2'-chloro-4',5'-difluoroacetophenone
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With sodium hypochlorite Oxidation; | 90% |
With hydrogenchloride; sodium hypochlorite In dichloromethane | 85.1% |
With hydrogenchloride; sodium hypochlorite In dichloromethane | 85.1% |
With sodium hypochlorite for 6h; Heating; | 80% |
With hydrogenchloride; sodium hydroxide; sodium hypobromide; bromine; sodium hydrogensulfite In 1,4-dioxane; dichloromethane; water |
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With KF; benzenesulfonyl chloride In sulfolane; thionyl chloride | 75% |
2-chloro-4,5-difluoro-α-chloroacetophenone
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With sodium hypochlorite Oxidation; |
4-chloro-1,2-difluorobenzene
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / AlCl3 2: 90 percent / 5 percent NaOCl View Scheme | |
Multi-step reaction with 2 steps 1: 95 percent / AlCl3 2: 5 percent NaOCl View Scheme | |
Multi-step reaction with 2 steps 1: 75 percent / AlCl3 / 9 h / 60 °C 2: 80 percent / NaOCl / 6 h / Heating View Scheme |
2-fluoro-5-chloronitrobenzene
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: H2 / 5 percent Pt/C / 1,2-dimethoxy-ethane / 24 h / 2585.74 Torr 2: BF3*Et2O; t-BuONO / 1,2-dimethoxy-ethane / 1 h / -5 °C 3: 49 percent / 0.5 h / 170 °C 4: 80 percent / AlCl3 5: 90 percent / 5 percent NaOCl View Scheme | |
Multi-step reaction with 5 steps 1: H2 / 5 percent Pt/C / 1,2-dimethoxy-ethane / 24 h / 2585.74 Torr 2: BF3*Et2O; t-BuONO / 1,2-dimethoxy-ethane / 1 h / -5 °C 3: 49 percent / 0.5 h / 170 °C 4: 95 percent / AlCl3 5: 5 percent NaOCl View Scheme |
5-chloro-2-fluoroaniline
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: BF3*Et2O; t-BuONO / 1,2-dimethoxy-ethane / 1 h / -5 °C 2: 49 percent / 0.5 h / 170 °C 3: 80 percent / AlCl3 4: 90 percent / 5 percent NaOCl View Scheme | |
Multi-step reaction with 4 steps 1: BF3*Et2O; t-BuONO / 1,2-dimethoxy-ethane / 1 h / -5 °C 2: 49 percent / 0.5 h / 170 °C 3: 95 percent / AlCl3 4: 5 percent NaOCl View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 52 percent / KF; 18-crown-6 / tetrahydrothiophene 1,1-dioxide / 32 h / 180 °C 2: H2 / 5 percent Pt/C / 1,2-dimethoxy-ethane / 24 h / 2585.74 Torr 3: BF3*Et2O; t-BuONO / 1,2-dimethoxy-ethane / 1 h / -5 °C 4: 49 percent / 0.5 h / 170 °C 5: 80 percent / AlCl3 6: 90 percent / 5 percent NaOCl View Scheme | |
Multi-step reaction with 6 steps 1: 52 percent / KF; 18-crown-6 / tetrahydrothiophene 1,1-dioxide / 32 h / 180 °C 2: H2 / 5 percent Pt/C / 1,2-dimethoxy-ethane / 24 h / 2585.74 Torr 3: BF3*Et2O; t-BuONO / 1,2-dimethoxy-ethane / 1 h / -5 °C 4: 49 percent / 0.5 h / 170 °C 5: 95 percent / AlCl3 6: 5 percent NaOCl View Scheme |
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 49 percent / 0.5 h / 170 °C 2: 80 percent / AlCl3 3: 90 percent / 5 percent NaOCl View Scheme | |
Multi-step reaction with 3 steps 1: 49 percent / 0.5 h / 170 °C 2: 95 percent / AlCl3 3: 5 percent NaOCl View Scheme |
ortho-difluorobenzene
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / FeCl3, Cl2 / 3 h / 50 °C 2: 75 percent / AlCl3 / 9 h / 60 °C 3: 80 percent / NaOCl / 6 h / Heating View Scheme |
2-chloro-4,5-difluorobenzotrichloride
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With sulfuric acid | |
With sulfuric acid |
Conditions | Yield |
---|---|
With sulfuric acid In water; acetic acid |
water
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; bromine In sodium hypobromide |
2-chloro-4,5-difluoro-α-chloroacetophenone
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In sodium hypobromide |
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In sodium hypochlorite |
tert.-butylnitrite
2-amino-4,5-difluorobenzoic acid
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetonitrile |
2-amino-4,5-difluorobenzoic acid
