2,5-Difluorobenzoic acid supplier

Name
2,5-Difluorobenzoic acid
EINECS 221-060-6
CAS No. 2991-28-8
Article Data9
CAS DataBase
Density 1.432 g/cm³
Solubility Insoluble in water.
Melting Point 132-134 °C(lit.)
Formula C₇H₄F₂O₂
Boiling Point 244.7 °C at 760 mmHg
Molecular Weight 158.104
Flash Point 101.8 °C
Transport Information
Appearance white crystalline powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2,5-difluorobenzoate;2,5-Difluorobenzoicacid;
PSA 37.30000
LogP 1.66300

Synthetic route

: 399-94-0
2-bromo-1,4-difluorobenzene

: 124-38-9
carbon dioxide

: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
With n-butyllithium 1) hexane, Et2O, 2 min, -78 deg C. 2) ether; Yield given. Multistep reaction;

: 124-38-9
carbon dioxide

: 540-36-3
para-difluorobenzene

: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
With sec.-butyllithium 1.) THF, -78 deg C, 0.5 h, 2.) THF, a) -78 deg C, 15 min, b) from -78 deg C to RT; Yield given. Multistep reaction;

: 2358-29-4
2,3,6-trifluorobenzoic acid

A: 455-38-9
3-fluorobenzoic acid

B: 65-85-0
benzoic acid

C: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
With ammonia; sodium at -45℃; for 0.25h; Reduction; Hydrodefluorination; Title compound not separated from byproducts;	A 9 % Spectr. B 9 % Spectr. C 16 % Spectr.

...Expand

: 1979-36-8
2',5'-difluoroacetophenone

: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
With potassium permanganate Oxidation;

: 540-36-3
para-difluorobenzene

: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: KMnO4 View Scheme

: 2367-82-0
1,2,3,5-tetrafluorobenzene

: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran / -70 °C 1.2: tetrahydrofuran 2.1: 9 percent Spectr. / Zn; NH3 / -45 °C 3.1: 16 percent Spectr. / Na; NH3 / 0.25 h / -45 °C View Scheme
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran / -70 °C 1.2: tetrahydrofuran 2.1: 12 percent Spectr. / Na; NH3 / 0.25 h / -45 °C 3.1: 16 percent Spectr. / Na; NH3 / 0.25 h / -45 °C View Scheme

: 367-23-7
1,2,4-trifluorobenzene

: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: BuLi / tetrahydrofuran / -70 °C 1.2: tetrahydrofuran 2.1: 16 percent Spectr. / Na; NH3 / 0.25 h / -45 °C View Scheme

: 32890-92-9
2,3,4,6-tetrafluorobenzoic acid

: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 9 percent Spectr. / Zn; NH3 / -45 °C 2: 16 percent Spectr. / Na; NH3 / 0.25 h / -45 °C View Scheme
Multi-step reaction with 2 steps 1: 12 percent Spectr. / Na; NH3 / 0.25 h / -45 °C 2: 16 percent Spectr. / Na; NH3 / 0.25 h / -45 °C View Scheme

: 2,5-difluoro-α,α-dichloroacetophenone

: sodium disulfite

: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
With hydrogenchloride In sodium hypobromide; water

: C7H3F2O2(1-)*C25H30N3(1+)

A: 467-63-0
crystal violet carbinol base

B: 2991-28-8
2,5-difluorobenzoic acid

Conditions

Conditions	Yield
With water In chlorobenzene at 28℃; Equilibrium constant; Further Variations:; Temperatures;

: 2991-28-8
2,5-difluorobenzoic acid

: 35730-09-7
2,5-difluorobenzoyl chloride

Conditions

Conditions	Yield
Stage #1: 2,5-difluorobenzoic 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;	97%
With sulfuryl dichloride for 4h; Heating;	73%

: 64-17-5
ethanol

: 2991-28-8
2,5-difluorobenzoic acid

: 708-25-8
ethyl 2,5-difluorobenzoate

Conditions

Conditions	Yield
With sulfuric acid at 100℃; for 12h; Sealed tube;	95%
With sulfuric acid Reflux;
With sulfuric acid for 10h; Reflux;

