56473-96-2

Basic information

• Product Name: 3-azido-2-furaldehyde
• Synonyms: 3-azido-2-furaldehyde
• CAS NO: 56473-96-2
• Molecular Formula: C₅H₃N₃O₂
• Molecular Weight: 137.09622
• Mol File: 56473-96-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-azido-2-furaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-azido-2-furaldehyde(56473-96-2)
• EPA Substance Registry System: 3-azido-2-furaldehyde(56473-96-2)

Safety Data

• Hazardous Substances Data: 56473-96-2(Hazardous Substances Data)

Upstream product

• 14757-78-9 3-bromofurfural 

Downstream Products

• 898552-91-5 3-imino(triphenyl)phosphorane-furan-2-carbaldehyde 
• 83818-75-1 ethyl 2-phenylfuro<3,2-c><1λ⁴,2>thiazine-3-carboxylate 
• 272-62-8 furo[3,2-b]pyridine 
• 183448-68-2 3-amino-2-thioformylfuran 
• 56489-00-0 3-Amino-2-formylfuran 
• 56473-91-7 furo<3,2-b>pyridine-5-carboxylic acid 

Relevant articles and documents

3-Nitrene-2-formylthiophene and 3-Nitrene-2-formylfuran: Matrix Isolation, Conformation, and Rearrangement Reactions

Two new heteroarylnitrenes, 3-nitrene-2-formylthiophene (15/15′) and 3-nitrene-2-formylfuran (16/16′), in the triplet ground state have been generated in solid Ar (10.0 K) and N2 (15.0 K) matrices by the 266 nm laser photolysis of 3-azido-2-formylthiophene (13) and 3-azido-2-formylfuran (14), respectively. According to the characterization with matrix-isolation IR spectroscopy and quantum chemical calculations at the B3LYP/6-311++G(3df,3pd) level, both nitrenes exhibit two conformations depending on the orientation of the formyl groups. Upon subsequent green-light irradiation (532 nm), both the nitrenes 15/15′ and 16/16′ undergo ring closure to form 3,2-thienoisoxazole (17) and 3,2-furoisoxazole (18), respectively. Traces of 3-imino-4,5-dihydrothiophene-2-ketene (19), formally formed through the intramolecular 1,4-H shift in the corresponding nitrenes 15/15′, have been also identified among the laser photolysis products of the azide 13. In sharp contrast to the photochemistry, the high-vacuum flash pyrolysis (HVFP) of the azide 13 at ca. 1000 K mainly yields imino ketene in two conformations 19/19′ together with traces of isoxazole 17. In addition to the reversible conformational interconversion in the imino ketene 19 ? 19′, the photoisomerization from isoxazole 17 to imino ketene 19 has also been observed. The HVFP of the azide 14 at ca. 1000 K results in complete dissociation to HCN, C2H2, CO, CO2, H2O, and N2. Unlike the recently disclosed hydrogen-atom tunneling (HAT) in the transformation from the structurally related 2-formyl phenylnitrene (2) to imino ketene 3 in a cryogenic Ar-matrix, the absence of HAT in nitrenes 15 and 16 can be reasonably explained by the higher barrier heights and also larger barrier widths in the isomerization reactions.

Rigidified Compounds for Modulating Heparanase Activity

Disclosed are novel rigidified compounds having a rhodanine-like residue and at least one aryl or heteroaryl residue linked to the rhodanine-like residue, whereby a core structure of these compounds, as defined in the specification, is characterized as having one or zero free-to-rotate bonds. Also disclosed are pharmaceutical compositions containing these rigidified compounds and uses thereof for modulating the activity of heparanase and hence in the treatment of heparanase-associated diseases and disorders, and uses thereof for modulating the activity of heparin-binding proteins and hence in the treatment of heparin-binding proteins-associated diseases and disorders as well as in the treatment of medical conditions that are at least partially treatable by rhodanine or a rhodanine analog.