4-Fluorobenzoic acid supplier

Name
4-Fluorobenzoic acid
EINECS 207-259-0
CAS No. 456-22-4
Article Data359
CAS DataBase
Density 1.319 g/cm³
Solubility Soluble in alcohol, hot water, methanol, and ether. Very slightly soluble in cold water.
Melting Point 184 °C
Formula C₇H₅FO₂
Boiling Point 253.7 °C at 760 mmHg
Molecular Weight 140.114
Flash Point 107.2 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-39-24/25-22-37/39-36
Risk Codes 22-41-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Benzoic acid, p-fluoro-;p-Fluorobenzoic acid;Benzoic acid, 4-fluoro-;
PSA 37.30000
LogP 1.52390

Synthetic route

: 352-32-9
p-fluorotoluene

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide at 50℃; for 9h; Temperature; UV-irradiation;	96.8%
With oxygen; Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Green chemistry;	96%
With hydrogen bromide In water	95.2%

: 53458-16-5
1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With oxygen; sodium hydride In tetrahydrofuran; mineral oil at 25℃; under 760.051 Torr; for 0.5h;	74%
With diphenyl diselenide; dihydrogen peroxide In water; acetonitrile at 20℃; for 24h;	72%
Stage #1: 1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one With potassium cyanide; carbon dioxide In N,N-dimethyl-formamide at 12℃; under 760.051 Torr; for 1h; Stage #2: With titanium(IV)isopropoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 40℃; for 18h; Reagent/catalyst;	10 %Spectr.

: 124-38-9
carbon dioxide

: 460-00-4
1-Bromo-4-fluorobenzene

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide Ambient temperature; electrochemically;	94%
Stage #1: 1-Bromo-4-fluorobenzene With bromobenzene; trifluoroacetic acid; cobalt(II) bromide; zinc dibromide; zinc In acetonitrile Inert atmosphere; Stage #2: carbon dioxide With palladium diacetate; tricyclohexylphosphine In tetrahydrofuran; acetonitrile at 0℃; under 760.051 Torr; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate; acetonitrile	94%
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 2-(diphenylphosphino)-2’(3-(dimethylamino)-3-oxopropyl)-6’-(3-(icosyloxy)-3-oxopropyl)biphenyl; water; palladium diacetate; N-ethyl-N,N-diisopropylamine In toluene under 760.051 Torr; for 16h; Inert atmosphere; Schlenk technique; Irradiation;	88%

: 124-38-9
carbon dioxide

: 225916-39-2
2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With (1,3-bis(2,6-diisopropyl-4-(morpholinomethyl)phenyl)imidazolidin-2-ylidene)copper(I) bromide; potassium tert-butylate In tetrahydrofuran under 760.051 Torr; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;	96%
Stage #1: carbon dioxide; 2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane With [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl]; potassium tert-butylate In toluene at 100℃; under 760.051 Torr; for 15h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In water; ethyl acetate; toluene at 20℃;	96%
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;	89%

: 459-56-3
4-fluorobenzylic alcohol

A: 456-22-4
4-Fluorobenzoic acid

B: 459-57-4
4-fluorobenzaldehyde

Conditions

Conditions	Yield
With peracetic acid; C24H29INO5 In acetic acid at 30℃; for 48h;	A 67% B 19%
With tert.-butylhydroperoxide In hexane; water at 50℃; for 9.5h;	A 62% B 22%
With sodium hypochlorite; sodium hydrogencarbonate for 4h; Yield given. Yields of byproduct given;
With [Rh(III)(OEP)(Cl)]/C; sodium hydroxide In water at 25℃; Electrochemical reaction; Inert atmosphere;
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C40H32B2Cu2F10N8S2*2CH4O; potassium carbonate In water at 40℃; under 760.051 Torr; for 24h; Green chemistry;

