1513-65-1

Basic information

• Product Name: 2,6-Difluoropyridine
• Synonyms: 2,6-Difluoropyridine, 99% 5GR;2,6- twofluorine pyridine;2,6-Difluoropyridine, 97+%;2, 6-2 fluoride pyridine;2,6-difluoropyridi;Pyridine, 2,6-difluoro-;2,6-DIFLUOROPYRIDINE;2,6-Difluoropyridine, 95+%
• CAS NO: 1513-65-1
• Molecular Formula: C₅H₃F₂N
• Molecular Weight: 115.08
• EINECS: 216-152-8
• Product Categories: Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Heterocyclic Building Blocks;Heterocyclic Fluorinated Building Blocks;Other Fluorinated Heterocycles;Fluorine series;Fluorin-contained pyridine series;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine;Pyridines;Fluoropyridines;Halopyridines;C5;Heterocyclic Building Blocks
• Mol File: 1513-65-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 124.5 °C743 mm Hg(lit.)
• Flash Point: 93 °F
• Appearance: Clear purple-red/Liquid
• Density: 1.268 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.643mmHg at 25°C
• Refractive Index: n20/D 1.437(lit.)
• Storage Temp.: Flammables area
• Solubility: Not miscible or difficult to mix.
• PKA: -6.09±0.10(Predicted)
• BRN: 1422549
• CAS DataBase Reference: 2,6-Difluoropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Difluoropyridine(1513-65-1)
• EPA Substance Registry System: 2,6-Difluoropyridine(1513-65-1)

Safety Data

• Hazard Codes: Xi,T,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39-37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1513-65-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liquid

Uses

2,6-Difluoropyridine has been used in the preparation of poly(pyridine ether)s via polycondensation with silylated 1,1,1-tris(4-hydroxyphenyl)ethane.

General Description

Lithium diisopropylamide (LDA)-mediated ortholithiations of 2,6-difluoropyridine in tetrahydrofuran at -78°C has been studied using a combination of IR and NMR spectroscopic and computational methods. Polycondensation of bistrimethylsilyl derivatives of various diphenols with 2,6-difluoropyridine in N-methylpyrrolidone in the presence of K2CO3 has been investigated.

InChI:InChI=1/C5H4F3N3O/c6-5(7,8)2-1-3(12)11-4(9)10-2/h1H,(H3,9,10,11,12)

Synthetic route

2,6-dichloropyridine (2402-78-0) → 2,3-dichloro-pyridine (2402-77-9) + 2,6-difluoro pyridine (1513-65-1)

Conditions	Yield
In dimethyl sulfoxide	A 96.3% B n/a

2,6-dichloropyridine (2402-78-0) → 2,6-difluoro pyridine (1513-65-1)

Conditions	Yield
With HF; KF	94.7%
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 20℃; for 1.5h;
With p-methoxybenzoyl fluoride; 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere;	93 %Spectr.
With tetramethylammonium fluoride In N,N-dimethyl-formamide at 25℃; for 24h; Sealed tube;	95 %Spectr.
With tetramethylammonium fluoride In N,N-dimethyl-formamide at 20℃; for 24h;	95 %Spectr.

2,6-difluoro-3-iodopyridine (685517-67-3) → 2,6-difluoro-4-iodopyridine (685517-71-9) + 2,6-difluoro pyridine (1513-65-1)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -75℃; for 0.5h;	A 81% B 3%

2,6-Diaminopyridine (141-86-6) → 2,6-difluoro pyridine (1513-65-1)

Conditions	Yield
With ammonium hydroxide; hydrogen fluoride; sodium nitrite at 70℃; for 14h;	62%
With ammonium fluoride; HF; sodium nitrite In sodium hydroxide

Upstream product

• 109-09-1 2-chloropyridine 
• 110-86-1 pyridine 
• 2402-78-0 2,6-dichloropyridine 
• 700-16-3 Pentafluoropyridine 
• 2875-18-5 2,3,5,6-tetrafluoropyridine 
• 685517-67-3 2,6-difluoro-3-iodopyridine 
• 119071-51-1 C₅H₄ClFN⁽¹⁺⁾*BF₄^(1-) 
• 141-86-6 2.6-diaminopyridine 

Downstream Products

• 858675-60-2 2-ethoxy-6-fluoropyridine 
• 133635-20-8 (3aR,4R,6R,6aR)-4-(2,6-Difluoro-pyridin-3-yl)-2,2-dimethyl-6-trityloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 
• 58602-02-1 2,6-Difluoro-3-nitropyridine 
• 155601-70-0 2,6-Difluoropyridine-3-(α-oxo)acetic acid, t-butyl ester 
• 155601-65-3 2,6-difluoropyridine-3-carbaldehyde 
• 193481-62-8 6-fluoro-2-dimethylaminopyridine-3-carbaldehyde 
• 193481-63-9 2-fluoro-6-dimethylaminopyridine-3-carbaldehyde 
• 64741-27-1 2,6-bis(diphenylphosphino)pyridine 
• 345966-40-7 1-(2-methoxyphenyl)-4-(2-(2-(6-fluoro)aminopyridinyl)ethyl)piperazine 
• 1597-32-6 6-fluoro-pyridin-2-ylamine 
• 685517-67-3 2,6-difluoro-3-iodopyridine 
• 171178-29-3 4-(3-bromoanilino)-7-fluoropyrido[2,3-d]pyrimidine 
• 86724-80-3 2-amino-6-fluoropyridine-3-carboxamide 
• 171178-51-1 2,6-difluoropyridine-3-carboxamide 

Relevant articles and documents

Highly reactive and regenerable fluorinating agent for oxidative fluorination of aromatics

A newly synthesized copper aluminum fluoride of nominal composition CuAl2F8 exhibits excellent reactivity towards direct oxidative fluorination of aromatic compounds, as well as fluorodechlorination of chloroaromatics. The spent CuAl2F8 reagent can be regenerated by treatment with O2 and HF, and the fluorination process has been demonstrated to retain high conversions through 20 reaction cycles. The main advantages of this new process are safety, minimal waste, and potentially low cost.

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PROCESS FOR FLUORINATING COMPOUNDS

Disclosed are mild temperature (e.g., from 0 to 80°C) SNAr fluorinations of a variety of halide and sulfonate substituted aryl and heteroaryl substrates using NMe4F.

Anhydrous Tetramethylammonium Fluoride for Room-Temperature SNAr Fluorination

This paper describes the room-temperature SNAr fluorination of aryl halides and nitroarenes using anhydrous tetramethylammonium fluoride (NMe4F). This reagent effectively converts aryl-X (X = Cl, Br, I, NO2, OTf) to aryl-F under mild conditions (often room temperature). Substrates for this reaction include electron-deficient heteroaromatics (22 examples) and arenes (5 examples). The relative rates of the reactions vary with X as well as with the structure of the substrate. However, in general, substrates bearing X = NO2 or Br react fastest. In all cases examined, the yields of these reactions are comparable to or better than those obtained with CsF at elevated temperatures (i.e., more traditional halex fluorination conditions). The reactions also afford comparable yields on scales ranging from 100 mg to 10 g. A cost analysis is presented, which shows that fluorination with NMe4F is generally more cost-effective than fluorination with CsF.