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Feist's acid

Feist's acid
	Skeletal formula of the (−)-enantiomer of Feist's acid
Names
	IUPAC name trans-3-methylidenecyclopropane-1,2-dicarboxylic acid
	Preferred IUPAC name rel-(1R,2R)-3-methylidenecyclopropane-1,2-dicarboxylic acid
	Other names trans-3-methylenecyclopropane-1,2-dicarboxylic acid; trans-3-methylidenecyclopropane-1,2-dicarboxylic acid; 3-methylenecyclopropane-trans-1,2-dicarboxylic acid; Feist's acid;
Identifiers
CAS Number	(±): 499-02-5; (−): 148152-68-5;
3D model (JSmol)	(±): Interactive image; (−): Interactive image;
ChemSpider	(±): 643905;
EC Number	(±): 207-874-4;
PubChem CID	(±): 736804;
	InChI (±): InChI=1/C6H6O4/c1-2-3(5(7)8)4(2)6(9)10/h3-4H,1H2,(H,7,8)(H,9,10)/t3-,4-/s2 Key: XZVHROKAQFFOCA-SEFKMRKONA-N; (−): InChI=1S/C6H6O4/c1-2-3(5(7)8)4(2)6(9)10/h3-4H,1H2,(H,7,8)(H,9,10)/t3-,4-/m1/s1 Key: XZVHROKAQFFOCA-QWWZWVQMSA-N;
	SMILES (±): C(O)(=O)[C@H]1[C@H](C(O)=O)C1=C; (−): C(O)(=O)[C@H]1[C@H](C(O)=O)C1=C;
Properties
Chemical formula	C6H6O4
Molar mass	142.110 g·mol−1
Melting point	200 °C (392 °F; 473 K)
Structure
Crystal structure	triclinic
Space group	P1
Lattice constant	a = 4.83±0.02 Å, b = 7.60±0.03 Å, c = 9.15±0.04 Å α = 94°50′ ± 1°, β = 96°18′ ± 1°, γ = 101°30′ ± 1°
Lattice volume (V)	326.5 Å3
Formula units (Z)	2
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H315, H318, H335
Safety data sheet (SDS)	Sigma-Aldrich
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tracking categories (test):

SizeSet

Feist's acid is an organic dicarboxylic acid with the formula C₆H₆O₄.

History

Feist's acid was discovered in 1893 by Franz Feist [de]. He proposed a structural formula featuring a cyclopropene ring with a double bond between the carbon atoms connected to the two carboxyl groups.

Preparation

Notes

^ The prefix rel is preferred over cis/trans when used to indicate relative stereochemistry between two substituents in a ring system.^[1]

References

^ Favre, Henry A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013. Cambridge, England: Royal Society of Chemistry. p. 1245. doi:10.1039/9781849733069. ISBN 978-1-84973-306-9. OCLC 865143943.
^ Coffey, S., ed. (2008). Alicyclic Compounds: Monocarbocyclic Compounds to and Including Five Ring Atoms. Vol. II (2nd ed.). Elsevier. p. 60. ISBN 978-0-444-53345-6. {{cite book}}: |work= ignored (help)
^ Downie, Thomas Cochrane (1952). Studies in crystal structure: Acid salts of salicylic acid (Part A); Feist's acid and its salts (Part B) (PDF) (PhD thesis). University of Glasgow.

Bibliography

Lloyd, Douglas, ed. (1969). Feist's Acid. Springer, Boston, MA. doi:10.1007/978-1-4684-8270-6_5. {{cite book}}: |work= ignored (help)

[2] The prefix rel is preferred over cis/trans when used to indicate relative stereochemistry between two substituents in a ring system.^[1]

[1] Favre, Henry A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013. Cambridge, England: Royal Society of Chemistry. p. 1245. doi:10.1039/9781849733069. ISBN 978-1-84973-306-9. OCLC 865143943.

[3] Coffey, S., ed. (2008). Alicyclic Compounds: Monocarbocyclic Compounds to and Including Five Ring Atoms. Vol. II (2nd ed.). Elsevier. p. 60. ISBN 978-0-444-53345-6. {{cite book}}: |work= ignored (help)

[4] Downie, Thomas Cochrane (1952). Studies in crystal structure: Acid salts of salicylic acid (Part A); Feist's acid and its salts (Part B) (PDF) (PhD thesis). University of Glasgow.

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