: 459-57-4
4-fluorobenzaldehyde

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;	99%
With 4H3N4H(1+)CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;	99%
With tert.-butylnitrite; N-hydroxyphthalimide; oxygen In water at 60℃; under 760.051 Torr; for 48h; Schlenk technique;	99%

: 459-46-1
4-Fluorobenzyl bromide

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With sodium periodate; sulfuric acid In water at 95℃; for 12h;	86%
With tert.-butylhydroperoxide at 100℃; for 5h;	80%
With tert.-butylhydroperoxide In water at 80℃; for 12h; Green chemistry;
Multi-step reaction with 2 steps 1: silver(I) nitrite / diethyl ether / 5 h / 0 °C / Reflux 2: tetra-(n-butyl)ammonium iodide; zinc diacetate; water / 24 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h / Inert atmosphere 1.2: 5 h / Inert atmosphere; Reflux 2.1: bis(acetylacetonate)oxovanadium; sodium acetate; methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen / 48 h / 120 °C View Scheme

: 14660-45-8
potassium monomethylcarbonate

: 214360-58-4
2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Sealed tube;	89%

: 403-33-8
methyl 4-flurobenzoate

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With iodine; aluminium In acetonitrile at 80℃; for 18h;	98%
With high-silica Hβ-75 zeolite In water at 130℃; for 24h; Reagent/catalyst;	75%

: 352-34-1
4-fluoro-1-iodobenzene

: 201230-82-2
carbon monoxide

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h;	96%
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 5h;	92%
With water; sodium carbonate; palladium diacetate at 20 - 165℃; under 10501.1 - 22502.3 Torr; for 0.333333h; microwave irradiation;	77%
With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; bis-triphenylphosphine-palladium(II) chloride; water; sodium carbonate In water at 100℃; under 7600.51 Torr; for 24h; Catalytic behavior; Autoclave;	74%

: 1-(4-fluorophenyl)-2-[(4-methylphenyl)sulfonyl]-1-ethanone

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate; oxygen In acetonitrile at 20 - 50℃; for 4h;	89%

: 459-56-3
4-fluorobenzylic alcohol

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With sodium hypochlorite; sodium hydrogencarbonate for 1.33333h;	100%
With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication;	97%
With oxygen at 120℃; for 10h; Green chemistry;	95%

: 352-11-4
1-chloromethyl-4-fluorobenzene

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With 4 Angstroem MS; methyl tri-n-octyl ammonium hydrogen sulfate; sodium tungstate at 90℃; for 10h;	86%
With Oxone In water; acetonitrile for 12h; Reflux;	85%

: 403-42-9
1-(4-fluorophenyl)ethanone

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
Stage #1: 1-(4-fluorophenyl)ethanone With tert.-butylhydroperoxide; sodium hydroxide; tungsten(VI) oxide In water at 80℃; for 8h; Stage #2: With hydrogenchloride In water	93%
Stage #1: 1-(4-fluorophenyl)ethanone With iodine; dimethyl sulfoxide In chlorobenzene at 130℃; for 3h; Stage #2: With tert.-butylhydroperoxide In chlorobenzene at 20 - 130℃; for 3h;	93%
With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate In acetic acid at 100℃; under 760.051 Torr; for 15h;	88%

: 352-34-1
4-fluoro-1-iodobenzene

: 124-38-9
carbon dioxide

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; diethylzinc In N,N-dimethyl acetamide at 70℃; under 760.051 Torr;	60%
Stage #1: 4-fluoro-1-iodobenzene With copper In tetrahydrofuran at 25℃; for 0.5h; Stage #2: carbon dioxide In tetrahydrofuran for 24h;	42%

: 1765-93-1
4-fluoroboronic acid

: 141-97-9
ethyl acetoacetate

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;	80%

: 124-38-9
carbon dioxide

: 1765-93-1
4-fluoroboronic acid

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate In N,N-dimethyl acetamide at 70℃; for 24h; Schlenk technique; Sealed tube;	73%

