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; |
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
3-bromo-4-hydroxybenzonitrile
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
3-bromo-4-hydroxybenzonitrile
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
3-bromo-4-hydroxybenzonitrile
Conditions | Yield |
---|---|
With sodium hydroxide |
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; |
Conditions | Yield |
---|---|
With paraffinic wax films; 10percentw Synperonic Reagent/catalyst; Irradiation; |
Bromoxynil
A
3,4-dihydroxybenzonitrile
B
3-bromo-4-hydroxybenzonitrile
C
4-cyanophenol
Conditions | Yield |
---|---|
With water Irradiation; |
3-bromo-4-hydroxybenzonitrile
2-(tert-butyldimethylsilyloxy)ethyl bromide
2-(2-bromo-4-cyanophenoxy)-1-(tert-butyldimethylsiloxy)-ethane
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
3-bromo-4-hydroxybenzonitrile
tert-butyl (2-bromo-4-cyanophenoxy)acetate
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
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% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis; Inert atmosphere; | 98% |
3-bromo-4-hydroxybenzonitrile
allyl bromide
4-(allyloxy)-3-bromobenzonitrile
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
2-bromo-4-(1H-tetrazole-5-yl)phenol
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
3-bromo-4-hydroxybenzonitrile
3-bromo-4-isobutoxybenzonitrile
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
3-(bromomethyl)benzonitrile
3-cyanobenzyl 2-bromo-4-cyanophenyl ether
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
phenylacetylene
2-phenylbenzofuran-5-carbonitrile
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% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; | 96% |
3-(2-hydroxyethyl)thiophene
3-bromo-4-hydroxybenzonitrile
3-bromo-4-(2-thiophen-3-ylethoxy)benzonitrile
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; | 95% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; |
3-bromo-4-hydroxybenzonitrile
benzyl bromide
4-(benzyloxy)-3-bromobenzonitrile
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 |
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
3-bromo-4-hydroxybenzonitrile
3-Bromo-4-(2-methoxyethoxymethoxy)-benzonitrile
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
3-bromo-4-hydroxybenzonitrile
3-bromo-4-(2-fluoroethoxy)benzonitrile
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In dimethyl sulfoxide at 85℃; for 1h; | 92% |
3-bromo-4-hydroxybenzonitrile
tert-butyl 4-(chloromethyl)-3,6-dihydropyridine-1(2H)-carboxylate
4-(2-bromo-4-cyano-phenoxymethyl)-3,6-dihydro-(2H)-pyridine-1-carboxylic acid tert-butyl ester
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
4-cyanobenzyl bromide
4-cyanobenzyl 2-bromo-4-cyanophenyl ether
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% |
Conditions | Yield |
---|---|
With sodium carbonate; sodium iodide In butanone for 34h; Reflux; Darkness; | 91.5% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃; | 91% |
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
3-bromo-4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.25h; Green chemistry; | 90% |
CYANAMID
3-bromo-4-hydroxybenzonitrile
molybdenum hexacarbonyl
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
methyl iodide
3-bromo-4-methoxybenzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 25℃; for 6h; | 89% |
In DMF (N,N-dimethyl-formamide) at 20℃; for 3 - 12h; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 88% |
Bromocyclobutane
3-bromo-4-hydroxybenzonitrile
3-bromo-4-cyclobutoxybenzonitrile
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
benzyl chloride
4-(benzyloxy)-3-bromobenzonitrile
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone at 48℃; for 16h; | 86% |
The Benzonitrile,3-bromo-4-hydroxy- with the CAS number 2315-86-8 is also called 2-Bromo-4-cyanophenol. Both the systematic name and IUPAC name are 3-bromo-4-hydroxybenzonitrile. Its molecular formula is C7H4BrNO. The EINECS registry number is 219-022-9. This chemical belongs to the following product categories: (1)Aromatic Nitriles; (2)Nitrile; (3)Bromine Compounds; (4)Nitriles; (5)Phenols; (6)C6 to C7; (7)Cyanides/Nitriles; (8)Nitrogen Compounds.
The properties of the Benzonitrile,3-bromo-4-hydroxy- are: (1)ACD/LogP: 2.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.24; (4)ACD/LogD (pH 7.4): 1.17; (5)ACD/BCF (pH 5.5): 28.46; (6)ACD/BCF (pH 7.4): 2.46; (7)ACD/KOC (pH 5.5): 366.83; (8)ACD/KOC (pH 7.4): 31.67; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 33.02 Å2; (13)Index of Refraction: 1.656; (14)Molar Refractivity: 40.57 cm3; (15)Molar Volume: 110.3 cm3; (16)Polarizability: 16.08×10-24cm3; (17)Surface Tension: 69.9 dyne/cm; (18)Enthalpy of Vaporization: 52.98 kJ/mol; (19)Vapour Pressure: 0.00396 mmHg at 25°C.
Uses: This chemical can react with 1-chloromethoxy-2-methoxy-ethane to prepare 3-bromo-4-(2-methoxy-ethoxymethoxy)-benzonitrile. This reaction needs reagent NaH and solvent pyridine. The yield is 92%. The type of this reaction is alkylation.
While using this chemical, you should be very cautious. This chemical is harmful if swallowed. Therefore, you should take the following instructions. You should wear suitable protective clothing and gloves.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc1cc(C#N)ccc1O
(2)InChI: InChI=1/C7H4BrNO/c8-6-3-5(4-9)1-2-7(6)10/h1-3,10H
(3)InChIKey: HLHNOIAOWQFNGW-UHFFFAOYAB
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