2315-86-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-4-hydroxybenzonitrile is used as a reactant for the synthesis of various tetrazoles, which are important in the development of pharmaceutical compounds. Tetrazoles have a wide range of applications in the medical field, including their use as anti-inflammatory, antifungal, and antimicrobial agents.
Used in Chemical Synthesis:
3-Bromo-4-hydroxybenzonitrile serves as a key intermediate in the synthesis of various organic compounds, particularly those with potential applications in the chemical, pharmaceutical, and materials science industries. Its unique structure allows for further functionalization and modification, making it a versatile building block for the creation of new molecules with specific properties and functions.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 3-Bromo-4-hydroxybenzonitrile is also utilized in research and development settings. It can be employed in the study of chemical reactions, mechanisms, and the development of new synthetic methods, contributing to the advancement of scientific knowledge and the discovery of novel compounds with potential applications in various fields.

InChI:InChI=1/C7H4BrNO/c8-6-3-5(4-9)1-2-7(6)10/h1-3,10H

Synthetic route

3-bromo-4-hydroxybenzylaldehyde (2973-78-6) → 3-bromo-4-hydroxybenzonitrile (2315-86-8)

Conditions	Yield
With HCl·DMPU; hydroxylamine hydrochloride In acetonitrile at 60℃;	95%
With formic acid; hydroxylamine hydrochloride; sodium formate at 105 - 110℃; for 5h;	70%
Stage #1: 3-bromo-4-hydroxybenzylaldehyde With formic acid In water for 0.25h; Stage #2: With hydroxylamine hydrochloride; sodium formate at 105 - 110℃; for 5h;	70%
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride / dimethyl sulfoxide / 90 °C 2: hydroxylamine hydrochloride; dimethyl sulfoxide / 90 °C View Scheme
With hydroxylamine hydrochloride In dimethyl sulfoxide at 90℃; for 2h;

4-cyanophenol (767-00-0) → 3-bromo-4-hydroxybenzonitrile (2315-86-8)

Conditions	Yield
With N-Bromosuccinimide; trifluorormethanesulfonic acid In acetonitrile	94%
With 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide at 20℃; for 0.5h;	93%
With N-Bromosuccinimide; trifluorormethanesulfonic acid at -15 - 10℃;	93%

C8H8BrNO2 (1428637-13-1) → 3-bromo-4-hydroxybenzonitrile (2315-86-8)

Conditions	Yield
With [Ru(η6-p-cymene)Cl2]2; diphenyl acetylene In isopropyl alcohol at 100℃; for 16h; Inert atmosphere; regioselective reaction;	93%

3-bromo-4-hydroxybenzaldehyde oxime (938300-85-7) → 3-bromo-4-hydroxybenzonitrile (2315-86-8)

Conditions	Yield
With oxalyl dichloride; Triphenylphosphine oxide In chloroform at 20℃; for 1h;	85%
With hydroxylamine hydrochloride; dimethyl sulfoxide at 90℃;

2-bromo-4-cyanophenyl acetate (78338-69-9) → 3-bromo-4-hydroxybenzonitrile (2315-86-8)

Conditions	Yield
With sodium hydroxide

4-cyanophenol (767-00-0) → 3-bromo-4-hydroxybenzonitrile (2315-86-8) + Bromoxynil (1689-84-5)

Conditions	Yield
With tetrafluoroboric acid diethyl ether; N-Bromosuccinimide In acetonitrile for 24h; Product distribution; Ambient temperature; other acids; bromination of phenols and anisoles with NBS in the presence or absence of strong acids;
With tetrafluoroboric acid diethyl ether; N-Bromosuccinimide In acetonitrile for 24h; Ambient temperature; Yield given. Yields of byproduct given;
With chloroform; bromine
With N-Bromosuccinimide In acetonitrile for 5.5h; Ambient temperature;

Bromoxynil (1689-84-5) → 3-bromo-4-hydroxybenzonitrile (2315-86-8) + 4-cyanophenol (767-00-0)

Conditions	Yield
With paraffinic wax films; 10percentw Synperonic Reagent/catalyst; Irradiation;

Bromoxynil (1689-84-5) → 3,4-dihydroxybenzonitrile (17345-61-8) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) + 4-cyanophenol (767-00-0)

Conditions	Yield
With water Irradiation;

3-bromo-4-hydroxybenzonitrile (2315-86-8) + 2-(tert-butyldimethylsilyloxy)ethyl bromide (86864-60-0) → 2-(2-bromo-4-cyanophenoxy)-1-(tert-butyldimethylsiloxy)-ethane (325147-51-1)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃;	100%
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 16h;	94%
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 16h;

bromoacetic acid tert-butyl ester (5292-43-3) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → tert-butyl (2-bromo-4-cyanophenoxy)acetate (1240286-84-3)

