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5467-56-1

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5467-56-1 Usage

Uses

1-[4-(Pentyloxy)phenyl]-ethanone is a useful reagent for organic synthesis, can be used in the synthesis of antibiotic compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 5467-56-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,6 and 7 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 5467-56:
(6*5)+(5*4)+(4*6)+(3*7)+(2*5)+(1*6)=111
111 % 10 = 1
So 5467-56-1 is a valid CAS Registry Number.
InChI:InChI=1/C13H18O2/c1-3-4-5-10-15-13-8-6-12(7-9-13)11(2)14/h6-9H,3-5,10H2,1-2H3

5467-56-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(4-pentoxyphenyl)ethanone

1.2 Other means of identification

Product number -
Other names 4-n-pentyloxyacetophenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5467-56-1 SDS

5467-56-1Synthetic route

1-Bromopentane
110-53-2

1-Bromopentane

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In water; ethyl acetate; acetone100%
With potassium carbonate In N,N-dimethyl-formamide for 16h; Reflux;92%
With potassium carbonate; potassium iodide In acetone Inert atmosphere; Reflux;78%
(pentyloxy)benzene
2050-04-6

(pentyloxy)benzene

acetic anhydride
108-24-7

acetic anhydride

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
With zinc(II) chloride
phenol
108-95-2

phenol

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3; CS2
2: methanol. NaOH
View Scheme
4-Iodoacetophenone
13329-40-3

4-Iodoacetophenone

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: copper(l) iodide; 8-Hydroxyquinoline-N-oxide / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere
1.2: 28 h / 100 °C / Inert atmosphere
2.1: cesiumhydroxide monohydrate; tetra-(n-butyl)ammonium iodide / water; dimethyl sulfoxide / 12 h / 100 °C / Inert atmosphere
View Scheme
para-bromoacetophenone
99-90-1

para-bromoacetophenone

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: copper(l) iodide; 8-Hydroxyquinoline-N-oxide / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere
1.2: 24 h / 110 °C / Inert atmosphere
2.1: cesiumhydroxide monohydrate; tetra-(n-butyl)ammonium iodide / water; dimethyl sulfoxide / 12 h / 100 °C / Inert atmosphere
View Scheme
1-Chloropentane

1-Chloropentane

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60 - 80℃; for 4h; Inert atmosphere;
4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

pentyl halide

pentyl halide

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃;
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

(R)-1-(4-Pentyloxy-phenyl)-ethanol

(R)-1-(4-Pentyloxy-phenyl)-ethanol

Conditions
ConditionsYield
With Trimethyl borate; (S)-diphenylprolinol; dimethylsulfide borane complex In tetrahydrofuran; toluene at 25 - 30℃;99%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

4-pentyloxy-benzoic acid ethyl ester
177715-63-8

4-pentyloxy-benzoic acid ethyl ester

1,3-Di-(p-n-pentyloxyphenyl)propane-1,3-dione
107265-33-8

1,3-Di-(p-n-pentyloxyphenyl)propane-1,3-dione

Conditions
ConditionsYield
With sodium hydride90%
With sodium hydride
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

C22H24O4

C22H24O4

Conditions
ConditionsYield
With caesium carbonate In ethanol; water at 50℃; for 5h;84.6%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

4-amyloxy-3-nitroacetophenone
134221-17-3

4-amyloxy-3-nitroacetophenone

Conditions
ConditionsYield
With sulfuric acid; nitric acid at -8 - -5℃; for 2h;83%
With sulfuric acid; nitric acid at 0℃; for 0.5h;
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

thiosemicarbazide
79-19-6

thiosemicarbazide

2-(1-(4-pentoxyphenyl)ethylidene)hydrazine-1-carbothioamide

2-(1-(4-pentoxyphenyl)ethylidene)hydrazine-1-carbothioamide

Conditions
ConditionsYield
With acetic acid In ethanol at 50 - 80℃; for 3h;82%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

C20H22O3

C20H22O3

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; Claisen Condensation; Inert atmosphere;50%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

