Conditions | Yield |
---|---|
With aluminium trichloride at 100℃; for 2h; | 100% |
With hydrogenchloride; AlCl3 | 76% |
With aluminium trichloride at 180℃; | 75% |
Conditions | Yield |
---|---|
With sulfuric acid; C18H16Br4N2O3V; dihydrogen peroxide; potassium bromide In methanol; water at 20℃; for 0.333333h; Catalytic behavior; | 100% |
With perchloric acid; dihydrogen peroxide; potassium bromide In water at 20℃; for 3h; | 99% |
With o-xylylene bis(triethylammonium tribromide) In acetonitrile at 20℃; for 0.116667h; regioselective reaction; | 90% |
5-bromo-2-methoxyacetophenone
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -5 - 25℃; | 98% |
Conditions | Yield |
---|---|
aluminium trichloride | 89% |
1-(5-bromo-2-hydroxyphenyl)ethan-1-one oxime
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With sodium perborate In acetic acid for 5h; deoximation; Heating; | 88% |
Conditions | Yield |
---|---|
With aluminum (III) chloride at 130℃; for 2h; | 87% |
With aluminum (III) chloride Friedel-Crafts Acylation; | 79% |
Stage #1: 4-bromo-phenol; acetyl chloride Heating; Stage #2: With aluminium trichloride at 125 - 1300℃; |
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With hydrogenchloride | 79% |
Conditions | Yield |
---|---|
Stage #1: 4-bromo-phenol; acetic anhydride Stage #2: With boron trifluoride diacetate In neat (no solvent) Fries Phenol Ester Rearrangement; | 77% |
With aluminium trichloride In nitrobenzene for 4h; 1.) to 120 deg C, 1 h, 2.) 150 deg C, 3 h; | 51% |
o-hydroxyacetophenone
A
3,5-dibromo-2-hydroxyacetophenone
B
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
Stage #1: o-hydroxyacetophenone In acetonitrile at 80℃; for 0.166667h; Stage #2: With N-Bromosuccinimide In acetonitrile at 80℃; for 8h; regioselective reaction; | A 6 %Chromat. B 77% |
Conditions | Yield |
---|---|
Stage #1: 4-bromophenyl acetate With aluminum (III) chloride at 150℃; for 3h; Stage #2: ethyl acetate In water | 70% |
o-hydroxyacetophenone
A
3’-bromo-2’-hydroxylacetophenone
B
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With Oxone; ammonium bromide In methanol at 20℃; for 4.5h; regioselective reaction; | A 26% B 61% |
With trimethylsilyl bromide; bis(4-chlorophenyl)sulfoxide In acetonitrile at 25℃; for 6h; Inert atmosphere; regioselective reaction; | A n/a B 52% |
Conditions | Yield |
---|---|
With aluminium trichloride In carbon disulfide for 2.5h; Heating; | 43% |
1-(3-Bromophenyl)ethanone
A
3-bromo-4-hydroxyacetophenone
B
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With (difluoroboryl)dimethylglyoximatocobalt(II) bis(acetonitrile); water; 3-cyano-1-methylquinolinium cation In acetonitrile at 20℃; for 5h; Inert atmosphere; Irradiation; Green chemistry; | A 15% B 15% |
Conditions | Yield |
---|---|
With boron trifluoride at 120℃; unter Druck; |
Conditions | Yield |
---|---|
With aluminium trichloride |
o-hydroxyacetophenone
A
5-Bromo-2-hydroxyacetophenone
B
2-(2-bromoacetyl)hydroxybenzene
Conditions | Yield |
---|---|
With bromine; acetic acid |
aluminium trichloride
4-bromophenyl acetate
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
at 150 - 160℃; |
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With sodium ethanolate |
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With sodium ethanolate |
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With sodium sulfide In ethanol for 1h; Heating; |
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With sodium sulfide In ethanol for 1h; Heating; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2SO4 / 120 °C 2: AlCl3 / 160 °C View Scheme | |
Multi-step reaction with 2 steps 1: 83.87 percent / pyridine / CH2Cl2 / 5 °C 2: 50 percent / aluminium chloride / 2 h / 140 °C View Scheme | |
Multi-step reaction with 2 steps 1: 99 percent / pyridine / CH2Cl2 / 20 °C 2: 75 percent / AlCl3 / 180 °C View Scheme | |
Multi-step reaction with 2 steps 1: conc. H2SO4 2: AlCl3 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 83 percent / Et3N / CH2Cl2 / 21 h / Ambient temperature 2: 72 percent / AlCl3 / 0.5 h / 150 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent 2: 66 percent / AlCl3 View Scheme | |
Multi-step reaction with 2 steps 1: 97 percent / pyridine / 2 h / 100 °C 2: 62 percent / aluminium trichloride / 3 h / 150 °C View Scheme | |
Multi-step reaction with 2 steps 2: AlCl3 / 150 - 160 °C View Scheme |
Conditions | Yield |
---|---|
aluminium trichloride In hexane; ethyl acetate |
