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24700

Sigma-Aldrich

3-Chloro-2,4(3H,5H)-furandione

≥98.0% (HPLC)

Synonym(s):

3-Chlorotetronic acid

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About This Item

Empirical Formula (Hill Notation):
C4H3ClO3
CAS Number:
4971-55-5
Molecular Weight:
134.52
Beilstein:
113477
MDL number:
MFCD00134273
UNSPSC Code:
12352100
PubChem Substance ID:
57648093
NACRES:
NA.22

Assay

≥98.0% (HPLC)

mp

206 °C (dec.) (lit.)

SMILES string

ClC1C(=O)COC1=O

InChI

1S/C4H3ClO3/c5-3-2(6)1-8-4(3)7/h3H,1H2

InChI key

DJEJYZZJYYNADA-UHFFFAOYSA-N

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Application

3-Chloro-2,4(3H,5H)-furandione (3-Chlorotetronic acid) is a C4-heterocyclic building block and has been used in synthesis of:
  • pure tetronic acid
  • pyridinium-, isoquinolinium-, quinolinium- and N-methyl imidazolium zwitterions
  • pyridine-, isoquinoline-, quinoline- and N-methylimidazole ylides
  • rubrolide L, a marine ascidian butenolide and a potent inhibitor of human aldose reductase

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T. Meul et al.
Chimia, 41, 73-73 (1987)
Synthesis of the human aldose reductase inhibitor rubrolide L.
Boukouvalas J and McCann LC.
Tetrahedron Letters, 51(35), 4636-4639 (2010)
Synthesis of highly stable unusual charge-separated pyridinium-, isoquinolinium-, quinolinium-, and N-methylimidazolium-tetronic acid zwitterions.
Shaabani A, et al.
Tetrahedron, 65(31), 6063-6068 (2009)

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