4-OC5H11-C6H4-COOAlk

4-OC5H11-C6H4-COOAlk

1,3-Di-(p-n-pentyloxyphenyl)propane-1,3-dione
107265-33-8

1,3-Di-(p-n-pentyloxyphenyl)propane-1,3-dione

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 5h; Heating;30%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

ethyl 2-hydroxy-4-oxo-4-(4-pentoxyphenyl)-2-butenoate
84424-70-4

ethyl 2-hydroxy-4-oxo-4-(4-pentoxyphenyl)-2-butenoate

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 50℃; for 2h; Claisen Condensation; Reflux;23%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

C22H24O4

C22H24O4

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane20%
4-(prop-1-yl)piperidine
22398-09-0

4-(prop-1-yl)piperidine

formaldehyd
50-00-0

formaldehyd

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

1-(4-pentyloxy-phenyl)-3-(4-propyl-piperidino)-propan-1-one

1-(4-pentyloxy-phenyl)-3-(4-propyl-piperidino)-propan-1-one

Conditions
ConditionsYield
With hydrogenchloride; ethanol
4-ethylpiperidine
3230-23-7

4-ethylpiperidine

formaldehyd
50-00-0

formaldehyd

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

3-(4-ethyl-piperidino)-1-(4-pentyloxy-phenyl)-propan-1-one

3-(4-ethyl-piperidino)-1-(4-pentyloxy-phenyl)-propan-1-one

Conditions
ConditionsYield
With ethanol
formaldehyd
50-00-0

formaldehyd

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

piperidine hydrochloride
6091-44-7

piperidine hydrochloride

1-(4-pentyloxy-phenyl)-3-piperidino-propan-1-one; hydrochloride
63957-33-5

1-(4-pentyloxy-phenyl)-3-piperidino-propan-1-one; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; nitromethane; ethanol; toluene
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

o-tolidin
119-93-7

o-tolidin

3,3'-dimethyl-N,N'-bis(α-methyl-4-pentoxybenzylidene)biphenyl-4,4'-diamine

3,3'-dimethyl-N,N'-bis(α-methyl-4-pentoxybenzylidene)biphenyl-4,4'-diamine

Conditions
ConditionsYield
With acetic acid In benzene Heating;
1-Bromopentane
110-53-2

1-Bromopentane

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In water; ethyl acetate; acetone100%
With potassium carbonate In N,N-dimethyl-formamide for 16h; Reflux;92%
With potassium carbonate; potassium iodide In acetone Inert atmosphere; Reflux;78%
(pentyloxy)benzene
2050-04-6

(pentyloxy)benzene

acetic anhydride
108-24-7

acetic anhydride

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
With zinc(II) chloride
phenol
108-95-2

phenol

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3; CS2
2: methanol. NaOH
View Scheme
4-Iodoacetophenone
13329-40-3

4-Iodoacetophenone

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: copper(l) iodide; 8-Hydroxyquinoline-N-oxide / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere
1.2: 28 h / 100 °C / Inert atmosphere
2.1: cesiumhydroxide monohydrate; tetra-(n-butyl)ammonium iodide / water; dimethyl sulfoxide / 12 h / 100 °C / Inert atmosphere
View Scheme
para-bromoacetophenone
99-90-1

para-bromoacetophenone

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: copper(l) iodide; 8-Hydroxyquinoline-N-oxide / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere
1.2: 24 h / 110 °C / Inert atmosphere
2.1: cesiumhydroxide monohydrate; tetra-(n-butyl)ammonium iodide / water; dimethyl sulfoxide / 12 h / 100 °C / Inert atmosphere
View Scheme
1-Chloropentane
543-59-9

1-Chloropentane

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60 - 80℃; for 4h; Inert atmosphere;
4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

pentyl halide

pentyl halide

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃;
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

(R)-1-(4-Pentyloxy-phenyl)-ethanol

(R)-1-(4-Pentyloxy-phenyl)-ethanol

Conditions
ConditionsYield
With Trimethyl borate; (S)-diphenylprolinol; dimethylsulfide borane complex In tetrahydrofuran; toluene at 25 - 30℃;99%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

