2-Butenoic acid, 3-methyl-, ethyl ester

Formula: C₇H₁₂O₂
Molecular weight: 128.1690
IUPAC Standard InChI: InChI=1S/C7H12O2/c1-4-9-7(8)5-6(2)3/h5H,4H2,1-3H3
IUPAC Standard InChIKey: UTXVCHVLDOLVPC-UHFFFAOYSA-N
CAS Registry Number: 638-10-8
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: Crotonic acid, 3-methyl-, ethyl ester; Ethyl β,β-dimethylacrylate; Ethyl dimethylacrylate; Ethyl isopropylideneacetate; Ethyl senecioate; Ethyl 3-methyl-2-butenoate; Ethyl 3-methylcrotonate; Ethyl 3,3-dimethylacrylate; Ethyl β-methylcrotonate; Ethyl 3-methylbut-2-enoate; 3-Methyl-2-butenoic acid, ethyl ester; 3,3-Dimethylacrylic acid ethyl ester; Ethyl isobutenoate; NSC 61853; NSC 99208
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Other data available:
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Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity	Value	Units	Method	Reference	Comment
T_boil	426.7	K	N/A	Weast and Grasselli, 1989	BS
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	11.8 ± 0.05	kcal/mol	GS	Emel'yanenko, Toktonov, et al., 2008	Based on data from 274. to 319. K.; AC

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	SE-30	150.	902.	Ashes and Haken, 1975	He, Celatom silanized (62-72 mesh); Column length: 3.7 m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-5	924.	Engel and Ratel, 2007	60. m/0.32 mm/1. μm, 40. C @ 2. min, 3. K/min, 230. C @ 10. min

Van Den Dool and Kratz RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1217.	Cantergiani, Brevard, et al., 2001	30. m/0.25 mm/0.25 μm; Program: 20C(30s) => fast => 60C => 4C/min => 220C (20min)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	ZB-1	911.	Mierendorff, Stahl-Biskup, et al., 2008	30. m/0.25 mm/0.25 μm, Nitrogen, 3. K/min; T_start: 45. C; T_end: 230. C
Capillary	ZB-1	911.	Mierendorff, Stahl-Biskup, et al., 2003	30. m/0.25 mm/0.25 μm, N2, 3. K/min; T_start: 45. C; T_end: 230. C

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1219.	Beck, Higbee, et al., 2008	60. m/0.32 mm/0.25 μm, Helium, 30. C @ 4. min, 2. K/min, 200. C @ 30. min

References

Go To: Top, Phase change data, Gas Chromatography, Notes

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Emel'yanenko, Toktonov, et al., 2008
Emel'yanenko, Vladimir N.; Toktonov, Alexey V.; Kozlova, Svetlana A.; Verevkin, Sergey P.; Andrushko, Vasyl; Andrushko, Natalia; Börner, Armin, Structure-Energy Relationships in Unsaturated Esters of Carboxylic Acids. Thermochemical Measurements and ab Initio Calculations, J. Phys. Chem. A, 2008, 112, 17, 4036-4045, https://doi.org/10.1021/jp7115033 . [all data]

Ashes and Haken, 1975
Ashes, J.R.; Haken, J.K., Gas chromatography of homologous esters. IX. Structure-retention increments of unsaturated esters, J. Chromatogr., 1975, 111, 1, 171-187, https://doi.org/10.1016/S0021-9673(01)80159-X . [all data]

Engel and Ratel, 2007
Engel, E.; Ratel, J., Correction of the data generated by mass spectrometry analyses of biological tissues: Application to food authentication, J. Chromatogr. A, 2007, 1154, 1-2, 331-341, https://doi.org/10.1016/j.chroma.2007.02.012 . [all data]

Cantergiani, Brevard, et al., 2001
Cantergiani, E.; Brevard, H.; Krebs, Y.; Feria-Morales, A.; Amadò, R.; Yeretzian, C., Characterisation of the aroma of green Mexican coffee and identification of mouldy/earthy defect, Eur. Food Res. Technol., 2001, 212, 6, 648-657, https://doi.org/10.1007/s002170100305 . [all data]

Mierendorff, Stahl-Biskup, et al., 2008
Mierendorff, H.-G.; Stahl-Biskup, E.; Posthumus, M.A.; van Beek, T.A., Composition of commercial Cape chamomile oil (Eriocephalus punctuatus / Eriocephalus tenuifolius), 2008, retrieved from http://www.chemische-analysen-hamburg.de/Publikationen?Cape_Chamomile_Oil/. [all data]

Mierendorff, Stahl-Biskup, et al., 2003
Mierendorff, H.-G.; Stahl-Biskup, E.; Posthumus, M.A.; van Beek, T.A., Composition of commercial Cape chamomile oil (Eriocephalus punctulatus), Flavour Fragr. J., 2003, 18, 6, 510-514, https://doi.org/10.1002/ffj.1259 . [all data]

Beck, Higbee, et al., 2008
Beck, J.J.; Higbee, B.S.; Marrill, G.B.; Roitman, J.N., Comparison of volatile emissions from undamaged and mechanically damaged almonds, J, Sci. Food Argic., 2008, 88, 8, 1363-1368, https://doi.org/10.1002/jsfa.3224 . [all data]

Notes

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Symbols used in this document:

T_boil Boiling point

Δ_vapH° Enthalpy of vaporization at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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T_boil	Boiling point
Δ_vapH°	Enthalpy of vaporization at standard conditions