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With sodium nitrate; copper(l) chloride In hydrogenchloride; water |
2-chloro-4,5-difluorobenzoic acid
2-chloro-4,5-difluorobenzoyl chloride
Conditions | Yield |
---|---|
With pyridine; thionyl chloride In toluene | 92.1% |
With N,N-dimethyl-formamide In dichloromethane for 3h; Ambient temperature; | |
With thionyl chloride; N,N-dimethyl-formamide for 2h; Heating; |
methanol
2-chloro-4,5-difluorobenzoic acid
2-Chloro-4,5-difluorobenzoic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid at 60℃; for 48h; | 86.6% |
With acetyl chloride at 0℃; | 84% |
With acetyl chloride at 20℃; Cooling with ice; | |
With acetyl chloride for 65h; Reflux; |
2-chloro-4,5-difluorobenzoic acid
acetyl chloride
2-Chloro-4,5-difluorobenzoic acid methyl ester
Conditions | Yield |
---|---|
In methanol | 84% |
copper (I) acetate
2-chloro-4,5-difluorobenzoic acid
3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine
4,5-difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid
Conditions | Yield |
---|---|
With potassium carbonate; acetic acid In N,N-dimethyl-formamide | 81% |
With potassium carbonate; acetic acid In N,N-dimethyl-formamide | 81% |
2-chloro-4,5-difluorobenzoic acid
metronidazole
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-chloro-4,5-difluorobenzoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 80% |
3-methyl-1-(6-methylpyridin-2-yl)-1H-pyrazol-5-amine
copper (I) acetate
2-chloro-4,5-difluorobenzoic acid
A
4-chloro-6,7-difluoro-3-methyl-1-(6-methyl-2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline
B
4,5-difluoro-2-[[3-methyl-1-(6-methyl-2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide | A 39% B 79% |
2-chloro-4,5-difluorobenzoic acid
4-amino-5-(3-pyridyl)-4H-1,2,4-triazole-3-thiol
Conditions | Yield |
---|---|
With trichlorophosphate for 6h; Reflux; | 79% |
2-chloro-4,5-difluorobenzoic acid
phenylmethanethiol
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 6h; | 79% |
2-chloro-4,5-difluorobenzoic acid
2-chloro-4,5-difluorobenzamide
Conditions | Yield |
---|---|
Stage #1: 2-chloro-4,5-difluorobenzoic acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Stage #2: With ammonia In water; N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; | 76% |
Stage #1: 2-chloro-4,5-difluorobenzoic acid With thionyl chloride In toluene at 60℃; for 1.5h; Heating / reflux; Stage #2: With pyridine In toluene at 60℃; for 1.5h; Stage #3: With ammonia In toluene at 20 - 35℃; |
2-chloro-4,5-difluorobenzoic acid
benzylamine
N-benzyl-2-chloro-4,5-difluorobenzamide
Conditions | Yield |
---|---|
Stage #1: 2-chloro-4,5-difluorobenzoic acid With triethylamine; isobutyl chloroformate In dichloromethane for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: benzylamine In dichloromethane at 0℃; | 76% |
2-chloro-4,5-difluorobenzoic acid
4-amino-3-(2-furyl)-5-mercapto[4H]-1,2,4-triazole
Conditions | Yield |
---|---|
With trichlorophosphate Reflux; | 75% |
4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol
2-chloro-4,5-difluorobenzoic acid
6-(2-chloro-4,5-difluorophenyl)-3-(pyridin-4-yl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
Conditions | Yield |
---|---|
With trichlorophosphate Reflux; | 74% |
2-Amino-4,6-dimethylpyridine
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With O-phenyl phosphorodichloridate; triethylamine In 1,2-dichloro-ethane at 20℃; for 24h; | 72% |
3-ethyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine
copper (I) acetate
2-chloro-4,5-difluorobenzoic acid
A
4-chloro-3-ethyl-6,7-difluoro-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline
B
4,5-difluoro-2-[[3-ethyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide | A 50% B 66% |
ethanamine hydrochloride
2-chloro-4,5-difluorobenzoic acid
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 140℃; for 1.5h; Microwave irradiation; | 65% |
