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116751-24-7

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    Cas No: 116751-24-7

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116751-24-7 Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 116751-24-7 differently. You can refer to the following data:
1. 2,4,5-Trifluoro-3-hydroxybenzoic Acid can be used to prepare quinoline derivatives as Antibacterial Agents.
2. 3-Hydroxy-2,4,5-trifluorobenzoic acid may be used to synthesize methyl 3-methoxy-2,4,5-trifluorobenzoate and ethyl 3-ethoxy-2,4,5-trifluorobenzoate.

Check Digit Verification of cas no

The CAS Registry Mumber 116751-24-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,6,7,5 and 1 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 116751-24:
(8*1)+(7*1)+(6*6)+(5*7)+(4*5)+(3*1)+(2*2)+(1*4)=117
117 % 10 = 7
So 116751-24-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H3F3O3/c8-3-1-2(7(12)13)4(9)6(11)5(3)10/h1,11H,(H,12,13)/p-1

116751-24-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Hydroxy-2,4,5-trifluorobenzoic acid

1.2 Other means of identification

Product number -
Other names 3-Hydroxy-2,4,5-trif

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:116751-24-7 SDS

116751-24-7Synthetic route

3,4,5,6-tetrafluorophthalic acid
652-03-9

3,4,5,6-tetrafluorophthalic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: 3,4,5,6-tetrafluorophthalic acid With sodium hydroxide In water at 90℃; for 9h;
Stage #2: With hydrogenchloride; tri-n-propylamine In water at 140℃; under 7500.75 Torr; for 7h; pH=1; Temperature;
90.35%
3,4,6-trifluoro-5-hydroxyphthalic acid
28749-88-4

3,4,6-trifluoro-5-hydroxyphthalic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
In water90%
In water90%
4-methoxy-3,5,6-trifluorophthalic acid
28889-41-0

4-methoxy-3,5,6-trifluorophthalic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
In water74%
In water74%
2-bromo-3,4,6-trifluoro-5-hydroxy-benzoic acid

2-bromo-3,4,6-trifluoro-5-hydroxy-benzoic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; zinc In water at 25℃; for 2h;1.92 g
triisopropyl(2,3,6-trifluorophenoxy)silane

triisopropyl(2,3,6-trifluorophenoxy)silane

carbon dioxide
124-38-9

carbon dioxide

A

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

B

2,3,5-trifluoro-4-hydroxybenzoic acid
156839-10-0

2,3,5-trifluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: triisopropyl(2,3,6-trifluorophenoxy)silane With 2,2,6,6-tetramethylpiperidinyl-lithium In diethyl ether
Stage #2: carbon dioxide In diethyl ether
Stage #3: With hydrogenchloride Title compound not separated from byproducts;
carbon dioxide
124-38-9

carbon dioxide

1,2,4-trifluoro-3-(methoxymethoxy)benzene

1,2,4-trifluoro-3-(methoxymethoxy)benzene

A

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

B

2,3,5-trifluoro-4-hydroxybenzoic acid
156839-10-0

2,3,5-trifluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: 1,2,4-trifluoro-3-(methoxymethoxy)benzene With n-butyllithium In tetrahydrofuran
Stage #2: carbon dioxide In tetrahydrofuran; hexane
Stage #3: With hydrogenchloride In water Title compound not separated from byproducts;
Stage #1: 1,2,4-trifluoro-3-(methoxymethoxy)benzene With lithium diisopropyl amide In tetrahydrofuran
Stage #2: carbon dioxide In tetrahydrofuran
Stage #3: With hydrogenchloride In water Title compound not separated from byproducts;
1-bromo-2,3,5-trifluoro-4-(methoxymethoxy)benzene
851341-31-6

1-bromo-2,3,5-trifluoro-4-(methoxymethoxy)benzene

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 2,2,6,6-tetramethylpiperidine; potassium tert-butoxide; N,N,N',N'',N''-pentamethylenediamine / butyllithium / tetrahydrofuran; hexane / 0.75 h / -125 °C
1.2: tetrahydrofuran; hexane
2.1: HCl / H2O
3.1: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C
View Scheme
2-bromo-3,4,6-trifluoro-5-methoxymethoxy-benzoic acid

2-bromo-3,4,6-trifluoro-5-methoxymethoxy-benzoic acid

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / H2O
2: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C
View Scheme
2,3,6-trifluorophenol
113798-74-6

2,3,6-trifluorophenol

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 82 percent / imidazole / dimethylformamide / 20 h / 25 °C
2.1: lithium 2,2,6,6-tetramethylpiperidide / diethyl ether
2.2: diethyl ether
2.3: hydrochloric acid
View Scheme
Multi-step reaction with 5 steps
1.1: 87 percent / N-bromosuccinimide / CHCl3 / 2 h / 0 °C
2.1: 88 percent / N-ethyldiisopropylamine / CH2Cl2 / 2 h / 25 °C
3.1: 2,2,6,6-tetramethylpiperidine; potassium tert-butoxide; N,N,N',N'',N''-pentamethylenediamine / butyllithium / tetrahydrofuran; hexane / 0.75 h / -125 °C
3.2: tetrahydrofuran; hexane
4.1: HCl / H2O
5.1: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 87 percent / N-ethyldiisopropylamine / CH2Cl2 / 25 °C
2.1: lithium diisopropylamide / tetrahydrofuran
2.2: tetrahydrofuran
2.3: HCl / H2O
View Scheme
4-bromo-2,3,6-trifluorophenol
192446-70-1

