712-79-8

Basic information

• Product Name: 2-(difluoromethoxy)naphthalene
• Synonyms: 2-(difluoromethoxy)naphthalene;2-(Difluoromethoxy)
• CAS NO: 712-79-8
• Molecular Formula: C₁₁H₈F₂O
• Molecular Weight: 194.1774264
• EINECS: -0
• Mol File: 712-79-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-(difluoromethoxy)naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(difluoromethoxy)naphthalene(712-79-8)
• EPA Substance Registry System: 2-(difluoromethoxy)naphthalene(712-79-8)

Safety Data

• Hazardous Substances Data: 712-79-8(Hazardous Substances Data)

Usage

General Description

2-(difluoromethoxy)naphthalene is a chemical compound with the molecular formula C12H8F2O. It is a white to light yellow solid that is slightly soluble in water. 2-(difluoromethoxy)naphthalene is used as a precursor in the synthesis of various pharmaceuticals and agrochemicals. It is also used as a building block for the preparation of aromatic compounds and as a reagent in organic chemistry reactions. Additionally, 2-(difluoromethoxy)naphthalene is used in the production of dyes and pigments, as well as in the manufacturing of electronic materials. It is important to handle this compound with care, as it may cause irritation to the skin, eyes, and respiratory system if not used properly.

Upstream product

• 1717-59-5 2,2-difluoro-2-(fluorosulfonyl)acetic acid 
• 135-19-3 β-naphthol 
• 354-08-5 bromodifluoroacetic acid 
• 91-20-3 naphthalene 

Relevant articles and documents

Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C?H Di- and Trifluoromethoxylation

Applications of TEMPO. catalysis for the development of redox-neutral transformations are rare. Reported here is the first TEMPO.-catalyzed, redox-neutral C?H di- and trifluoromethoxylation of (hetero)arenes. The reaction exhibits a broad substrate scope, has high functional-group tolerance, and can be employed for the late-stage functionalization of complex druglike molecules. Kinetic measurements, isolation and resubjection of catalytic intermediates, UV/Vis studies, and DFT calculations support the proposed oxidative TEMPO./TEMPO+ redox catalytic cycle. Mechanistic studies also suggest that Li2CO3 plays an important role in preventing catalyst deactivation. These findings will provide new insights into the design and development of novel reactions through redox-neutral TEMPO. catalysis.

Catalytic radical difluoromethoxylation of arenes and heteroarenes

Intermolecular C-H difluoromethoxylation of (hetero)arenes remains a long-standing and unsolved problem in organic synthesis. Herein, we report the first catalytic protocol employing a redox-active difluoromethoxylating reagent 1a and photoredox catalysts for the direct C-H difluoromethoxylation of (hetero)arenes. Our approach is operationally simple, proceeds at room temperature, and uses bench-stable reagents. Its synthetic utility is highlighted by mild reaction conditions that tolerate a wide variety of functional groups and biorelevant molecules. Experimental and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1a forming a neutral radical intermediate that liberates the OCF2H radical exclusively. Addition of this radical to (hetero)arenes gives difluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of difluoromethoxylation.

A SIMPLE CONVENIENT METHOD FOR PREPARATION OF DIFLUOROMETHYL ETHERS USING FLUOROSULFONYLDIFLUOROACETIC ACID AS A DIFLUOROCARBENE PRECURSOR

In the presence of catalytic amounts of sodium sulfate or cuprous iodide, a variety of alkyl and aryl difluoromethyl ethers were synthesized in moderate yields by the reaction of the corresponding alcohols and phenols with fluorosulfonyldifluoroacetic acid (1) in acetonitrile under mild conditions.Fluorosulfonyldifluoroacetate anion (5) is believed to readily eliminate SO2, CO2 and F(1-), thus liberating CF2:; insertion of difluorocarbene into O-H bonds and its capture by fluorode ion then result in the formation of ethers and by-product CF3H, respectively.