2105-94-4

Basic information

• Product Name: 4-Bromo-2-fluorophenol
• Synonyms: 4-BROMO-2-FLUOROPHENOL;2-Fluoro-4-Bromophenol;4-Bromo-2-fluorophenol 98%;4-Bromo-2-fluorophenol98%;4-Bromo-2-fluorophenol, 97+%;4-Bromo-2-fluorophen;4-BroMo-2-fluorophenol, 98% 5GR;2-Fluoro-4-BroMophonel
• CAS NO: 2105-94-4
• Molecular Formula: C₆H₄BrFO
• Molecular Weight: 191
• EINECS: 218-284-1
• Product Categories: Fluorobenzene Series;Aromatic Phenols;Fluorobenzene;Phenol&Thiophenol&Mercaptan;Bromine Compounds;Fluorine Compounds;Phenols;Building Blocks for Liquid Crystals;Functional Materials;Phenols (Building Blocks for Liquid Crystals);Organic Building Blocks;Oxygen Compounds;alcohol| alkyl bromide|alkyl Fluorine
• Mol File: 2105-94-4.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 79 °C7 mm Hg(lit.)
• Flash Point: 210 °F
• Appearance: Clear colorless to brown/Liquid
• Density: 1.744 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.156mmHg at 25°C
• Refractive Index: n20/D 1.566(lit.)
• Storage Temp.: Room temperature.
• PKA: 8.14±0.18(Predicted)
• BRN: 1861281
• CAS DataBase Reference: 4-Bromo-2-fluorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-fluorophenol(2105-94-4)
• EPA Substance Registry System: 4-Bromo-2-fluorophenol(2105-94-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2105-94-4(Hazardous Substances Data)

Usage

Description

4-Bromo-2-fluorophenol is an organic compound characterized by the presence of a bromine atom at the 4th position and a fluorine atom at the 2nd position on a phenol molecule. It is a clear, colorless to brownish liquid with versatile chemical properties that make it a valuable starting material for the synthesis of various compounds.

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-fluorophenol is used as a starting material for the synthesis of various pharmaceutical compounds, such as 4-Bromo-2-fluoro-6-iodoanisole, which can be further modified through iodination and methylation processes. 4-Bromo-2-fluorophenol serves as a key intermediate in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 4-Bromo-2-fluorophenol is utilized as a starting material for the synthesis of 2-Phenylpyran-4-ones. These compounds are evaluated for their potential as active cyclooxygenase-2 (COX-2) inhibitors, which are important targets for the development of anti-inflammatory and pain-relieving medications.
Used in Organic Synthesis:
4-Bromo-2-fluorophenol is also used as a starting material for the synthesis of 1,4-disubstituted 3-cyano-2-pyridones. These compounds have a wide range of applications in organic chemistry, including the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Material Science:
In the material science field, 4-Bromo-2-fluorophenol is used as a starting material for the synthesis of dicationic imidazolium-based compounds. These ionic liquids have potential applications in various industries, such as energy storage, catalysis, and green chemistry, due to their unique properties like high thermal stability and low vapor pressure.
Overall, 4-Bromo-2-fluorophenol is a versatile compound with a wide range of applications across different industries, including pharmaceuticals, chemical research, organic synthesis, and material science. Its unique chemical properties and reactivity make it a valuable starting material for the development of new compounds and technologies.

