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Urethane
• Formula: C3H7NO2
• Molecular weight: 89.09
• IUPAC International Chemical Identifer:
o InChI=1/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
o Download the identifier in a file.
• CAS Registry Number: 51-79-6

• Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d Mol file.
• Other names: Carbamic acid, ethyl ester; Ethyl carbamate; Ethyl urethane; O-
Ethylurethane; Leucethane; NSC 746; Pracarbamine; Urethan; NH2COOC2H5; A
11032; Aethylcarbamat; Aethylurethan; Carbamidsaeure-aethylester; Estane 5703;
Ethyl urethan; Leucothane; Pracarbamin; U-Compound; Uretan; X 41; Ethylester
kyseliny karbaminove; Rcra waste number U238; Uretan etylowy; Ethyl ester of
carbamic acid
• Information on this page:
o Condensed phase thermochemistry data
o Phase change data
o Reaction thermochemistry data
o Gas phase ion energetics data
o References
o Notes / Error Report
• Other data available:
o Gas phase thermochemistry data
o IR Spectrum
o Mass Spectrum
o Gas Chromatography
• Data at other NIST sites:
o Computational Chemistry Comparison and Benchmark Database (on SRD
web site)
• Options:
o Switch to calorie-based units

Condensed phase thermochemistry data

 Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion
energetics data, References, Notes / Error Report

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 - H.Y. Afeefy, J.F. Liebman, and S.E. Stein
DH - E.S. Domalski and E.D. Hearing

Quantity Value Units Method Reference Comment

Bernard, Boukari, et al., hfusion=20.9±0.8 kJ/mol;
ΔfH°liquid -497.3 kJ/mol Cm
1976 ALS
Quantity Value Units Method Reference Comment
Schmidt and Becker,
ΔfH°solid -517.1 kJ/mol Ccb ALS
1933
Quantity Value Units Method Reference Comment
Schmidt and Becker,
ΔcH°solid -1663.8 kJ/mol Ccb ALS
1933

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment

156.43 300. DeWit, DeKruif, et al., 1983 T = 90 to 330 K.; DH

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry
data, Gas phase ion energetics data, References, Notes / Error Report

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 - R.L. Brown and S.E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, M. Frenkel
director
ALS - H.Y. Afeefy, J.F. Liebman, and S.E. Stein
C - J.S. Chickos
DH - E.S. Domalski and E.D. Hearing
Quantity Value Units Method Reference Comment
Aldrich Chemical
Tboil 456.2 K N/A BS
Company Inc., 1990
Uncertainty assigned by TRC
Tboil 458.40 K N/A Lecat, 1947
= 0.6 K; TRC
Quantity Value Units Method Reference Comment
322. ± Average of 6 values;
Tfus K AVG N/A
4. Individual data points
Quantity Value Units Method Reference Comment
De Wit, De Kruif, et Uncertainty assigned by TRC
Ttriple 321.41 K N/A
al., 1983 = 0.02 K; TRC
Quantity Value Units Method Reference Comment
51. ± Bernard, Boukari, et hfusion=20.9±0.8 kJ/mol;
ΔvapH° kJ/mol V
2.5 al., 1976 ALS
Quantity Value Units Method Reference Comment
DeWit, Van
ΔsubH° 76.3 kJ/mol N/A C
Miltenburg, et al., 1983

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)

View plot Requires a Java capable browser.

Temperature
A B C Reference Comment
(K)
-41.70 Coefficents calculated by NIST
338.9 - 457. 5.48918 2278.150 Stull, 1947
7 from author's data.

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment

DeWit, Van Miltenburg, et al.,
77.7 256. - 273. TE ME C
1983
 71.9 322. N/A Barnard, 1976 C
89.1 ± 0.8 292. - 307. GS Davies and Jones, 1959 C

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment

16.794 321.41 DeWit, DeKruif, et al., 1983 DH
20.900 321.7 Bernard, Boukari, et al., 1976 DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment

52.25 321.41 DeWit, DeKruif, et al., 1983 DH
64.8 321.7 Bernard, Boukari, et al., 1976 DH

In addition to the Thermodynamics Research Center (TRC) data available from this site,
much more physical and chemical property data is available from the NIST/TRC Table
Database This database contains more than 497,000 property data points and 4,450 sets of
equation coefficients for 7,468 compounds and 33 properties.

Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase
ion energetics data, References, Notes / Error Report

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the

U.S.A. All rights reserved.

Data compiled by: J.E. Bartmess

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
C3H6NO2- +H = +

By formula: C3H6NO2- + H+ = C3H7NO2

Quantity Value Units Method Reference Comment

1514. ± gas phase; value altered from reference
ΔrH° kJ/mol G+TS Taft, 1987
9.6 due to change in acidity scale
Quantity Value Units Method Reference Comment
1485. ± gas phase; value altered from reference
ΔrG° kJ/mol IMRE Taft, 1987
9.2 due to change in acidity scale

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction
thermochemistry data, References, Notes / Error Report

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:

B - J.E. Bartmess
LLK - S.G. Lias, R.D. Levin, and S.A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment

10.2 PE Overman, Taylor, et al., 1978 LLK
10.62 PE Overman, Taylor, et al., 1978 Vertical value; LLK

De-protonation reactions

C3H6NO2- +H = +

By formula: C3H6NO2- + H+ = C3H7NO2

Quantity Value Units Method Reference Comment
1514. ± gas phase; value altered from reference
ΔrH° kJ/mol G+TS Taft, 1987
9.6 due to change in acidity scale; B
Quantity Value Units Method Reference Comment
1485. ± gas phase; value altered from reference
ΔrG° kJ/mol IMRE Taft, 1987
9.2 due to change in acidity scale; B

References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction
thermochemistry data, Gas phase ion energetics data, Notes / Error Report

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the

U.S.A. All rights reserved.

Bernard, Boukari, et al., 1976

Bernard, M.A.; Boukari, Y.; Busnot, F., Thermodynamic study of methyl and ethyl
carbamates and their eutectic, Thermochim. Acta, 1976, 16, 267-275. [all data]

Schmidt and Becker, 1933

Schmidt, V.A.; Becker, F., Die Bildungswarme von Nitrocellulofen, Nitroglycerin und
anderen widuigen Beltandteilen von Treibmitteln, Z. Gesamte Schiess Sprengstoffwes.,
1933, 33, 280-282. [all data]

DeWit, DeKruif, et al., 1983

DeWit, H.G.M.; DeKruif, C.G.; Van Miltenburg, J.C., Thermodynamic properties of
molecular organic crystals containing organic crystals containing nitrogen, oxygen, and
sulfur. II. Molar heat capacities of eight compounds by adiabatic calorimetry, J. Chem.
Thermodynam., 1983, 15, 891-902. [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]

Lecat, 1947
Lecat, M., Orthobaric Azeotropes of Sulfides, Bull. Cl. Sci., Acad. R. Belg., 1947, 33,
160-82. [all data]

De Wit, De Kruif, et al., 1983

De Wit, H.G.M.; De Kruif, C.G.; Van Miltenburg, J.C., J. Chem. Thermodyn., 1983,
891. [all data]
DeWit, Van Miltenburg, et al., 1983
DeWit, H.G.M.; Van Miltenburg, J.C.; DeKruif, C.G., J. Chem. Thermodyn., 1983, 15,
651. [all data]

Stull, 1947
Stull, D.R., Vapor Pressure of Pure Substances Organic Compounds, Ind. Eng. Chem.,
1947, 39, 517-540. [all data]

Barnard, 1976
Barnard, M., Thermochim. Acta, 1976, 16, 267. [all data]

Davies and Jones, 1959

Davies, M.; Jones, A.H., Trans. Faraday Soc., 1959, 55, 1329. [all data]

Taft, 1987
Taft, R.W., Personal communication. See also Prog. Phys. Org. Chem., 1987, 16,
1. [all data]

Overman, Taylor, et al., 1978

Overman, L.E.; Taylor, G.F.; Houk, K.N.; Domelsmith, L.N., Diels-Alder reactions
between trans-1-N-acylamino-1,3-dienes and methyl acrylate. A correlation between
diene photoelectron ionization potentials and reactivity, stereoselectivity, and
regioselectivity, J. Am. Chem. Soc., 1978, 100, 3182. [all data]

Notes / Error Report

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction
thermochemistry data, Gas phase ion energetics data, References

• Data from NIST Standard Reference Database 69, June 2005 Release: NIST
Chemistry WebBook
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