4889-69-4

Basic information

• Product Name: 1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)-
• CAS NO: 4889-69-4
• Molecular Formula: C14H9ClO2
• Molecular Weight: 244.677
• Mol File: 4889-69-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 224 °C
• Boiling Point: 395.4±42.0 °C(Predicted)
• Density: 1.342±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)-(4889-69-4)
• EPA Substance Registry System: 1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)-(4889-69-4)

Safety Data

• Hazardous Substances Data: 4889-69-4(Hazardous Substances Data)

Usage

Description

1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)-, commonly known as coumarin, is a chemical compound characterized by its distinctive sweet smell and a bitter taste. It is widely recognized for its applications in the fragrance and flavor industries, as well as its utility in the synthesis of pharmaceuticals, dyes, and anticoagulant drugs. Despite its diverse uses, coumarin's consumption is regulated due to potential health risks such as liver damage and medication interactions.

Uses

Used in Perfumery:
1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)is used as a fragrance ingredient for its sweet, distinctive scent, contributing to the creation of various perfumes and colognes.
Used in Flavor Industry:
In the flavor industry, 1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)is used as a flavoring agent to impart a unique taste to a range of foods and beverages.
Used in Pharmaceutical Synthesis:
Coumarin is utilized as a precursor in the synthesis of various pharmaceuticals, highlighting its importance in the development of new medications.
Used in Dye Production:
1(3H)-Isobenzofuranone, 3-(4-chlorophenyl)serves as an intermediate in the production of dyes, playing a crucial role in the coloring of different materials.
Used in Anticoagulant Drug Manufacturing:
Coumarin is also used in the manufacturing process of anticoagulant drugs, where it acts as an essential intermediate for the development of these life-saving medications.

Upstream product

• 85-56-3 2-(4-chlorobenzoyl)benzoic acid 
• 1679-18-1 4-Chlorophenylboronic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 7468-67-9 o-formylbenzonitrile 
• 4122-56-9 methyl o-formylbenzoate 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 88070-48-8 N-methylbenzamide 
• 104-88-1 4-chlorobenzaldehyde 
• 65-85-0 benzoic acid 
• 119-67-5 o-carboxybenzaldehyde 
• 84761-77-3 2-formylphenyl triflate 
• 593-51-1 methylamine hydrochloride 
• 74-89-5 methylamine 
• 610-97-9 o-iodo-methyl-benzoic acid 

Downstream Products

• 1401613-06-6 C₁₈H₁₁ClOS 
• 1401613-08-8 2-(4-chlorobenzoyl)phenyl(thiophene-2-yl)methanone 
• 1401613-13-5 C₂₈H₃₁ClO₄S 

Relevant articles and documents

Efficient One-Pot Synthesis of 3-Substituted Phthalides via Additive Arylation of Organozinc Intermediate

In recent years, substitution at the third position on phthalides has been proven a valua-ble synthetic intermediate for developing active molecules. We reported a direct and efficient one-pot method for the synthesis of 3-aryl Phthalides performed by adding organo-zinc reagent on methyl-2-formylbenzoate; reagent formed in-situ by the reaction between diethylzinc and different aryl boronic acid derivatives without using any ligand. The possible mechanism involved a coordi-nated zinc carbonyl transition state, arylation, and followed by the intramolecular cyclization. The substituents groups in boronic having different electronic and steric properties played an important role in the reaction completion time and yield. The structure elucidation and confirmation of the synthesized compounds were done by using H-NMR analytical data. The method can be useful for synthesizing various scaffolds and intermediates in search of potentially active compounds.

Catalytic asymmetric synthesis of 3-aryl phthalides enabled by arylation-lactonization of 2-formylbenzoates

The catalytic asymmetric synthesis of 3-aryl phthalides is reported through a sequential asymmetric arylation-lactonization reaction. The reaction is enabled by a boron-zinc exchange to generate reactive arylating agents, which react with 2-formylbenzoates in the presence of a chiral amino naphthol ligand. The enantiodetermining step is the arylation of the aldehyde, which then undergoes a lactonization event to yield the corresponding phthalides in good yields and enantioselectivities.

Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation

The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.