652-12-0

Basic information

• Product Name: Tetrafluorophthalic anhydride
• Synonyms: 3,4,5,6-TETRAFLUOROPHTHALIC ANHYDRIDE;TETRAFLUOROPHTHALIC ANHYDRIDE;Tetrafluorophathlic Anhydride;3,4,5,6-Tetrafluorophthalic anhydride 98%;3,4,5,6-Tetrafluorophthalicanhydride98%;4,5,6,7-Tetrafluoro-1,3-dihydroisobenzofuran-1,3-dione;4,5,6,7-Tetrafluoro-1,3-isobenzofurandione;Tetrafluoroisobenzofuran-1,3-dione
• CAS NO: 652-12-0
• Molecular Formula: C₈F₄O₃
• Molecular Weight: 220.08
• EINECS: 211-485-5
• Product Categories: Phthalic Acids, Esters and Derivatives;Fluorobenzene;Highly Purified Reagents;Other Categories;Refined Products by Sublimation;Anhydride Monomers;Monomers;Polymer Science
• Mol File: 652-12-0.mol

Chemical Properties

• Melting Point: 94-96 °C(lit.)
• Boiling Point: 332.6 °C at 760 mmHg
• Flash Point: 149.9 °C
• Appearance: Light grayish to beige/Powder
• Density: 1.843 g/cm³
• Vapor Pressure: 1.07mmHg at 25°C
• Refractive Index: 1.38
• Solubility: Soluble in most organic solvents and acetic acid.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: Tetrafluorophthalic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrafluorophthalic anhydride(652-12-0)
• EPA Substance Registry System: Tetrafluorophthalic anhydride(652-12-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• WGK Germany: 3
• HazardClass: IRRITANT, MOISTURE SENSITIVE
• Hazardous Substances Data: 652-12-0(Hazardous Substances Data)

Usage

Chemical Properties

Light greyish to beige powder

InChI:InChI=1/C8F8O/c9-2-1(7(17)8(14,15)16)3(10)5(12)6(13)4(2)11

Upstream product

• 652-03-9 3,4,5,6-tetrafluorophthalic acid 
• 5292-39-7 3,4,5,6-tetrafluorophthaloyldifluoride 
• 50-84-0 2,4 dichlorobenzoic acid 
• 170574-02-4 perfluorophthalide 
• 59514-37-3 perfluorobenzocyclobutenedione 
• 117-08-8 tetrachlorophthalic anhydride 
• 31039-74-4 4,5,6,7-tetrachloro-2-phenylphthalimide 
• 116508-58-8 tetrafluoro-N-phenylphthalimide 

Downstream Products

• 5938-44-3 2-benzoyl-3,4,5,6-tetrafluorobenzoic acid 
• 5292-41-1 2-methoxycarbonyl-3,4,5,6-tetrafluorobenzoic acid 
• 114798-45-7 N-[4-(2-Butyl-4-chloro-5-methoxycarbonylmethyl-imidazol-1-ylmethyl)-phenyl]-3,4,5,6-tetrafluoro-phthalamic acid 
• 13628-92-7 Octafluorbiphenylen 
• 194225-51-9 (R)-2-[1-(4-nitrophenyl)ethyl]-4,5,6,7-tetrafluoro-1H-isoindole-1,3-dione 
• 194225-52-0 (S)-2-[1-(4-nitrophenyl)ethyl]-4,5,6,7-tetrafluoro-1H-isoindole-1,3-dione 
• 179033-27-3 methyl 3-tetrafluorophthalimido-3-(3,4-dimethoxyphenyl)propanoate 
• 1026222-44-5 3,4,5,6-tetrafluoro-N-(3-methyl-2-oxo-piperidin-3-yl)-phthalamic acid 

Relevant articles and documents

Perfluoropentacene: High-performance p-n junctions and complementary circuits with pentacene

