Phenothiazine
- Formula: C12H9NS
- Molecular weight: 199.272
- IUPAC Standard InChIKey: WJFKNYWRSNBZNX-UHFFFAOYSA-N
- CAS Registry Number: 92-84-2
- 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: 10H-Phenothiazine; Contaverm; Danikoropa; Dibenzothiazine; Dibenzo-1,4-thiazine; Early bird wormer; ENT 38; Feeno; Fenoverm; Nemazene; Nexarbol; Orimon; Padophene; Penthazine; Phenegic; Phenoverm; Phenovis; Phenoxur; Phenthiazine; Phenzeen; Reconox; Thiodiphenylamine; AFI-Tiazin; Agrazine; Antiverm; Dibenzo-p-thiazine; Fenothiazine; Fenotiazina; Fentiazin; Helmetina; Lethelmin; Nemazine; Phenosan; Souframine; Thiodifenylamine; Thiodiphenylamin; Tiodifenilamina; Vermitin; Wurm-Thional; XL-50; Biverm; Dibenzoparathiazine; 10H-Phenothiazin; EPA Pesticide Chemical Code 064501; Promethazine M (ring); Alimemazine M (ring); Dixyrazine M (ring); Perazine M (ring); Pecazine M (ring); Mequitazine M (ring)
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 66.49 ± 0.45 | kcal/mol | Ccr | Sabbah and El Watik, 1992 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 39.84 ± 0.45 | kcal/mol | Ccr | Sabbah and El Watik, 1992 | |
ΔfH°solid | 11.88 | kcal/mol | Ccb | Tavernier and Lamouroux, 1957 | Author's hf298_condensed=12.415 kcal/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1619.7 ± 0.38 | kcal/mol | Ccr | Sabbah and El Watik, 1992 | |
ΔcH°solid | -1591.80 | kcal/mol | Ccb | Tavernier and Lamouroux, 1957 | Author's hf298_condensed=12.415 kcal/mol |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 644.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 458.39 | K | N/A | Donnelly, Drewes, et al., 1990 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 457.5 | K | N/A | Plato and Glasgow, 1969 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 458.5 | K | N/A | Plato and Glasgow, 1969 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 457.55 | K | N/A | Cullinane and Rees, 1940 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 26.637 ± 0.088 | kcal/mol | C | Sabbah and El Watik, 1992 | ALS |
ΔsubH° | 27.37 ± 0.1 | kcal/mol | C | Sabbah and El Watik, 1992 | AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.6 | 351. | A | Stephenson and Malanowski, 1987 | Based on data from 336. to 395. K. See also Nelson and Smith, 1942.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.1329 | 458.40 | N/A | Sabbah and El Watik, 1992 | DH |
6.79 | 457.2 | DSC | Gupta, Singh, et al., 2007 | AC |
6.14 | 458.4 | N/A | Sabbah and El Watik, 1992 | AC |
6.434 | 458.2 | N/A | Acree, 1991 | AC |
Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
6.74 ± 0.07 | CTS | Poltorakov, Pirnazarova, et al., 1973 | LLK |
6.87 | CTS | Pozharskii, Kashparov, et al., 1971 | LLK |
7.625 | S | Kitagawa, 1968 | RDSH |
7.7 | PI | Kitagawa, 1968 | RDSH |
6.96 ± 0.19 | CTS | Fulton and Lyons, 1968 | RDSH |
7.26 ± 0.08 | PE | Domelsmith, Munchausen, et al., 1977 | Vertical value; LLK |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLID (KBr PELLET) $$ SEE 697 FOR CHCl3 SOLUTION; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLUTION (5% CHCl3); Not specified, most likely a grating spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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
Spectrum
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Additional Data
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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 | Tox21 Consortium/NIST Mass Spectrometry Data Center, 2012 |
NIST MS number | 408667 |
UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | VanAllan, Reynolds, et al., 1962 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 318 |
Instrument | n.i.g. |
Melting point | 187.5 |
Boiling point | 371 |
Gas Chromatography
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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
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | OV-101 | 2010. | Maurer and Pfleger, 1988 | N2, Chromosorb G HP, 100. C @ 3. min, 30. K/min, 310. C @ 5. min; Column length: 0.6 m |
Packed | OV-101 | 2010. | Maurer and Pfleger, 1988 | N2, Chromosorb G HP, 100. C @ 3. min, 30. K/min, 310. C @ 5. min; Column length: 0.6 m |
