437-81-0

Basic information

• Product Name: 2,6-Difluorobenzaldehyde
• Synonyms: 2,6-DIFLUOROBENZALDEHYDE;TIMTEC-BB SBB006685;2,6-Difluorobenzaldehyde,97%;3,4,5-triflurobenzenenitrile;2,6-Difluorobenzaldehyde 98%;2,6-Difluorobenzaldehyde98%;2,6-DIFLUORLOBENZALDEHYDE;2-6-Difluorbenzaldehyd
• CAS NO: 437-81-0
• Molecular Formula: C₇H₄F₂O
• Molecular Weight: 142.1028664
• EINECS: -0
• Product Categories: Fluorobenzene;Carbonyl Compounds;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;API intermediates;Miscellaneous;Aldehydes;C7;Carbonyl Compounds;Aryl Fluorinated Building Blocks;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Fluorine series
• Mol File: 437-81-0.mol
• Article Data: 34

Chemical Properties

• Melting Point: 15-17 °C(lit.)
• Boiling Point: 82-84 °C15 mm Hg(lit.)
• Flash Point: 164 °F
• Appearance: Clear light yellow to bright yellow/Liquid
• Density: 1.317 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.46mmHg at 25°C
• Refractive Index: n20/D 1.502(lit.)
• Storage Temp.: 2-8°C
• Sensitive: Air Sensitive
• BRN: 1935273
• CAS DataBase Reference: 2,6-Difluorobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Difluorobenzaldehyde(437-81-0)
• EPA Substance Registry System: 2,6-Difluorobenzaldehyde(437-81-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39-36/37
• WGK Germany: 2
• F: 10-23
• HazardClass: IRRITANT
• Hazardous Substances Data: 437-81-0(Hazardous Substances Data)

Usage

Description

2,6-Difluorobenzaldehyde is an organic compound characterized by the presence of two fluorine atoms at the 2nd and 6th positions on a benzene ring, with an aldehyde functional group attached to the carbon atom at the 1st position. This molecule is known for its reactivity and is commonly used as a building block in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
2,6-Difluorobenzaldehyde is used as a reactant for the synthesis of 5-Cyano-6-(2,6-difluorophenyl)-5,6-dihydro-2-thiouracil, a compound with potential pharmaceutical applications. This synthesis is achieved through a one-pot cyclocondensation reaction with ethyl cyanoacetate and thiourea.
Used in Organic Synthesis:
In the field of organic synthesis, 2,6-Difluorobenzaldehyde serves as a reactant for the preparation of 1-(2,6-Difluorobenzyl)-2-(2,6-difluorophenyl)-benzimidazole. 2,6-Difluorobenzaldehyde is synthesized by reacting 2,6-difluorobenzaldehyde with 1,2-phenylenediamine in the presence of a catalytic amount of p-toluenesulfonic acid.
Used in the Synthesis of (3E)-4-(2,6-Difluorophenyl)-3-buten-2-one:
2,6-Difluorobenzaldehyde is also used in the Wittig olefination reaction to produce (3E)-4-(2,6-difluorophenyl)-3-buten-2-one. This reaction involves the use of acetylmethylidenetriphenyl phosphorane, resulting in the formation of a conjugated diene with potential applications in various chemical processes.
Used in the Preparation of Methyl 4-Fluorobenzo[b]thiophene-2-carboxylate:
Furthermore, 2,6-difluorobenzaldehyde is utilized in the synthesis of methyl 4-fluorobenzo[b]thiophene-2-carboxylate by treating it with methyl thioglycolate in the presence of K2CO3. This reaction leads to the formation of a heterocyclic compound with potential applications in various chemical and pharmaceutical industries.

InChI:InChI=1/C7H4F2O/c8-6-2-1-3-7(9)5(6)4-10/h1-4H

Upstream product

• 372-18-9 1,3-Difluorobenzene 
• 93-61-8 N-methyl-N-phenylformamide 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 2751-90-8 tetraphenylphosphonium bromide 
• 207226-37-7 1,3-difluoro-2-vinyl-benzene 
• 64-18-6 formic acid 
• 13697-89-7 2,6-difluoroiodobenzene 
• 109-94-4 formic acid ethyl ester 
• 446-52-6 2-Fluorobenzaldehyde 
• 617-84-5 N-formyldiethylamine 
• 93343-10-3 3,5-difluoroanisol 
• 1897-52-5 2,6 difluorobenzonitrile 
• 19064-18-7 2,6-difluorobenzyl alcohol 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 1673-75-2 3-(2,6-difluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 124466-13-3 -(2,6-Difluoro-phenyl)-N,N'-bis-[1,3,4]thiadiazol-2-yl-methanediamine 
• 157224-28-7 1,3-Difluoro-2-((E)-2-nitro-propenyl)-benzene 
• 133214-28-5 meso-N,N'-Disalicylidene-1,2-bis(2,6-difluorophenyl)ethylenediamine 
• 146137-75-9 2-Benzylsulfanyl-6-fluoro-benzaldehyde 
• 133214-34-3 1,2-Bis-(2,6-difluoro-phenyl)-N,N'-bis-[1-(2,6-difluoro-phenyl)-meth-(E)-ylidene]-ethane-1,2-diamine 
• 91624-89-4 2-(difluoromethyl)-1,3-difluorobenzene 
• 157042-75-6 (4S,5R)-5-(2,6-difluorophenyl)-2-oxazoline-4-(N,N-dimethyl)carboxamide 

Relevant articles and documents

Latent Nucleophilic Carbenes

Using DFT and ab initio calculations, we demonstrate that noncyclic formamidines can undergo thermal rearrangement into their isomeric aminocarbenes under rather mild conditions. We synthesized the silylformamidine, for which the lowest activation energy in this process was predicted. Experimental studies proved it to serve as a very reactive nucleophilic carbene. The reactions with acetylenes, benzenes, and trifluoromethane proceeded via insertion into sp, sp2, and spCH bonds. The carbene also reacted with the functional groups, such as CHO, COR, and CN at double or triple bonds, displaying high mobility of the trimethylsilyl group. The obtained silylformamidine can be considered as a latent nucleophilic carbene. It can be prepared in bulk quantities, stored, and used when the need arises. Calculation results predict similar behavior for some other silylated formamidines and related compounds.

Method for efficiently synthesizing fluorine-containing compound

The invention discloses a method for efficiently synthesizing a fluorine-containing compound, and relates to the field of fluorine-containing compound synthesis. The method is a method for generating a corresponding fluorine atom substituted fluorine-containing compound by reacting aromatic chloride or activated chloride serving as a raw material with potassium fluoride under the action of a novel catalyst. The method disclosed by the invention has the advantages of good product selectivity, high efficiency, mild reaction conditions, simplicity and convenience in operation, convenience in application and the like.

Pd-Catalyzed, ortho C-H Methylation and Fluorination of Benzaldehydes Using Orthanilic Acids as Transient Directing Groups

The direct, Pd-catalyzed ortho C-H methylation and fluorination of benzaldehydes have been accomplished using commercially available orthanilic acids as transient directing groups. In these reactions, the 1-fluoro-2,4,6-trimethylpyridinium salts can be either a bystanding F+ oxidant or an electrophilic fluorinating reagent. An X-ray crystal structure of a benzaldehyde ortho C-H palladation intermediate was obtained using triphenylphosphine as the stabilizing ligand.