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3011-34-5

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3011-34-5 Usage

Uses

Different sources of media describe the Uses of 3011-34-5 differently. You can refer to the following data:
1. 4-Hydroxy-3-nitrobenzaldehyde is an Intermediate used in synthesis of novel amodiaquine analogs as potential antimalarial and antifilarial compounds.
2. 4-Hydroxy-3-nitrobenzaldehyde was used in the synthesis of:4-hydroxy-3-nitrocinnamic acid solvated benzohydrazone derivatives: N′-(4-hydroxy-3-nitrobenzylidene)-3-methylbenzohydrazide-methanol-water

General Description

4-Hydroxy-3-nitrobenzaldehyde reacts with 3-bromo-benzohydrazide in methanol to yield (E)-3-bromo-N′-(4-hydroxy-3-nitrobenzylidene)benzohydrazide.

Check Digit Verification of cas no

The CAS Registry Mumber 3011-34-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,0,1 and 1 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3011-34:
(6*3)+(5*0)+(4*1)+(3*1)+(2*3)+(1*4)=35
35 % 10 = 5
So 3011-34-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NO4/c9-4-5-1-2-7(10)6(3-5)8(11)12/h1-4,10H/p-1

3011-34-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A17972)  4-Hydroxy-3-nitrobenzaldehyde, 98%   

  • 3011-34-5

  • 5g

  • 803.0CNY

  • Detail
  • Alfa Aesar

  • (A17972)  4-Hydroxy-3-nitrobenzaldehyde, 98%   

  • 3011-34-5

  • 25g

  • 2963.0CNY

  • Detail
  • Alfa Aesar

  • (A17972)  4-Hydroxy-3-nitrobenzaldehyde, 98%   

  • 3011-34-5

  • 100g

  • 9508.0CNY

  • Detail

3011-34-5SDS

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 4-Hydroxy-3-nitrobenzaldehyde

1.2 Other means of identification

Product number -
Other names 4-Hydroxy-3-nitrobenzaldeyde

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:3011-34-5 SDS

3011-34-5Synthetic route

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With dinitrogen tetraoxide; ferric nitrate In acetone for 2.5h; Ambient temperature;100%
With magnesium(II) nitrate hexahydrate; AMA at 20℃; for 0.583333h; Neat (no solvent); regioselective reaction;98%
With tetrachlorosilane; silica gel; sodium nitrite In dichloromethane at 20℃; for 1.5h;97%
4-hydroxymethyl-2-nitrophenol
41833-13-0

4-hydroxymethyl-2-nitrophenol

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With manganese(II) nitrate hexahydrate; copper(II) nitrate trihydrate; acetic acid In α,α,α-trifluorotoluene at 50℃; for 2h; In air; chemoselective reaction;91%
With potassium hydroxide; permanganate(VII) ion at 90 - 100℃;
4-methyl-2-nitrophenol
119-33-5

4-methyl-2-nitrophenol

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With oxygen; cobalt(II) diacetate tetrahydrate; sodium hydroxide In ethylene glycol at 80℃; under 760.051 Torr; for 8h;87%
With oxygen; sodium hydroxide In 2-methoxy-ethanol at 80℃; for 7h; chemoselective reaction;
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

A

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

B

4-hydroxy-2-nitrobenzaldehyde
90151-04-5

4-hydroxy-2-nitrobenzaldehyde

Conditions
ConditionsYield
With Nitrogen dioxide under 225.02 Torr; for 12h;A 77%
B 17%
4-fluoro-3-nitrobenzaldehyde
42564-51-2

4-fluoro-3-nitrobenzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene; 4-methoxyphenylboronic acid; tetrabutylammomium bromide; palladium diacetate; caesium carbonate In 1,2-dimethoxyethane at 70℃; for 48h; Suzuki-Miyaura Coupling; Inert atmosphere;75%
With sodium hydroxide; N,N-dimethyl-formamide anschliessendes Behandeln mit Saeure;
(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol
501-36-0

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

A

(E)-3,4',5-trihydroxy-α-nitrostilbene

(E)-3,4',5-trihydroxy-α-nitrostilbene

rac-(2RS,3RS)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydrobenzofuran-5-carbaldehyde

rac-(2RS,3RS)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydrobenzofuran-5-carbaldehyde