: 124-38-9
carbon dioxide

: C8H10FS(1+)*CF3O3S(1-)

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With 2.9-dimethyl-1,10-phenanthroline; neocuproine; zinc In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h;	74%

: 201230-82-2
carbon monoxide

: 460-00-4
1-Bromo-4-fluorobenzene

A: 456-22-4
4-Fluorobenzoic acid

B: 403-33-8
methyl 4-flurobenzoate

Conditions

Conditions	Yield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 7h; Irradiation;	A 8% B 81.5%

...Expand

: 24133-58-2
1,2-bis(4-fluorophenyl)-1,2-ethanediol

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With oxygen In dichloromethane at 20℃; under 760.051 Torr; for 12h; Irradiation;	88%
Stage #1: 1,2-bis(4-fluorophenyl)-1,2-ethanediol With oxygen; sodium t-butanolate In tetrahydrofuran at 20℃; under 760.051 Torr; for 3h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=1; chemoselective reaction;	70%

: 405-99-2
para-fluorostyrene

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
Stage #1: para-fluorostyrene With tert.-butylhydroperoxide; iodine; sodium hydroxide In water at 105℃; for 16h; Sealed tube; Stage #2: With hydrogenchloride In water	52%

: 459-57-4
4-fluorobenzaldehyde

A: 459-56-3
4-fluorobenzylic alcohol

B: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 25℃; for 3.5h; Cannizzaro Reaction;	A n/a B 86%
With potassium hydroxide
With barium dihydroxide; formaldehyd at 100 - 110℃; for 0.2h;	A 88 % Chromat. B 11 % Chromat.
Stage #1: 4-fluorobenzaldehyde In neat (no solvent) for 0.0333333h; Green chemistry; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 40℃; for 0.00416667h; Reagent/catalyst; Cannizzaro Reaction; Microwave irradiation; Green chemistry;

: 201230-82-2
carbon monoxide

: 460-00-4
1-Bromo-4-fluorobenzene

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 2h; Irradiation;	97%
With dicobalt octacarbonyl; potassium carbonate; methyloxirane In methanol at 60℃; under 760 Torr; for 6h;	89%

: 124-38-9
carbon dioxide

: 132993-23-8
4-fluorophenyl trifluoromethanesulfonate

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 90℃; electrochemical reaction;	92%
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine; DavePhos In N,N-dimethyl acetamide at 20℃; for 36h; Irradiation; Green chemistry; chemoselective reaction;	62%
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; tetrabutylammomium bromide; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 4h; Irradiation;

: 403-41-8
1-(4-Fluorophenyl)ethanol

A: 456-22-4
4-Fluorobenzoic acid

B: 403-42-9
1-(4-fluorophenyl)ethanone

Conditions

Conditions	Yield
Stage #1: 1-(4-Fluorophenyl)ethanol With oxygen; sodium hydride In tetrahydrofuran at 0 - 20℃; for 6h; Stage #2: With hydrogenchloride In water	A 32% B 64%

: 403-33-8
methyl 4-flurobenzoate

: 75-05-8
acetonitrile

A: 456-22-4
4-Fluorobenzoic acid

B: 4640-67-9
3-(4-fluorophenyl)-3-oxopropionitrile

Conditions

Conditions	Yield
With sodium hydride In tert-butyl methyl ether; water at 90℃;	A 17.5% B 64%

...Expand

: 316142-60-6
N-(4-cyanophenyl)-4-fluorobenzamide

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With hydrogenchloride at 120℃; for 24h;	98%

: 462-06-6
fluorobenzene

: 124-38-9
carbon dioxide

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
With aluminum tri-bromide; triisopropylsilyl chloride at 80℃; under 22502.3 Torr; for 48h; Autoclave;	53%
With aluminium trichloride; aluminium at 40℃; under 42754.3 Torr; for 18h;	47%
With triethylamine In acetonitrile at 20℃; under 760.051 Torr; for 24h; Irradiation;	62 %Spectr.

