Mucobromic acid

Mucobromic acid
Names
	IUPAC name 2,3-dibromo-4-oxobut-2-enoic acid 3,4-dibromo-5-hydroxy-2,5-dihydrofuran-2-one
	Systematic IUPAC name (2Z)-2,3-Dibromo-4-oxo-2-butenoic acid/(±)-3,4-dibromo-5-hydroxy-2(5H)-furanone (1:1)
	Other names 2,3-Dibromomalealdehydic acid Dibromomalealdehydic acid Dibromoaldehydoacrylic acid
Identifiers
CAS Number	488-11-9;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	22236714;
ECHA InfoCard	100.006.973
EC Number	207-670-5;
PubChem CID	24897300;
CompTox Dashboard (EPA)	DTXSID20883397 ;
	InChI InChI=1S/2C4H2Br2O3/c5-1-2(6)4(8)9-3(1)7;5-2(1-7)3(6)4(8)9/h3,7H;1H,(H,8,9)/b;3-2+;
	SMILES C(=O)C(=C(C(=O)O)Br)Br; C1(O)C(Br)=C(Br)C(=O)O1;
Properties
Chemical formula	C4H2Br2O3
Molar mass	257.865 g·mol−1
Appearance	white solid
Melting point	122 to 124 °C (252 to 255 °F; 395 to 397 K)
Boiling point	619.7 °C (1,147.5 °F; 892.9 K)
Solubility in methanol	0.1 g/mL
Vapor pressure	5.96−18 mmHg
Hazards
Main hazards	burns skin and eyes
Safety data sheet	MSDS
EU classification (DSD) (outdated)	C
R-phrases (outdated)	34-37
S-phrases (outdated)	26-36/37/39-45
Flash point	328.6 °C (623.5 °F; 601.8 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Mucobromic acid is an organic compound that consists of a dibrominated alkene with aldehyde and carboxylic acid functional groups.[1] It easily tautomerizes to a furanone hemiacetal form. This compound, and the analogous mucochloric acid (CAS #87-56-9), form the group of known mucohalic acids. The bromide appears to behave similarly to the more heavily studied chloride.

Synthesis and structure

Mucobromic acid can be synthesized by bromination of furfural via an oxidation/decarboxylation process:[1]

C₄H₄OCHO + 3 Br₂ + 3 H₂O → C₂Br₂CHO(CO₂H) + CO₂ + 8 HBr

Mucobromic acid exists as a mixture acyclic and cyclic isomers. The compound can be reduced using sodium borohydride to give the lactone.[2]

Hydrolysis under basic conditions of either the chloro or bromo compound involves substitution of the halide adjacent to the acid. The resulting mucoxyhalic acids exist as a mixture of keto and enol forms.[3] The reaction occurs via a conjugate addition/elimination of the alkene–aldehyde part of the structure.[4]

Hazards

Mucohalic acids have received attention since they are products of the halogenation of biomass. They are genotoxins and potential carcinogens. They have the ability to alkylate certain DNA bases, specifically guanosine, adenosine, and cytosine.[3]

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References

Taylor, G. A. "Mucobromic Acid". Organic Syntheses.; Collective Volume, 4, p. 688
Cunha, Silvio; Oliveira, Caio C.; Sabinob, José R. (2011). "Synthesis of 3-Bromotetronamides via Amination of 3,4-Dibromofuran-2(5H)-one" (PDF). J. Braz. Chem. Soc. 22 (3): 598–603. doi:10.1590/s0103-50532011000300026.
Gómez-Bombarelli, R.; González-Pérez, M.; Calle, E.; Casado, J. (2011). "Reactivity of mucohalic acids in water". Water Research. 45 (2): 714–720. doi:10.1016/j.watres.2010.08.040. PMID 20855100.
Wasserman, H. H.; Precopio, F. M. (1952). "Studies on the mucohalic acids .1. The structure of mucoxychloric acid". J. Am. Chem. Soc. 74 (2): 326–328. doi:10.1021/ja01122a009.

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[OS-1] Taylor, G. A. "Mucobromic Acid". Organic Syntheses.; Collective Volume, 4, p. 688

[2] Cunha, Silvio; Oliveira, Caio C.; Sabinob, José R. (2011). "Synthesis of 3-Bromotetronamides via Amination of 3,4-Dibromofuran-2(5H)-one" (PDF). J. Braz. Chem. Soc. 22 (3): 598–603. doi:10.1590/s0103-50532011000300026.

[Reactions-3] Gómez-Bombarelli, R.; González-Pérez, M.; Calle, E.; Casado, J. (2011). "Reactivity of mucohalic acids in water". Water Research. 45 (2): 714–720. doi:10.1016/j.watres.2010.08.040. PMID 20855100.

[4] Wasserman, H. H.; Precopio, F. M. (1952). "Studies on the mucohalic acids .1. The structure of mucoxychloric acid". J. Am. Chem. Soc. 74 (2): 326–328. doi:10.1021/ja01122a009.