Product Name

  • Name

    2-Fluoro-4-hydroxybenzoic acid

  • EINECS 613-746-2
  • CAS No. 65145-13-3
  • Article Data10
  • CAS DataBase
  • Density 1.492 g/cm3
  • Solubility
  • Melting Point 199-202 °C
  • Formula C7H5FO3
  • Boiling Point 334.6 °C at 760 mmHg
  • Molecular Weight 156.113
  • Flash Point 156.2 °C
  • Transport Information
  • Appearance
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 65145-13-3 (2-Fluoro-4-hydroxybenzoic acid)
  • Hazard Symbols IrritantXi
  • Synonyms 2-Fluoro-4-hydroxybenzoicacid;4-Hydroxy-2-fluorobenzoic acid;
  • PSA 57.53000
  • LogP 1.22950

Synthetic route

2-fluoro-4-hydroxybenzonitrile
82380-18-5

2-fluoro-4-hydroxybenzonitrile

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: 2-fluoro-4-hydroxybenzonitrile With sodium hydroxide In water for 4h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 20℃;		100%
With sodium hydroxide In water for 60h; Yield given;
With potassium hydroxide In ethanol; water
2-fluoro-4-propoxybenzoic acid

2-fluoro-4-propoxybenzoic acid

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78 - 20℃;89%
3-chloro-2-fluoro-4-hydroxybenzoic acid
860296-15-7

3-chloro-2-fluoro-4-hydroxybenzoic acid

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol at 25℃; for 20h;89%
3-(fluorophenyloxy)triisopropylsilane
860296-18-0

3-(fluorophenyloxy)triisopropylsilane

carbon dioxide
124-38-9

carbon dioxide

A

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

B

6-fluorosalicylic acid
67531-86-6

6-fluorosalicylic acid

Conditions
ConditionsYield
Stage #1: 3-(fluorophenyloxy)triisopropylsilane With N,N,N',N'',N'''-pentamethyldiethylenetriamine; sec.-butyllithium In tetrahydrofuran at -75℃; for 2h;
Stage #2: carbon dioxide In tetrahydrofuran		A 51%
B 5%
...Expand
2,4-difluoro-benzoic acid
1583-58-0

2,4-difluoro-benzoic acid

A

4-fluorosalicylic acid
345-29-9

4-fluorosalicylic acid

B

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide for 7h; Heating; Title compound not separated from byproducts;
2-fluoro-4-hydroxy-3-trimethylsilanyl-benzoic acid

2-fluoro-4-hydroxy-3-trimethylsilanyl-benzoic acid

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 25℃; for 6h;3.24 g
carbon dioxide
124-38-9

carbon dioxide

3-(methoxymethoxy)-2-(trimethylsilyl)fluorobenzene
146746-69-2

3-(methoxymethoxy)-2-(trimethylsilyl)fluorobenzene

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: 3-(methoxymethoxy)-2-(trimethylsilyl)fluorobenzene With n-butyllithium; potassium tert-butylate In tetrahydrofuran; hexane at -75℃; for 2h;
Stage #2: carbon dioxide In tetrahydrofuran; hexane
Stage #3: With hydrogenchloride In water at 25℃; for 6h;
2-chloro-1-fluoro-3-(methoxymethoxy)benzene
860296-13-5

2-chloro-1-fluoro-3-(methoxymethoxy)benzene

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 2 h / -75 °C
1.2: tetrahydrofuran; hexane
1.3: 73 percent / HCl / H2O / pH 1
2.1: 89 percent / ammonium formate / Pd/C / methanol / 20 h / 25 °C
View Scheme
3-fluorophenol
372-20-3

3-fluorophenol

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 83 percent / imidazole / dimethylformamide / 20 h / 25 °C
2.1: sec-BuLi; PMDTA / tetrahydrofuran / 2 h / -75 °C
2.2: 51 percent / tetrahydrofuran
View Scheme
Multi-step reaction with 3 steps
1: 61 percent / bromine / CHCl3 / 0.01 h
2: 1-methyl-2-pyrrolidinone / 2 h / 180 °C
3: sodium hydroxide / H2O / 60 h
View Scheme
1-fluoro-3-(methoxy-methoxy)benzene
126940-10-1