C

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

D

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

Conditions
ConditionsYield
With phosphate buffer; sodium nitrite In methanol at 20℃; for 3h; pH=3.0; Further byproducts given;A 4%
B 2%
C 1%
D 4%
4-bromo-3-nitrobenzaldehyde
163596-75-6

4-bromo-3-nitrobenzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With sodium carbonate
4-acetamido-3-nitrobenzaldehyde
51818-98-5

4-acetamido-3-nitrobenzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With sodium hydroxide
potassium acetate
127-08-2

potassium acetate

4-chloro-3-nitro-benzaldehyde
16588-34-4

4-chloro-3-nitro-benzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
at 150℃;
at 150℃;
4-chloro-3-nitro-benzaldehyde
16588-34-4

4-chloro-3-nitro-benzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With potassium hydroxide
With potassium acetate at 140 - 150℃;
With sodium carbonate at 140 - 150℃;
4-hydroxy-3-nitro-benzyl chloride
6694-75-3

4-hydroxy-3-nitro-benzyl chloride

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With hexamethylenetetramine; acetic acid anschliessendes Erhitzen mit wss.HCl;
4-hydroxybenzaldehyde oxime
699-06-9, 60221-52-5, 60221-53-6

4-hydroxybenzaldehyde oxime

A

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

B

4-hydroxy-3-nitro-benzaldehyde-oxime
26879-83-4

4-hydroxy-3-nitro-benzaldehyde-oxime

Conditions
ConditionsYield
With nitric acid; acetic acid
nitric acid
7697-37-2

nitric acid

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

cis-nitrous acid
7782-77-6

cis-nitrous acid

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

4-chloro-3-nitro-benzaldehyde
16588-34-4

4-chloro-3-nitro-benzaldehyde

alkali hydroxide

alkali hydroxide

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

HNO3+H2SO4

HNO3+H2SO4

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

4-chloro-3-nitro-benzaldehyde
16588-34-4

4-chloro-3-nitro-benzaldehyde

natrium carbonate

natrium carbonate

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
at 140 - 150℃;
at 140 - 150℃;
nitric acid
7697-37-2

nitric acid

acetic acid
64-19-7

acetic acid

4-hydroxybenzaldehyde oxime
699-06-9, 60221-52-5, 60221-53-6

4-hydroxybenzaldehyde oxime

A

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

B

3-nitro-4-hydroxy-benzaldehyde-oxime

3-nitro-4-hydroxy-benzaldehyde-oxime

4-aminobenzaldehyde
556-18-3

4-aminobenzaldehyde

nitric acid
7697-37-2

nitric acid

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
man verduennt mit Wasser.Diazotization;
hydrochloride of p-amino-benzaldehyde

hydrochloride of p-amino-benzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With water; nitric acid Diazotization;
4-hydroxymethyl-2-nitrophenol
41833-13-0

4-hydroxymethyl-2-nitrophenol

permanganate

permanganate

aqueous KOH-solution

aqueous KOH-solution

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
at 90 - 100℃;
4-hydroxybenzaldehyde oxime
699-06-9, 60221-52-5, 60221-53-6

4-hydroxybenzaldehyde oxime

A

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

B

3-nitro-4-hydroxy-benzaldehyde-oxime

3-nitro-4-hydroxy-benzaldehyde-oxime

Conditions
ConditionsYield
With nitric acid; acetic acid
4-acetamido-3-nitrobenzaldehyde
51818-98-5

4-acetamido-3-nitrobenzaldehyde

diluted NaOH-solution

diluted NaOH-solution

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

4-(1,3-dithiolan-2-yl)phenol
22068-49-1

4-(1,3-dithiolan-2-yl)phenol

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

C

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

D

4-[1,3]dithiolan-2-yl-2-nitro-phenol

4-[1,3]dithiolan-2-yl-2-nitro-phenol

Conditions
ConditionsYield
With bismuth(III) nitrate; water In benzene at 20℃; for 8h; Product distribution;
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HNO3; water; H2SO4
2: DMF; aq. NaOH solution / anschliessendes Behandeln mit Saeure
View Scheme
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated sulfuric acid; nitric
2: natrium carbonate
View Scheme
2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated hydrochloric acid
2: permanganate; diluted KOH-solution / 90 - 100 °C
View Scheme
Multi-step reaction with 2 steps
1: formaldehyde; concentrated hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser
2: permanganate; diluted KOH-solution / 90 - 100 °C
View Scheme
C38H42N6O10
1375797-26-4

