403-14-5

Basic information

• Product Name: 3'-Fluoro-4'-hydroxyacetophenone
• Synonyms: 3'-FLUORO-4'-HYDROXYACETOPHENONE;3-FLUORO-4-HYDROXYACETOPHENONE;1-(3-FLUORO-4-HYDROXYPHENYL)-1-ETHANONE;1-(3-FLUORO-4-HYDROXYPHENYL)ETHANONE;BUTTPARK 153\33-64;3'-Fluoro-4'-hydroxyacetophenone, 98+%;1-(3-fluoro-4-hydroxyphenyl)-1-ethanone (en);1-(3-fluoro-4-hydroxyphenyl)ethan-1-one
• CAS NO: 403-14-5
• Molecular Formula: C₈H₇FO₂
• Molecular Weight: 154.14
• EINECS: -0
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Adehydes, Acetals & Ketones;Fluorine Compounds;Phenols;Fluorine series
• Mol File: 403-14-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 127-129°C
• Boiling Point: 276.1 °C at 760 mmHg
• Flash Point: 120.8 °C
• Appearance: /
• Density: 1.247 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.91±0.18(Predicted)
• BRN: 1936529
• CAS DataBase Reference: 3'-Fluoro-4'-hydroxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Fluoro-4'-hydroxyacetophenone(403-14-5)
• EPA Substance Registry System: 3'-Fluoro-4'-hydroxyacetophenone(403-14-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 403-14-5(Hazardous Substances Data)

Usage

Uses

3''-Fluoro-4''-hydroxyacetophenone

Preparation

Preparation by reaction of pyridinium chloride on 3-fluoro-4- methoxyacetophenone at reflux (78%).

Upstream product

• 455-91-4 1-(3-fluoro-4-methoxyphenyl)ethanone 
• 122399-89-7 1-(4-(pyridin-2-yloxy)phenyl)ethan-1-one 
• 29650-44-0 2-fluorophenyl acetate 
• 7440-44-0 pyrographite 
• 367-12-4 2-fluorophenol 
• 321-28-8 1-fluoro-2-methoxybenzene 
• 99-93-4 4-Hydroxyacetophenone 
• 75-36-5 acetyl chloride 

Downstream Products

• 343564-44-3 4-acetyl-2-fluorophenyl trifluoromethane sulfonate 
• 81227-99-8 1-(4-(benzyloxy)-3-fluorophenyl)ethan-1-one 
• 403-20-3 3-fluoro-p-anisic acid 
• 3907-15-1 3-fluoro-4-methoxybenzoylchloride 
• 392621-13-5 4-{[tert-Butyl(diphenyl)silyl]oxy}-3-fluorophenol 

Relevant articles and documents

Development of pH-activatable fluorescent probes for rapid visualization of metastatic tumours and fluorescence-guided surgeryviatopical spraying

A series of pH-activatable aza-BODIPY-based fluorescent probes were developed for rapid cancer visualization and real-time fluorescence-guided surgery by harnessing topical spraying. These probes exhibited good water-solubility, a tunable pKafrom 5.0 to 7.9, and stable intense NIR emission at ～725 nm under acidic conditions.AzaB5with a pKavalue of 6.7 was able to rapidly and clearly visualize pulmonary and abdominal metastatic tumours including tiny metastases less than 2 mmviatopical spraying, further improving intraoperative fluorescence-guided resection. We believe thatAzaB5is promising as a powerful tool to rapidly delineate a broad range of malignancies and assist surgical tumour resection.

Synthesis of 2 - fluoro phenol compounds

The present invention provides a method for synthetizing a 2-fluoro phenol compound shown in a formula IV. The phenol compound shown in the formula I is prepared into a 2-pyridine oxygroup arene compound shown in a formula II through an Ullmann reaction, the 2-pyridine oxygroup arene compound shown in the formula II is mixed with a palladium catalyst, a fluorinating reagent, an additive and an organic solvent, the mixture is stirred under the temperature of 30-160 DEG C to perform a fluorination reaction to obtain an ortho-position fluoridated 2-pyridine oxygroup arene compound shown in a formula III, and the ortho-position fluoridated 2-pyridine oxygroup arene compound shown in the formula III is prepared into the 2-fluoro phenol compound shown in the formula IV through the action of alkali. The method provided by the present invention has the advantages of mild reaction conditions, simplicity in operations, good substrate adaptability, high fluorination selectivity and the like. The 2-fluoro phenol compound is shown in the figure below.

Fries rearrangement: Scalable synthesis of key fluoro building blocks 3-fluoro-4-methoxybenzoyl chloride and 1,2-diethoxy-3-fluorobenzene

Lewis acid catalyzed Fries rearrangement of 2-fluorophenyl acetate (3) was performed on kg scale. The ortho 5 and para 4 isomers obtained were separated in an industrially feasible way. Compound 4 was then converted into fluorinated building block 3-fluoro-4-methoxybenzoyl chloride (1) while compound 5 was converted into 1,2-diethoxy-3-fluorobenzene (2) in high yields.