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Chemical Structure| 445-29-4 Chemical Structure| 445-29-4
Chemical Structure| 445-29-4

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CAS No.: 445-29-4

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Abbas, Muhammad ; Murari, Bhargavasairam ; Sheybani, Simin ; Joy, Monu ; Balkus Jr, Kenneth J ;

Abstract: Tuning a material’s hydrophobicity is desirable in several industrial applications, such as hydrocarbon storage, separation, selective CO2 capture, oil spill cleanup, and water purification. The introduction of fluorine into rare-earth (RE) metal–organic frameworks (MOFs) can make them hydrophobic. In this work, the linker bis(trifluoromethyl)terephthalic acid (TTA) was used to make highly fluorinated MOFs. The reaction of the TTA and RE3+ (RE: Y, Gd, or Eu) ions resulted in the primitive cubic structure (pcu) exhibiting RE dimer nodes (RE-TTA-pcu). The crystal structure of the RE-TTA-pcu was obtained. The use of the in the synthesis resulted in fluorinated hexaclusters in the face-centered cubic (fcu) framework (RE-TTA-fcu), analogous to the UiO-66 MOF. The RE-TTA-fcu has fluorine on the linker as well as in the cluster. The MOFs were characterized by powder X-ray diffraction, X-ray photoelectron spectroscopy, thermogravimetric analysis, and contact angle measurements.

Keywords: metal-organic frameworks ; ; hydrophobic materials ; coordination polymers

Purchased from AmBeed: ;

Miller, Lars ;

Abstract: This work explores the synthesis and characterization of redox active rare-earth (RE) metal–organic frameworks (MOFs). MOFs are of interest due to their unique properties including permanent porosity, high surface area, and stability. Redox active MOFs have shown promise in a variety of applications including catalysis and molecular electronics. The second chapter will explore materials composed of Ce(IV) clusters bridged by ditopic carboxylate-based linkers. The synthesis of a series of UiO-66 analogues using the redox active metal Ce(IV) is completed with the original linker benzene-1,4-dicarboxylic acid as well as with various functionalized linkers including: 2-aminobenzene-1,4-dicarboxylic acid, 2-fluorobenzene1,4-dicarboxylic acid, 2-bromobenzene-1,4-dicarboxylic acid, 2,5-dihydroxybenzene-1,4- dicarboxylic acid, and 2,3,5,6-tetrafluorobenzene-1,4-dicarboxylic acid. The electrochemical differences between the analogues is explored via cyclic voltammetry. The third chapter delves into the synthesis of a series of redox active MOFs using the tetratopic tetrathiaflvalene-3,4,5,6-tetrakis(4-benzoic acid) (TTFTBA) redox active linker. Synthesis of a 3D cluster based MOF is attempted using Ce(III/IV), Yb(III), and Lu(III). Two new MOFs with shp topology are synthesized using TTFTBA and Yb(III) or Lu(III). The materials are characterized, and their redox properties are explored.

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Alternative Products

Product Details of 2-Fluorobenzoic acid

CAS No. :445-29-4
Formula : C7H5FO2
M.W : 140.11
SMILES Code : C1=CC=CC(=C1C(O)=O)F
MDL No. :MFCD00002405
InChI Key :NSTREUWFTAOOKS-UHFFFAOYSA-N
Pubchem ID :9935

Safety of 2-Fluorobenzoic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Fluorobenzoic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 445-29-4 ]