InChI:InChI=1/C6H5ClFN/c7-4-1-2-5(8)6(9)3-4/h1-3H,9H2

Synthetic route

2-fluorophenol (367-12-4) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
With bromine In dichloromethane; water	90%
With bromine In dichloromethane; water	90%
With bromine In dichloromethane; water	90%

2-(2-fluoro-4-bromophenoxy)pyridine → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
Stage #1: 2-(2-fluoro-4-bromophenoxy)pyridine With methyl trifluoromethanesulfonate In toluene at 100℃; for 2h; Inert atmosphere; Stage #2: With sodium ethanolate for 1h; Reflux; Inert atmosphere;	82%
Stage #1: 2-(2-fluoro-4-bromophenoxy)pyridine With methyl trifluoromethanesulfonate In toluene at 100℃; Stage #2: With methanol; sodium at 90℃;	76%

4-bromo-phenol (106-41-2) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
With acetic acid; Selectfluor; eosin y In water at 20℃; for 6h; Irradiation; Green chemistry;	68%

2-fluorophenol (367-12-4) → 4-bromo-2-fluorophenol (2105-94-4) + 2,4-dibromo-6-fluorophenol (576-86-3) + 2-bromo-6-fluorophenol (2040-89-3)

Conditions	Yield
With 4-morpholineethanesulfonic acid; VBrPO(AnI) bromoperoxidase; dihydrogen peroxide; sodium bromide In water; tert-butyl alcohol at 23℃; pH=6.2; Overall yield = 37 %;	A n/a B 18% C n/a

3-fluoro-4-methoxyphenyl bromide (2357-52-0) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
With hydrogen bromide at 190℃;

4-amino-2-fluorophenol (399-96-2) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
2., HBr, CuBr; Yield given. Multistep reaction;

3-fluorobromobenzene (1073-06-9) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
With microsomal protein; NADPH In phosphate buffer at 37℃; for 0.166667h; pH=7.6; Enzyme kinetics; Oxidation;

4-bromo-phenol (106-41-2) → 4-bromo-2-fluorophenol (2105-94-4) + 4-bromo-2,6-difluorophenol (104197-13-9)

Conditions	Yield
With formic acid; fluorine at 10℃; for 1.75h; Fluorination; Title compound not separated from byproducts;	A 22 % Spectr. B 4 % Spectr.

2-fluoro-4-nitrophenol (403-19-0) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98.5 percent / hydrogen / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr 2: 2., HBr, CuBr View Scheme

3-fluoro-4-methoxyaniline (366-99-4) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; aqueous sodium nitrite solution / Behandeln des Reaktionsgemisches mit Kupfer(I)-bromid und wss. Bromwasserstoffsaeure 2: aqueous hydrobromic acid / 190 °C View Scheme

sodium metabisulfite + 2-fluorophenol (367-12-4) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
With bromine In carbon disulfide
With bromine In carbon disulfide

2-fluorophenol (367-12-4) + sodium thiosulfate → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
With bromine In carbon disulfide

1-bromo-3,4-difluorobenzene (348-61-8) → 4-bromo-2-fluorophenol (2105-94-4) + 5-Bromo-2-fluorophenol (112204-58-7)

Conditions	Yield
Stage #1: 1-bromo-3,4-difluorobenzene With potassium trimethylsilonate In diethylene glycol dimethyl ether at 120℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In diethylene glycol dimethyl ether; water at 20℃; Inert atmosphere;

2-fluorophenol (367-12-4) → 4-bromo-2-fluorophenol (2105-94-4) + 2,4-dibromo-6-fluorophenol (576-86-3)

Conditions	Yield
With vanadate(V)-dependent bromoperoxidase I from Ascophyllum nodosum; dihydrogen peroxide; sodium bromide In water; tert-butyl alcohol at 23℃; for 72h; pH=6.2; Enzymatic reaction; Overall yield = 106 mg;
Stage #1: 2-fluorophenol In acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-Bromosuccinimide In acetonitrile at 20℃; for 24h;

2-hydroxybromobenzene (95-56-7) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: copper(l) iodide; 2-Picolinic acid; potassium phosphate / dimethyl sulfoxide / 24 h / 80 °C / Inert atmosphere 2.1: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide / ethyl acetate / 5 h / 80 °C 3.1: methyl trifluoromethanesulfonate / toluene / 2 h / 100 °C / Inert atmosphere 3.2: 1 h / Reflux; Inert atmosphere View Scheme