4-pentyloxy-benzoic acid ethyl ester
177715-63-8

4-pentyloxy-benzoic acid ethyl ester

1,3-Di-(p-n-pentyloxyphenyl)propane-1,3-dione
107265-33-8

1,3-Di-(p-n-pentyloxyphenyl)propane-1,3-dione

Conditions
ConditionsYield
With sodium hydride90%
With sodium hydride
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

C22H24O4

C22H24O4

Conditions
ConditionsYield
With caesium carbonate In ethanol; water at 50℃; for 5h;84.6%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

4-amyloxy-3-nitroacetophenone
134221-17-3

4-amyloxy-3-nitroacetophenone

Conditions
ConditionsYield
With sulfuric acid; nitric acid at -8 - -5℃; for 2h;83%
With sulfuric acid; nitric acid at 0℃; for 0.5h;
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

thiosemicarbazide
79-19-6

thiosemicarbazide

2-(1-(4-pentoxyphenyl)ethylidene)hydrazine-1-carbothioamide

2-(1-(4-pentoxyphenyl)ethylidene)hydrazine-1-carbothioamide

Conditions
ConditionsYield
With acetic acid In ethanol at 50 - 80℃; for 3h;82%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

C20H22O3

C20H22O3

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; Claisen Condensation; Inert atmosphere;50%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

4-OC5H11-C6H4-COOAlk

4-OC5H11-C6H4-COOAlk

1,3-Di-(p-n-pentyloxyphenyl)propane-1,3-dione
107265-33-8

1,3-Di-(p-n-pentyloxyphenyl)propane-1,3-dione

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 5h; Heating;30%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

ethyl 2-hydroxy-4-oxo-4-(4-pentoxyphenyl)-2-butenoate
84424-70-4

ethyl 2-hydroxy-4-oxo-4-(4-pentoxyphenyl)-2-butenoate

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 50℃; for 2h; Claisen Condensation; Reflux;23%
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

C22H24O4

C22H24O4

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane20%
4-(prop-1-yl)piperidine
22398-09-0

4-(prop-1-yl)piperidine

formaldehyd
50-00-0

formaldehyd

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

1-(4-pentyloxy-phenyl)-3-(4-propyl-piperidino)-propan-1-one

1-(4-pentyloxy-phenyl)-3-(4-propyl-piperidino)-propan-1-one

Conditions
ConditionsYield
With hydrogenchloride; ethanol
4-ethylpiperidine
3230-23-7

4-ethylpiperidine

formaldehyd
50-00-0

formaldehyd

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

3-(4-ethyl-piperidino)-1-(4-pentyloxy-phenyl)-propan-1-one

3-(4-ethyl-piperidino)-1-(4-pentyloxy-phenyl)-propan-1-one

Conditions
ConditionsYield
With ethanol
formaldehyd
50-00-0

formaldehyd

4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

piperidine hydrochloride
6091-44-7

piperidine hydrochloride

1-(4-pentyloxy-phenyl)-3-piperidino-propan-1-one; hydrochloride
63957-33-5

1-(4-pentyloxy-phenyl)-3-piperidino-propan-1-one; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; nitromethane; ethanol; toluene
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

o-tolidin
119-93-7

o-tolidin

3,3'-dimethyl-N,N'-bis(α-methyl-4-pentoxybenzylidene)biphenyl-4,4'-diamine

3,3'-dimethyl-N,N'-bis(α-methyl-4-pentoxybenzylidene)biphenyl-4,4'-diamine

Conditions
ConditionsYield
With acetic acid In benzene Heating;
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

p,p'-diaminobiphenyl
92-87-5

p,p'-diaminobiphenyl

N,N'-bis(α-methyl-4-pentoxybenzylidene)biphenyl-4,4'-diamine

N,N'-bis(α-methyl-4-pentoxybenzylidene)biphenyl-4,4'-diamine

Conditions
ConditionsYield
With acetic acid In benzene Heating;
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

formic acid ethyl ester
109-94-4

formic acid ethyl ester

Sodium; (E)-3-oxo-3-(4-pentyloxy-phenyl)-propen-1-olate

Sodium; (E)-3-oxo-3-(4-pentyloxy-phenyl)-propen-1-olate

Conditions
ConditionsYield
With sodium In 1,4-dioxane for 8h; Ambient temperature;
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