: 2991-28-8
2,5-difluorobenzoic acid

: 111608-81-2
4,7-difluoro-3-hydroxy-1(3H)-isobenzofuranone

Conditions

Conditions	Yield
With sec-BuLi In tetrahydrofuran; hydrogenchloride; N,N-dimethyl-formamide	93%
With sec-BuLi In tetrahydrofuran; hydrogenchloride; N,N-dimethyl-formamide	93%
Multi-step reaction with 5 steps 1: 73 percent / SO2Cl / 4 h / Heating 2: CH2Cl2 / 6 h / Ambient temperature 3: SOCl2 / 12 h 4: 1.) sec-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h 5: 5 N HCl / Heating View Scheme

: 56-36-0
tributyltin acetate

: 2991-28-8
2,5-difluorobenzoic acid

: tri-n-butyltin 2,5-difluorobenzoate

Conditions

Conditions	Yield
In ethanol; toluene byproducts: acetic acid; equimolar amts. of Sn-compd. and the benzoic acid are mixed with toluene/EtOH (3:1), mixt. refluxed (4 h); the azeotrope acetic acid/EtOH/toluene followed by the azeotrop toluene/EtOH is distilled off to 50% of the initial vol., evapn. (reduced pressure);	92%

: 870-46-2
t-butoxycarbonylhydrazine

: 2991-28-8
2,5-difluorobenzoic acid

: 1079843-62-1
C12H14F2N2O3

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide	91%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 3h;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In tetrahydrofuran; N,N-dimethyl-formamide for 16h;

: 2991-28-8
2,5-difluorobenzoic acid

: 223444-58-4
N-t-Butyl-2,5-difluorobenzamide

Conditions

Conditions	Yield
	91%

: europium(III) hydroxide

: 2991-28-8
2,5-difluorobenzoic acid

: C21H13EuF6O8

Conditions

Conditions	Yield
In methanol; acetone at 60℃; for 1h;	91%

: 67-56-1
methanol

: 2991-28-8
2,5-difluorobenzoic acid

: methyl 2,5-difluorobenzoate

Conditions

Conditions	Yield
With thionyl chloride Reflux;	90.7%
With sulfuric acid for 12h; Reflux;	66%
With thionyl chloride at 60℃; for 3h; Cooling with ice;

: 183067-65-4
2-(3,4-bis(benzyloxy)phenyl)-7-(benzyloxy)-3,5-dihydroxy-4H-chromen-4-one

: 2991-28-8
2,5-difluorobenzoic acid

: C36H24F2O8

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 50℃; for 5h;	84%

: 28957-04-2, 28957-10-0
oridonin

: 2991-28-8
2,5-difluorobenzoic acid

: (1S,5S,6S,6aR,9S,11aS,11bS,14R)-1,5,6-trihydroxy-4,4-dimethyl-8-methylene-7-oxododecahydro-1H-6,11b-(epoxymethano)-6a,9-methanocyclohepta[a]naphthalen-14-yl 2,5-difluorobenzoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane	83%

: 75-65-0
tert-butyl alcohol

: 2991-28-8
2,5-difluorobenzoic acid

: 129589-71-5
N-(tert-Butoxycarbonyl)-2,5-difluoroaniline

Conditions

Conditions	Yield
With diphenylphosphoranyl azide; triethylamine for 2h; Heating;	81%

: 51507-18-7
methyl 2-diazohydrocinnamate

: 2991-28-8
2,5-difluorobenzoic acid

A: (S)-3-methoxy-3-oxo-2-phenylpropyl 2,5-difluorobenzoate

B: C17H14F2O4

Conditions

Conditions	Yield
With C2HF6NO4S2*C27H30BNO In dichloromethane at -78℃; for 1h; Inert atmosphere; enantioselective reaction;	A 75% B n/a

...Expand

: 2991-28-8
2,5-difluorobenzoic acid

: 741721-49-3
2,5-difluoro-3-nitro-benzoic acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid	72%
With sulfuric acid; nitric acid at 0 - 20℃; for 1h;	31.3%
With sulfuric acid; nitric acid In water at 0 - 20℃;	31.3%
With sulfuric acid; nitric acid at 0 - 20℃;	31.3%
With sulfuric acid; nitric acid at 0 - 20℃;	31.3%