[ 445-29-4 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 594-19-4 ]
  • [ 445-29-4 ]
  • [ 1077-58-3 ]
  • 1-(2-fluorophenyl)-2,2-dimethylpropan-1-one [ No CAS ]
  • 2
  • [ 445-29-4 ]
  • [ 148461-16-9 ]
  • 3
  • [ 445-29-4 ]
  • [ 52833-63-3 ]
  • 4
  • [ 445-29-4 ]
  • [ 1006-19-5 ]
  • 5
  • [ 13754-19-3 ]
  • [ 445-29-4 ]
  • [ 878287-56-0 ]
YieldReaction ConditionsOperation in experiment
88.5% A mixture of <strong>[13754-19-3]4,5-diaminopyrimidine</strong> (0.500 g), 2-fluorobenzoic acid (0.700 g) and polyphosphoric acid (25 mL) was heated at 180 C. for 3 hours. Then the reaction mixture was cooled and poured into water (500 mL). The solution was adjusted to pH=8-9 by addition of solid NaOH and the resulting precipitate was collected by filtration, washed with water and dried to give 8-(2-fluorophenyl)-purine (off-white powder, 88.5%). 1H NMR (200 MHz, DMSO-d6) delta 13.79 (br s, 1H, NH), 9.14 (s, 1H, purine-H), 8.95 (s, 1H, purine-H), 8.23 (m, 1H, phenyl-H), 7.73-7.41 (m, 3H, phenyl-H).
  • 8
  • [ 3537-14-2 ]
  • [ 445-29-4 ]
  • [ 1186224-49-6 ]
YieldReaction ConditionsOperation in experiment
With Eaton's reagent; at 150℃;Autoclave; To a pressure vessel containing <strong>[3537-14-2]5-nitropyridine-2,3-diamine</strong> 106 (125 mg, 0.8 mmol) and 2-fluorobenzoic acid 107 (1 12.17 mg, 0.8 mmol) was added Eaton's reagent (2 ml, 12.73 mmol). The reaction mixture was stirred at 150 C. The mixture was cooled to room temperature and quenched with water. The precipitate was collected and dried under vacuum to provide compound 108. The compound was used for subsequent reaction without purification.
  • 10
  • [ 337915-79-4 ]
  • [ 445-29-4 ]
  • 6-bromo-2-(3-fluorophenyl)-1-methyl-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
2-Fluorobenzoic acid (128 mg, 0.91 mmol) and carbonyl diimidazole (170 mg, 1.05 mmol) were dissolved in butyronitrile (3 mL). After stirring at room temperature for 15 minutes, Example 271B (183 mg, 0.91 mmol) was added. The reaction mixture was heated at 180 C. for 30 minutes in a Biotage Initiator microwave reactor. The reaction mixture was concentrated and acetic acid (2 mL) was added. After heating at 150 C. for 20 minutes, the residue was partitioned between 50 mL of ethyl acetate and 50 mL of water. The aqueous layer was removed and the organic layer was washed with aqueous saturated sodium bicarbonate (30 mL), dried over sodium sulfate, filtered and concentrated. Purification by silica gel flash chromatography eluting with 20% ethyl acetate in hexanes gave the title compound. MS (DCI) m/e 305.0 (M+H)+
  • 11
  • [ 6638-79-5 ]
  • [ 445-29-4 ]
  • [ 198967-24-7 ]
YieldReaction ConditionsOperation in experiment
73% With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; for 2h; 2-Fluoro-N-methoxy-N-methylbenzamide was prepared in 73% yield according to the Example 1 , Step A substituting 6-bromopicolinic acid for 2-fluorobenzoic acid.
  • 12
  • [ 881676-32-0 ]
  • [ 445-29-4 ]
  • [ 881674-56-2 ]
YieldReaction ConditionsOperation in experiment
