Furan-3-carboxylic acid

Structural formula
General
Surname	Furan-3-carboxylic acid
other names	3-furoic acid
Molecular formula	C 5 H 4 O 3
Brief description	white solid
External identifiers / databases
CAS number 488-93-7 EC number 207-689-9 ECHA InfoCard 100.006.991 PubChem 10268 Wikidata Q21045227
properties
Molar mass	112.08 g mol −1
Physical state	firmly
density	1.32 g cm −3
Melting point	120-122 ° C
pK s value	4.0 (25 ° C)
solubility	almost insoluble in water soluble in ethanol and ethyl acetate
Refractive index	1.471
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Furan-3-carboxylic acid is a chemical compound from the group of furan derivatives and carboxylic acids .

Occurrence

Furan-3-carboxylic acid was first isolated from the root bark of Euonymus atropurpurea by Rogerson in 1912 . It is also found in the roots of the bean and sweet potato , which were infected with the Ceratostomella fimbriate fungus , and in the essential oil from tobacco leaves.

Extraction and presentation

Furan-3-carboxylic acid can be obtained by aromatizing 3-trichloroacetyl-4,5-dihydrofuran with N -bromo succinimide in carbon tetrachloride , followed by a nucleophilic shift with hydroxides, alcohols and amines (e.g. sodium hydroxide and benzene ).

Synthesis by reaction of 3-furyllithium with carbon dioxide is also possible , the former in turn being obtained by oxidative cyclization of 2-butyne-1,4-diol .

properties

Furan-3-carboxylic acid is a white solid.

use

Furan-3-carboxylic acid can be used for the synthesis of other chemical compounds (such as resmethrin ) or of furan-2,5- and furan-2,4-dicarboxylic acid under solvent-free conditions via a disproportionation reaction .

See also

• Furan-2-carboxylic acid

Individual evidence

1. ↑ ^{a b c} Data sheet furan-3-carboxylic acid (PDF) from Merck , accessed on September 2, 2015.
2. ^ ^{A b} Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 65 ( limited preview in Google Book search).
3. ↑ ^{a b c d e} data sheet 3-Furoic acid, 98% from Sigma-Aldrich , accessed on September 2, 2015 ( PDF ).
4. ^ Alan R. Katritzky: Handbook of Heterocyclic Chemistry . Elsevier, 2013, ISBN 978-1-4832-9342-4 , pp. 281 ( limited preview in Google Book search).
5. ^ William M. Haynes: CRC Handbook of Chemistry and Physics, 94th Edition . CRC Press, 2013, ISBN 978-1-4665-7115-0 , pp. 3–280 ( limited preview in Google Book search).
6. ↑ R. Hegnauer: Chemotaxonomie der Pflanzen An overview of the distribution and the systematic importance of plant substances. Volume 3: Dicotyledoneae: Acanthaceae - Cyrillaceae . Springer-Verlag, 2013, ISBN 978-3-0348-9385-5 , pp. 556 ( limited preview in Google Book search).
7. ^ Chemicals and Drugs (CI – G) . Springer-Verlag, 2013, ISBN 978-3-642-80620-9 , pp. 1071 ( limited preview in Google Book search).
8. ↑ Julio Alvarez-Builla, Juan José Vaquero, José Barluenga: Modern Heterocyclic Chemistry Vol. 1 . John Wiley & Sons, 2011, ISBN 978-3-527-33201-4 , pp. 2407 ( limited preview in Google Book search).
9. ↑ Wataru Ando, ​​Daniel Bellus, Uwe Bergsträßer, David Black, Heinrich Heydt, Burkhard König, Gerhard Maas, Francois Mathey, Manfred Regitz, Jürgen Schatz, Norihiro Tokitoh, Klaus-Peter Zeller: Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 9 Fully Unsaturated Small-Ring Heterocycles and Monocyclic Five-Membered Hetarenes with One Heteroatom . Georg Thieme Verlag, 2014, ISBN 3-13-112231-5 , p. 210 ( limited preview in Google Book search).