4-bromo-2,3,6-trifluorophenol

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 88 percent / N-ethyldiisopropylamine / CH2Cl2 / 2 h / 25 °C
2.1: 2,2,6,6-tetramethylpiperidine; potassium tert-butoxide; N,N,N',N'',N''-pentamethylenediamine / butyllithium / tetrahydrofuran; hexane / 0.75 h / -125 °C
2.2: tetrahydrofuran; hexane
3.1: HCl / H2O
4.1: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C
View Scheme
N-methyl-tetrafluorophthalimide
33795-85-6

N-methyl-tetrafluorophthalimide

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: N-methyl-tetrafluorophthalimide With sodium hydroxide for 10h; Reflux;
Stage #2: With sulfuric acid at 70 - 105℃; for 8h; Temperature; Reagent/catalyst;
Multi-step reaction with 2 steps
1: sodium hydroxide; zinc(II) chloride / water / 8 h / 100 °C / Large scale
2: hydrogenchloride / Reflux
View Scheme
Multi-step reaction with 2 steps
1: water; zinc(II) chloride; sodium hydroxide / 8 h / 100 °C / Large scale
2: hydrogenchloride / water / Reflux
View Scheme
C8F3O5(3-)*3Na(1+)

C8F3O5(3-)*3Na(1+)

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

Conditions
ConditionsYield
With hydrogenchloride Reflux;
With hydrogenchloride In water Reflux;
ethyl iodide
75-03-6

ethyl iodide

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl 3-ethoxy-2,4,5-trifluorobenzoate
172602-80-1

ethyl 3-ethoxy-2,4,5-trifluorobenzoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 18h;92%
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

methyl iodide
74-88-4

methyl iodide

methyl 3-methoxy-2,4,5-trifluorobenzoate
136897-64-8

methyl 3-methoxy-2,4,5-trifluorobenzoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 18h;91%
With sodium hydride In N,N-dimethyl-formamide
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 3-methoxy-2,4,5-trifluorobenzoate
136897-64-8

methyl 3-methoxy-2,4,5-trifluorobenzoate

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester
137234-92-5

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl acetamide; water91%
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3-methoxy-2,4,5-trifluorobenzoic acid
112811-65-1

3-methoxy-2,4,5-trifluorobenzoic acid

Conditions
ConditionsYield
With potassium dihydrogenphosphate; N-ethyl-N,N-diisopropylamine In water at 170℃; for 8h; Reagent/catalyst; Solvent; Temperature; Autoclave;85.2%
Stage #1: 2,4,5-trifluoro-3-hydroxybenzoic acid; carbonic acid dimethyl ester With sodium hydroxide at 55 - 60℃; for 2h; pH=8 - 10; Large scale;
Stage #2: With hydrogenchloride In water at 35℃; Large scale;
85%
methanol
67-56-1

methanol

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester
137234-92-5

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester

Conditions
ConditionsYield
sulfuric acid at 70℃; for 18h; Sealed tube; Heating / reflux;79%
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

methyl 3-methoxy-2,4,5-trifluorobenzoate
136897-64-8

methyl 3-methoxy-2,4,5-trifluorobenzoate

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester
137234-92-5

2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester

Conditions
ConditionsYield
With dmap; potassium iodide In water; carbonic acid dimethyl ester78%
2-(tert-butyldimethylsilyloxy)ethyl bromide
86864-60-0

2-(tert-butyldimethylsilyloxy)ethyl bromide

2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl-3-[(2-{[(1,1-dimethylethyl)(dimethyl)siyl]oxy}ethyl)oxy]-2,4,5-trifluorobenzoate
838856-71-6

2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl-3-[(2-{[(1,1-dimethylethyl)(dimethyl)siyl]oxy}ethyl)oxy]-2,4,5-trifluorobenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 15h;23%
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

2,4,5-Trifluoro-3-hydroxy-benzoyl chloride
1042641-60-0

2,4,5-Trifluoro-3-hydroxy-benzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

3-ethoxy-2,4,5-trifluorobenzoyl chloride
172602-81-2

3-ethoxy-2,4,5-trifluorobenzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

3-ethoxy-2,4,5-trifluorobenzoic acid
169507-61-3

3-ethoxy-2,4,5-trifluorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl (3-ethoxy-2,4,5-trifluorobenzoyl)acetate
172602-82-3

ethyl (3-ethoxy-2,4,5-trifluorobenzoyl)acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

(Z)-3-Ethoxy-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester

(Z)-3-Ethoxy-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

(Z)-3-Cyclopropylamino-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester
1027303-55-4

(Z)-3-Cyclopropylamino-2-(3-ethoxy-2,4,5-trifluoro-benzoyl)-acrylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylic acid
172602-86-7