copper (I) acetate
2-chloro-4,5-difluorobenzoic acid
A
4-chloro-6,7-difluoro-3-methyl-1-(3-pyridinyl)-1H-pyrazolo[3,4-b]quinoline
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide | A 8% B 63% |
2-chloro-4,5-difluorobenzoic acid
1,1,1,3,3,3-hexamethyl-disilazane
Conditions | Yield |
---|---|
With iodine In neat (no solvent) at 20℃; for 96h; Green chemistry; | 62% |
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; palladium diacetate; potassium carbonate; Tri(p-tolyl)phosphine In N,N-dimethyl-formamide at 140℃; for 12h; Schlenk technique; Inert atmosphere; | 58% |
2-chloro-4,5-difluorobenzoic acid
1,2-cyclooctene
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 5,6-difluoro-2-(1-phenylethyl)benzo[d][1,2]selenazol-3(2H)-one In dichloromethane at 20℃; for 8h; | 56% |
copper (I) acetate
2-chloro-4,5-difluorobenzoic acid
1-(2-pyridinyl)-1H-pyrazol-5-ylamine
4,5-difluoro-2-[[1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide | 55% |
Conditions | Yield |
---|---|
Stage #1: dysprosium(III) nitrate hexahydrate; N-Methyldiethanolamine; chromium(III) chloride hexahydrate; 2-chloro-4,5-difluorobenzoic acid With triethylamine In acetonitrile for 2h; Stage #2: methanol In diethyl ether | 49% |
Conditions | Yield |
---|---|
Stage #1: terbium(III) nitrate hexahydrate; N-Methyldiethanolamine; chromium(III) chloride hexahydrate; 2-chloro-4,5-difluorobenzoic acid With triethylamine In acetonitrile for 2h; Stage #2: methanol In diethyl ether | 42% |
Conditions | Yield |
---|---|
Stage #1: holmium(III) nitrate hexahydrate; N-Methyldiethanolamine; chromium(III) chloride hexahydrate; 2-chloro-4,5-difluorobenzoic acid With triethylamine In acetonitrile for 2h; Stage #2: methanol In diethyl ether | 39% |
The 2-Chloro-4,5-difluorobenzoic acid with CAS registry number of 110877-64-0 is also known as Benzoicacid, 2-chloro-4,5-difluoro-. The IUPAC name and product name are the same. It belongs to product categories of Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Aromatic Compound; Benzoic Acid; C7; Carbonyl Compounds; Carboxylic Acids. Its EINECS registry number is 405-380-5. In addition, the formula is C7H3ClF2O2 and the molecular weight is 192.55. This chemical is a white to light yellow crystal powder and should be sealed in cool, dry place away from oxidants.
Physical properties about 2-Chloro-4,5-difluorobenzoic acid are: (1)ACD/LogP: 1.90; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 2; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.534; (11)Molar Refractivity: 38.06 cm3; (12)Molar Volume: 122.3 cm3; (13)Surface Tension: 46.5 dyne/cm; (14)Density: 1.573 g/cm3; (15)Flash Point: 119.4 °C; (16)Enthalpy of Vaporization: 54.1 kJ/mol; (17)Boiling Point: 273.8 °C at 760 mmHg; (18)Vapour Pressure: 0.00273 mmHg at 25 °C.
Preparation of 2-Chloro-4,5-difluorobenzoic acid: it is prepared by reaction of 2-chloro-4,5-difluoroacetophenone. The reaction needs reagent NaOCl and other condition of heating for 6 hours. The yield is about 80%.
Uses of 2-Chloro-4,5-difluorobenzoic acid: it is used to produce 2-chloro-N-(4,6-dimethyl-pyridin-2-yl)-4,5-difluoro-benzamide by reaction with 4,6-dimethyl-pyridin-2-ylamine. The reaction occurs with reagents triethylamine, phenyl dichlorophosphate and solvent 1,2-dichloro-ethane at the temperature of 20 °C for 24 hours. The yield is about 72%.
When you are using this chemical, please be cautious about it. As a chemical, it is harmful by inhalation, in contact with skin and if swallowed. Besides, it has risk of serious damage to eyes and may cause sensitisation by skin contact. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=C(C(=CC(=C1F)F)Cl)C(=O)O
2. InChI: InChI=1S/C7H3ClF2O2/c8-4-2-6(10)5(9)1-3(4)7(11)12/h1-2H,(H,11,12)
3. InChIKey: CGFMLBSNHNWJAW-UHFFFAOYSA-N
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