1-fluoro-3-(methoxy-methoxy)benzene

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sec-BuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C
1.2: 86 percent / tetrahydrofuran; cyclohexane / 0.75 h / -75 °C
2.1: BuLi; KOtBu / tetrahydrofuran; hexane / 2 h / -75 °C
2.2: tetrahydrofuran; hexane
3.1: 3.24 g / HCl / H2O / 6 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sec-BuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C
1.2: 86 percent / tetrahydrofuran; cyclohexane / 0.75 h / -75 °C
2.1: K-OtBu; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C
2.2: tetrahydrofuran; hexane
2.3: HCl / H2O / 6 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sec-BuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C
1.2: 83 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; cyclohexane / 0.75 h / -75 °C
2.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 2 h / -75 °C
2.2: tetrahydrofuran; hexane
2.3: 73 percent / HCl / H2O / pH 1
3.1: 89 percent / ammonium formate / Pd/C / methanol / 20 h / 25 °C
View Scheme
3-(methoxymethoxy)-2-(trimethylsilyl)fluorobenzene
146746-69-2

3-(methoxymethoxy)-2-(trimethylsilyl)fluorobenzene

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: BuLi; KOtBu / tetrahydrofuran; hexane / 2 h / -75 °C
1.2: tetrahydrofuran; hexane
2.1: 3.24 g / HCl / H2O / 6 h / 25 °C
View Scheme
4-bromo-3-fluorophenol
121219-03-2

4-bromo-3-fluorophenol

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-2-pyrrolidinone / 2 h / 180 °C
2: sodium hydroxide / H2O / 60 h
View Scheme
2-fluoro-2-hydroxybenzonitrile

2-fluoro-2-hydroxybenzonitrile

2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

2-Fluoro-4-hydroxybenzoic acid Specification

The Benzoicacid, 2-fluoro-4-hydroxy-, with the CAS registry number 65145-13-3, is also known as 2-Fluoro-4-hydroxybenzoicacid. It belongs to the product categories of Fine Chemical & Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzoic acid; Acids & Esters; Fluorine Compounds; Phenols. This chemical's molecular formula is C7H5FO3 and molecular weight is 156.11. Its systematic name is called 2-fluoro-4-hydroxybenzoic acid. The product should be sealed and stored in cool and dry place. What's more, it should be protected from strong oxides.

Physical properties of Benzoicacid, 2-fluoro-4-hydroxy-: (1)ACD/LogP: 1.78; (2)ACD/LogD (pH 5.5): -0.19; (3)ACD/LogD (pH 7.4): -1.37; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 2.4; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.585; (12)Molar Refractivity: 35.05 cm3; (13)Molar Volume: 104.6 cm3; (14)Surface Tension: 60.3 dyne/cm; (15)Density: 1.492 g/cm3; (16)Flash Point: 156.2 °C; (17)Enthalpy of Vaporization: 60.96 kJ/mol; (18)Boiling Point: 334.6 °C at 760 mmHg; (19)Vapour Pressure: 4.99E-05 mmHg at 25°C.

Preparation of Benzoicacid, 2-fluoro-4-hydroxy-: this chemical can be prepared by 2-fluoro-4-propoxybenzoic acid. This reaction will need reagent BBr3 and solvent CH2Cl2. The reaction temperature is -78 - 20 °C. The yield is about 89%.

Benzoicacid, 2-fluoro-4-hydroxy- can be prepared by 2-fluoro-4-propoxybenzoic acid

Uses of Benzoicacid, 2-fluoro-4-hydroxy-: it can be used to produce 4-butoxy-2-fluorobenzoic acid with 1-bromo-butane by heating. This reaction will need reagents ethanol, potassium hidroxide and solvent H2O with reaction time of 25 hours. The yield is about 64%.

Benzoicacid, 2-fluoro-4-hydroxy- can be used to produce 4-butoxy-2-fluorobenzoic acid with 1-bromo-butane by heating

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: Fc1c(C(=O)O)ccc(O)c1
(2)InChI: InChI=1/C7H5FO3/c8-6-3-4(9)1-2-5(6)7(10)11/h1-3,9H,(H,10,11)
(3)InChIKey: NXWTWYULZRDBSA-UHFFFAOYAX

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