2,4-difluoro-3-(triethylsilyl)benzoic acid
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water for 2h; Heating; | 98% |
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 80℃; for 18h; | 98% |
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With 1,3-Dichloro-2-propanol; boron trifluoride diethyl etherate; water at 50℃; for 1.83333h; Temperature; | 97% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -75℃; | 92% |
Stage #1: 2,4-difluoro-1-iodobenzene With copper In tetrahydrofuran at 25℃; for 0.5h; Stage #2: carbon dioxide In tetrahydrofuran for 24h; | 76% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.5h; Green chemistry; | 92% |
2,4-difluoroethynylbenzene
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 Torr; for 48h; | 92% |
2,4-difluoro-3-chlorobenzoic acid
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; zinc for 2h; Heating; | 91% |
dicobalt octacarbonyl
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 90% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube; | 87% |
Conditions | Yield |
---|---|
With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate; acetic acid at 180℃; under 18751.9 Torr; for 1.5h; Reagent/catalyst; Temperature; Green chemistry; | 85% |
With sodium percarbonate; potassium tert-butylate; sphingosylphosphorylcholine; meta-dinitrobenzene In tert-butyl alcohol at 80℃; for 5h; | 23% |
With potassium permanganate Oxidation; |
dicobalt octacarbonyl
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 82% |
Conditions | Yield |
---|---|
With potassium fluoride; cetyltrimethylammonim bromide In N,N-dimethyl-formamide at 120℃; for 7h; | 72.4% |
Conditions | Yield |
---|---|
With potassium permanganate |
2,4-difluorobromobenzene
carbon dioxide
A
3-bromo-2,6-difluorobenzoic acid
B
2,4-difluoro-benzoic acid
C
2,6-difluorobenzoic acid
Conditions | Yield |
---|---|
With n-butyllithium 1) hexane, Et2O, 2 min, -78 deg C. 2) ether; Yield given. Multistep reaction. Yields of byproduct given; | |
With n-butyllithium 1) hexane, THF; 2 min, -78 deg C. 2) ether; Yield given. Multistep reaction. Yields of byproduct given; |
4-Fluorobenzoic acid
A
2,3,4,5-tetrafluorobenzoic acid
B
3,4-Difluorobenzoic acid
C
2,4,5-trifluorobenzoic acid
D
2,3,4,-trifluorobenzoic acid
E
3,4,5-trifluorobenzoic acid
F
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With fluorine In sulfuric acid Product distribution; various substrate to fluorine ratios; also in 98percent HCOOH; |
2,4-difluorobenzaldehyde
A
2,4-difluorophenol
B
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With 4-hydroxyacetophenone monooxygenase from P. fluorescens ACB; oxygen; NADPH In phosphate buffer at 30℃; for 1h; pH=8.0; Enzyme kinetics; Baeyer-Villiger oxidation; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: BuLi / hexane; tetrahydrofuran / 0.75 h / -75 °C 1.2: 74 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / 0.75 h / -75 °C 2.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 2 h / -75 °C 2.2: 90 percent / tetrahydrofuran; hexane 3.1: 91 percent / Zn; aq. NaOH / 2 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 89 percent / butyllithium / hexane; tetrahydrofuran / -75 °C 2: 89 percent / sec-butyllithium / cyclohexane; tetrahydrofuran / 0.75 h 3: 98 percent / potassium hydroxide / ethanol; H2O / 2 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 98 percent / sec-BuLi; I2 / tetrahydrofuran; cyclohexane / -75 °C 2: 48 percent / LDA / tetrahydrofuran; hexane / -75 °C 3: 92 percent / BuLi / tetrahydrofuran; hexane / -75 °C View Scheme | |
Multi-step reaction with 2 steps 2: KMnO4 View Scheme |
1-chloro-2,6-difluorobenzene
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 90 percent / tetrahydrofuran; hexane 2.1: 91 percent / Zn; aq. NaOH / 2 h / Heating View Scheme |
1-triethylsilyl-2,6-difluorobenzene
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / sec-butyllithium / cyclohexane; tetrahydrofuran / 0.75 h 2: 98 percent / potassium hydroxide / ethanol; H2O / 2 h / Heating View Scheme |