Conditions	Yield
Stage #1: 3-bromo-4-hydroxybenzonitrile With potassium carbonate In acetone for 0.166667h; Stage #2: bromoacetic acid tert-butyl ester In acetone at 65℃; for 18h; Product distribution / selectivity;	100%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 12h;
Stage #1: 3-bromo-4-hydroxybenzonitrile With potassium carbonate In acetone for 0.166667h; Stage #2: bromoacetic acid tert-butyl ester In acetone at 65℃; for 18h;

3-bromo-4-hydroxybenzonitrile (2315-86-8) + cesium trifluoromethanethiolate → 2,2-difluoro-5-cyano-1,3-benzoxathiolane-7-carbaldehyde

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; cesium fluoride In 1,4-dioxane at 100℃; for 4h; Inert atmosphere; Glovebox; Sealed tube;	99%

3-bromo-4-hydroxybenzonitrile (2315-86-8) + 4-bromomethyltrifluoromethylbenzene (402-49-3) → 3-bromo-4-((4-(trifluoromethyl)benzyl)oxy)benzonitrile

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis; Inert atmosphere;	98%

3-bromo-4-hydroxybenzonitrile (2315-86-8) + allyl bromide (106-95-6) → 4-(allyloxy)-3-bromobenzonitrile (851437-35-9)

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 7h;	97%
With potassium carbonate In dichloromethane at 20℃; for 24h;	96%
With potassium carbonate; potassium iodide In acetone for 2h; Reflux;	87%
With potassium carbonate In acetone Reflux;

3-bromo-4-hydroxybenzonitrile (2315-86-8) → 2-bromo-4-(1H-tetrazole-5-yl)phenol (1007128-18-8)

Conditions	Yield
With sodium azide; ammonium cerium (IV) nitrate In N,N-dimethyl-formamide at 110℃; for 6h; Inert atmosphere; Green chemistry;	96%
With sodium azide; gold In N,N-dimethyl-formamide at 80℃; for 1.3h; Reagent/catalyst; Inert atmosphere;	94%
With sodium azide In N,N-dimethyl-formamide at 100℃; for 4h; Reagent/catalyst; Temperature;	89%

Isobutyl bromide (78-77-3) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-isobutoxybenzonitrile (208665-95-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;	96%
Stage #1: 3-bromo-4-hydroxybenzonitrile With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: Isobutyl bromide In N,N-dimethyl-formamide at 100℃; for 5h; Inert atmosphere;	91%
With potassium carbonate; potassium iodide at 80℃; Inert atmosphere;	82%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70 - 75℃; for 12h;

3-bromo-4-hydroxybenzonitrile (2315-86-8) + 3-(bromomethyl)benzonitrile (28188-41-2) → 3-cyanobenzyl 2-bromo-4-cyanophenyl ether (1456777-71-1)

Conditions	Yield
Stage #1: 3-bromo-4-hydroxybenzonitrile With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: m-(bromomethyl)benzonitrile In N,N-dimethyl-formamide	96%

3-bromo-4-hydroxybenzonitrile (2315-86-8) + phenylacetylene (536-74-3) → 2-phenylbenzofuran-5-carbonitrile (79008-77-8)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 24h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;	96%

1-bromo-octane (111-83-1) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-(octyloxy)benzonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	96%

3-(2-hydroxyethyl)thiophene (13781-67-4) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-(2-thiophen-3-ylethoxy)benzonitrile (1189815-96-0)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;	95%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;

3-bromo-4-hydroxybenzonitrile (2315-86-8) + benzyl bromide (100-39-0) → 4-(benzyloxy)-3-bromobenzonitrile (317358-76-2)

Conditions	Yield
With potassium carbonate In acetone for 20h; Inert atmosphere; Reflux;	95%
With potassium carbonate In acetone at 50℃;
With potassium carbonate In N,N-dimethyl-formamide at 10 - 50℃;	28.8 g

3-bromo-3,3-difluropropene (420-90-6) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-(1,1-difluoroallyloxy)benzonitrile

Conditions	Yield
With palladium diacetate; sodium hydride; triphenylphosphine In tetrahydrofuran at 0 - 40℃; for 0.5h; Tsuji-Trost Allylation; Inert atmosphere; regioselective reaction;	95%

2-Methoxyethoxymethyl chloride (3970-21-6) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-Bromo-4-(2-methoxyethoxymethoxy)-benzonitrile (219671-91-7)

Conditions	Yield
With sodium hydride In pyridine Alkylation;	92%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5 - 2h; Product distribution / selectivity;

2-fluoroethyl bromide (762-49-2) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-(2-fluoroethoxy)benzonitrile (1037078-83-3)

Conditions	Yield
With potassium carbonate; potassium iodide In dimethyl sulfoxide at 85℃; for 1h;	92%