: 80983-36-4
5-(propylthio)-1H-benzimidazol-2-ylamine

: 2991-28-8
2,5-difluorobenzoic acid

: 2,4-difluoro-N-(5-(propylthio)-1H-benzo[d]imidazol-2-yl)benzamide

Conditions

Conditions	Yield
Stage #1: 2,5-difluorobenzoic acid With potassium carbonate; 1,1'-carbonyldiimidazole In tetrahydrofuran for 0.5h; Stage #2: 5-(propylthio)-1H-benzimidazol-2-ylamine In tetrahydrofuran Reflux;	71%

: 140-88-5
ethyl acrylate

: 2991-28-8
2,5-difluorobenzoic acid

: ethyl 2-(4,7-difluoro-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetate

Conditions

Conditions	Yield
With silver hexafluoroantimonate; potassium acetate; dichloro[η5-1-(3,5-bis(trifluoromethyl)phenyl)-3-(2-(2,3,4,5-tetramethylcyclopentadienyl)ethyl)urea][(6-oxo-1,6-dihydropyridin-2-yl)diphenylphosphine]rhodium(III); copper(II) trifluoroacetate In toluene at 120℃; for 16h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	70%

: 30235-26-8
4-pyridin-2-yl-thiazol-2-ylamine

: 2991-28-8
2,5-difluorobenzoic acid

: 2-[(2,5-difluorobenzoyl)amino]-4-(pyridin-2-yl)thiazole

Conditions

Conditions	Yield
Stage #1: 2,5-difluorobenzoic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 23℃; for 0.5h; Inert atmosphere; Stage #2: 4-pyridin-2-yl-thiazol-2-ylamine In N,N-dimethyl-formamide at 23℃; for 16h; Inert atmosphere;	69%

: 109-99-9
tetrahydrofuran

: [Ru2II,III(CH3CO2)4(THF)2]BF4

: 2991-28-8
2,5-difluorobenzoic acid

: [Ru2II,II(2,5-F2PhCO2)4(THF)2]*0.5THF

Conditions

Conditions	Yield
Stage #1: [Ru2II,III(CH3CO2)4(THF)2]BF4; 2,5-difluorobenzoic acid In N,N-dimethyl-aniline for 12h; Schlenk technique; Glovebox; Reflux; Stage #2: tetrahydrofuran	67%

...Expand

: {2‐azabicyclo[2.1.1]hexan‐1‐yl}methanamine

: 2991-28-8
2,5-difluorobenzoic acid

: N‐({2‐benzyl‐2‐azabicyclo[2.1.1]hexan‐1‐yl}methyl)‐2,5‐difluorobenzamide

Conditions

Conditions	Yield
Stage #1: 2,5-difluorobenzoic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Stage #2: {2‐azabicyclo[2.1.1]hexan‐1‐yl}methanamine In dichloromethane at 20℃; for 1h;	65%

: 4-(6-(4-amino-4-methylpiperidin-1-yl)pyridin-3-yl)-6-(2-hydroxy-2-methylpropoxy)pyrazolo[1,5-a]pyridine-3-carbonitrile

: 2991-28-8
2,5-difluorobenzoic acid

: N-(1-(5-(3-cyano-6-(2-hydroxy-2-methylpropoxy)pyrazolo[1,5-a]pyridin-4-yl)pyridin-2-yl)-4-methylpiperidin-4-yl)-2,5-difluorobenzamide

Conditions

Conditions	Yield
With N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridine-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	64%

: 95-25-0
5-chloro-2-benzoxazolinone

: 2991-28-8
2,5-difluorobenzoic acid

: 230628-47-4
5-chloro-6-(2,5-difluoro-benzoyl)-3H-benzooxazol-2-one

Conditions

Conditions	Yield
With PPA Acylation;	62%

: 1182669-71-1
N-(2-methylbenzoyl)-8-aminoquinoline

: 2991-28-8
2,5-difluorobenzoic acid

: 2-fluoro-7-methyl-5-(quinolin-8-yl)-5,6-dihydrophenanthridin-6-one

Conditions

Conditions	Yield
Stage #1: 2,5-difluorobenzoic acid With sodium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: N-(2-methylbenzoyl)-8-aminoquinoline With nickel(II) acetate tetrahydrate; silver nitrate In N,N-dimethyl acetamide at 170℃; for 24h; Schlenk technique; Inert atmosphere;	62%

