Standard Reference

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Urethane • • •

Formula: C3H7NO2 Molecular weight: 89.09 IUPAC International Chemical Identifer: o o

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InChI=1/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)

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; OEthylurethane; 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 ALS H.Y. Afeefy, J.F. Liebman, DH - E.S. Domalski and E.D. Hearing Quantity Value Units Method ΔfH°liquid

-497.3 kJ/mol

Cm

Quantity Value Units Method ΔfH°solid

-517.1 kJ/mol

Ccb

Quantity Value Units Method ΔcH°solid

-1663.8 kJ/mol

Ccb

in and

Reference

comments: S.E. Stein

Comment

Bernard, Boukari, et al., hfusion=20.9±0.8 kJ/mol; 1976 ALS Reference Schmidt and Becker, 1933

Comment ALS

Reference Schmidt and Becker, 1933

Comment ALS

Constant pressure heat capacity of solid Cp,solid (J/mol*K) Temperature (K) 156.43

Reference

Comment

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

Tboil

456.2

K

N/A

Aldrich Chemical Company Inc., 1990

BS

Tboil

458.40

K

N/A

Lecat, 1947

Uncertainty assigned by TRC = 0.6 K; TRC

Quantity Value Units Method 322. ± 4.

Tfus

Reference

321.41

K

Reference

51. ± kJ/mol 2.5

76.3 kJ/mol

Uncertainty assigned by TRC = 0.02 K; TRC

Reference

Comment

Bernard, Boukari, et al., 1976

V

Quantity Value Units Method ΔsubH°

Comment

De Wit, De Kruif, et al., 1983

N/A

Quantity Value Units Method ΔvapH°

Average of 6 values; Individual data points

K AVG N/A

Quantity Value Units Method Ttriple

Comment

hfusion=20.9±0.8 kJ/mol; ALS

Reference

Comment

DeWit, Van C Miltenburg, et al., 1983

N/A

Antoine Equation Parameters log10(P)

=

A

− =

P

(B

/ vapor

(T pressure

+

C)) (bar)

T = temperature (K) View plot Requires a Java capable browser. Temperature (K)

A

B

338.9 - 457. 5.48918 2278.150

C

Reference

Comment

-41.70 Coefficents calculated by NIST Stull, 1947 7 from author's data.

Enthalpy of sublimation ΔsubH (kJ/mol) Temperature (K) Method 77.7

256. - 273. TE ME

Reference DeWit, Van Miltenburg, et al., 1983

Comment C

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 kJ/mol G+TS Taft, 1987 9.6 due to change in acidity scale

ΔrH°

Quantity Value

Units Method Reference

Comment

1485. ± gas phase; value altered from reference kJ/mol IMRE Taft, 1987 9.2 due to change in acidity scale

ΔrG°

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

in

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

comments: Bartmess

Quantity Value ΔrH°

Comment

1514. ± gas phase; value altered from reference kJ/mol G+TS Taft, 1987 9.6 due to change in acidity scale; B

Quantity Value ΔrG°

Units Method Reference

Units Method Reference

Comment

1485. ± gas phase; value altered from reference 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, Barnard, M., Thermochim. Acta, 1976, 16, 267. [all data]

1976

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

1959

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 • •

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Data from NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database. If you believe that this page may contain an error, please fill out the error report form for this page.

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