: 124-38-9
carbon dioxide

: 352-33-0
1-Chloro-4-fluorobenzene

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
Stage #1: carbon dioxide; 1-Chloro-4-fluorobenzene With manganese; bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; triphenylphosphine In 1,3-dimethyl-2-imidazolidinone at 25℃; under 760.051 Torr; for 20h; Stage #2: With hydrogenchloride; water In diethyl ether at 20℃; for 0.166667h;	81%
With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; tetraethylammonium iodide; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;	62%
Stage #1: 1-Chloro-4-fluorobenzene With bis(cyclopentadienyl)titanium dichloride; butyl magnesium bromide In tetrahydrofuran at 40℃; for 6h; Inert atmosphere; Schlenk technique; Stage #2: carbon dioxide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;	59%
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 4h; Electrolysis;	51%

: 150-13-0
4-amino-benzoic acid

: 456-22-4
4-Fluorobenzoic acid

Conditions

Conditions	Yield
	100%
With pyridine hydrogenfluoride; sodium nitrite 1.) O deg C, 20 min, 2.) 100 deg C, 1 h;	89%
With hydrogen fluoride; sodium nitrite

4-Fluorobenzoic acid Specification

The 4-Fluorobenzoic acid, with the CAS registry number 456-22-4, is a kind of white to light yellow crystal powder. This chemical is insoluble in water while soluble in alcohol, ether and other organic solvent, with its product categories including Fluorin-contained Benzoic acid series; Benzene derivatives; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Carboxylic Acids; Phenyls & Phenyl-Het; Fluorobenzene; API intermediates; Carboxylic Acids; Phenyls & Phenyl-Het; C7; Carbonyl Compounds.

The physical properties of this chemical are as below: (1)ACD/LogP: 2.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.7; (4)ACD/LogD (pH 7.4): -0.83; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 13.6; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.3; (13)Index of Refraction: 1.537; (14)Molar Refractivity: 33.17 cm³; (15)Molar Volume: 106.1 cm³; (16)Polarizability: 13.15 ×10^-24 cm³; (17)Surface Tension: 46 dyne/cm; (18)Density: 1.319 g/cm³; (19)Flash Point: 107.2 °C; (20)Enthalpy of Vaporization: 51.89 kJ/mol; (21)Boiling Point: 253.7 °C at 760 mmHg; (22)Vapour Pressure: 0.00936 mmHg at 25°C; (23)Exact Mass: 140.027358; (24)MonoIsotopic Mass: 140.027358; (25)Topological Polar Surface Area: 37.3; (26)Heavy Atom Count: 10; (27)Complexity: 128.

Use of this chemical: 4-Fluorobenzoic acid could react to produce 4-fluoro-benzoyl chloride. This reaction could happen in the presence of the reagent of SOCl₂.

Production method of this chemical: 4-fluoro-benzaldehyde could react to produce 4-Fluorobenzoic acid. This reaction could happen in the presence of the reagent of aqueous KOH.

As to its usage, it is widely applied in many ways. It could be used as the intermediate of fungicide flumorph, and also as the organic synthesis intermediate; In addition, it could also be used as the standard reagent of testing the fluorin.

When you deal with this chemical, you should be careful. For one thing, it is irritant to eyes, respiratory system and skin, which may also cause inflammation to the skin or other mucous membranes. For another thing, it is harmful which may cause damage to health and may have risk of serious damage to eyes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection, and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Then avoid contacting with skin and eyes and remember not to breathe dust.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1=CC(=CC=C1C(=O)O)F
(2)InChI: InChI=1S/C7H5FO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)
(3)InChIKey: BBYDXOIZLAWGSL-UHFFFAOYSA-N

Product Name

4-Fluorobenzoic acid

Synthetic route

4-Fluorobenzoic acid Specification

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