C38H42N6O10

A

NH-pyrazole
288-13-1

NH-pyrazole

B

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

C

N,N-bis(2-hydroxyphenylmethyl)-N-(2-pyridylmethyl)ethane-1,2-diamine
1375797-17-3

N,N-bis(2-hydroxyphenylmethyl)-N-(2-pyridylmethyl)ethane-1,2-diamine

Conditions
ConditionsYield
With water; 2-hydroxyethanethiol; magnesium chloride; β-galactosidase at 37℃; for 3h; pH=7.2; Kinetics; aq. phosphate buffer; Enzymatic reaction;
C41H43N7O10
1375797-28-6

C41H43N7O10

A

1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

B

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

C

N,N-bis(2-hydroxyphenylmethyl)-N-(2-pyridylmethyl)ethane-1,2-diamine
1375797-17-3

N,N-bis(2-hydroxyphenylmethyl)-N-(2-pyridylmethyl)ethane-1,2-diamine

Conditions
ConditionsYield
With water; 2-hydroxyethanethiol; magnesium chloride; β-galactosidase at 37℃; for 3h; pH=7.2; Kinetics; aq. phosphate buffer; Enzymatic reaction;
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

allyl bromide
106-95-6

allyl bromide

3-nitro-4-(2-propenyloxy)benzaldehyde
125872-98-2

3-nitro-4-(2-propenyloxy)benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 60℃;100%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 1h;99%
With potassium carbonate; potassium iodide In acetonitrile for 20h; Inert atmosphere; Reflux;97%
With potassium carbonate In acetonitrile at 60℃; for 72h; Inert atmosphere;92%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

ethyl iodide
75-03-6

ethyl iodide

4-ethoxy-3-nitrobenzaldehyde
132390-61-5

4-ethoxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20 - 70℃;99%
With potassium carbonate In acetonitrile for 15h; Heating;82%
With potassium carbonate In N,N-dimethyl-formamide
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

ethylene glycol
107-21-1

ethylene glycol

4-(1,3-dioxolan-2-yl)-2-nitrophenyl trifluoromethanesulfonate
697306-05-1

4-(1,3-dioxolan-2-yl)-2-nitrophenyl trifluoromethanesulfonate

Conditions
ConditionsYield
Stage #1: trifluoromethylsulfonic anhydride; 4-hydroxy-3-nitrobenzaldehyde With triethylamine In dichloromethane at 0℃; for 0.666667h;
Stage #2: ethylene glycol With methanesulfonic acid In toluene for 14h; Heating / reflux;
99%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

4-hydroxymethyl-2-nitrophenol
41833-13-0

4-hydroxymethyl-2-nitrophenol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;98%
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 3h;97%
With sodium tetrahydroborate In methanol at 0℃; for 1h; Inert atmosphere;80%
bromethyl methyl ether
13057-17-5

bromethyl methyl ether

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

3-nitro-(4-methoxymethoxy)benzaldehyde
105183-11-7

3-nitro-(4-methoxymethoxy)benzaldehyde

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;98%
N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine
14384-45-3

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

2-(4-hydroxy-3-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol
1169932-83-5

2-(4-hydroxy-3-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol

Conditions
ConditionsYield
In methanol at 20℃; for 3h;98%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester
3082-95-9, 72692-06-9, 73464-50-3

2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester

(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
148579-93-5

(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions
ConditionsYield
Stage #1: 2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester With hydrogen bromide; acetic acid In dichloromethane at 0 - 20℃;
Stage #2: 4-hydroxy-3-nitrobenzaldehyde With silver(l) oxide In acetonitrile at 20℃; Darkness;
98%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

4-(1-(4-hydroxy-3-nitrobenzyl)-1H-benzo[d]imidazol-2-yl)-2-nitrophenol
111664-46-1

4-(1-(4-hydroxy-3-nitrobenzyl)-1H-benzo[d]imidazol-2-yl)-2-nitrophenol

Conditions
ConditionsYield
at 30℃; for 0.366667h; Catalytic behavior; Mechanism; Reagent/catalyst; Temperature; Time; Inert atmosphere; Green chemistry; chemoselective reaction;97%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester
21085-72-3

