345-16-4

Basic information

• Product Name: 5-Fluorosalicylic acid
• Synonyms: BUTTPARK 34\01-09;5-FLUORO-2-HYDROBENZOIC ACID;5-fluoro-2-hydroxybenzoic;5-FLUORO-2-HYDROXYBENZOIC ACID;5-FLUOROSALICYLIC ACID;2-HYDROXY-5-FLUOROBENZOIC ACID;RARECHEM AL BE 0856;5-Fluoro-2-Hydroxy Benzoic Acid 5-Fluoro Sallicylic Acid 2-Hydroxy-5-Fluoro Benzoic Acid
• CAS NO: 345-16-4
• Molecular Formula: C₇H₅FO₃
• Molecular Weight: 156.11
• EINECS: 206-455-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Acids & Esters;Fluorine Compounds;Phenols;Aryl Fluorinated Building Blocks;Building Blocks;C7;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Fluorine series
• Mol File: 345-16-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 177-179 °C(lit.)
• Boiling Point: 307.4 °C at 760 mmHg
• Flash Point: 139.7 °C
• Appearance: light brown/
• Density: 1.3290 (estimate)
• Vapor Pressure: 0.0624mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 2.68±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 2209120
• CAS DataBase Reference: 5-Fluorosalicylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluorosalicylic acid(345-16-4)
• EPA Substance Registry System: 5-Fluorosalicylic acid(345-16-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-37/38-36
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 345-16-4(Hazardous Substances Data)

Usage

Chemical Properties

light yellow powder

Uses

5-Fluorosalicylic acid was used as internal standard in the quantification of salicylic acid.

Synthesis Reference(s)

Tetrahedron, 52, p. 23, 1996 DOI: 10.1016/0040-4020(95)00867-8

InChI:InChI=1/C6H3ClFNO2/c7-5-2-1-4(8)3-6(5)9(10)11/h1-3H

Upstream product

• 347-54-6 5-fluoro-2-hydroxybenzaldehyde 
• 1998-90-9 2-acetoxy-5-fluoro benzyl acetate 
• 445-82-9 1-(5-fluoro-2-methoxyphenyl)ethanone 
• 455-38-9 3-fluorobenzoic acid 
• 448-40-8 2-acetoxy-5-fluoro benzoic acid 
• 399-54-2 4-fluoro-2-methylanisole 
• 452-72-2 4-fluoro-2-methylphenol 
• 452-71-1 4-fluor-2-methylaniline 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 141362-06-3 4-fluorophenyl methoxymethyl ether 
• 371-41-5 4-Fluorophenol 
• 368422-23-5 5-fluoro-2-(methoxymethoxy)benzoic acid 
• 124-38-9 carbon dioxide 
• 2357-33-7 5-fluoro-2-hydroxy-benzyl alcohol 

Downstream Products

• 149428-79-5 5-fluoro-2-(2-phenylethoxy]benzyl Alcohol 
• 55411-47-7 3',5'-dichloro-2,4'-dihydroxy-5-fluorobenzanilide 
• 391-92-4 methyl 5-fluoro-2-hydroxybenzoate 
• 1334312-06-9 C₁₃H₁₁FN₂O₂ 
• 1334312-07-0 C₁₃H₁₁FN₂O₂ 
• 84376-25-0 phenyl 5-fluoro-2-hydroxybenzoate 
• 4068-69-3 methyl 5-fluoro-3-iodosalicylate 
• 371-41-5 4-Fluorophenol 
• 99517-44-9 methyl 3-allyl-5-fluoro-2-hydroxybenzoate 
• 2728-74-7 5-fluoro-2-hydroxy-benzoyl chloride 
• 443-12-9 ethyl 5-fluoro-2-hydroxybenzoate 

Relevant articles and documents

A versatile approach for the synthesis of para -substituted arenes via palladium-catalyzed C-H functionalization and protodecarboxylation of benzoic acids

While a great number of ortho C-H functionalization reactions have been developed and several breakthroughs have been achieved in meta C-H activation, para C-H functionalization is still in its infancy stage. In this article, a versatile strategy for the synthesis of para-substituted arenes has been developed via a tandem process consisting of palladium-catalyzed C-H functionalization and subsequent copper-catalyzed protodecarboxylation of benzoic acids. Both electron-withdrawing and electron-donating functionalities can be introduced into the para positions of arenes bearing a variety of substituents.

Fluorophenols and (trifluoromethyl)phenols as substrates of site-selective metalation reactions: To protect or not to protect

O-Methoxymethyl (MOM) protected fluorophenols can be cleanly metalated and subsequently be submitted to site-selective electrophilic substitution. The 2- and 4-isomers exhibit ambivalent reactivity: deprotonation occurs at the position adjacent to the oxygen when butyllithium is employed whereas the position adjacent to the fluorine is attacked by the superbasic mixture of butyllithium and potassium tert-butoxide (LIC-KOR). The MOM-protected (trifluoromethyl)-phenols react exclusively at oxygen-neighboring positions. The meta isomer provides another example of optional site selectivity, undergoing hydrogen/metal exchange at the 2-position with the LIC-KOR reagent and at the 6-position with sec-butyllithium. Unprotected (trifluoromethyl)phenols can also be ortho-metalated after O-deprotonation, although the products are formed in only moderate yields.

Synthesis of 5-fluoro salicylic acid

A short synthesis of 5-fluoro salicylic acid starting from 4- fluorophenol is reported.