2,6-difluoroiodobenzene
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 48 percent / LDA / tetrahydrofuran; hexane / -75 °C 2: 92 percent / BuLi / tetrahydrofuran; hexane / -75 °C View Scheme |
phenylhydrazine hydrochloride
2,4-difluorobenzoyl chloride
A
benzoic acid hydrazide
B
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
In pyridine | A 98 g (79%) B n/a |
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
In ethanol; dichloromethane at 25℃; Kinetics; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; water / 16 h / 20 °C / Schlenk technique; Inert atmosphere View Scheme |
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In tetrahydrofuran at 50℃; for 18h; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: 2,4-dinitrotoluene With ammonium chloride In ethanol at 75 - 85℃; for 1.16667h; Stage #2: With manganese(IV) oxide; tetrabutylammomium bromide; dihydrogen peroxide at 40 - 60℃; for 1h; Stage #3: With tetrabutylammomium bromide; sodium fluoride In N,N-dimethyl-formamide at 100 - 115℃; for 5.5h; |
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; tris[2-phenylpyridinato-C2,N]iridium(III) / acetonitrile / 48 h / 60 °C / Sealed tube; Inert atmosphere; Photolysis 2: hydrogenchloride / 18 h / 80 °C View Scheme |
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; tris[2-phenylpyridinato-C2,N]iridium(III) / acetonitrile / 48 h / 60 °C / Sealed tube; Inert atmosphere; Photolysis 3: hydrogenchloride / 18 h / 80 °C View Scheme |
2,4,6-trifluoro-3,5-dichlorobenzoic acid
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / 4 h / 70 °C 2: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; tris[2-phenylpyridinato-C2,N]iridium(III) / acetonitrile / 48 h / 60 °C / Sealed tube; Inert atmosphere; Photolysis 4: hydrogenchloride / 18 h / 80 °C View Scheme |
2,4-difluoro-benzoic acid
2,4-difluorobenzoyl chloride
Conditions | Yield |
---|---|
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Cooling with ice; | 100% |
Stage #1: 2,4-difluoro-benzoic acid With N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.0833333h; Stage #2: With oxalyl dichloride In dichloromethane at 20℃; for 12h; | 100% |
With thionyl chloride Heating; | 96% |
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With N-iodo-succinimide; sulfuric acid at 0℃; for 4h; | 100% |
With N-iodo-succinimide; trifluorormethanesulfonic acid at 5 - 50℃; for 1.5h; Product distribution / selectivity; | 100% |
With N-Iodosuccinamide; sulfuric acid at 0 - 5℃; for 5h; | 94% |
(2S,4S)-2-(3,3-difluoropyrrolidine-1-carbonyl)-4-piperazin-1-ylpyrrolidine-1-carboxylic acid tert-butyl ester
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
Stage #1: (2S,4S)-2-(3,3-difluoropyrrolidine-1-carbonyl)-4-piperazin-1-ylpyrrolidine-1-carboxylic acid tert-butyl ester; 2,4-difluoro-benzoic acid With O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Stage #2: With sodium hydrogencarbonate In dichloromethane; water | 100% |
2,4-difluoro-benzoic acid
2,4-difluoro-5-nitro-benzoic acid
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 0 - 20℃; for 16.5h; | 98% |
With sulfuric acid; nitric acid In water at 20 - 50℃; for 3.5h; | 98% |
With sulfuric acid; nitric acid at 0 - 20℃; for 16.5h; | 98% |
3,4,5-Trimethoxyaniline
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; | 98% |
2,4-difluoro-benzoic acid
methyl 2,4-difluorobenzoate
Conditions | Yield |
---|---|
With thionyl chloride In methanol | 97% |
Multi-step reaction with 2 steps 1: thionyl chloride; sulfuric acid / 0.2 h / Inert atmosphere; Reflux 2: triethylamine / dichloromethane / 0 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With 1,3-dimethyl-2-imidazolidinone; sodium hydroxide at 130℃; for 4h; | 95.1% |
With sodium hydroxide In dimethyl sulfoxide at 130℃; for 8h; | 90% |
With 1,3-dimethyl-2-imidazolidinone; sodium hydroxide at 135℃; for 4h; | 68% |