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
148579-93-5

(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions
ConditionsYield
With silver(l) oxide In acetonitrile for 4h; Koenigs-Knorr reaction;96%
With silver(l) oxide In acetonitrile for 4h; Koenigs-Knorr reaction;96%
With silver(l) oxide In acetonitrile at 20℃; for 12h; Koenigs-Knorr Glycosidation; Schlenk technique; Inert atmosphere; Molecular sieve; Darkness;96%
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

tert-butyl 2-(4-formyl-2-nitrophenoxy)acetate

tert-butyl 2-(4-formyl-2-nitrophenoxy)acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 30h; Inert atmosphere;96%
With potassium carbonate In acetonitrile Alkylation;
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

1-amino-naphthalene
134-32-7

1-amino-naphthalene

malononitrile
109-77-3

malononitrile

2-amino-4-(4-hydroxy-3-nitrophenyl)benzo[h]quinoline-3-carbonitrile

2-amino-4-(4-hydroxy-3-nitrophenyl)benzo[h]quinoline-3-carbonitrile

Conditions
ConditionsYield
In ethanol for 5h; Heating;96%
tetrahydrofuran-2,4-dione
4971-56-6

tetrahydrofuran-2,4-dione

6-aminoquinoline
580-15-4

6-aminoquinoline

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

11-(4-hydroxy-3-nitrophenyl)-8,11-dihydrofuro[3,4-b][4,7]phenanthrolin-10(7H)-one
1049682-10-1

11-(4-hydroxy-3-nitrophenyl)-8,11-dihydrofuro[3,4-b][4,7]phenanthrolin-10(7H)-one

Conditions
ConditionsYield
In water at 120℃; for 0.116667h; microwave irradiation;96%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

acetone
67-64-1

acetone

urea
57-13-6

urea

C19H18N6O8

C19H18N6O8

Conditions
ConditionsYield
potassium hydrogensulfate In acetic acid at 80℃; for 1.5h;95%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

benzyl bromide
100-39-0

benzyl bromide

4-phenylmethoxy-3-nitrobenzaldehyde
22955-07-3

4-phenylmethoxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide95%
With potassium carbonate In N,N-dimethyl-formamide95%
With potassium carbonate In N,N-dimethyl-formamide95%
6-aminoquinoline
580-15-4

6-aminoquinoline

4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

14-(4-hydroxy-3-nitrophenyl)-7H-chromeno[3,4-b][4,7]phenanthrolin-13(14H)-one
1038883-16-7

14-(4-hydroxy-3-nitrophenyl)-7H-chromeno[3,4-b][4,7]phenanthrolin-13(14H)-one

Conditions
ConditionsYield
In water at 140℃; for 0.0833333h; microwave irradiation;95%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

dimedone
126-81-8

dimedone

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

7,8-dihydro-4-(4-hydroxy-3-nitrophenyl)-7,7-dimethyl-2-(4-nitrophenyl)quinolin-5(1H,4H,6H)-one
1107620-89-2

7,8-dihydro-4-(4-hydroxy-3-nitrophenyl)-7,7-dimethyl-2-(4-nitrophenyl)quinolin-5(1H,4H,6H)-one

Conditions
ConditionsYield
With ammonium acetate at 100℃; for 0.15h; Microwave irradiation;95%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

dimedone
126-81-8

dimedone

β-naphthol
135-19-3

β-naphthol

12-(4-hydroxy-3-nitrophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
1254077-26-3

12-(4-hydroxy-3-nitrophenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one

Conditions
ConditionsYield
With silica supported perchloric acid at 80℃; for 1h; neat (no solvent);95%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

N-acetylglycine
543-24-8

N-acetylglycine

4-(4-Hydroxy-3-nitrobenzylidene)-2-methyloxazol-5(4H)-one
346633-49-6

4-(4-Hydroxy-3-nitrobenzylidene)-2-methyloxazol-5(4H)-one

Conditions
ConditionsYield
With sodium acetate In acetic anhydride for 4h; Inert atmosphere; Reflux;95%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

