Methyl 5-fluoronicotinate

Base Information

• Chemical Name: Methyl 5-fluoronicotinate
• CAS No.: 455-70-9
• Molecular Formula: C7H6FNO2
• Molecular Weight: 155.129
• Hs Code.: 2933399090
• European Community (EC) Number: 692-234-0
• DSSTox Substance ID: DTXSID40196537
• Wikidata: Q83069574
• Mol file: 455-70-9.mol

Synonyms:Methyl 5-fluoronicotinate;455-70-9;methyl 5-fluoropyridine-3-carboxylate;Methyl 5-fluoro-3-pyridinecarboxylate;5-Fluoro-nicotinic acid methyl ester;3-Pyridinecarboxylic acid, 5-fluoro-, methyl ester;5-Fluoropyridine-3-carboxylic acid methyl ester;BRN 0128573;MFCD01692049;Nicotinic acid, 5-fluoro-, methyl ester;Nicotinic acid, 5-fluoro-, methyl ester (9CI);SCHEMBL1419312;DTXSID40196537;Methyl5-fluoro-3-pyridinecarboxylate;BBL101816;STL555613;AKOS005257350;AS-5625;PB12769;LS-130954;CS-0043948;FT-0682781;EN300-128748;J-522482

Chemical Property of Methyl 5-fluoronicotinate

Chemical Property:

• Vapor Pressure: 0.441mmHg at 25°C
• Melting Point: 48 °C
• Boiling Point: 194.5°Cat760mmHg
• PKA: 0.77±0.20(Predicted)
• Flash Point: 71.4°C
• PSA: 39.19000
• Density: 1.243g/cm³
• LogP: 1.00730
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 155.03825660
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 5-fluoronicotinate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=CN=C1)F
• Uses: Methyl 5-fluoronicotinate

Technology Process of Methyl 5-fluoronicotinate

There total 16 articles about Methyl 5-fluoronicotinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 5-fluoropyridine-3-carboxylic acid (402-66-4) → 5-fluoro-3-pyridinecarboxylic acid methyl ester (455-70-9)

Guidance literature:

In diethyl ether; 1.) 0 deg C, 2.) RT, overnight;

DOI:10.1021/jo00250a019

Reference yield: 69.0%

methyl 5-hydroxy-3-pyridinecarboxylate (30766-22-4) → 5-fluoro-3-pyridinecarboxylic acid methyl ester (455-70-9)

Guidance literature:

With Cl^(1-)*C₂₇H₃₆ClN₂⁽¹⁺⁾*Cs⁽¹⁺⁾*F^(1-); In toluene; at 23 - 110 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol5035518

Reference yield: 58.0%

5-(methoxycarbonyl)pyridine-3-diazonium tetrafluoroborate → 5-fluoro-3-pyridinecarboxylic acid methyl ester (455-70-9)

Guidance literature:

With boron trifluoride diethyl etherate; 1-fluoro-3,3-dimethyl-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole; In chlorobenzene; at 45 ℃; for 36h; Temperature; Reagent/catalyst; Catalytic behavior; Glovebox; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.201802466

upstream raw materials:

5-amino-nicotinic acid methyl ester

diazomethane

5-fluoropyridine-3-carboxylic acid

methanol

Downstream raw materials:

5-fluoropyridine-3-carbohydrazide

3-(chloromethyl)-5-fluoropyridine

(2-Amino-3,5-difluoro-phenyl)-(5-fluoro-pyridin-3-yl)-methanone

5-fluoropyridine-3-carboxaldehyde

Refernces

• 1、 Knight, Brian J.,Tolchin, Zachary A.,Smith, Joel M.. "A predictive model for additions to: N -alkyl pyridiniums". supporting information. p. 2693 - 2696. Retrieved 2021/03/18.
• 2、 Xing, Bo,Ni, Chuanfa,Hu, Jinbo. "Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions". . p. 9896 - 9900. Retrieved 2018/07/31.