With 1,3-dimethyl-2-imidazolidinone; sodium hydroxide at 135℃; for 6h; | 67.52% |
With sodium hydroxide In 1-methyl-pyrrolidin-2-one at 150℃; for 1h; |
benzo[1,3]dioxolo-5-ylamine
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; | 93% |
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; | 93% |
Conditions | Yield |
---|---|
With water; sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 170 - 175℃; for 15h; Sealed tube; | 92.8% |
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; | 91% |
Conditions | Yield |
---|---|
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
In methanol; acetone at 60℃; for 1h; | 89% |
tert-butyl alcohol
2,4-difluoro-benzoic acid
tert-butyl 2,4-difluorobenzoate
Conditions | Yield |
---|---|
With dmap; di-tert-butyl dicarbonate for 48h; | 86% |
With dmap; di-tert-butyl dicarbonate at 20℃; for 24h; | 84% |
With dmap; di-tert-butyl dicarbonate In dichloromethane at 20℃; for 24h; | 84% |
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Heating; | 85% |
With hydrogenchloride at 80℃; for 24.25h; | 76% |
Stage #1: ethanol; 2,4-difluoro-benzoic acid With hydrogenchloride for 5.33333h; Heating / reflux; Stage #2: With sodium hydroxide In diethyl ether; water | |
With hydrogenchloride | |
With sulfuric acid Heating; |
3,5-dimethylphenyl iodide
2,4-difluoro-benzoic acid
3,5-difluoro-3',5'-dimethyl-1,1'-biphenyl
Conditions | Yield |
---|---|
With palladium diacetate; acetic acid; silver carbonate at 130℃; for 16h; regioselective reaction; | 85% |
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
With trichlorophosphate Reflux; | 85% |
ethyl 3-(dimethylamino)acrylate
2,4-difluoro-benzoic acid
Conditions | Yield |
---|---|
Stage #1: 2,4-difluoro-benzoic acid With thionyl chloride at 80℃; for 2h; Stage #2: ethyl 3-(dimethylamino)acrylate With triethylamine In toluene at 90℃; for 12h; | 85% |
di-tert-butyl dicarbonate
tert-butyl alcohol
2,4-difluoro-benzoic acid
tert-butyl 2,4-difluorobenzoate
Conditions | Yield |
---|---|
dmap In dichloromethane at 20℃; for 24h; | 84% |
di-tert-butyl dicarbonate
2,4-difluoro-benzoic acid
tert-butyl 2,4-difluorobenzoate
Conditions | Yield |
---|---|
With dmap In dichloromethane; tert-butyl alcohol at 20℃; for 24h; | 84% |
dmap In tert-butyl alcohol at 40℃; for 18h; | 81% |
The IUPAC name of this chemical is 2,4-difluorobenzoic acid. With the CAS registry number 1583-58-0, it is also named as Benzoic acid, 2,4-difluoro-. The product's categories are Fluorin-contained Benzoic Acid Series; Fine Chemical & Intermediates; Blocks; Carboxes; Fluoro Compounds; API intermediates; Miscellaneous; Acids & Esters; Fluorine Compounds; Fluorobenzoic acids; Carbonyl Compounds; Carboxylic Acids. It is white to light yellow crystal powder which is soluble in water and stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.17; (4)ACD/LogD (pH 7.4): -1.04; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.85; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.512; (13)Molar Refractivity: 33.17 cm3; (14)Molar Volume: 110.3 cm3; (15)Polarizability: 13.14×10-24 cm3; (16)Surface Tension: 43.6 dyne/cm; (17)Enthalpy of Vaporization: 50.34 kJ/mol; (18)Vapour Pressure: 0.0218 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 158.017936; (21)MonoIsotopic Mass: 158.017936; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 11; (24)Complexity: 161.
Uses of 2,4-Difluorobenzoic acid: It is used as intermediate of pharmaceutical and liquid crystal. And it also can react with ethanol to get 2,4-difluoro-benzoic acid ethyl ester. This reaction needs reagent conc. H2SO4 by heating. The reaction time is 3 hours. The yield is 85%.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)c1ccc(F)cc1F
2. InChI:InChI=1/C7H4F2O2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3H,(H,10,11)
3. InChIKey:NJYBIFYEWYWYAN-UHFFFAOYAW
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