We report the synthesis and characterization of perfluoropentacene as an n-type semiconductor for organic field-effect transistors (OFETs). Perfluoropentacene is a planar and crystalline material that adopts a herringbone structure as observed for pentacene. OFETs with perfluoropentacene were constructed using top-contact geometry, and an electron mobility of 0.11 cm2 V-1 s-1 was observed. Bipolar OFETs with perfluoropentacene and pentacene function at both negative and positive gate voltages. The improved p-n junctions are probably due to the similar d-spacings of both acenes. Complementary inverter circuits were fabricated, and the transfer characteristics exhibit a sharp inversion of the output signal with a high-voltage gain. Copyright

Novel functionalized indigo derivatives for organic electronics

A series of nine novel indigo derivatives, including diiodoindigo, octahalogenated indigoids and compounds with extended π-conjugated system, were synthesized, characterized and investigated as semiconductor materials in organic field-effect transistors (OFETs). Among them, 6,6′-diiodoindigo demonstrated the ambipolar behavior with balanced p-type and n-type mobilities. The complete substitution of hydrogens at the indigo core with halogen atoms led to low electron mobilities in OFETs. An extension of the conjugated system through the introduction of small aromatic substituents (thiophene and phenyl) resulted in predominant p-type behavior. Fusion of aromatic rings resulted in z-shaped dibenzoindigo, which showed poor charge transport properties due to the non-optimal arrangement of molecules along each other in the crystal lattice. The acquired data fulfilled the previously reported model based on the relationship between the chemical nature of substituents and their positions at the indigo core, optoelectronic properties of materials and their performance in OFETs. The results of this study will be useful for rational design of a new generation of the indigo-based semiconductors for biocompatible organic electronics.

Synthesis and structures of gold perfluorophthalimido complexes

Compounds of the new tetrafluorophthalimido anion, [C6F 4(CO)2N]-, are readily accessible by treatment of tetrafluorophthalimide with either LiNPri2 or mixtures of NEt3 and Me3ECl (E = Si or Sn), to give C 6F4(CO)2N-X (X = Li 3, SiMe34, and SnMe35). The reaction of the trimethylsilyl derivative 4 with AgF leads cleanly to the ion pair complex [Ag(NCMe)2][Ag(N(CO) 2C6F4)2] (6·2MeCN), which contains a linear [Ag{N(CO)2C6F4} 2]- anion and a tetracoordinate Ag+ cation. Compound 6 reacts with iodine to give the N-iodo compound C6F 4(CO)2NI 7, which crystallises as an acetonitrile adduct. Treatment of 6 with LAuCl affords LAu{N(CO)2C6F 4} (L = Ph3P 8a, Cy3P 8b, or THT 9), whereas the reaction with AuCl in acetonitrile affords the heterobinuclear compound [Ag(MeCN)2][Au{N(CO)2C6F4} 2]·MeCN (10·3MeCN). The tetrafluorophthalimido ligand is not readily displaced by donor ligands; however, the addition of B(C 6F5)3(Et2O) to a diethyl ether solution of 8a leads to the salt [Au(PPh3)2][N{COB(C 6F5)3}2C6F4)] 11. The analogous reaction of (THT)Au{N(CO)2C6F 4} with B(C6F5)3 in toluene in the presence of excess norbornene (nb) gives [Au(nb)3][N{COB(C 6F5)3}2C6F4)] 12. Compounds 11 and 12 contain a new non-coordinating phthalimido-bridged diborate anion with O-bonded boron atoms. The crystal structures of compounds 2-11 are reported.

Reaction of perfluorobenzocycloalkenes with SiO2-SbF5 and skeleton transformations of their carbonyl derivatives in SbF5 medium

The reaction of perfluorinated benzocyclobutene and tetraline with SiO 2-SbF5 led to the formation in a high yield of their mono- and further dicarbonyl derivatives. The monocarbonyl derivatives on heating with SbF5 underwent disproportionation into the corresponding perfluorobenzocycloalkenes and diketones. Both mono- and diketones in the SbF5 medium are liable to suffer skeleton rearrangements yielding five- and six-membered oxygen-containing heterocycles and/or products of the opening of the alicyclic fragment of the substrate, and from the perfluorobenzocyclobutenone compounds were also obtained with a number of carbon atoms greater than that of the initial ketone.