Packed | OV-101 | 2010. | Maurer and Pfleger, 1988 | N2, Chromosorb G HP, 100. C @ 3. min, 30. K/min, 310. C @ 5. min; Column length: 0.6 m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | OV-101 | 2030. | McLinden and Stenhouse, 1979 | N2, Chromosorb W; Column length: 2. m; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 2010. | Perrigo and Peel, 1981 | N2, Chromosorb W, 130. C @ 2. min, 8. K/min, 290. C @ 8. min; Column length: 1.8 m |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Other | Methyl Silicone | 2024. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Subscription Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sabbah and El Watik, 1992
Sabbah, R.; El Watik, L.,
Etude thermodynamique de la phenoxazine et de la phenotiazine,
Thermochim. Acta, 1992, 197, 381-390. [all data]
Tavernier and Lamouroux, 1957
Tavernier, P.; Lamouroux, M.,
Determinations calorimetriques relatives a vingt et une substances organiques,
Mem. Poudres, 1957, 39, 335-356. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Donnelly, Drewes, et al., 1990
Donnelly, J.R.; Drewes, L.A.; Johnson, R.L.; Munslow, W.D.; Knapp, K.K.; Sovocool, G.W.,
Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry,
Thermochim. Acta, 1990, 167, 2, 155, https://doi.org/10.1016/0040-6031(90)80476-F
. [all data]
Plato and Glasgow, 1969
Plato, C.; Glasgow, A.R., Jr.,
Differential scanning calorimetry as a general method for determining the purity and heat of fusion of high-purity organic chemicals. Application to 95 compounds,
Anal. Chem., 1969, 41, 2, 330, https://doi.org/10.1021/ac60271a041
. [all data]
Cullinane and Rees, 1940
Cullinane, N.M.; Rees, W.T.,
Isomorphous relationships of some organic compounds of analogous constitution,
Trans. Faraday Soc., 1940, 36, 507. [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]
Nelson and Smith, 1942
Nelson, O.A.; Smith, L.E.,
The Vapor Pressure of Phenothiazine 1,
J. Am. Chem. Soc., 1942, 64, 12, 3035-3037, https://doi.org/10.1021/ja01264a086
. [all data]
Gupta, Singh, et al., 2007
Gupta, R.K.; Singh, S.K.; Singh, R.A.,
Some physicochemical studies on organic eutectics,
Journal of Crystal Growth, 2007, 300, 2, 415-420, https://doi.org/10.1016/j.jcrysgro.2006.12.017
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Poltorakov, Pirnazarova, et al., 1973
Poltorakov, A.P.; Pirnazarova, F.N.; But, P.G.; Piruzyan, L.A.; Chibrikin, V.M.; Vikjlyaev, Yu.I.; Ul'yanova, O.V.,
Ionization potentials of phenothiazine derivatives and their correlation with the parmacologic effect,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1973, 22, 2050, In original 2106. [all data]
Pozharskii, Kashparov, et al., 1971
Pozharskii, A.F.; Kashparov, I.S.; Holls, P.J.; Zaletov, V.G.,
Hetrocyclic pleiadiene analogs. VI. Electronic properties of perimidine,
Chem. Heterocycl. Compd., 1971, 4, 503, In original 543. [all data]
Kitagawa, 1968
Kitagawa, T.,
Absorption spectra and photoionization of polycyclic aromatics in vacuum ultraviolet region,
J. Mol. Spectry., 1968, 26, 1. [all data]
Fulton and Lyons, 1968
Fulton, A.; Lyons, L.E.,
The ionization energies of some phenothiazine tranquillizers and molecules of similar structure,
Australian J. Chem., 1968, 21, 873. [all data]
Domelsmith, Munchausen, et al., 1977
Domelsmith, L.N.; Munchausen, L.L.; Houk, K.N.,
Photoelectron spectra of psychotropic drugs. 2. Phenothiazine and related tranquilizers,
J. Am. Chem. Soc., 1977, 99, 6506. [all data]
VanAllan, Reynolds, et al., 1962
VanAllan, J.A.; Reynolds, G.A.; Adel, R.E.,
Polynuclear heterocycles. I. 1H-benzo[b]pyrido[1,2,3-mn]phenoxazin-1-one and related substances,
J. Org. Chem., 1962, 27, 1659-1664. [all data]
Maurer and Pfleger, 1988
Maurer, H.; Pfleger, K.,
Identification of phenothiazine antihistamines and their metabolites in urine,
Arch. Toxicol., 1988, 62, 2-3, 185-191, https://doi.org/10.1007/BF00570138
. [all data]
McLinden and Stenhouse, 1979
McLinden, V.J.; Stenhouse, A.M.,
A chromatography system for drug identification,
Forensic Sci. Int., 1979, 13, 71-79, https://doi.org/10.1016/0379-0738(79)90265-2
. [all data]
Perrigo and Peel, 1981
Perrigo, B.J.; Peel, H.W.,
The use of retention indices and temperature-programmed gas chromatography in analytical toxicology,
J. Chromatogr. Sci., 1981, 19, 5, 219-226, https://doi.org/10.1093/chromsci/19.5.219
. [all data]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Subscription Links, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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