652-39-1

Basic information

• Product Name: 3-Fluorophthalic anhydride
• Synonyms: 3-FLUOROPHTHALIC ANHYDRIDE;5-FLUORO-ISOBENZOFURANDIONE;1,3-Isobenzofurandione, 4-fluoro-;4-Fluoro-2-benzofuran-1,3-dione;3-FluorophthalicAnhydride,~97%;3-Fluorophthalic anhydride 98%;3-Fluorophthalicanhydride98%;4-Fluoro-isobenzofuran-1,3-dione,3-Fluorophthalic Anhydride
• CAS NO: 652-39-1
• Molecular Formula: C₈H₃FO₃
• Molecular Weight: 166.11
• EINECS: 211-491-8
• Product Categories: Phthalic Acids, Esters and Derivatives;Carbonyl Compounds;Carboxylic Acid Anhydrides;Organic Building Blocks;Building Blocks;Carbonyl Compounds;Carboxylic Acid Anhydrides;Chemical Synthesis;Fluorinated Building Blocks;Heterocyclic Fluorinated Building Blocks;Organic Building Blocks;Other Fluorinated Heterocycles;Others
• Mol File: 652-39-1.mol

Chemical Properties

• Melting Point: 159-163 °C
• Boiling Point: 283°C(lit.)
• Flash Point: 132.8 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.4338 (estimate)
• Vapor Pressure: 0.000941mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Benzene (Slightly), DMSO (Slightly)
• Water Solubility: insoluble
• Sensitive: Moisture Sensitive
• BRN: 1283580
• CAS DataBase Reference: 3-Fluorophthalic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluorophthalic anhydride(652-39-1)
• EPA Substance Registry System: 3-Fluorophthalic anhydride(652-39-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 42/43-36/37/38-22
• Safety Statements: 45-36/37/39-26-36
• WGK Germany: 3
• HazardClass: IRRITANT, MOISTURE SENSITIVE
• Hazardous Substances Data: 652-39-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluorophthalic anhydride is used as a starting reagent for the synthesis of substituted benzamides with potential neuroleptic activity, which are important for the development of medications targeting neurological disorders.
Used in Agricultural Industry:
3-Fluorophthalic anhydride is used in the preparation of flubendiamide, an insecticide that helps control pests in various crops, contributing to increased agricultural productivity and crop protection.
Used in Chemical Synthesis:
3-Fluorophthalic anhydride may be employed as a starting reagent for the synthesis of 8-fluoro-10-methyl-1,2-benzanthracene, a compound with potential applications in various chemical and material science fields.

InChI:InChI=1/C8H3FO3/c9-5-3-1-2-4-6(5)8(11)12-7(4)10/h1-3H

Upstream product

• 443-82-3 3-fluoro-o-xylene 
• 167412-23-9 4-(3,5-difluorophenyl)semicarbazide 
• 117-21-5 3-chlorophthalic anhydride 
• 321-38-0 1-Fluoronaphthalene 
• 603-11-2 3-nitrophthalic acid 
• 24564-71-4 3-Nitrophthaloyl dichloride 
• 1583-67-1 3-fluorophthalic acid 
• 641-70-3 3-nitrophthalic acid anhydride 

Downstream Products

• 869720-39-8 2-fluoro-6-[7-nitro-5-trifluoromethyl-1H-benzo[d]imidazol-2-yl]benzoic acid 
• 2244520-92-9 4-fluoro-2-(1-methyl-2,6-dioxopiperidin-3-yI)-2,3-dihydro-1H-isoindole-1,3-dione 

Relevant articles and documents

A New Synthesis of 3-Fluorophthalic Anhydride

A high yield, one pot synthesis of 3-fluorophthalic anhydride from the easily accessible 3-nitrophthaloyl dichloride is described.The mechanistic implications of the fluorodenitration process are also discussed.

Protein degradation targeting chimeric compound, application and preparation method thereof

The invention provides a novel protein degradation targeting chimeric compound, application and a preparation method thereof. The protein degradation targeting chimeric compound is 2-(2, 6-dioxo-piperidine-3-yl)-4-fluoro-isoindole-1, 3-dione. The preparation method comprises the following steps: S1, carrying out a fluorination reaction on 3-chlorophthalic anhydride to generate 3-fluorophthalic anhydride; and step S2, carrying out a condensation reaction on the 3-fluorophthalic anhydride and 3-amino-2, 6-piperidinedione hydrochloride so as to obtain the 2-(2, 6-dioxo-piperidine-3-yl)-4-fluoro-isoindole-1, 3-dione. According to the protein degradation targeting chimeric body, the compound is moderate in molecular size, good in fluorine leaving performance, small in molecular weight and stable in performance, target protein and E3 ubiquitin enzyme can be effectively close to each other, and the protein degradation targeting chimeric body can be effectively used for preparing targeting drugs. And the preparation method is simple and convenient, less in three wastes and low in raw material price, so that the preparation cost is low, and the method is suitable for industrial large-scaleproduction.