formic acid ethyl ester
109-94-4

formic acid ethyl ester

3-Oxo-3-(4-pentyloxy-phenyl)-propionaldehyde

3-Oxo-3-(4-pentyloxy-phenyl)-propionaldehyde

Conditions
ConditionsYield
With sodium In 1,4-dioxane for 2h; Heating;
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

p-n-Pentyloxyphenylglyoxal
14333-55-2

p-n-Pentyloxyphenylglyoxal

Conditions
ConditionsYield
(i) SeO2, aq. dioxane, (ii) H2O; Multistep reaction;
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

2-(4-pentyloxyphenyl)-5-cyanopyridine
107503-54-8

2-(4-pentyloxyphenyl)-5-cyanopyridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Na wire / dioxane / 8 h / Ambient temperature
2: piperidine / acetic acid; H2O / 1.)r.t., 8 h 2.)reflux, 16 h
3: 73 percent / PhPOCl2 / 3 h / 140 - 160 °C
4: 48 percent / H2/Et3N / 10percent Pd/C / dimethylformamide / 3800 Torr / Ambient temperature
View Scheme
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

2-Oxo-6-(4-pentyloxy-phenyl)-1,2-dihydro-pyridine-3-carbonitrile
107488-03-9

2-Oxo-6-(4-pentyloxy-phenyl)-1,2-dihydro-pyridine-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Na wire / dioxane / 8 h / Ambient temperature
2: piperidine / acetic acid; H2O / 1.)r.t., 8 h 2.)reflux, 16 h
View Scheme
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

2-Chloro-6-(4-pentyloxy-phenyl)-nicotinonitrile
106793-10-6

2-Chloro-6-(4-pentyloxy-phenyl)-nicotinonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Na wire / dioxane / 8 h / Ambient temperature
2: piperidine / acetic acid; H2O / 1.)r.t., 8 h 2.)reflux, 16 h
3: 73 percent / PhPOCl2 / 3 h / 140 - 160 °C
View Scheme
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

(Z)-3-(4-Iodo-phenylamino)-1-(4-pentyloxy-phenyl)-propenone

(Z)-3-(4-Iodo-phenylamino)-1-(4-pentyloxy-phenyl)-propenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium / dioxane / 2 h / Heating
2: dioxane; ethanol; diethyl ether / Ambient temperature
View Scheme
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

(Z)-3-(4-Hexyl-phenylamino)-1-(4-pentyloxy-phenyl)-propenone

(Z)-3-(4-Hexyl-phenylamino)-1-(4-pentyloxy-phenyl)-propenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium / dioxane / 2 h / Heating
2: dioxane; ethanol; diethyl ether / Ambient temperature
View Scheme
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

(Z)-3-(4-Hexyloxy-phenylamino)-1-(4-pentyloxy-phenyl)-propenone

(Z)-3-(4-Hexyloxy-phenylamino)-1-(4-pentyloxy-phenyl)-propenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium / dioxane / 2 h / Heating
2: dioxane; ethanol; diethyl ether / Ambient temperature
View Scheme
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

(Z)-3-(4-Nitro-phenylamino)-1-(4-pentyloxy-phenyl)-propenone

(Z)-3-(4-Nitro-phenylamino)-1-(4-pentyloxy-phenyl)-propenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium / dioxane / 2 h / Heating
2: dioxane; ethanol; diethyl ether / Ambient temperature
View Scheme
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

3,5-Bis-(4-pentyloxy-phenyl)-3,4-dihydro-[1,2]dithiol-1-ylium; chloride

3,5-Bis-(4-pentyloxy-phenyl)-3,4-dihydro-[1,2]dithiol-1-ylium; chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 30 percent / sodium hydride / tetrahydrofuran / 5 h / Heating
2: 1.) phosphorous pentasulfide, 2.) lithium chloride / 1.) 150 deg C, 1 h, 2.) acetic acid, reflux, 30 min
View Scheme
4-pentyloxyacetophenone
5467-56-1

