	kJ/mol	Joback Calculated Property
ΔfH°gas	202.00	kJ/mol	NIST
ΔfH°liquid	132.00	kJ/mol	NIST
ΔfH°solid	[109.00; 142.50]	kJ/mol
ΔfH°solid	130.00 ± 1.50	kJ/mol	NIST
ΔfH°solid	142.50	kJ/mol	NIST
ΔfH°solid	117.40 ± 2.10	kJ/mol	NIST
ΔfH°solid	131.00	kJ/mol	NIST
ΔfH°solid	109.00	kJ/mol	NIST
ΔfusH°	19.68	kJ/mol	Measurement and prediction of (solid + liquid) equilibria of gun powder's and propellant's stabilizers mixtures
ΔsubH°	110.00	kJ/mol	NIST
ΔvapH°	[55.23; 70.00]	kJ/mol
ΔvapH°	55.23	kJ/mol	NIST
ΔvapH°	69.90	kJ/mol	NIST
ΔvapH°	70.00	kJ/mol	NIST
IE	[7.14; 7.44]	eV
IE	7.19 ± 0.05	eV	NIST
IE	7.18 ± 0.01	eV	NIST
IE	7.14 ± 0.03	eV	NIST
IE	7.25 ± 0.03	eV	NIST
IE	7.44	eV	NIST
log10WS	[-3.51; -3.50]
log10WS	-3.51		Aq. Solubility Prediction
log10WS	-3.50		Estimated Solubility
logPoct/wat	3.430		Crippen Calculated Property
McVol	142.400	ml/mol	McGowan Calculated Property
NFPA Fire	1		KDB
NFPA Health	3		KDB
Pc	[8140.00; 8409.97]	kPa
Pc	8140.00	kPa	PSRK revision IV (2005), critical constants and acentric factors of 1000 components Compiled value
Pc	8409.97 ± 405.30	kPa	NIST
Inp	[274.57; 1637.00]
Inp	1619.00		NIST
Inp	1567.00		NIST
Inp	1621.00		NIST
Inp	1625.00		NIST
Inp	1622.00		NIST
Inp	1637.00		NIST
Inp	1588.00		NIST
Inp	1602.00		NIST
Inp	1637.00		NIST
Inp	1568.00		NIST
Inp	1617.00		NIST
Inp	1634.00		NIST
Inp	1575.00		NIST
Inp	1575.00		NIST
Inp	1601.00		NIST
Inp	274.57		NIST
Inp	276.00		NIST
Inp	279.32		NIST
Inp	275.74		NIST
Inp	279.27		NIST
Inp	1634.00		NIST
Inp	1602.00		NIST
Ip	[2517.00; 2521.00]
Ip	2517.00		NIST
Ip	2517.00		NIST
Ip	2521.00		NIST
Ip	2521.00		NIST
Ip	2517.00		NIST
Ip	2521.00		NIST
Tboil	[575.15; 582.15]	K
Tboil	575.15	K	KDB
Tboil	575.20	K	NIST
Tboil	582.15 ± 2.00	K	NIST
Tc	[931.15; 931.15]	K
Tc	931.15	K	PSRK revision IV (2005), critical constants and acentric factors of 1000 components Compiled value
Tc	931.15 ± 3.00	K	NIST
Tfus	[323.85; 327.40]	K
Tfus	325.60	K	Experimental and modeling studies of binary organic eutectic systems to be used as stabilizers for nitrate esters-based energetic materials
Tfus	326.65	K	DSC measurement and prediction of phase diagrams for binary mixtures of energetic materials' stabilizers
Tfus	326.15	K	Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) Compiled value
Tfus	325.85	K	KDB
Tfus	326.23	K	Aq. Solubility Prediction
Tfus	326.40 ± 0.20	K	NIST
Tfus	326.40 ± 0.50	K	NIST
Tfus	326.30 ± 0.20	K	NIST
Tfus	326.15 ± 0.30	K	NIST
Tfus	326.25 ± 0.40	K	NIST
Tfus	326.15 ± 0.50	K	NIST
Tfus	327.40 ± 3.00	K	NIST
Tfus	326.35 ± 0.50	K	NIST
Tfus	326.09 ± 0.25	K	NIST
Tfus	326.15 ± 0.15	K	NIST
Tfus	326.15 ± 1.00	K	NIST
Tfus	327.15 ± 2.00	K	NIST
Tfus	325.95 ± 0.50	K	NIST
Tfus	Outlier 324.05 ± 0.30	K	NIST
Tfus	Outlier 323.85 ± 0.30	K	NIST
Tfus	327.15 ± 2.00	K	NIST
Tfus	326.15 ± 1.50	K	NIST
Tfus	325.15 ± 0.60	K	NIST
Tfus	326.08 ± 1.00	K	NIST
Tfus	326.00 ± 1.50	K	NIST
Tfus	327.15 ± 1.50	K	NIST
Vc	0.520	m3/kmol	PSRK revision IV (2005), critical constants and acentric factors of 1000 components Compiled value