Design, synthesis, and biological evaluation of proteolysis targeting chimeras (PRoTACS) for the dual degradation of IGF-1R and SrC

A focused PROTAC library was developed to degrade both IGF-1R and Src proteins, which are associated with various cancers. PROTACs with IGF-1R and Src degradation potentials were synthesized by tethering different inhibitor warhead units and the E3 ligase (CRBN) recruiting-pomalidomide with various linkers. The designed PROTACs 12a–b inhibited the proliferation and migration of MCF7 and A549 cancer cells with low micromolar potency (1–5 μM) in various cellular assays.

Simultaneous Inhibition of SIRT2 Deacetylase and Defatty-Acylase Activities via a PROTAC Strategy

As a member of the sirtuin family of enzymes, SIRT2 promotes tumor growth and regulates various biological pathways through lysine deacetylation and defatty-acylation. In the past few years, many SIRT2-selective small molecule inhibitors have been developed, but none have demonstrated simultaneous inhibition of both SIRT2 activities in cells. To further scrutinize the physiological importance and significance of SIRT2 deacetylase and defatty-acylase activities, small molecules that can selectively inhibit both activities of SIRT2 in living cells are needed. Here, we have applied the Proteolysis Targeting Chimera (PROTAC) strategy and synthesized a new SIRT2 inhibitor (TM-P4-Thal) to degrade SIRT2 selectively, which led to simultaneous inhibition of its deacetylase and defatty-acylase activities in living cells. Additionally, this compound exemplifies the advantage of the PROTAC strategy that allows complete eradication of an enzyme and its activity in biological settings.

IMIDE-BASED MODULATORS OF PROTEOLYSIS AND METHODS OF USE

The description relates to imide-based compounds, including bifunctional compounds comprising the same, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins which are degraded and/or otherwise inhibited by bifunctional compounds according to the present invention. In particular, the description provides compounds, which contain on one end a ligand which binds to the cereblon E3 ubiquitin ligase and on the other end a moiety which binds a target protein such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. Compounds can be synthesized that exhibit a broad range of pharmacological activities consistent with the degradation/inhibition of targeted polypeptides of nearly any type.

A 3 - phthalic acid synthetic method (by machine translation)

The invention discloses a 3 - phthalic acid synthetic method, the raw material 3 - nitrophthalic acid is dissolved by acetyl chloride solvent dehydration is carried out, after the dehydration by the fluorination potassium [...], then adding thionyl chloride to remove the by-product generated in the process of fluoro, purification to obtain the target compound 3 - phthalic acid. The invention relates to 3 - nitrophthalic acid as the synthetic 3 - phthalic acid raw material, the raw material is cheap, simple process, high yield; by adjusting the PH of the method, the product from the sulfolane solvent in very good separation out, solves the high boiling point of the solvent is not easily evaporated difficult; using acetyl chloride as dehydration solvent, not only replacing the drug control acetic anhydride, but also reduces the acetic anhydride in the dehydration process of the acetic acid by-product, mild reaction conditions after processing is simple and convenient. (by machine translation)

SMALL MOLECULES

Compounds having the general structure A - L - B are presented wherein A and B are independently an E3 ubiquitin ligase protein binding ligand compound of formula 1A or 1 B. Pharmaceutical compositions comprising these compounds and methods of use are also presented.

RAF-DEGRADING CONJUGATE COMPOUNDS

The present disclosure provides, inter alia, RAF-Degrading Conjugate Compounds that are useful in the treatment of cancer and other RAF related diseases. Also provided are, pharmaceutical compositions, methods of treatment, and kits comprising a RAF- Degrading Conjugate Compound.

IMIDE-BASED MODULATORS OF PROTEOLYSIS AND ASSOCIATED METHODS OF USE

The description relates to imide-based compounds, including bifunctional compounds comprising the same, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins which are degraded and/or otherwise inhibited by bifunctional compounds according to the present invention. In particular, the description provides compounds, which contain on one end a ligand which binds to the cereblon E3 ubiquitin ligase and on the other end a moiety which binds a target protein such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. Compounds can be synthesized that exhibit a broad range of pharmacological activities consistent with the degradation/inhibition of targeted polypeptides of nearly any type.

Dual fluorescent N-Aryl-2,3-naphthalimides: Applications in ratiometric DNA detection and white organic light-emitting devices

A ten element matrix of 5- and 6-substituted-(2,3)-naphthalimides was prepared for the appropriate placement of substituents necessary to promote dual fluorescence (DF). As prescribed by our balanced seesaw photophysical model this matrix yielded nine new DF dyes out of a possible ten compounds. From this set of nine DF dyes, 4-fluoronaphthalic amide (37) was selected as a probe for ratiometric detection of DNA and demonstration of panchromatic emission.