o-hydroxyacetophenone
A
3,5-dibromo-2-hydroxyacetophenone
B
3’-bromo-2’-hydroxylacetophenone
C
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With N-Bromosuccinimide at 80℃; for 10h; regioselective reaction; | A 8 %Chromat. B 6 %Chromat. C 45 %Chromat. |
With N-Bromosuccinimide In acetonitrile at 20℃; for 2h; | A 52 %Chromat. B 6 %Chromat. C 19 %Chromat. |
Cyclopentyl bromide
5-Bromo-2-hydroxyacetophenone
1-(5-bromo-2-cyclopentyloxyphenyl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 13.5h; | 100% |
5-Bromo-2-hydroxyacetophenone
4-bromo-2-(1-iminoethyl)phenol
Conditions | Yield |
---|---|
With ammonia In methanol at 20℃; Cooling with ice; | 100% |
5-Bromo-2-hydroxyacetophenone
1-(5-bromo-2-hydroxyphenyl)ethan-1-one oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In ethanol; water at 70℃; for 2h; | 100% |
With hydroxylamine hydrochloride; sodium acetate In methanol at 0 - 20℃; for 2h; Reflux; | 90% |
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water | |
With hydroxylamine hydrochloride |
5-Bromo-2-hydroxyacetophenone
dimethyl amine
1-(5-(dimethylamino)-2-hydroxyphenyl)ethan-1-one
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane; DavePhos In tetrahydrofuran at 80℃; for 2h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere; | 100% |
5-Bromo-2-hydroxyacetophenone
(E)-4-nitrocinnamic acid chloride
(E)-2-acetyl-4-bromophenyl-3-(4-nitrophenyl)acrylate
Conditions | Yield |
---|---|
With pyridine at 20℃; for 1h; | 99.2% |
With pyridine at 20℃; for 1h; | 99.2% |
With pyridine at 20℃; for 2h; | 96.2% |
5-Bromo-2-hydroxyacetophenone
p-methoxybenzyl chloride
1-(5-bromo-2-((4-methoxybenzyl)oxy)phenyl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate microwave irradiation; | 99% |
With potassium carbonate; potassium iodide In acetone Reflux; | 99% |
5-Bromo-2-hydroxyacetophenone
N-tert-butyloxycarbonylpiperidin-4-one
tert-butyl 6-bromo-4-oxo-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate
Conditions | Yield |
---|---|
Stage #1: 5-Bromo-2-hydroxyacetophenone With pyrrolidine In methanol Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In methanol at 80℃; | 99% |
Stage #1: 5-Bromo-2-hydroxyacetophenone With pyrrolidine In toluene at 20℃; for 0.333333h; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In toluene for 15h; Reflux; | 97% |
With pyrrolidine In methanol for 11h; Reflux; | 94% |
5-Bromo-2-hydroxyacetophenone
allyl bromide
1-(2-(allyloxy)-5-bromophenyl)ethan-1-one
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 50℃; | 98% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; | 87% |
Stage #1: 5-Bromo-2-hydroxyacetophenone With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; Further stages.; | 86% |
3,6-dimethyl-1-benzofuran-2-carbaldehyde
5-Bromo-2-hydroxyacetophenone
(E)-1-(5-Bromo-2-hydroxy-phenyl)-3-(3,6-dimethyl-benzofuran-2-yl)-propenone
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water Ambient temperature; | 98% |
5-Bromo-2-hydroxyacetophenone
methyl iodide
5-bromo-2-methoxyacetophenone
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 45℃; | 98% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 97.2% |
With potassium carbonate In acetone for 2h; | 95% |
5-Bromo-2-hydroxyacetophenone
ethyl bromoacetate
(2-acetyl-4-bromophenoxy)acetic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 98% |
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 12h; | 97% |
Stage #1: 5-Bromo-2-hydroxyacetophenone With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃; | 64% |
1-Bromopentane
5-Bromo-2-hydroxyacetophenone
1-(5-bromo-2-(pentyloxy)phenyl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; | 98% |
5-Bromo-2-hydroxyacetophenone
benzyl bromide
1-(2-(benzyloxy)-5-bromophenyl)ethanone
Conditions | Yield |
---|---|
Stage #1: 5-Bromo-2-hydroxyacetophenone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide for 3h; Inert atmosphere; | 98% |
With potassium carbonate In ethanol for 4h; Reflux; | 84% |
With potassium carbonate In ethanol for 4h; Inert atmosphere; Reflux; | 84% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 63% |
Conditions | Yield |
---|---|
With C19H25F6N3S In toluene at 0℃; for 72h; Aldol Addition; Inert atmosphere; enantioselective reaction; | 97% |
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 16h; | 97% |
5-Bromo-2-hydroxyacetophenone
4-methoxy-benzoyl chloride
4-methoxybenzoic acid 2-acetyl-4-bromophenyl ester
Conditions | Yield |
---|---|
With pyridine for 0.583333h; | 96.5% |