2-(4-bromophenyloxy)pyridine (4783-82-8) → 4-bromo-2-fluorophenol (2105-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide / ethyl acetate / 5 h / 80 °C 2.1: methyl trifluoromethanesulfonate / toluene / 2 h / 100 °C / Inert atmosphere 2.2: 1 h / Reflux; Inert atmosphere View Scheme

4-bromo-2-fluorophenol (2105-94-4) + benzyl bromide (100-39-0) → 1-benzyloxy-4-bromo-2-fluorobenzene (133057-82-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	100%
With potassium carbonate In acetonitrile at 20℃; for 15h;	93%

4-bromo-2-fluorophenol (2105-94-4) + chloroformic acid ethyl ester (541-41-3) → 4-bromo-2-fluorophenyl ethyl carbonate (661463-10-1)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	100%
With triethylamine In dichloromethane at 0℃; for 1h;	100%
With triethylamine In dichloromethane at 0℃; for 1h;	93%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	93%

4-bromo-2-fluorophenol (2105-94-4) + 1,3-chlorobromopropane (109-70-6) → 4-bromo-1-(3-chloro-propoxy)-2-fluoro-benzene (181807-91-0)

Conditions	Yield
With potassium carbonate In acetonitrile for 3h; Product distribution / selectivity; Heating / reflux;	100%

4-bromo-2-fluorophenol (2105-94-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (4-bromo-2-fluorophenoxy)(tert-butyl)dimethylsilane (203926-74-3)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 25℃; for 18h;	85.4%
With 1H-imidazole In N,N-dimethyl-formamide

4-bromo-2-fluorophenol (2105-94-4) + tert-butyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate (161975-39-9) → tert-butyl 4-((4-bromo-2-fluorophenoxy)methyl)piperidine-1-carboxylate

Conditions	Yield
With caesium carbonate In acetonitrile for 12h; Reflux;	100%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;	86%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;	86%
With potassium carbonate In dimethyl sulfoxide at 110℃; for 16h;	83.1%
With potassium carbonate In dimethyl sulfoxide at 110℃; for 16h;	83.1%

ethyl bromide (74-96-4) + 4-bromo-2-fluorophenol (2105-94-4) → 3-fluoro-4-ethoxy bromobenzene (115467-08-8)

Conditions	Yield
With potassium carbonate In butanone for 24h; Heating / reflux;	99%
With tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 6h; Inert atmosphere;	90%
With potassium carbonate In acetone at 20℃;

4-bromo-2-fluorophenol (2105-94-4) + cyclopropylcarbinyl bromide (7051-34-5) → 4-Bromo-1-cyclopropylmethoxy-2-fluoro-benzene (622386-52-1)

Conditions	Yield
With caesium carbonate; tetra-(n-butyl)ammonium iodide In 1-methyl-pyrrolidin-2-one at 50 - 80℃; for 2.16667h;	99%

4-bromo-2-fluorophenol (2105-94-4) + ethyl iodide (75-03-6) → 3-fluoro-4-ethoxy bromobenzene (115467-08-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	99%
With potassium carbonate In acetone for 6h; Inert atmosphere; Reflux;	98%

4-bromo-2-fluorophenol (2105-94-4) + isopropyl alcohol (67-63-0) → 4-bromo-2-fluoro-1-isopropoxybenzene (202865-80-3)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 45℃; for 1h; Reflux;	99%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 45℃; for 1h; Reflux;	99%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 45℃; for 1h; Reflux;	99%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 45℃; for 1h; Reflux;
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 45℃; for 1h; Reflux;

triisopropylsilyl chloride (13154-24-0) + 4-bromo-2-fluorophenol (2105-94-4) → 1-bromo-3-fluoro-4-triisopropylsilyloxybenzene

Conditions	Yield
With 1H-imidazole In dichloromethane at 25℃; for 3h;	99%
With 1H-imidazole In dichloromethane at 20℃; for 12h;	94%
With 1H-imidazole In dichloromethane at 20℃; for 1h;