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
ΔfusH	[17.86; 19.90]	kJ/mol	[326.10; 326.20]
ΔfusH	19.90	kJ/mol	326.10	NIST
ΔfusH	17.86	kJ/mol	326.20	NIST
ΔfusH	17.86	kJ/mol	326.20	NIST
ΔsubH	[96.70; 110.00]	kJ/mol	[310.50; 311.00]
ΔsubH	96.70 ± 2.50	kJ/mol	310.50	NIST
ΔsubH	96.70 ± 2.50	kJ/mol	310.50	NIST
ΔsubH	110.00 ± 1.00	kJ/mol	311.00	NIST
ΔvapH	[54.20; 64.10]	kJ/mol	[478.00; 623.00]
ΔvapH	64.10	kJ/mol	478.00	NIST
ΔvapH	54.20	kJ/mol	623.00	NIST
Psub	[4.00e-05; 2.03e-03]	kPa	[293.10; 326.70]
Psub	4.00e-05	kPa	293.10	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	4.00e-05	kPa	293.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	6.00e-05	kPa	296.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	7.00e-05	kPa	298.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	8.00e-05	kPa	298.40	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.00e-04	kPa	300.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.20e-04	kPa	301.00	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.30e-04	kPa	302.10	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.50e-04	kPa	302.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.40e-04	kPa	303.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.70e-04	kPa	305.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	2.00e-04	kPa	305.50	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	2.40e-04	kPa	308.00	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	2.50e-04	kPa	308.00	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	2.60e-04	kPa	308.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	2.90e-04	kPa	309.10	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	3.00e-04	kPa	309.30	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	3.40e-04	kPa	310.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	4.20e-04	kPa	312.30	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	4.50e-04	kPa	313.00	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	5.00e-04	kPa	313.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	5.40e-04	kPa	315.00	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	5.50e-04	kPa	315.00	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	6.10e-04	kPa	315.40	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	6.00e-04	kPa	315.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	6.50e-04	kPa	316.00	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	7.00e-04	kPa	316.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	7.50e-04	kPa	317.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	8.30e-04	kPa	318.00	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	8.60e-04	kPa	318.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	8.50e-04	kPa	318.30	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	8.50e-04	kPa	318.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.11e-03	kPa	320.30	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.10e-03	kPa	320.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.38e-03	kPa	322.30	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.53e-03	kPa	323.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.43e-03	kPa	323.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.69e-03	kPa	324.10	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.64e-03	kPa	324.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	1.86e-03	kPa	325.20	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
Psub	2.03e-03	kPa	326.70	Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[161.72; 438.26]	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			-7.70400e+01
Coefficient B			1.06220e+00
Coefficient C			-7.40000e-04
Coefficient D			1.93100e-07
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	161.72	J/mol×K	273.00	Calculated Property
Cp,gas	214.68	J/mol×K	353.78	Calculated Property
Cp,gas	260.65	J/mol×K	434.56	Calculated Property
Cp,gas	300.25	J/mol×K	515.33	Calculated Property
Cp,gas	334.10	J/mol×K	596.11	Calculated Property
Cp,gas	362.79	J/mol×K	676.89	Calculated Property
Cp,gas	386.94	J/mol×K	757.67	Calculated Property
Cp,gas	407.16	J/mol×K	838.44	Calculated Property
Cp,gas	424.06	J/mol×K	919.22	Calculated Property
Cp,gas	438.26	J/mol×K	1000.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
Pvap	[1.33; 202.66]	kPa	[428.54; 610.47]	The Yaws Handbook of Vapor Pressure
Equation			ln(Y) = A + B/(T + C) Y is Pvap in kPa, T in K
Coefficient A			1.53095e+01
Coefficient B			-5.43887e+03
Coefficient C			-6.64740e+01
Temperature range, min.			428.54
Temperature range, max.			610.47
Pvap	1.33	kPa	428.54	Calculated Property
Pvap	2.95	kPa	448.75	Calculated Property
Pvap	6.03	kPa	468.97	Calculated Property
Pvap	11.51	kPa	489.18	Calculated Property
Pvap	20.70	kPa	509.40	Calculated Property
Pvap	35.37	kPa	529.61	Calculated Property
Pvap	57.81	kPa	549.83	Calculated Property
Pvap	90.81	kPa	570.04	Calculated Property
Pvap	137.78	kPa	590.26	Calculated Property
Pvap	202.66	kPa	610.47	Calculated Property
Pvap	[0.13; 100.93]	kPa	[381.50; 575.00]	NIST
Equation			ln(Y) = A + B/(T + C) Y is Pvap in kPa, T in K
Coefficient A			1.63440e+01
Coefficient B			-6.28464e+03
Coefficient C			-3.92070e+01
Reference			Stull, 1947
Comment			Coefficents calculated by NIST from author's data.
Temperature range, min.			381.50
Temperature range, max.			575.00
Pvap	0.13	kPa	381.50	Calculated Property
Pvap	0.39	kPa	403.00	Calculated Property
Pvap	1.03	kPa	424.50	Calculated Property
Pvap	2.45	kPa	446.00	Calculated Property
Pvap	5.31	kPa	467.50	Calculated Property
Pvap	10.72	kPa	489.00	Calculated Property
Pvap	20.27	kPa	510.50	Calculated Property
Pvap	36.27	kPa	532.00	Calculated Property
Pvap	61.81	kPa	553.50	Calculated Property
Pvap	100.93	kPa	575.00	Calculated Property