5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
10: 90 percent / 1.0 N aq. NaOH / ethanol / 18 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate
172602-83-4

ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate
172602-85-6

ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-4-oxo-3-quinolinecarboxylate

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-5-nitro-4-oxo-3-quinolinecarboxylate
172602-84-5

ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-ethoxy-5-nitro-4-oxo-3-quinolinecarboxylate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

5-Amino-7-(3-amino-piperidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

5-Amino-7-(3-amino-piperidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
10: 90 percent / 1.0 N aq. NaOH / ethanol / 18 h / Ambient temperature
11: 1.) Et3N, 2.) TFA / 1.) DMSO, CH3CN, RT, 18 h, 2.) CH2Cl2, from 0 deg C to RT, 1 h
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

5-Amino-7-(3-amino-pyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

5-Amino-7-(3-amino-pyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
10: 90 percent / 1.0 N aq. NaOH / ethanol / 18 h / Ambient temperature
11: 1.) Et3N, 2.) TFA / 1.) DMSO, CH3CN, RT, 18 h, 2.) CH2Cl2, from 0 deg C to RT, 1 h
View Scheme
2,4,5-trifluoro-3-hydroxybenzoic acid
116751-24-7

2,4,5-trifluoro-3-hydroxybenzoic acid

5-Amino-7-(3-aminomethyl-3-methyl-pyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

5-Amino-7-(3-aminomethyl-3-methyl-pyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 92 percent / NaH / dimethylformamide / 18 h
2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h
5: acetic anhydride / 18 h / Heating
6: ethanol / 18 h
7: NaH / tetrahydrofuran / 5 h / Ambient temperature
8: 61 percent / KNO3, conc. H2SO4 / 18 h / Ambient temperature
9: 89 percent / H2 / Raney nickel / tetrahydrofuran / 4 h / 24 - 30 °C / 1241.2 - 1551.4 Torr
10: 90 percent / 1.0 N aq. NaOH / ethanol / 18 h / Ambient temperature
11: 1.) Et3N, 2.) TFA / 1.) DMSO, CH3CN, RT, 18 h, 2.) CH2Cl2, from 0 deg C to RT, 1 h
View Scheme

116751-24-7Relevant articles and documents

Synthesis method of 2, 4, 5-trifluoro-3-methoxybenzoyl chloride

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Paragraph 0053; 0059-0062; 0073; 0077-0078; 0083; 0087-0088, (2020/09/16)

The invention discloses a synthesis method of 2, 4, 5-trifluoro-3-methoxybenzoyl chloride. The method comprises the following steps of: (1) using a metal halide as a catalyst, putting N-methyltetrafluorophthalimide in an alkaline environment, and carrying out hydroxylation reaction to obtain a sodium salt of 4-hydroxy-3, 5, 6-trifluorophthalic acid; (2) adding acid into the reaction system, and carrying out decarboxylation reaction to obtain 2, 4, 5-trifluoro-3-hydroxybenzoic acid; (3) sequentially adding a methylation reagent and acid into the reaction system under an alkaline condition, andcarrying out methylation reaction and acidification reaction to obtain 2, 4, 5-trifluoro-3-methoxybenzoic acid; and (4) mixing the 2, 4, 5-trifluoro-3-methoxybenzoic acid with thionyl chloride, and carrying out acylation reaction so as to obtain the 2, 4, 5-trifluoro-3-methoxybenzoyl chloride. The synthesis method disclosed by the invention is short in route, small in alkali dosage and few in sidereaction, the total molar yield of the reaction reaches 82.5%, and the purity of the product reaches 99.6% or above.

Preparation method of 2,4,5-trifluoro-3-methoxybenzoyl chloride and intermediate thereof

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Paragraph 0034; 0045; 0046; 0049-0064, (2020/07/02)

The invention discloses a preparation method of 2,4,5-trifluoro-3-methoxybenzoyl chloride and intermediate thereof. The preparation method of 2,4,5-trifluoro-3-methoxybenzoyl chloride comprises the following steps: by taking tetrafluorophthalic acid as a raw material, carrying out defluorination hydroxylation and acidification decarboxylation to obtain 2,4,5-trifluoro-3-hydroxybenzoic acid, thenreacting with dimethyl carbonate to obtain 2,4,5-trifluoro-3-methoxybenzoic acid, and finally carrying out acylating chlorination to obtain 2,4,5-trifluoro-3-methoxybenzoyl chloride. The preparation process is simple, the total reaction yield is high, the product quality is good, the process route is environment-friendly, and the method has a good industrial application prospect.

The site-selective functionalization of halogen-bearing phenols: An exercise in diversity-oriented organometallic synthesis

Marzi, Elena,Schlosser, Manfred

, p. 3393 - 3401 (2007/10/03)

The organometallic approach to diversity-oriented organic synthesis was subjected to a further test, this time in the phenol series. The model compounds selected were 2,3,6-trifluorophenol, the three isomers of (trifluoromethoxy) phenol and the three isomers of chlorophenol. A combination of optionally site selective metalations and protective group-controlled metalations enabled the selective generation of several isomeric intermediates in each case and their subsequent conversion into functionalized derivatives, in particular hydroxybenzoic acids.

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