3-bromo-4-hydroxybenzonitrile (2315-86-8) + tert-butyl 4-(chloromethyl)-3,6-dihydropyridine-1(2H)-carboxylate (159635-23-1) → 4-(2-bromo-4-cyano-phenoxymethyl)-3,6-dihydro-(2H)-pyridine-1-carboxylic acid tert-butyl ester (1025687-92-6)

Conditions	Yield
With potassium carbonate In acetone for 60h; Reflux; Inert atmosphere;	92%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone Heating;	67%

3-bromo-4-hydroxybenzonitrile (2315-86-8) + 4-cyanobenzyl bromide (17201-43-3) → 4-cyanobenzyl 2-bromo-4-cyanophenyl ether (1456777-69-7)

Conditions	Yield
Stage #1: 3-bromo-4-hydroxybenzonitrile With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: 4-cyanobenzyl bromide In N,N-dimethyl-formamide	92%

3-bromo-4-hydroxybenzonitrile (2315-86-8) + 1-chloro-3-hydroxypropane (627-30-5) → 3-bromo-4-(3-hydroxypropoxy)benzonitrile

Conditions	Yield
With sodium carbonate; sodium iodide In butanone for 34h; Reflux; Darkness;	91.5%

3-bromo-4-hydroxybenzonitrile (2315-86-8) + propargyl bromide (106-96-7) → 3-bromo-4-(prop-2-yn-1-yloxy)benzonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃;	91%

3-bromo-4-hydroxybenzonitrile (2315-86-8) → Bromoxynil (1689-84-5)

Conditions	Yield
With iron(III) chloride; N-Bromosuccinimide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 40℃; for 2.5h; regioselective reaction;	91%

3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-hydroxy-benzoic acid (14348-41-5)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.25h; Green chemistry;	90%

CYANAMID (420-04-2) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → 2-amino-4-oxo-4H-benzo[e][1,3]oxazine-6-carbonitrile

Conditions	Yield
Stage #1: molybdenum hexacarbonyl With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 65℃; for 20h; Inert atmosphere; Stage #2: CYANAMID; 3-bromo-4-hydroxybenzonitrile With palladium diacetate; triethylamine; bis[2-(diphenylphosphino)phenyl] ether In 1,4-dioxane at 65℃; for 20h; Inert atmosphere;	90%

3-bromo-4-hydroxybenzonitrile (2315-86-8) + methyl iodide (74-88-4) → 3-bromo-4-methoxybenzonitrile (117572-79-9)

Conditions	Yield
With potassium carbonate In acetonitrile at 25℃; for 6h;	89%
In DMF (N,N-dimethyl-formamide) at 20℃; for 3 - 12h;

3-bromo-4-hydroxybenzonitrile (2315-86-8) + bromoacetic acid methyl ester (96-32-2) → C10H8BrNO3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	88%

Bromocyclobutane (4399-47-7) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-cyclobutoxybenzonitrile (1065640-60-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 72h;	86%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 72h;

3-bromo-4-hydroxybenzonitrile (2315-86-8) + benzyl chloride (100-44-7) → 4-(benzyloxy)-3-bromobenzonitrile (317358-76-2)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 48℃; for 16h;	86%

Upstream product

• 78338-69-9 2-bromo-4-cyanophenyl acetate 
• 767-00-0 4-cyanophenol 
• 938300-85-7 3-bromo-4-hydroxybenzaldehyde oxime 
• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 1428637-13-1 C₈H₈BrNO₂ 
• 1689-84-5 Bromoxynil 

Downstream Products

• 101579-22-0 3,3'-dibromo-4,4'-but-2-ynediyldioxy-di-benzonitrile 
• 50381-88-9 3,3'-dibromo-4,4'-pentanediyldioxy-di-benzonitrile 
• 219671-91-7 3-Bromo-4-(2-methoxyethoxymethoxy)-benzonitrile 
• 867281-15-0 3-bromo-4-(fluoromethoxy)benzonitrile 
• 325147-51-1 2-(2-bromo-4-cyanophenoxy)-1-(tert-butyldimethylsiloxy)-ethane 
• 935742-51-1 3-bromo-4-(3-methyl-but-3-enyloxy)-benzonitrile 
• 1072073-77-8 3-allyl-5-bromo-4-hydroxybenzonitrile 
• 779331-40-7 2-(2-bromo-4-cyanophenoxy)-(2S)-propanoic acid 
• 851437-35-9 4-(allyloxy)-3-bromobenzonitrile 
• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 909035-05-8 4-[(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methoxy]-3-bromobenzonitrile 
• 1025687-92-6 4-(2-bromo-4-cyano-phenoxymethyl)-3,6-dihydro-(2H)-pyridine-1-carboxylic acid tert-butyl ester 
• 317358-76-2 4-(benzyloxy)-3-bromobenzonitrile 
• 1007128-18-8 2-bromo-4-(1H-tetrazole-5-yl)phenol 

Relevant academic research and scientific papers

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