5310-45-2

Usage

Synonyms

1,3-Difluorophenylmalonyl difluoride

Physical state

Colorless liquid at room temperature

Pharmaceutical industry

Intermediate in the synthesis of various active pharmaceutical ingredients

Agrochemicals

Building block in the production of agrochemicals

Specialty chemicals

Building block in the production of other specialty chemicals

Reactivity

Highly reactive compound

Skin irritation

Potential for causing skin irritation

Eye irritation

Potential for causing eye irritation

Respiratory issues

Potential for causing respiratory issues if inhaled

Handling

Should be handled with care due to its reactivity and potential health risks

InChI:InChI=1/C14H10Cl3N5/c1-7(8-2-4-9(19)5-3-8)21-22-14-12(16)11(15)10(6-18)13(17)20-14/h2-5H,19H2,1H3,(H,20,22)/b21-7+

Upstream product

• 121-91-5 isophthalic acid 
• 99-63-8 benzene-1,3-dicarbonyl dichloride 

Downstream Products

• 421552-88-7 methyl 3-(1H-benzo[d]imidazol-2-yl)benzoate 
• 20000-55-9 methyl 3-(benzo[d]oxazol-2-yl)benzoate 
• 20000-51-5 methyl 3-(1,3-benzothiazol-2-yl)benzoate 

Relevant academic research and scientific papers

Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles

A series of acyl fluorides was synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at room temperature, followed by extraction and distillation. Isolated acyl fluorides (usually 7-20 g) display excellent purity and can be transformed into sterically hindered amides and esters when treated with lithium amide bases and alkoxides under mild conditions.

Use of C,N-chelated di-n-butyltin(IV) fluoride for the synthesis of acyl fluorides, fluoroformates and fluorophosgene

{2-[(CH3)2NCH2]C6H4}(n-Bu)2SnF (1) reacts with various chloroformates, acyl chlorides, methanesulfonyl chloride, 4,4′-dimethoxytrityl chloride and phosgene precursors or derivatives to form fluorinated analogues. All reactions proceed rapidly and under mild conditions. The use of a catalytic amount of 1 and KF in toluene led to a relatively high yield of a selected fluoroformate.

Liquid-phase synthesis of 2-substituted benzimidazoles, benzoxazoles and benzothiazoles

A novel acid fluoride for use in the liquid-phase synthesis of substituted benzimidazoles, benzoxazoles and benzothiazoles was developed. Its synthetic utility is exemplified by a structurally diverse set of aromatic heterocycles. Final cleavage is achiev

The Relationship between 19F Substituent Chemical Shifts and Electron Densities: meta- and para-Substituted Benzoyl Fluorides

The 19F substituent chemical shifts (SCS) of meta- and para-benzoyl fluorides are found to correlate well with substituent parameters using the dual substituent parameter (DSP) equation, indicating that they reflect electronic perturbations induced by the substituent.The direction of the SCS values is such that donating substituents cause upfield shifts whilst acceptors cause downfield shifts.STO-3G calculations indicate that substituents induce only very small changes in ?-electron density about the fluorine atom, but that these changes correlate reasonably well with the observed SCS values.For the para series, the slope of the relationship between Δq?F and 19F SCS is 5000 ppm/electron, indicating the great sensitivity of the fluorine atom to small changes in electron density.