N'-(4-hydroxy-3-nitrobenzylidene)-4-methylbenzohydrazide

N'-(4-hydroxy-3-nitrobenzylidene)-4-methylbenzohydrazide

Conditions
ConditionsYield
In methanol for 2h; Reflux;95%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

ethyl acetoacetate
141-97-9

ethyl acetoacetate

malononitrile
109-77-3

malononitrile

C14H11N5O4

C14H11N5O4

Conditions
ConditionsYield
With hydrazine hydrate In water at 20℃; for 0.583333h;95%
4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

C25H15NO9

C25H15NO9

Conditions
ConditionsYield
With ethanolpyridole based semi-dendrimer supported on silica-coated magnetic Fe3O4 nanoparticles In neat (no solvent) for 0.25h;95%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside
3068-32-4

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-formyl-2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
121358-46-1, 77667-26-6

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-formyl-2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions
ConditionsYield
With silver(l) oxide In acetonitrile94%
With silver(l) oxide In acetonitrile for 4h; Inert atmosphere;83%
With silver(l) oxide In acetonitrile at 20℃; for 4h; Inert atmosphere;83%
2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester
6919-98-8

2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

(2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-formyl-2-nitro-phenoxy)tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-formyl-2-nitro-phenoxy)tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
silver(l) oxide In acetonitrile at 23℃; for 16h;94%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

4-hydroxy-3-nitrobenzonitrile
3272-08-0

4-hydroxy-3-nitrobenzonitrile

Conditions
ConditionsYield
With sodium azide; trifluorormethanesulfonic acid In acetonitrile at 20℃; for 0.0333333h; Schmidt reaction;94%
With trifluorormethanesulfonic acid; trimethylsilylazide In acetonitrile at 20℃; for 0.75h; Schmidt Reaction; Sealed tube; Inert atmosphere;82%
With hydroxylamine hydrochloride; sodium formate In formic acid; water
5-methylcyclohexan-1,3-dione
4341-24-6

5-methylcyclohexan-1,3-dione

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one
18940-21-1

5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one

C28H28N2O5
1026246-66-1

C28H28N2O5

Conditions
ConditionsYield
With acetic acid at 120℃; for 0.0333333h; microwave irradiation;94%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

propargyl bromide
106-96-7

propargyl bromide

rac-4-(1-hydroxybut-3-yn-1-yl)-2-nitrophenol
1313026-26-4

rac-4-(1-hydroxybut-3-yn-1-yl)-2-nitrophenol

Conditions
ConditionsYield
Stage #1: propargyl bromide With aluminium; mercury dichloride In tetrahydrofuran; toluene at 65℃; for 0.5h; Inert atmosphere;
Stage #2: 4-hydroxy-3-nitrobenzaldehyde In tetrahydrofuran; toluene Inert atmosphere;
94%
Stage #1: propargyl bromide With aluminium; mercury dichloride In tetrahydrofuran; toluene for 6h; Reflux;
Stage #2: 4-hydroxy-3-nitrobenzaldehyde In tetrahydrofuran; toluene at 0℃; for 0.5h;
94%
Stage #1: propargyl bromide With aluminium; mercury dichloride In tetrahydrofuran; toluene for 6h; Reflux;
Stage #2: 4-hydroxy-3-nitrobenzaldehyde In tetrahydrofuran; toluene at 0℃; for 0.5h;
45%
Stage #1: propargyl bromide With aluminium; mercury dichloride In tetrahydrofuran for 6h; Reflux;
Stage #2: 4-hydroxy-3-nitrobenzaldehyde In tetrahydrofuran at 0℃; for 30h; Inert atmosphere;
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

dimedone
126-81-8

dimedone

9-(4-hydroxy-3-nitrophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

9-(4-hydroxy-3-nitrophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

Conditions
ConditionsYield
With ammonium acetate Hantzsch Dihydropyridine Synthesis; Reflux;94%
2,3-dihydrophthalazine-1,4-dione
1445-69-8

2,3-dihydrophthalazine-1,4-dione

4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

malononitrile
109-77-3

malononitrile

3‐amino‐1‐(4‐hydroxy‐3‐nitrophenyl)‐5,10‐dioxo‐5,10‐dihydro‐1H‐pyrazolo[1,2‐b]phthalazine‐2‐carbonitrile