With pyridine at 0 - 20℃; for 0.5h; | 96.5% |
5-Bromo-2-hydroxyacetophenone
2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde
(E)-1-(5-bromo-2-hydroxyphenyl)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)prop-2-en-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 40h; Ambient temperature; | 96% |
With potassium hydroxide In ethanol Ambient temperature; | 96% |
With sodium hydroxide In methanol at 20℃; | 58.33% |
5-Bromo-2-hydroxyacetophenone
benzoyl chloride
5'-bromo-2'-benzoyloxy-acetophenone
Conditions | Yield |
---|---|
With pyridine at 70℃; | 96% |
In pyridine | |
With pyridine at 0℃; for 0.333333h; |
5-Bromo-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With pyrrolidine; cerium(III) chloride; Decaborane In methanol at 50℃; for 8h; Product distribution; Further Variations:; Reaction partners; Reagents; | 96% |
5-Bromo-2-hydroxyacetophenone
N-tert-butyloxycarbonylpiperidin-4-one
6-bromospiro[chroman-2,4'-piperidin]-4-one hydrochloride
Conditions | Yield |
---|---|
Stage #1: 5-Bromo-2-hydroxyacetophenone; N-tert-butyloxycarbonylpiperidin-4-one With pyrrolidine In methanol at 80℃; for 16h; Stage #2: With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 16h; | 96% |
Stage #1: 5-Bromo-2-hydroxyacetophenone; N-tert-butyloxycarbonylpiperidin-4-one With pyrrolidine In methanol Heating / reflux; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃; for 4h; |
Conditions | Yield |
---|---|
With C19H25F6N3S In toluene at 0℃; Aldol Addition; Inert atmosphere; enantioselective reaction; | 96% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 30℃; for 0.5h; Inert atmosphere; | 96% |
1-phenylmethyl-4-piperidone
5-Bromo-2-hydroxyacetophenone
1'-benzyl-6-bromospiro[chroman-2,4'-piperidin]-4-one
Conditions | Yield |
---|---|
Stage #1: 1-phenylmethyl-4-piperidone With pyrrolidine; butyric acid In dimethyl sulfoxide for 0.25h; Kabe Chromanone Synthesis; Stage #2: 5-Bromo-2-hydroxyacetophenone In dimethyl sulfoxide at 20℃; for 3h; Kabe Chromanone Synthesis; | 95% |
With pyrrolidine In methanol for 8h; Heating; | 80% |
With pyrrolidine In methanol for 11h; Reflux; | 66% |
With pyrrolidine In methanol Reflux; | 66% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 60℃; for 16h; | 95% |
5-Bromo-2-hydroxyacetophenone
2-(trifluoromethyl)phenylboronic acid
1-[4-hydroxy-2'-(trifluoromethyl)biphenyl-3-yl]ethanone
Conditions | Yield |
---|---|
Stage #1: 5-Bromo-2-hydroxyacetophenone; 2-(trifluoromethyl)phenylboronic acid With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 50℃; for 48h; Suzuki Coupling; Inert atmosphere; Stage #2: With trifluoroacetic acid In dichloromethane for 1h; | 95% |
5-Bromo-2-hydroxyacetophenone
(E)-1-(5-bromo-2-hydroxyphenyl)ethanone oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; potassium acetate In ethanol for 16h; Reflux; | 95% |
5-Bromo-2-hydroxyacetophenone
malononitrile
6-bromo-3-cyano-4-methyl coumarin
Conditions | Yield |
---|---|
With iodine In N,N-dimethyl-formamide for 0.0666667h; Temperature; Microwave irradiation; | 95% |
Molecular Structure of 5-Bromo-2-hydroxyacetophenone (CAS NO.1450-75-5):
IUPAC Name: 1-(5-bromo-2-hydroxyphenyl)ethanone
Empirical Formula: C8H7BrO2
Molecular Weight: 215.044
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 26.3Å2
Index of Refraction: 1.591
Molar Refractivity: 45.85 cm3
Molar Volume: 135.5 cm3
Surface Tension: 48.5 dyne/cm
Density: 1.586 g/cm3
Flash Point: 124.7 °C
Enthalpy of Vaporization: 54.24 kJ/mol
Boiling Point: 282.6 °C at 760 mmHg
Vapour Pressure: 0.00194 mmHg at 25°C
Melting point: 58-61 °C(lit.)
InChI
InChI=1/C8H7BrO2/c1-5(10)7-4-6(9)2-3-8(7)11/h2-4,11H,1H3
Smiles
c1(C(=O)C)c(ccc(c1)Br)O
Product Categories: Aromatic Acetophenones & Derivatives (substituted); Adehydes, Acetals & Ketones; Bromine Compounds; Phenols; C7 to C8; Carbonyl Compounds; Ketones
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 1gm/kg (1000mg/kg) | Indian Journal of Chemistry, Section B: Organic Chemistry, Including Medicinal Chemistry. Vol. 20, Pg. 480, 1981. |
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: KM5556350
Hazard Note: Irritant
HazardClass: Irritant
5-Bromo-2-hydroxyacetophenone , with CAS number of 1450-75-5, can be called 5'-Bromo-o-hydroxyacetophenone ; Acetophenone,5'-bromo-2'-hydroxy- (6CI,7CI,8CI) ; 1-(5-Bromo-2-hydroxyphenyl)ethanone ; 2-Acetyl-4-bromophenol ; 2'-Hydroxy-5'-bromoacetophenone .
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