405-50-5

Basic information

• Product Name: 4-Fluorophenylacetic acid
• Synonyms: 4-Fluorobenzeneacetic acid;4-fluoro-benzeneaceticaci;Acetic acid, (p-fluorophenyl)-;NSC 402;4-FLUOROPHENYLACETIC ACID FOR SYNTHESIS;The fluorine benzene acetic acid;A085 4-Fluorophenylacetic acid;Ba 2821
• CAS NO: 405-50-5
• Molecular Formula: C₈H₇FO₂
• Molecular Weight: 154.14
• EINECS: 206-972-4
• Product Categories: Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Phenylacetic acid series;Aromatic Phenylacetic Acids and Derivatives;Fluorobenzene;API intermediates;Carboxylic Acids;Phenyls & Phenyl-Het;C8;Carbonyl Compounds;Aryl Fluorinated Building Blocks;Building Blocks;C7-C8;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks
• Mol File: 405-50-5.mol
• Article Data: 41

Chemical Properties

• Melting Point: 81-83 °C(lit.)
• Boiling Point: 164°C (2.25 torr)
• Flash Point: >100°C
• Appearance: White/Shiny Crystalline Powder or Flakes
• Density: 1.1850 (estimate)
• Vapor Pressure: 0.00461mmHg at 25°C
• Storage Temp.: Store below +30°C.
• PKA: pK1:4.25 (25°C)
• Water Solubility: Insoluble in water.
• Merck: 14,4177
• BRN: 972145
• CAS DataBase Reference: 4-Fluorophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorophenylacetic acid(405-50-5)
• EPA Substance Registry System: 4-Fluorophenylacetic acid(405-50-5)

Safety Data

• Hazard Codes: Xi
• Statements: 38-36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 405-50-5(Hazardous Substances Data)

Usage

Chemical Properties

white shiny crystalline powder or flakes

Uses

4-Fluorophenylacetic acid is used as an intermediate in the production of fluorinated anesthetics.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 6037, 1956 DOI: 10.1021/ja01604a023

Purification Methods

Crystallise it from heptane, but it is best purified by distillation at high vacuum. [Bergmann et al. J Am Chem Soc 78 6037 1956, Beilstein 9 III 2261, 9 IV 1672.]

InChI:InChI=1/C8H7FO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)/p-1

Upstream product

• 67-56-1 methanol 
• 143659-27-2 1-Naphthylmethyl 4-fluorophenylacetate 
• 352-34-1 4-fluoro-1-iodobenzene 
• 201230-82-2 carbon monoxide 
• 459-46-1 4-Fluorobenzyl bromide 
• 321547-57-3 4-(2-methoxy-3-triisopropylsilanyloxy-benzoyl)-piperidine 
• 459-04-1 4-Fluorophenylacetyl chloride 
• 797755-07-8 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid 
• 64-19-7 acetic acid 
• 124-38-9 carbon dioxide 
• 401514-49-6 [(4-fluorophenyl)methylidene]hydrazine 
• 64-18-6 formic acid 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 702-11-4 4-fluoro-N,N-dimethylbenzylamine 

Downstream Products

• 143033-77-6 Acetic acid 6-(4-fluoro-phenyl)-7-oxo-7H-dibenzo[a,c]cyclohepten-5-yl ester 
• 718-25-2 (E)-4-fluorostilbene 
• 405-86-7 (E)-4-(4-fluorostyryl)-N,N-dimethylaniline 
• 221121-30-8 2-(4-fluorophenyl)-1-(1H-imidazol-1-yl)ethan-1-one 
• 186690-18-6 (E)-2-(4-Fluoro-phenyl)-3-(2-methoxy-4-methylsulfanyl-phenyl)-acrylic acid 
• 207509-64-6 methyl 4-fluoro-α,α-dimethoxyphenylacetate 
• 1027423-24-0 N-[5-(2,4-Dioxo-thiazolidin-5-ylmethyl)-2-hydroxy-phenyl]-2-(4-fluoro-phenyl)-acetamide 
• 293731-49-4 benzyl 2-(4-fluorophenyl)ethanoate 
• 34837-84-8 4-fluorobenzeneacetic acid methyl ester 
• 51230-93-4 2-(4-fluorophenyl)pent-4-enoic acid 
• 473225-47-7 (4-fluoro-phenyl)-acetic acid 2-oxo-2-phenyl-ethyl ester 
• 163563-22-2 (Z)-2-(4'-fluorophenyl)-3-N,N-dimethylaminopropenal 
• 864960-93-0 N-cyclopropyl-2-(4-fluorophenyl)acetamide 
• 959958-63-5 2-(4-fluorobenzyl)-5-aminobenzoxazole 

Relevant articles and documents

Potential proinsecticides of fluorinated carboxylic acids and β-ethanolamines. IV. Evaluation of the Δ2-oxazoline-1,3 structure by 19F NMR monitoring of the in vitro metabolism in locust tissues

The enzymatic effect of locust tissues upon hydrolysis of the fluorinated Δ2-oxazoline-1,3 Ia was elucidated using 19F[1H] NMR monitoring. In a phosphate buffer at pH = 7.4 (mean physiological pH of locust tissues), the substrate Ia hydrolyses slowly into the corresponding fluorinated hydroxylamide VIa. If diluted, locust haemolymph (12.5% in phosphate buffer) catalyses slightly this hydrolytic pathway, it overall triggers the unmasking of carboxylate IIIa, corresponding to the expected proinsecticide behaviour of Ia. This behaviour is spectacularly almost the unique reaction observed during in vitro assays in concentrated fat body and mesenteron. Inasmuch as β-hydroxylamide VIa is not hydrolysed into carboxylate IIIa during such conditions, it must be concluded that carboxylate formation exclusively results from hydration and hydrolysis of substrate Ia via the aminoester Va. The formation of this intermediate aminoester is demonstrated by complementary assays. The enzymes supposed to intervene are of the α-chymotrypsine type for the first step (hydration) and of the esterase type for subsequent hydrolysis of intermediate aminoester Va. Thus, this work constitutes the first example of a Δ2-oxazoline-1,3 structure exploited for elaborating proinsecticides of carboxylates III and/or β-ethanolamines II based on enzymatic activation in insects.

Desulfonylative Electrocarboxylation with Carbon Dioxide

Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.

Method for converting benzyl borate compounds into phenylacetic acid and derivatives thereof by carbon dioxide

The invention discloses a method for converting benzyl borate compounds into phenylacetic acid and derivatives thereof by carbon dioxide. The method comprises the steps: dissolving the benzyl borate compounds and an alkali in an organic solvent in the absence of a metal catalyst, introducing carbon dioxide into the reaction system, carrying out a reaction at the temperature of 50-150 DEG C for 3-72 hours, and acidifying to obtain phenylacetic acid or the derivatives thereof. The method is a green, simple and efficient method for synthesizing phenylacetic acid and the derivatives thereof, greenhouse gas carbon dioxide is used as a carbon source in the reaction, no transition metal catalyst is used, and the method is environmentally friendly, economical and high in efficiency.