o-Toluidine
- Formula: C7H9N
- Molecular weight: 107.1531
- IUPAC Standard InChIKey: RNVCVTLRINQCPJ-UHFFFAOYSA-N
- CAS Registry Number: 95-53-4
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Benzenamine, 2-methyl-; o-Aminotoluene; o-Methylaniline; o-Methylbenzenamine; o-Tolylamine; 1-Amino-2-methylbenzene; 2-Aminotoluene; 2-Methyl-1-aminobenzene; 2-Methylaniline; 2-Methylbenzenamine; 2-Toluidine; 2-Amino-1-methylbenzene; 1-Methyl-2-aminobenzene; o-Toluide; o-Toluidin; o-Toluidyna; Aniline, 2-methyl-; C.I. 37077; Rcra waste number U328; NSC 15348
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 53.2 ± 0.5 | kJ/mol | Ccr | Steele, Chirico, et al., 1994 | see Steele, Chirico, et al., 1990; ALS |
ΔfH°gas | 54.8 | kJ/mol | Ccb | Draeger, 1984 | ALS |
ΔfH°gas | 51.4 | kJ/mol | N/A | Pushin, 1954 | Value computed using ΔfHliquid° value of -6.5 kj/mol from Pushin, 1954 and ΔvapH° value of 57.9 kj/mol from Steele, Chirico, et al., 1994.; DRB |
Condensed phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -4.72 ± 0.96 | kJ/mol | Ccr | Steele, Chirico, et al., 1994 | see Steele, Chirico, et al., 1990; ALS |
ΔfH°liquid | -6.49 | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=-4.0 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -4036.09 ± 0.88 | kJ/mol | Ccr | Steele, Chirico, et al., 1994 | see Steele, Chirico, et al., 1990; ALS |
ΔcH°liquid | -4034. | kJ/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=-4.0 kcal/mol; ALS |
ΔcH°liquid | -4064.0 | kJ/mol | Ccb | Swarts, 1909 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
164.4 | 303.15 | Guseinov, Mirzaliev, et al., 1988 | T = 303 to 463 K. p= 0.1 MPa. Unsmoothed experimental datum. Cp(liq) = 0.8056 + 0.0023634T + (0.0017364 - 8.1591x10-6T)P kJ/kg*K (303.15 to 523.15 K, 0.1 to 25 MPa).; DH |
209.6 | 302.5 | de Kolossowsky and Udowenko, 1934 | DH |
209.6 | 302.5 | Kolosovskii and Udovenko, 1934 | DH |
201.7 | 288. | Radulescu and Jula, 1934 | DH |
211.3 | 298. | von Reis, 1881 | T = 294 to 485 K.; DH |
Phase change data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 473. ± 2. | K | AVG | N/A | Average of 16 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 252. ± 8. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 258.730 | K | N/A | Steele, Chirico, et al., 1994, 2 | Uncertainty assigned by TRC = 0.005 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 694.15 | K | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 37.4902 | bar | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 2.5331 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 57. ± 10. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
57.8 | 300. | EB,IP | Steele, Chirico, et al., 1994 | Based on data from 290. to 517. K.; AC |
54.5 | 340. | EB,IP | Steele, Chirico, et al., 1994 | Based on data from 290. to 517. K.; AC |
51.5 | 380. | EB,IP | Steele, Chirico, et al., 1994 | Based on data from 290. to 517. K.; AC |
48.6 | 420. | EB,IP | Steele, Chirico, et al., 1994 | Based on data from 290. to 517. K.; AC |
45.7 | 460. | EB,IP | Steele, Chirico, et al., 1994 | Based on data from 290. to 517. K.; AC |
42.7 | 500. | EB.IP | Steele, Chirico, et al., 1994 | Based on data from 290. to 517. K.; AC |
50.0 | 406. | A | Stephenson and Malanowski, 1987 | Based on data from 391. to 474. K. See also Dreisbach and Shrader, 1949 and Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
391.61 to 473.5 | 4.19168 | 1617.232 | -87.126 | Dreisbach and Shrader, 1949 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.100 | 249.55 | Meva'a and Lichanot, 1990 | DH |
11.66 | 287.6 | Steele, Chirico, et al., 1994 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
32. | 249.55 | Meva'a and Lichanot, 1990 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
By formula: C7H5NO + C7H9N = C14H14N2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -93.0 | kJ/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
IR Spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 290511 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Steele, Chirico, et al., 1994
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Knipmeyer, S.E.,
The thermodynamic properties of 2-methylaniline and trans-(r,S)-decahydroquinoline,
J. Chem. Thermodyn., 1994, 26, 515-544. [all data]
Steele, Chirico, et al., 1990
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Knipmeyer, S.E.,
The thermodynamic properties of 2-methylaniline and trans-(R,S)-decahydroquinoline,
Topical Rept., work performed under cooperative agreement No. FC22-83FE60149, Bartlesville,OK, (NIPER-459), 1990, 1-52. [all data]
Draeger, 1984
Draeger, J.A.,
Chemical-thermodynamic properties of molecules that undergo inversion. II. The methylanilines,
J. Chem. Thermodyn., 1984, 16, 1067-1073. [all data]
Pushin, 1954
Pushin, N.A.,
Heats of combustion and heats of formation of isomeric organic compounds,
Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]
Swarts, 1909
Swarts, M.F.,
Sur la chaleur de formation de l'aniline et de quelquesuns de ses derives,
Recl. Trav. Chim. Pays-Bas, 1909, 28, 155-165. [all data]
Guseinov, Mirzaliev, et al., 1988
Guseinov, S.O.; Mirzaliev, A.A.; Shakhmuradov, Sh.G.,
Investigation of the isobaric heat capacity of meta- and ortho-toluidine over a wide interval ov varying temperature and pressure, Iaz. Vyssh. Ucheb. Zaved.,
Neft i Gaz 31(9), 1988, 13, 35. [all data]
de Kolossowsky and Udowenko, 1934
de Kolossowsky, N.; Udowenko, W.W.,
Determination des chaleurs specifiques des liquides,
Compt. rend., 1934, 198, 1394-1395. [all data]
Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W.,
Specific heat of liquids. II.,
Zhur. Obshchei Khim., 1934, 4, 1027-1033. [all data]
Radulescu and Jula, 1934
Radulescu, D.; Jula, O.,
Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen,
Z. Phys. Chem., 1934, B26, 390-393. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [all data]
Steele, Chirico, et al., 1994, 2
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Knipmeyer, S.E.,
The thermodynamic properties of 2-methylaniline and trans-(R,S)-decahydroquinoline,
J. Chem. Thermodyn., 1994, 26, 5, 515, https://doi.org/10.1006/jcht.1994.1061
. [all data]
Glaser and Ruland, 1957
Glaser, F.; Ruland, H.,
Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen,
Chem. Ing. Techn., 1957, 29, 772. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A.,
Vapor Pressure--Temperature Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Meva'a and Lichanot, 1990
Meva'a, L.M.; Lichanot, A.,
Proprietes thermodynamiques en phase condensee des ortho, meta et para fluorotoluene, cresol et toluidine,
Thermochim. Acta, 1990, 158, 335-345. [all data]
Pannone and Macosko, 1987
Pannone, M.C.; Macosko, C.W.,
Kinetics of isocyanate amine reactions,
J. Appl. Polym. Sci., 1987, 34, 2409-2432. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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