487047-30-3

Basic information

• Product Name: 2(5H)-Furanone, 3-chloro-4-[4-(methylthio)phenyl]-
• CAS NO: 487047-30-3
• Molecular Formula: C11H9ClO2S
• Molecular Weight: 240.71
• Mol File: 487047-30-3.mol

Chemical Properties

• CAS DataBase Reference: 2(5H)-Furanone, 3-chloro-4-[4-(methylthio)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(5H)-Furanone, 3-chloro-4-[4-(methylthio)phenyl]-(487047-30-3)
• EPA Substance Registry System: 2(5H)-Furanone, 3-chloro-4-[4-(methylthio)phenyl]-(487047-30-3)

Safety Data

• Hazardous Substances Data: 487047-30-3(Hazardous Substances Data)

Upstream product

• 62674-12-8 3,4-dichloro-5H-furan-2-one 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 

Downstream Products

• 162011-90-7 rofecoxib 
• 487047-31-4 3-chloro-4-(4'-methylsulfonylphenyl)-5H-furan-2-one 
• 162012-30-8 4-(4-(methylthio)phenyl)-3-phenylfuran-2(5H)-one 

Relevant articles and documents

Preparation of aryl-substituted butenolides using mucohalic acids

Methods and materials for preparing 3-aryl-2-buten-4-olides and 2,3-bisaryl-2-buten-4-olides are disclosed. The methods include reacting a mucohalic acid with a reducing agent to give a 2,3-dihalo-2-buten-4-olide, which undergoes at least one Pd catalyzed cross-coupling reaction with an arylboronic acid.

Mucochloric acid: A useful synthon for the selective synthesis of 4-aryl-3-chloro-2(5H)-furanones, (Z)-4-aryl-5-[1-(aryl)methylidenel-3-chloro-2(5H)-furanones and 3,4-diaryl-2(5H)-furanones

3,4-Dichloro-2(5H)-furanone, which has been prepared efficiently from mucochloric acid, has been transformed selectively into 4-aryl-3-chloro-2(5H)-furanones either by Suzukior Stille-type reactions. These monochloro derivatives have been used as precursors either to (Z)-4-aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones, including naturally occurring rubrolide M, or to unsymmetrical 3,4-diaryl-2(5H)-furanones. Some 2(5H)-furanone derivatives so prepared have been found to exhibit significant cytotoxic activity in vitro against the NCI three-cell-line panel, but limited cytotoxicity against the NCI human tumor 60 cell-line panel. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Reinvestigation of mucohalic acids, versatile and useful building blocks for highly functionalized alpha,beta-unsaturated gamma-butyrolactones.

[reaction: see text] Mucohalic acids (mucochloric acid (1, 3,4-dichloro-5-hydroxy-5H-furan-2-one) and mucobromic acid (2, 3,4-dibromo-5-hydroxy-5H-furan-2-one)) are inexpensive, commercially available starting materials with multiple functional groups. These compounds have been modified by way of reduction followed by Suzuki cross-coupling reactions involving arylboronic acids to afford highly functionalized alpha,beta-unsaturated gamma-butyrolactones in excellent yield. The synthetic utility of these building blocks was effectively demonstrated through preparation of the antiinflammatory drug Vioxx.