Mucobromic acid

Structural formula
General
Surname	Mucobromic acid
other names	2,3-dibromomale aldehyde acid
Molecular formula	C 4 H 2 Br 2 O 3
Brief description	beige solid
External identifiers / databases
CAS number 488-11-9 EC number 207-670-5 ECHA InfoCard 100.006.973 PubChem 3033972 ChemSpider 22236714 Wikidata Q6931218
properties
Molar mass	257.86 g mol −1
Physical state	firmly
Melting point	120-124 ° C
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 314 P: 280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mucobromic acid is a chemical compound from the group of aldehydic acids .

Extraction and presentation

A practical synthesis for industrial production starts from furfural , which is oxidatively brominated to mucobromic acid with ring opening .

${\displaystyle \mathrm {C_{4}H_{4}OCHO+3\ Br_{2}+3\ H_{2}O\rightarrow C_{2}Br_{2}CHO(CO_{2}H)+CO_{2}+8\ HBr} }$

properties

Mucobromic acid is a beige solid. Mucobromic acid exists as a mixture of acyclic and cyclic isomers. The compound can be reduced to the lactone using sodium borohydride .

use

Mucobromic acid is used as an intermediate in the preparation of the sodium salt of nitromalondialdehyde , which is a valuable intermediate in the synthesis of heterocyclic compounds, or of hexanitroethane .

Individual evidence

1. ↑ ^{a b c d e f} data sheet Mucobromic acid, 99% from Sigma-Aldrich , accessed on December 12, 2015 ( PDF ).
2. ↑ Gallaghan, JA; Lomond, B .; Reed, WL: Synthesis of Hexanitroethane , Patent US 3,101,379 (1963). Google Patents
3. ↑ Taylor, GA: Mucobromic Acid. In: Organic Syntheses , Coll. Vol. 4 (1963), p. 688, doi : 10.1002 / 0471264180.os900.13 ( PDF ).
4. ↑ Silvio Cunha, Caio C Oliveira, José R Sabino: Synthesis of 3-bromotetronamides via amination of 3,4-dibromofuran-2 (5H) -one. In: Journal of the Brazilian Chemical Society. 22, 2011, p. 598, doi : 10.1590 / S0103-50532011000300026 .
5. ↑ Data sheet Mucobromic acid, 98 +% from AlfaAesar, accessed on December 12, 2015 ( PDF )(JavaScript required) .