20357-65-7

Basic information

• Product Name: 6-CHLOROPYRAN-2H-ONE 97
• Synonyms: 6-CHLOROPYRAN-2H-ONE 97;6-chloropyran-2h-one;6-Chloro-2H-pyran-2-one;6-Chloro-2-pyrone;6-Chloro-α-pyrone
• CAS NO: 20357-65-7
• Molecular Formula: C₅H₃ClO₂
• Molecular Weight: 130.53
• Mol File: 20357-65-7.mol

Chemical Properties

• Boiling Point: 193-194 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.356 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.035mmHg at 25°C
• Refractive Index: n20/D 1.5560(lit.)
• CAS DataBase Reference: 6-CHLOROPYRAN-2H-ONE 97(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLOROPYRAN-2H-ONE 97(20357-65-7)
• EPA Substance Registry System: 6-CHLOROPYRAN-2H-ONE 97(20357-65-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37-45
• WGK Germany: 3
• Hazardous Substances Data: 20357-65-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 2318, 1968 DOI: 10.1021/ja01011a020

InChI:InChI=1/C5H3ClO2/c6-4-2-1-3-5(7)8-4/h1-3H

Upstream product

• 628-48-8 glutaconic acid 
• 1724-02-3 glutaconic acid 
• 75-36-5 acetyl chloride 

Downstream Products

• 24203-77-8 6-pent-1-ynyl-pyran-2-one 
• 518062-89-0 6-phenylethynyl-pyran-2-one 
• 27593-23-3 6-pentyl-2H-pyran-2-one 
• 73178-43-5 (E)-diethyl glutaconate 

Relevant articles and documents

A flexible route to bioactive 6-alkyl-α-pyrones

Both 6-chloro-α-pyrones and 3-chlorobenzopyran-1-ones react with malonates followed by a double decarboalkoxylation to give the corresponding alkyl and alkenyl products.

Catalytic asymmetric diastereodivergent deracemization

Your wish is my command: Deracemization is a powerful strategy wherein a racemate is converted into a 100 % yield of a single enantiopure product. A new concept in catalytic deracemization is presented, in which a racemate with n stereogenic elements can be selectively converted into each one of 2m (m=number of chiral centers of the product) different enantiopure products, by simple tuning of the reaction conditions. Copyright

First total synthesis of naturally occurring (-)-nitidon and its enantiomer

The first total synthesis of naturally occurring (-)-nitidon and its enantiomer is reported. The best of the routes investigated for preparation of these enantiomerically pure compounds involves a modification of the Cadiot-Chodkiewicz reaction and the Sharpless asymmetric epoxidation of an (E)-2-ene-4,6-diyn-1-ol as key steps and proceeds in five steps and 18% overall yield. Both enantiomers of nitidon and some related 6-(1,3-diyn-1-yl)-2H-pyran- 2-ones have been found to exhibit significant cytotoxic activity against human cancer cell lines in vitro. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

6-Chloro-2(2H)-pyranone: A new 2(2H)-pyranone synthon

6-Chloro-2(2H)-pyranone, which can be prepared in high yield from commercially available trans-glutaconic acid, undergoes facile Pd/Cu-catalyzed reaction with various 1-alkynes to give rise to the corresponding 6-(1-alkynyl)-2(2H)-pyranones in moderate to good yields. These last hitherto unknown compounds have been used as direct precursors to 6-alkyl- and 6-[(Z)-1-alkenyl]-2(2H)-pyranones.