Hydrogen adsorption in microporous organic framework polymer

A microporous organic framework polymer (OFP) based on a polyimide framework exhibits a high surface area (1159 m2 g-1) and shows a reversible H2 storage capacity of 3.94 wt% at 10 bar and 77 K, the highest yet reported for an organic polymer. The Royal Society of Chemistry.

9,10-Dichlorooctafluoroanthracene as a building block for n-type organic semiconductors

(Chemical Equation Presented) 9,10-Dichlorooctafluoroanthracene (1) was synthesized from commercially available tetrafluorophthalic acid by an optimized solution-phase route. To establish 1 as a synthon for n-type organic semiconductors, the compound was reacted with phenylboronic acid under modified Suzuki-Miyaura coupling conditions to generate octafluoro-9,10- diphenylanthracene (7) in high yield. Cyclic voltammetry and X-ray crystallography indicate that 7 has a stabilized LUMO energy level and exhibits extended π stacking, which should lead to efficient electron transport in solid-state devices. 1,2,3,4,5,6,7,8-Octafluoroanthracene (2) was also synthesized as a potential n-type building block, but suitable C-C coupling conditions for this compound were not found, and 2 could not be converted into 9,10-dibromooctafluoroanthracene or octafluoro-9,10-diiodoanthracene.

Processes for producing tetrafluorophthalic anhydride and fluorobenzoic acids

A process for producing tetrafluorophthalic anhydride, which comprises chlorinating tetrachlorophthalic anhydride to obtain 3,3,4,5,6,7-hexachloro-1-[3H]-isobenzofuranone, then fluorinating it to obtain 3,4,5,6-tetrafluorophthaloyldifluoride and/or 3,3,4,5,6,7-hexafluoro-1-[3H]-isobenzofuranone, and further reacting the tetrafluorophthalolyldifluoride and/or the hexafluoro-1-[3H]-isobenzofuranone with an inorganic base or an organic acid to obtain tetrafluorophthalic anhydride.

Process for the preparation of tetrafluorophthalic acid and/or tetrafluorophthalic anhydride

The present invention relates to a process for the preparation of tetrafluorophthalic acid and/or tetrafluorophthalic anhydride by reacting a compound of the formula STR1 in which X is a radical STR2 which is optionally mono- or polysubstituted on the aromatic nucleus by fluorine and/or chlorine and/or alkyl groups having 1 to 4 carbon atoms, or is a radical STR3 in which R1, R2 and R3 are as defined, with water, and subsequently removing the water still present by azeotropic distillation or extracting the tetrafluorophthalic acid and/or its anhydride with a water-insoluble solvent or solvent mixture.

Divinyl compounds and chromogenic recording-material prepared by using thereof

Disclosed herein are novel divinyl compounds represented by the formula (I): STR1 and a recording-material prepared by utilizing the divinyl compounds. The present divinyl compound is in itself almost colorless, extremely stable in the atmosphere and develops rapidly blakish color by a developer. The color image given by the present divinyl compound is excellect in light-resistance and moisture-resistance and the letters developed can be read by an optical letter-reading apparatus or a barcord reading apparatus.

Process for producing tetrafluorophthalic acid

A process for producing tetrafluorophthalic acid is disclosed, which comprises the steps of: (a) reacting an alkali metal fluoride and at least one imide compound represented by formula (I) or (II) STR1 wherein X1, X2, X3, and X4, which may be the same or different, each represents a chloride atom or a bromine atom, R1 represents a monovalent organic group, and R2 represents a divalent organic group, to provide an N-substituted tetrafluorophthalimide; and (b) hydrolyzing the tetrafluorophthalimide in the presence of an acid.