2315-86-8

Basic information

• Product Name: 3-BROMO-4-HYDROXYBENZONITRILE
• Synonyms: 2-BROMO-4-CYANOPHENOL;3-BROMO-4-HYDROXYBENZONITRILE;LABOTEST-BB LT01143437;TIMTEC-BB SBB005818;3-Bromo-4-hydroxybenzonitrile, 98+%;3-Bromo-4-hydroxybenzonitrile,99%;Benzonitrile, 3-broMo-4-hydroxy-;3-broMo-4-hydroxybenzonirile
• CAS NO: 2315-86-8
• Molecular Formula: C7H4BrNO
• Molecular Weight: 198.02
• EINECS: 219-022-9
• Product Categories: Aromatic Nitriles;Nitrile;Bromine Compounds;Nitriles;Phenols;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 2315-86-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 155-159 °C(lit.)
• Boiling Point: 271.1 °C at 760 mmHg
• Flash Point: 117.8 °C
• Appearance: brown crystals or needles
• Density: 1.79 g/cm³
• Vapor Pressure: 0.00396mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• PKA: 6.30±0.18(Predicted)
• BRN: 2207020
• CAS DataBase Reference: 3-BROMO-4-HYDROXYBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-HYDROXYBENZONITRILE(2315-86-8)
• EPA Substance Registry System: 3-BROMO-4-HYDROXYBENZONITRILE(2315-86-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2315-86-8(Hazardous Substances Data)

Usage

Chemical Properties

brown crystals or needles

Uses

3-Bromo-4-hydroxybenzonitrile is a reactant that has been used in the preparation of tetrazoles.

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

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

Downstream Products

• 50381-88-9 3,3'-dibromo-4,4'-pentanediyldioxy-di-benzonitrile 
• 219671-91-7 3-Bromo-4-(2-methoxyethoxymethoxy)-benzonitrile 
• 779331-40-7 2-(2-bromo-4-cyanophenoxy)-(2S)-propanoic acid 
• 252357-04-3 3-bromo-4-(ethoxymethoxy)benzonitrile 
• 488713-69-5 2-[3'-aminosulfonyl-5-(5-carbamimidoyl-1H-benzoimidazol-2-yl)-6-hydroxy-biphenyl-3-yl]-succinic acid 
• 909035-05-8 4-[(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methoxy]-3-bromobenzonitrile 
• 1123659-39-1 4-(tetrahydropyran-2-yloxy)-3-bromobenzonitrile 
• 208665-95-6 3-bromo-4-isobutoxybenzonitrile 
• 117572-79-9 3-bromo-4-methoxybenzonitrile 
• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 851437-35-9 4-(allyloxy)-3-bromobenzonitrile 
• 3849-66-9 3-Brom-5-jod-4-acetoxybenzonitril 
• 767-00-0 4-cyanophenol 
• 17345-61-8 3,4-dihydroxybenzonitrile 

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