1-Bromopentane (110-53-2) + 4-bromo-2-fluorophenol (2105-94-4) → 4-bromo-2-fluoro-1-(pentyloxy)benzene (127326-78-7)

Conditions	Yield
Stage #1: 4-bromo-2-fluorophenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Inert atmosphere; Stage #2: 1-Bromopentane In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	99%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 9h; Inert atmosphere;

4-bromo-2-fluorophenol (2105-94-4) + 2-Bromoethyl methyl ether (6482-24-2) → 4-bromo-2-fluoro-1-(2-methoxyethoxy)benzene (944279-01-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	99%

1-bromo-octane (111-83-1) + 4-bromo-2-fluorophenol (2105-94-4) → 1-Bromo-3-fluoro-4-octyloxybenzene (119259-26-6)

Conditions	Yield
With potassium carbonate	98%
With potassium carbonate In N,N-dimethyl-formamide; benzene for 4h; Reflux; Dean-Stark;	96%
With potassium carbonate; potassium iodide In acetone for 24h; Reflux; Inert atmosphere;	60.5%
With tetrabutylammomium bromide; potassium carbonate In butanone for 4h; Heating / reflux;

4-bromo-2-fluorophenol (2105-94-4) → 2-fluoro-4-bromo-6-nitro-phenol (320-76-3)

Conditions	Yield
With Nitrogen dioxide In pentane 35 min, 0 deg C then 20 min, room temperature;	98%

1-bromo-butane (109-65-9) + 4-bromo-2-fluorophenol (2105-94-4) → 4-bromo-1-butoxy-2-fluorobenzene (54509-63-6)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In water at 80℃; for 6h; Inert atmosphere;	98%
With caesium carbonate; tetra-(n-butyl)ammonium iodide In 1-methyl-pyrrolidin-2-one at 85℃; for 2h;	96%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	85%

methyl 2-bromomethyl-5-bromobenzoate (79670-17-0) + 4-bromo-2-fluorophenol (2105-94-4) → methyl 5-bromo-2-((4-bromo-2-fluorophenoxy)methyl)benzoate (1427423-10-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;	98%
With potassium carbonate In N,N-dimethyl-formamide at 50℃;	98%

zinc(II) cyanide (557-21-1) + 4-bromo-2-fluorophenol (2105-94-4) → 3-fluoro-4-hydroxybenzonitrile (405-04-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 120℃; for 2h;	98%

1-iodo-butane (542-69-8) + 4-bromo-2-fluorophenol (2105-94-4) → 4-bromo-1-butoxy-2-fluorobenzene (54509-63-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;	98%

4-bromo-2-fluorophenol (2105-94-4) + (S)-tert-butyl 3-{[(methylsulfonyl)oxy]methyl}pyrrolidine-1-carboxylate (274692-06-7) → tert-butyl (S)-3-((4-bromo-2-fluorophenoxy)methyl)pyrrolidine-1-carboxylate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; Solvent; Reagent/catalyst; Temperature;	98%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; Reagent/catalyst; Temperature;	98%

4-bromo-2-fluorophenol (2105-94-4) + tert-butyl-(5-iodo-pentyloxy)-diphenyl-silane (164025-54-1) → 2-fluoro-4-[5-(tert-butyldiphenylsilanyloxy)-pentylselanyl]-phenol (831223-27-9)

Conditions	Yield
Stage #1: 4-bromo-2-fluorophenol With tert.-butyl lithium In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: With selenium In tetrahydrofuran at 20℃; for 1h; Stage #3: tert-butyl-(5-iodo-pentyloxy)-diphenyl-silane In tetrahydrofuran at 0 - 20℃;	97%

4-bromo-2-fluorophenol (2105-94-4) + 2-bromoethanol (540-51-2) → 4-bromo-1-(2-bromoethoxy)-2-fluorobenzene (944278-92-6)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 2h;	97%