96.5% With bis-triphenylphosphine-palladium(II) chloride; 1,10-Phenanthroline; copper (I) acetate; sodium hydroxide; In dimethyl sulfoxide; at 140℃; for 5h;Inert atmosphere; Dimethyl sulfoxide (200 mL) was added to a 500 mL three-neck flask, and 2-fluorobenzoic acid (II) (14.2 g, 0.1 mol) was added under nitrogen.5-bromopyrrole-3-carbaldehyde (III) (35.5 g, 0.2 mol), sodium hydroxide (40.1 g, 1 mol), Pd(PPh3)2Cl2 (14.1 g, 0.02 mol), CuOAc (4.9 g, 0.04 mol) ,1,10-Phenanthroline (7.3g, 0.04mol), stirring, heating to 140C, reaction for 5h,The reaction was completed by HPLC (2-fluorobenzoic acid (II) content is less than 1%), the temperature was lowered to 20C, the pH was adjusted to 6 with 5% aqueous hydrochloric acid solution, and the solid was slowly precipitated by adding water.The solid was extracted with ethyl acetate (50 mL X 3).The resulting organic phase was washed with saturated sodium bicarbonate solution (100 mL) and saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to 80 g and re-crystallized by the dropwise addition of petroleum ether (150 mL).Filtration drying gave a reddish solid product (18.5 g, yield: 96.5% based on 2-fluorobenzoic acid (II)).
  • 13
  • [ 30465-68-0 ]
  • [ 445-29-4 ]
  • 2-fluoro-N-(5-methoxyquinolin-8-yl)-6-(trifluoromethylthio)benzamide [ No CAS ]
  • 14
  • [ 30465-68-0 ]
  • [ 445-29-4 ]
  • 2-fluoro-N-(5-methoxyquinolin-8-yl)benzamide [ No CAS ]
  • 15
  • [ 59878-57-8 ]
  • [ 445-29-4 ]
  • (4-(cyclopropanecarbonyl)piperazin-1-yl)(2-fluorophenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% To a round bottom flask was added, 2-fluorobenzoic acid (1.00 g, 7.14 mmol), DCM (40 mL), diisopropylethylamine (1.86 mL, 10.7 mmol) and HBTU (4.06 g, 10.7 mmol). The reaction mixture was then stirred for 30 minutes at room temperature before adding cyclopropylpiperazine-l-ylmethanone (1.52 mL, 10.7 mmol). The reaction was stirred overnight before the excess solvent with removed in vacuo and the cmde material purified via flash column chromatography (EtOAc:MeOH 10:1) affording (4- (Cyclopropanecarbonyl)piperazin-l-yl)(2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)methanone as a white solid (1.32 g, 4.78 mmol 67%) in a mixture of rotamers (2:1). In each case the shift relating to the minor rotamer has been donated with an asterisk.* NMR (400 MHz, CDCh) d = 7.40 - 7.29 (m, 2H + 2H*), 7.16 (td, / = 7.5, 1.1 Hz, 1H + 1H*), 7.04 (ddd, J = 9.4, 8.3, 1.1 Hz, 1H + 1H*), 3.88 - 3.46 (m, 6H + 6H*), 3.38 - 3.20 (m, 2H + 2H*), 1.76 - 1.58 (m, 1H + 1H*), 0.98 - 0.88 (m, 2H + 2H*), 0.83 - 0.62 (m, 2H + 2H*); 13C NMR (100 MHz, CDCb) d = 172.3 (1C + 1C*), 165.4 (1C + 1C*), 158.0 (d, 7 = 247.7 Hz, 1C + 1C*), 131.7 (d, 7 = 8.0 Hz, 1C + 1C*), 129.1 (1C + 1C*), 124.9 (d, 7 = 3.5 Hz, 1C + 1C*), 123.5 (d, 7 = 17.4, 1C + 1C*), 115.8 (d, 7 = 21.3, 1C + 1C*), 47.0 (1C*), 46.7 (1C), 45.6 (1C*), 45.1 (1C), 42.2 (2C), 41.9 (1C*), 41.7 (1C*), 11.0 (1C + 1C*), 7.64 (2C + 2C*); OH^F NMR (376 MHz, CDCb) d = - 115.0 (s, IF*), - 115.1 (s, IF); IR (v, cm x): 1630, 1460, 1219, 1004, 727; HRMS (ESI) for Ci5Hi819FN202 [M+H]+ requires 277.1282 found 277.1285; Mp: 65 - 67C.
 

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