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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.

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  • 437-81-0 Structure
  • Basic information

    1. Product Name: 2,6-Difluorobenzaldehyde
    2. 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
    3. CAS NO:437-81-0
    4. Molecular Formula: C7H4F2O
    5. Molecular Weight: 142.1028664
    6. EINECS: -0
    7. 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
    8. Mol File: 437-81-0.mol
  • Chemical Properties

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

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39-37/39-36/37
    4. WGK Germany: 2
    5. RTECS:
    6. F: 10-23
    7. HazardClass: IRRITANT
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 437-81-0(Hazardous Substances Data)

437-81-0 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 437-81-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,3 and 7 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 437-81:
(5*4)+(4*3)+(3*7)+(2*8)+(1*1)=70
70 % 10 = 0
So 437-81-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H4F2O/c8-6-2-1-3-7(9)5(6)4-10/h1-4H

437-81-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A18099)  2,6-Difluorobenzaldehyde, 97%   

  • 437-81-0

  • 5g

  • 555.0CNY

  • Detail
  • Alfa Aesar

  • (A18099)  2,6-Difluorobenzaldehyde, 97%   

  • 437-81-0

  • 25g

  • 2064.0CNY

  • Detail

437-81-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,6-Difluorobenzaldehyde

1.2 Other means of identification

Product number -
Other names 2,6-Difluorobenzalde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:437-81-0 SDS

437-81-0Relevant articles and documents

Latent Nucleophilic Carbenes

Marchenko, Anatoliy,Koidan, Georgyi,Hurieva, Anastasiya,Shvydenko, Kostiantyn,Rozhenko, Alexander B.,Rusanov, Eduard B.,Kyrylchuk, Andrii A.,Kostyuk, Aleksandr

, p. 373 - 385 (2021/12/27)

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

-

Paragraph 0071-0073, (2021/06/26)

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.

A Magnetically Recyclable Palladium-Catalyzed Formylation of Aryl Iodides with Formic Acid as CO Source: A Practical Access to Aromatic Aldehydes

You, Shengyong,Zhang, Rongli,Cai, Mingzhong

, p. 1962 - 1970 (2021/01/25)

A magnetically recyclable palladium-catalyzed formylation of aryl iodides under CO gas-free conditions has been developed by using a bidentate phosphine ligand-modified magnetic nanoparticles-anchored- palladium(II) complex [2P-Fe 3O 4@SiO 2-Pd(OAc) 2] as catalyst, yielding a wide variety of aromatic aldehydes in moderate to excellent yields. Here, formic acid was employed as both the CO source and the hydrogen donor with iodine and PPh 3as the activators. This immobilized palladium catalyst can be obtained via a simple preparative procedure and can be facilely recovered simply by using an external magnetic field, and reused at least 9 times without any apparent loss of catalytic activity.

Synthesis of 2, 6 - difluoro phenyl -1 - (4, 5 - [...]) -3 - ketone to make a new method

-

Paragraph 0040-0044, (2019/04/14)

The invention discloses a method for synthesizing 2, 6 - difluoro phenyl - 1 - (4, 5 - [...]) - 3 - ethyl ketone of the new method. This synthetic route avoids the synthetic intermediate 1, 3 - difluoro - 2 - steps of styrene, overcome prior art intermediate volatile not easy to store, and due to the synthetic process needs to be used sodium hydride synthesis of operation and great danger of defect, so that the synthesis process is more suitable for large-scale production; the synthetic route higher yield, and the final target 2, 6 - difluoro phenyl - 1 - (4, 5 - [...]) - 3 - ethyl ketone through re-crystallization mode is purified, high purity 98%; and this synthetic route uses the raw materials of the commercial production of the raw material, cheap and easy to obtain.

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

Chen, Xiao-Yang,Sorensen, Erik J.

supporting information, p. 2789 - 2792 (2018/03/08)

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.

A 2, 6 - difluoro toluene of continuous oxidation to prepare 2, 6 - difluorobenzaldehyde method (by machine translation)

-

Paragraph 0026; 0028; 0030; 0032; 0034; 0036; 0038; 0040, (2017/08/29)

The invention relates to a 2, 6 - difluoro toluene of continuous oxidation to prepare 2, 6 - difluorobenzaldehyde method, which belongs to the technical field of organic synthesis process. The method is to 2, 6 - difluoro toluene compound as a raw materia

Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation

Ganiek, Maximilian A.,Becker, Matthias R.,Berionni, Guillaume,Zipse, Hendrik,Knochel, Paul

supporting information, p. 10280 - 10284 (2017/08/07)

An ambient temperature continuous flow method for nucleophilic amidation and thioamidation is described. Deprotonation of formamides by lithium diisopropylamine (LDA) affords carbamoyllithium intermediates that are quenched in situ with various electrophi

DIRECT DYES AND COMPOSITION COMPRISING THE DYES

-

Page/Page column 32, (2016/07/27)

The present invention relates to novel direct dyes and compositions comprising them for dyeing keratin fibers especially human hair. The novel dyes of the present invention have benzothiophene structure providing intensive and homogeneous dyeing on kerati

Polyoxometalate-Intercalated Layered Double Hydroxides as Efficient and Recyclable Bifunctional Catalysts for Cascade Reactions

Liu, Kai,Xu, Yanqi,Yao, Zhixiao,Miras, Haralampos N.,Song, Yu-Fei

, p. 929 - 937 (2016/03/15)

The polyoxometalate (POM) intercalated layered double hydroxides (LDHs) have been widely used as heterogeneous catalysts. However, the application of POM-LDHs as bifunctional catalysts for cascade reaction has seldom been studied compared to the noble-metal-based catalysts. Herein, a series of POM-LDHs catalysts of Tris-LDH-X4(PW9)2 (X=Mn, Fe, Co, Ni, Cu, and Zn; Tris=Tris(hydroxymethtyl)aminomethane) have been prepared. The efficacy of Tris-LDH-Zn4(PW9)2 as efficient bifunctional catalyst has been demonstrated for cascade reactions involving oxidation of benzyl alcohol to benzaldehyde followed by Knoevenagel condensation with ethyl cyanoacetate to produce benzylidene ethyl cyanoacetate. The combination of POM's redox/acidic sites and LDHs's basic sites led to a composite catalyst with excellent activity (99 %) and selectivity (≥99 %) under mild and soluble-base-free conditions. This work offers a new design strategy for the fabrication of efficient bifunctional catalysts for the promotion of one-pot cascade reactions.

Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O2

Gonzalez-De-Castro, Angela,Xiao, Jianliang

supporting information, p. 8206 - 8218 (2015/07/15)

A mild and operationally simple iron-catalyzed protocol for the selective aerobic oxidation of aromatic olefins to carbonyl compounds is described. Catalyzed by a Fe(III) species bearing a pyridine bisimidazoline ligand at 1 atm of O2, α- and β-substituted styrenes were cleaved to afford benzaldehydes and aromatic ketones generally in high yields with excellent chemoselectivity and very good functional group tolerance, including those containing radical-sensitive groups. With α-halo-substituted styrenes, the oxidation took place with concomitant halide migration to afford α-halo acetophenones. Various observations have been made, pointing to a mechanism in which both molecular oxygen and the olefinic substrate coordinate to the iron center, leading to the formation of a dioxetane intermediate, which collapses to give the carbonyl product. (Chemical Equation).

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