31004-27-0

Basic information

• Product Name: 3-chlorofuran-2(5H)-one
• Synonyms: 3-chlorofuran-2(5H)-one;3-Chloro-2(5H)-furanone;3-Chloro-5H-furan-2-one
• CAS NO: 31004-27-0
• Molecular Formula: C₄H₃ClO₂
• Molecular Weight: 118.51842
• EINECS: 250-428-9
• Mol File: 31004-27-0.mol

Chemical Properties

• Melting Point: 25-27 °C
• Boiling Point: 273.2 °C at 760 mmHg
• Flash Point: 151.8 °C
• Appearance: /
• Density: 1.4 g/cm³
• Vapor Pressure: 0.00582mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: 3-chlorofuran-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chlorofuran-2(5H)-one(31004-27-0)
• EPA Substance Registry System: 3-chlorofuran-2(5H)-one(31004-27-0)

Safety Data

• Hazardous Substances Data: 31004-27-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Chlorofuran-2(5H)-one is used as a key intermediate in organic synthesis for the production of a wide range of compounds. Its unique reactivity and properties allow for the formation of various derivatives, making it a versatile building block in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-chlorofuran-2(5H)-one serves as a crucial component in the development of pharmaceuticals. Its structural features enable the creation of novel drug candidates with potential therapeutic applications.
Used in Agrochemicals Production:
3-Chlorofuran-2(5H)-one is also utilized in the production of agrochemicals, such as pesticides and herbicides. Its chemical properties make it suitable for the synthesis of active ingredients in these agricultural products, contributing to their effectiveness in controlling pests and weeds.
Used in Materials Science:
3-chlorofuran-2(5H)-one has potential applications in materials science, where it can be incorporated into the development of new materials with specific properties. Its unique structure and reactivity can contribute to the creation of advanced materials with applications in various industries.

InChI:InChI=1/C4H3ClO2/c5-3-1-2-7-4(3)6/h1H,2H2

Upstream product

• 108250-04-0 3,4-dichloro-2,5-dimethoxy-tetrahydro-furan-2-carboxylic acid methyl ester 
• 96-02-6 2-chloromaleic anhydride 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 62674-12-8 3,4-dichloro-5H-furan-2-one 
• 72167-53-4 3-bromo-2,5-dimethoxy-2,5-dihydro-furan 

Downstream Products

• 5837-72-9 methyl (E)-4-oxo-2-butenoate 
• 2960-66-9 4-oxo-but-2-enoic acid ethyl ester 

Relevant articles and documents

General, regiodefined access to α-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory Gorgonian lipid

(Chemical Equation Presented) A variety of α-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.

Efficient preparation of 3-substituted-furan-2(5H)-ones and their direct vinylogous aldol addition

The deprotonation of 3-substituted-furan-2(5H)-ones 1, obtained via the hydrolysis of 3-substituted-2,5-dihydro-2,5-dimethoxyfurans, affords in the reaction with both aromatic and aliphatic aldehydes regioselectively the unsaturated 3-substituted 5-(1′-hydroxy)-γ-butyrolactones, such as 4, 5, 6, 7, 8, 9 and 10. The use of Lewis acids allows modulation of the diastereoisomeric ratios. The subsequent reduction, carried out with nickel boride, gives rise to the formation of the corresponding saturated 5-(1′-hydroxy)-γ-butyrolactones, such as 11, 12 and 13.

Regioselectivity of metal hydride reductions of unsymmetrically substituted cyclic anhydrides. Systems where "steric hindrance along the preferred reaction path" rationalization is not applicable

Metal hydride reductions of planar cyclic anhydrides such as methylmaleic or 3-substituted phthalic anhydrides occur preferentially at the sterically more hindered carbonyl function.This regioselectivity cannot be rationalized in terms of "the most favourable pathway for non-perpendicular attack by a nucleophile" since both carbonyl groups present are equally accessible to non-perpendicular approach.A study which takes into account the alkaline cation and inductive, mesomeric, and steric effects has been conducted for the reduction of several conjugated and aromatic anhydrides.A qualitative interpretation for the regioselectivities observed in these reductions (as well as in reductions already reported in the literature) is suggested.An early transition state for the catalyzed versus late transition state for the non-catalyzed process is proposed.