4-pentyloxyacetophenone

N,N'-Bis-[1-(1-benzyl-1H-imidazol-2-yl)-meth-(E)-ylidene]-hydrazine
134221-21-9

N,N'-Bis-[1-(1-benzyl-1H-imidazol-2-yl)-meth-(E)-ylidene]-hydrazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 83 percent / HNO3, H2SO4 / 2 h / -8 - -5 °C
2: 20.4 percent / ethanol / 5 h
View Scheme

5467-56-1Relevant articles and documents

Design, synthesis, biological evaluation and inhibition mechanism of 3-/4-alkoxy phenylethylidenethiosemicarbazides as new, potent and safe tyrosinase inhibitors

Liao, Bing,Mai, Yuliang,Shi, Huahong,Song, Senchuan,Wang, Fei

, p. 369 - 379 (2020/05/14)

Tyrosinase plays important roles in many different disease related processes, and the development of its inhibitors is particularly important in biotechnology. In this study, thirty-nine 3-/4-alkoxyphenylethyli-denethiosemicarbazides were synthesized as novel tyrosinase inhibitors based on structure-based molecular design. Our experimental results demonstrated that thirty-one of them possess remarkable tyrosinase inhibitory activities with IC50 value below 1μM, and 5a, 6e, 6g and 6t did not display any toxicity to 293T cell line at the concentration of 1000μmol/L. According to the inhibitory activities, several compounds were selected for detail investigation on the structure–activity relationships (SARs), mechanisms of enzyme inhibition, inhibitory kinetics and cytotoxicity. In particular, the interaction between the selected inhibitors and the active center of tyrosinase was considered and discussed in detail based on their structural characteristics. Taken together, the results presented here demonstrated that the newly designed compounds are promising candidates for the treatment of tyrosinase-related disorders and further development of them may have significant contribution in biomedical science.

Synthesis and molecular docking studies of novel pyrimidine derivatives as potential antibacterial agents

Bai, Xue-Qian,Li, Chun-Shi,Cui, Ming-Yue,Song, Ze-Wen,Zhou, Xing-Yu,Zhang, Chao,Zhao, Yang,Zhang, Tian-Yi,Jiang, Tie-Yan

, p. 1165 - 1176 (2019/12/11)

Abstract: The present work describes the in vitro antibacterial evaluation of some new pyrimidine derivatives. Twenty-two target compounds were designed, synthesized and preliminarily explored for their antimicrobial activities. The antimicrobial assay revealed that some target compounds exhibited significantly inhibitory efficiencies toward bacteria and fungal including drug-resistant pathogens. Compound 7c presented the most potent inhibitory activities against Gram-positive bacteria (e.g., Staphylococcus aureus 4220), Gram-negative bacteria (e.g., Escherichia coli 1924) and the fungus Candida albicans 7535, with an MIC of 2.4?μmol/L. Compound 7c was also the most potent, with MICs of 2.4 or 4.8?μmol/L against four multidrug-resistant, Gram-positive bacterial strains. The toxicity evaluation of the compounds 7c, 10a, 19d and 26b was assessed in human normal liver cells (L02 cells). Molecular docking simulation and analysis suggested that compound 7c has a good interaction with the active cavities of dihydrofolate reductase (DHFR). In vitro enzyme study implied that compound 7c also displayed DHFR inhibition. Graphic abstract: [Figure not available: see fulltext.]

Synthesis and liquid crystalline properties of a new homologous series of 4,5-disubstituted 2H-[1,2,3]-triazoles via azide-chalcone oxidative cycloaddition reaction

Sowmya,Rai, K. M. Lokanatha

, p. 764 - 768 (2017/07/07)

A new homologous series of 4,5-disubstituted 2H-[1,2,3]-triazole derivatives were synthesized from chalcones and sodium azide via oxidative cycloaddition reaction; CuI was used as catalyst. Flexibility in the synthesized molecules was provided by attaching straight alkoxy chains. The synthesized compounds were characterized by elemental analysis, and 1HNMRand 13CNMRand LC-MS spectroscopies . The stability and range of the mesophases increased with the length of the chain on the triazoles. The melting point, transition temperatures, and enantiotropic liquid crystal morphologies were determined by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) equipped with a hot stage. Journal compilation

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