Similar Compounds

Find more compounds similar to Diphenylamine.

Mixtures

• Diphenylamine + N-Nitrosodiphenylamine
• Carbon dioxide + Diphenylamine
• Diphenylamine + N-ethyl-4-nitroaniline

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).
• PSRK revision IV (2005), critical constants and acentric factors of 1000 components ChEDL chemicals 1.5.2, from Horstmann, S.; Jabłoniec, A.; Krafczyk, J.; Fischer, K.; Gmehling, J. PSRK Group Contribution Equation of State: Comprehensive Revision and Extension IV, Including Critical Constants and α-Function Parameters for 1000 Components. Fluid Phase Equilib. 2005, 227, 157-164.
• Crippen Method
• Solubility of three natural compounds with insecticidal activity in supercritical carbon dioxide: Experimental measurements and predictive modeling with the GC-EoS
• Experimental and modeling studies of binary organic eutectic systems to be used as stabilizers for nitrate esters-based energetic materials
• Measurement and prediction of (solid + liquid) equilibria of gun powder's and propellant's stabilizers mixtures
• DSC measurement and prediction of phase diagrams for binary mixtures of energetic materials' stabilizers
• Thermochemistry of Drugs. Experimental and First-Principles Study of Fenamates
• Joback Method
• KDB
• Aqueous Solubility Prediction Method
• Estimated Solubility Method
• McGowan Method
• NIST Webbook
• The Yaws Handbook of Vapor Pressure

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