3‐amino‐1‐(4‐hydroxy‐3‐nitrophenyl)‐5,10‐dioxo‐5,10‐dihydro‐1H‐pyrazolo[1,2‐b]phthalazine‐2‐carbonitrile

Conditions
ConditionsYield
With piperazine immobilized on shell of NiFe2O4-TiO2 core-shell nanoparticles via propylsilyl linkage at 80℃; for 1h;94%
With N,N,2,2,6,6-hexamethyl-N-(3-(trimethoxysilyl)propyl)piperidin-4-ammonium iodide grafted onto TiO2-coated NiFe2O4 nanocatalyst at 80℃; for 0.583333h; Green chemistry;93%
4-hydroxy-3-nitrobenzaldehyde
3011-34-5

4-hydroxy-3-nitrobenzaldehyde

methyl iodide
74-88-4

methyl iodide

4-methoxy-3-nitrobenzaldehyde
31680-08-7

4-methoxy-3-nitrobenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;93.7%
With potassium carbonate
With sodium carbonate In N-methyl-acetamide

3011-34-5Relevant articles and documents

Design, synthesis and nonlinear optical properties of (E)-1-(4-substituted)-3-(4-hydroxy-3-nitrophenyl) prop-2-en-1-one compounds

Saha, Amrita,Shukla, Vijay,Choudhury, Sudip,Jayabalan

, p. 184 - 189 (2016)

A new series of (E)-1-(4-substituted)-3-(4-hydroxy-3-nitrophenyl) prop-2-en-1-one compounds have been synthesized by Claisen-Schmidt condensation reaction. Nonlinear optical characterization were carried out using z-scan technique with nanosecond pulses. These samples are found to exhibit strong nonlinear absorption at 532 nm and the nonlinear absorption coefficient of these samples exponentially increases with the increase of phonon characteristic energy. This relation speaks the role of phonon in the origin of nonlinear absorption in these compounds. The reported dependence of optical nonlinearity of the chalcone derivatives on the phonon characteristic energy will help in designing similar class of new molecules with high nonlinear coefficients.

Zeolite-based hybrid material as an efficient promoter in the green synthesis of mono/bis-phthalazinones

Bodaghifard, Mohammad Ali,Ghasemi, Meisam,Hamidinasab, Mahdia

, p. 3435 - 3448 (2021/09/29)

Hybrid structures containing organic-inorganic porous materials are of great interest as green, heterogeneous, and recyclable catalysts. In this study, a novel organic-inorganic hybrid material (Zeolite HY@DETA) via the surface-functionalization of the Zeolite HY was prepared. The structure of hybrid material was characterized using the Fourier-transform infrared spectroscopy (FT-IR), field emission scanning electron microscopy (FE-SEM), Energy-dispersive X-ray spectroscopy (EDS), thermogravimetric analysis (TGA), and Brunauer–Emmett–Teller (BET) surface area analysis. Subsequently, the catalytic activity of this novel hybrid material was considered in the one-pot three-component synthesis of 3-amino-1-aryl-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile and some bis phthalazine-dione derivatives under green and environmentally benign conditions. The products were synthesized in excellent yields within a short reaction time and identified using elemental analysis, FT-IR, 1H NMR, and 13C NMR spectroscopies. This protocol avoids the use of harmful catalysts, toxic solvents, and harsh reaction conditions. Besides, the catalyst could be recycled for five reaction runs with a slight loss of catalytic activity.

(±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis

Bernal, Freddy A.,Gerhards, Marcel,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.

, (2020/08/06)

Leishmaniasis, a neglected tropical disease caused by parasites of the genus Leishmania, causes a serious burden of disease around the world, represents a threat to the life of millions of people, and therefore is a major public health problem. More effective and non-toxic new treatments are required, especially for visceral leishmaniasis, the most severe form of the disease. On the backdrop that dihydrobenzofurans have previously shown antileishmanial activity, we present here the synthesis of a set of seventy trans-2-phenyl-2,3-dihydrobenzofurans and evaluation of their in vitro activity against Leishmania donovani as well as a discussion of structure-activity relationships. Compounds 8m-o and 8r displayed the highest potency (IC50 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico ADME-like properties and ligand efficiency metrics by a simple scoring function estimating druglikeness highlighted compounds 16c, 18 and 23 as promising candidates for further development. Overall, the potential of trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents was confirmed.

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