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Basic Information
CAS No.: 87-56-9
Name: Mucochloric acid
Article Data: 12
Molecular Structure:
Molecular Structure of 87-56-9 (Mucochloric acid)
Formula: C4H2 Cl2 O3
Molecular Weight: 168.964
Synonyms: 2-Butenoicacid, 2,3-dichloro-4-oxo-, (Z)-; Malealdehydic acid, dichloro- (7CI,8CI);Mucochloric acid (6CI); 2,3-Dichloromaleic aldehyde acid; Dichloromalealdehydicacid; a,b-Dichloro-b-formylacrylic acid
EINECS: 201-752-4 (CHO)CCl=CClCOOH
Density: 1.648 g/cm3
Melting Point: 124 - 128 C
Boiling Point: 271 °C at 760 mmHg
Flash Point: 186 C
Solubility: 27 (g/l) SOLVENT yellowish liquid
Hazard Symbols: 8 (Packing Group: II) UN NO.
Risk Codes: R25;R34;R37;R42/43
Safety: Poison by ingestion. Moderate skin and severe eye irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl.
Transport Information: 25kgs
PSA: 54.37000
LogP: 0.95910
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    Mucochloric acid

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Chemistry

Molecular Formula: C4H2Cl2O3
Molar mass: 168.96 g/mol
EINECS: 201-752-4
Density: 1.648 g/cm3
Flash Point: 117.7 °C
Index of Refraction: 1.532
Boiling Point: 271 °C at 760 mmHg
Vapour Pressure: 0.00186 mmHg at 25°C
Melting point: 125-128 °C(lit.)
Water solubility: slightly soluble in cold water, easily deliquescence
Appearance: Light beige white crystalline powder
Solubility: Soluble in hot water, ethanol, ether and hot benzene
Structure of Mucochloric acid (87-56-9):

XLogP3-AA: 1.2
H-Bond Donor: 1
H-Bond Acceptor: 3
IUPAC Name: (E)-2,3-Dichloro-4-oxobut-2-enoic acid
Canonical SMILES: C(=O)C(=C(C(=O)O)Cl)Cl
Isomeric SMILES: C(=O)/C(=C(/C(=O)O)\Cl)/Cl
InChI: InChI=1S/C4H2Cl2O3/c5-2(1-7)3(6)4(8)9/h1H,(H,8,9)/b3-2+ 
InChIKey: LUMLZKVIXLWTCI-NSCUHMNNSA-N

Uses

 Mucochloric acid (87-56-9) can be used for organic synthesis intermediates. It is not only used for the synthesis of novel broad-spectrum acaricide: Pyridaben, herbicide: Bjarnason, but also for medicines and sulfapyridine such as photosensitive materials synthesis.

Production

1. Furfural by oxidation and chlorination: leads chlorine in strong acidic solution.
2. Manganese Dioxide - Hydrochloric acid by oxidation-chlorination method: in the presence of hydrochloric acid, Furfural and Manganese dioxide is oxidated at low temperatures, and then increasing the temperature for chlorination.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 100mg/kg (100mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(12), Pg. 16, 1969.
guinea pig LDLo skin 1gm/kg (1000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" National Technical Information Service. Vol. OTS0546543,
mouse LD50 oral 84mg/kg (84mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 46, 1982.
mouse LDLo intraperitoneal 10mg/kg (10mg/kg)   National Technical Information Service. Vol. OTS0546543,
rabbit LD50 oral 160mg/kg (160mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(12), Pg. 16, 1969.
rat LD50 intraperitoneal 10mg/kg (10mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0546543,
rat LD50 oral 100mg/kg (100mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(12), Pg. 16, 1969.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by ingestion. Moderate skin and severe eye irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl.

Specification

 Mucochloric acid (87-56-9) also can be called Malealdehydic acid, dichloro- (8CI) ; Acrylic acid, 2,3-dichloro-3-formyl- ; 2-Butenoic acid, 2,3-dichloro-4-oxo-, (Z)- ; 2-Butenoic acid, 2,3-dichloro-4-oxo-, (2Z)- ; Malealdehydic acid, dichloro-4-oxo-, (Z)- (9CI) .It is stimulating effect on the skin.