4-bromo-2-fluorophenol (2105-94-4) + chloromethyl methyl ether (107-30-2) → 4-bromo-2-fluoro-1-methoxymethoxybenzene

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 2h; Inert atmosphere;	97%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Cooling with ice;	97%
With potassium carbonate In acetone at 20℃; for 2h;	82%
With triethylamine In dichloromethane at 0 - 20℃; for 25h; Inert atmosphere;	57%

4-bromo-2-fluorophenol (2105-94-4) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → (2-((4-bromo-2-fluorophenoxy)methoxy)ethyl)trimethylsilane

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	97%

4-bromo-2-fluorophenol (2105-94-4) + (S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester (82010-31-9) → (S)-tert-butyl (1-(4-bromo-2-fluorophenoxy)-4-methylpentan-2-yl)carbamate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h;	97%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h;	97%

4-bromo-2-fluorophenol (2105-94-4) + 4-i-propylbenzyl bromide (73789-86-3) → C16H16BrFO

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	97%

1-bromo-hexane (111-25-1) + 4-bromo-2-fluorophenol (2105-94-4) → 2-fluoro-4-bromo-1-(hexyloxy)benzene (54509-62-5)

Conditions	Yield
With potassium carbonate	96%

4-bromo-2-fluorophenol (2105-94-4) + C18H23ClN4O3 → C24H26BrFN4O4

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere;	95%

2-chloro-N-isopropylacetamide (2895-21-8) + 4-bromo-2-fluorophenol (2105-94-4) → 2-(4-bromo-2-fluoro-phenoxy)-N-isopropylacetamide

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 80℃; for 18h; Inert atmosphere;	95%

4-bromo-2-fluorophenol (2105-94-4) + (2R)-1-(3-chloropropyl)-2-methylpyrrolidine (862876-56-0) → (2R)-1-[3-(4-bromo-2-fluorophenoxy)propyl]-2-methylpyrrolidine (1152749-38-6)

Conditions	Yield
With caesium carbonate In acetonitrile at 100℃; for 4h;	94%

4-bromo-2-fluorophenol (2105-94-4) + (S)-tert-butyl 4-isobutyl-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide → (S)-tert-butyl (1-(4-bromo-2-fluorophenoxy)-2,4-dimethylpentan-2-yl)carbamate

Conditions	Yield
Stage #1: 4-bromo-2-fluorophenol With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.666667h; Stage #2: (S)-tert-butyl 4-isobutyl-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide In N,N-dimethyl-formamide at 80℃;	94%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h;	83%

Upstream product

• 2357-52-0 3-fluoro-4-methoxyphenyl bromide 
• 367-12-4 2-fluorophenol 
• 399-96-2 4-amino-2-fluorophenol 
• 1073-06-9 3-fluorobromobenzene 
• 106-41-2 4-bromo-phenol 
• 403-19-0 2-fluoro-4-nitrophenol 
• 366-99-4 3-fluoro-4-methoxyaniline 
• 348-61-8 1-bromo-3,4-difluorobenzene 
• 95-56-7 2-hydroxybromobenzene 
• 4783-82-8 2-(4-bromophenyloxy)pyridine 

Downstream Products

• 451-90-1 (4-bromo-2-fluoro-phenoxy)-acetic acid 
• 32862-01-4 C₁₃H₉BrFNO₄ 
• 32862-02-5 C₁₄H₁₁BrFNO₄ 
• 147992-27-6 4-bromo-1-(difluoromethoxy)-2-fluoro-benzene 
• 54509-62-5 4-bromo-2-fluoro-1-(hexyloxy)benzene 
• 119259-26-6 1-Bromo-3-fluoro-4-octyloxybenzene 
• 320-76-3 2-fluoro-4-bromo-6-nitro-phenol 
• 133057-82-6 1-benzyloxy-4-bromo-2-fluorobenzene 
• 396-86-1 3,3'-difluoro-4,4'-dihydroxybiphenyl 
• 122265-74-1 1-Bromo-3-fluoro-4-dodecyloxybenzene 
• 251300-28-4 5-bromo-3-fluoro-2-hydroxybenzaldehyde 
• 405-04-9 3-fluoro-4-hydroxybenzonitrile 
• 167683-93-4 2-fluoro-4-methoxy-phenol 
• 708276-52-2 2-(4-bromo-2-fluorophenoxy)-1-(4-methylsulfanylphenyl)ethanone 