: 20951-43-3
2-bromo-4-(methylsulfonyl)phenol

: 2991-28-8
2,5-difluorobenzoic acid

: C14H10BrFO5S

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;	62%

: 19879-84-6
tetraacetyl thioglucose

: 2991-28-8
2,5-difluorobenzoic acid

: 2,3,4,6-tetraacetate-1-(2,5-difluorobenzoate) β-D-glucopyranose

Conditions

Conditions	Yield
With copper acetylacetonate; silver carbonate at 130℃; for 0.25h; Microwave irradiation; Inert atmosphere; Sealed tube; stereoselective reaction;	62%

: 75-65-0
tert-butyl alcohol

: 2991-28-8
2,5-difluorobenzoic acid

: C11H12F2O2

Conditions

Conditions	Yield
With sulfuric acid; magnesium sulfate In toluene at 20℃; Sealed tube;	62%

: (R)-2-(3,8-diazabicyclo[3.2.1]octan-3-yl)-2-(4-cyanophenyl)-N-(cyclopropylmethyl)acetamide

: 2991-28-8
2,5-difluorobenzoic acid

: (R)-2-(4-cyanophenyl)-N-(cyclopropylmethyl)-2-(8-(2,5-difluorobenzoyl)-3,8-diazabicyclo[3.2.1]octan-3-yl)acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;	59%

: 59-49-4
2-Benzoxazolinone

: 2991-28-8
2,5-difluorobenzoic acid

: 230628-46-3
6-(2,5-difluoro-benzoyl)-3H-benzooxazol-2-one

Conditions

Conditions	Yield
With PPA Acylation;	58%
With PPA
With PPA at 140 - 160℃;

: 2991-28-8
2,5-difluorobenzoic acid

: 265644-03-9
2,5-difluorobenzohydrazide

Conditions

Conditions	Yield
Stage #1: 2,5-difluorobenzoic acid With thionyl chloride In dichloromethane at 20℃; Reflux; Stage #2: With hydrazine In dichloromethane for 4h; Reflux;	56%
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate / ethanol / Reflux View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 10 h / Reflux 2: hydrazine hydrate / ethanol / 8 h / Reflux View Scheme

: (Z)-N′-hydroxy-1H-benzo[d]imidazole-5-carboximidamide

: 2991-28-8
2,5-difluorobenzoic acid

: 3-(1H-benzo[d]imidazol-6-yl)-5-(2,5-difluorophenyl)-1,2,4-oxadiazol

Conditions

Conditions	Yield
Stage #1: 2,5-difluorobenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: (Z)-N′-hydroxy-1H-benzo[d]imidazole-5-carboximidamide In N,N-dimethyl-formamide at 110℃;	47.6%

: (R)-3-amino-N-(3-(cyclopropylmethyl)-7-fluoro-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl)piperidine-1-carboxamide

: 2991-28-8
2,5-difluorobenzoic acid

: (3R)-N-(3-(cyclopropylmethyl)-7-fluoro-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-6-yl)-3-((2,5-difluorobenzoyl)amino)-piperidine-1-carboxamide

Conditions

Conditions	Yield
With dmap; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 70℃; for 6h;	39.5%

: 1187890-09-0
N-biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride

: 2991-28-8
2,5-difluorobenzoic acid

: 1187889-55-9
N-Biphenyl-4-yl-3-[4-(2,5-difluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10 - 20℃;	37%

2,5-Difluorobenzoic acid Chemical Properties

2,5-Difluorobenzoic acid(2991-28-8) is also named as Benzoic acid, 2,5-difluoro-;2,5-Difluorobenzic acid;2-chloro-6-flurobenzyl cyanide;2,5-Difluorobenzoic;2,5-Difluorobenzoic acid 98%;2,5-Difluorobenzoicacid98%,and so on.2,5-Difluorobenzoic acid(2991-28-8) is usually white powder.

CAS: 2991-28-8
Molecular Formula: C₇H₄F₂O₂
MW: 158.1
EINECS: 221-060-6
Molecular structure:
Melting point: 132-134 °C(lit.)
BRN: 973351

2,5-Difluorobenzoic acid Uses

2,5-Difluorobenzoic acid(2991-28-8) is commonly used as the pharmaceutical intermediate.

2,5-Difluorobenzoic acid Safety Profile

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-37/39
WGK Germany: 3
Hazard Note: Irritant

Product Name

2,5-Difluorobenzoic acid

Synthetic route

2,5-Difluorobenzoic acid Chemical Properties

2,5-Difluorobenzoic acid Uses

2,5-Difluorobenzoic acid Safety Profile

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