Relevant articles and documents

Influence of the type of halogen substituent on in vivo and in vitro phase II metabolism of 2-fluoro-4-halophenol metabolites formed from 3-halo-fluorobenzenes

The influence of a change in the type of halogen substituent on phase II metabolism of 2-fluoro-4-halophenol metabolites formed from 3-halo-fluorobenzenes was studied in vivo and in vitro using 19F nmr and spectroscopic assays. The ratio of sulphation to glucuronidation of 2-fluoro-4-halophenol metabolites formed from 3-halofluorobenzenes decreased from 48 to 13 to 6 when the halogen substituent varied from fluorine to chlorine to bromine. When the 2-fluoro-4-halophenols themselves were administered to the rats, the ratio of sulphation to glucuronidation was not affected by the type of halogen substituent at C4 and at a constant value of 0.6, i.e. significantly lower. Kinetic data for P450 catalysed hydroxylation of the 3-halo-fluorobenzenes and for sulphation and glucuronidation of their 2-fluoro-4-halophenol metabolites were obtained from in vitro microsomal and cytosolic incubations. These data demonstrate that the effects of varying the halogen substituent on phase II metabolism of the 2-fluoro-4-halophenol metabolites can be mainly ascribed to an apparently decreased K(m) for the glucuronidation of the 2-fluoro-4-halophenols with a change in the halo substituent from fluorine to chlorine to bromine. Results from calculations on electronic and structural characteristics of the three 4-halo-2-fluorophenols demonstrate that the best explanation for the decrease in the apparent K(m) of the glucuronidation from 2,4-difluoro- to 4-chloro-2-fluoro- to 4-bromo-2-fluorophenol might be an increase in the hydrophobicity of the phenol. An increase in the hydrophobicity of the phenol would provide an increased possibility for substrate accumulation in the hydrophobic membrane environment of the UDP-glucuronyltransferases, resulting in an apparently decreased K(m).

A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide

A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.

Novel pleconaril derivatives: Influence of substituents in the isoxazole and phenyl rings on the antiviral activity against enteroviruses

Today, there are no medicines to treat enterovirus and rhinovirus infections. In the present study, a series of novel pleconaril derivatives with substitutions in the isoxazole and phenyl rings was synthesized and evaluated for their antiviral activity against a panel of pleconaril-sensitive and -resistant enteroviruses. Studies of the structure-activity relationship demonstrate the crucial role of the N,N-dimethylcarbamoyl group in the isoxazole ring for antiviral activity against pleconaril-resistant viruses. In addition, one or two substituents in the phenyl ring directly impact on the spectrum of antienteroviral activity. The 3-(3-methyl-4-(3-(3-N,N-dimethylcarbamoyl-isoxazol-5-yl)propoxy)phenyl)-5-trifluoromethyl-1,2,4-oxadiazole 10g was among the compounds exhibiting the strongest activity against pleconaril-resistant as well as pleconaril-susceptible enteroviruses with IC50 values from 0.02 to 5.25 μM in this series. Compound 10g demonstrated markedly less CYP3A4 induction than pleconaril, was non-mutagenic, and was bioavailable after intragastric administration in mice. These results highlight compound 10g as a promising potential candidate as a broad spectrum enterovirus and rhinovirus inhibitor for further preclinical investigations.