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1761-61-1

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1761-61-1 Usage

Chemical Properties

SLIGHTLY YELLOW TO YELLOW-BEIGE POWDER

Uses

5-Bromosalicylaldehyde was used for chemical derivatization during amine quantiifcation in poly (ethylene terephthalate) (PET) film and PET scaffold.

General Description

5-Bromosalicylaldehyde reacts with 1,2-bis(4-chloro-2-aminophenoxy)ethane to yield Schiff base ligand 1,2-bis(2-(5-bromo-2-hydroxybenzilidenamino)-4-chlorophenoxy)ethane. It is the starting reagent for the synthesis of diarylamino-substituted N-methyl tetrahydrosalen ligand.

Check Digit Verification of cas no

The CAS Registry Mumber 1761-61-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,6 and 1 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1761-61:
(6*1)+(5*7)+(4*6)+(3*1)+(2*6)+(1*1)=81
81 % 10 = 1
So 1761-61-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H5BrO2/c8-6-1-2-7(10)5(3-6)4-9/h1-4,10H

1761-61-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A11917)  5-Bromosalicylaldehyde, 98%   

  • 1761-61-1

  • 25g

  • 489.0CNY

  • Detail
  • Alfa Aesar

  • (A11917)  5-Bromosalicylaldehyde, 98%   

  • 1761-61-1

  • 100g

  • 1349.0CNY

  • Detail
  • Alfa Aesar

  • (A11917)  5-Bromosalicylaldehyde, 98%   

  • 1761-61-1

  • 500g

  • 5383.0CNY

  • Detail

1761-61-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Bromosalicylaldehyde

1.2 Other means of identification

Product number -
Other names 5-bromo-2-hydroxybenzaldehyde

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:1761-61-1 SDS

1761-61-1Synthetic route

salicylaldehyde
90-02-8

salicylaldehyde

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With sulfuric acid; C18H16Br4N2O3V; dihydrogen peroxide; potassium bromide In methanol; water at 20℃; for 2.16667h; Catalytic behavior;100%
With sulfuric acid; C20H22Br2N2O5V; dihydrogen peroxide In methanol; water at 20℃; for 1.16667h; Catalytic behavior;100%
With perchloric acid; dihydrogen peroxide; potassium bromide In water at 20℃; for 3.5h;99%
5-bromo-2-hydroxybenzyl alcohol
2316-64-5

5-bromo-2-hydroxybenzyl alcohol

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 0.05h; Microwave irradiation;99%
With potassium dichromate; sulfuric acid
With oxygen In aq. buffer at 45℃; pH=6; Green chemistry;
ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate
954374-78-8

ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate

p-toluidine
106-49-0

p-toluidine

A

C29H30NO7Br
954374-96-0

C29H30NO7Br

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;A 99%
B n/a
2-(5-bromo-2-trityloxyphenyl)-1,3-dioxolane

2-(5-bromo-2-trityloxyphenyl)-1,3-dioxolane

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water for 12h; Heating;98%
With iron(III) p-toluenesulfonate hexahydrate In methanol; water for 4h; Reflux;78%
With copper(II) sulfate; sodium iodide In acetone at 20℃; for 2.75h;67%
5-bromo-2-hydroxybenzaldehyde phenylhydrazone

5-bromo-2-hydroxybenzaldehyde phenylhydrazone

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With cetyltrimethylammonium peroxodisulphate In acetonitrile for 0.133333h; Reflux;93%
formaldehyd
50-00-0

formaldehyd

4-bromo-phenol
106-41-2

4-bromo-phenol

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
Stage #1: formaldehyd With triethylamine; magnesium chloride In tetrahydrofuran for 0.166667h; Inert atmosphere;
Stage #2: 4-bromo-phenol In tetrahydrofuran at 75℃; Inert atmosphere; regioselective reaction;
91%
With triethylamine; magnesium chloride In acetonitrile for 8h; Reflux;82%
Stage #1: 4-bromo-phenol With magnesium methanolate at 20℃; for 0.0166667h;
Stage #2: formaldehyd at 20℃; for 0.166667h;
Stage #3: With sulfuric acid at 20℃; for 0.166667h; regioselective reaction;
45%
ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate
954374-78-8

ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate

isopropylamine
75-31-0

isopropylamine

A

C25H30NO7Br

C25H30NO7Br

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;A 90%
B n/a
2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfonic acid functionalized silica In diethyl ether; acetonitrile at 20℃; for 1.58333h;87%
With N-Bromosuccinimide; 1,3-di-n-butyl-imidazolium tetrafluoroborate at 28 - 35℃; for 0.0833333h;84%
With 1,4-dioxane dibromide at 20℃; for 0.5h;82%
With perchloric acid; dihydrogen peroxide; potassium bromide; [K(H2O)2][VO2(pyridoxal-benzohydrazide)] In water for 4h;36.5%
salicylaldehyde
90-02-8

salicylaldehyde

A

2-hydroxy-3-bromobenzaldehyde
1829-34-1

2-hydroxy-3-bromobenzaldehyde

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With ammonium metavanadate; oxygen; aluminium bromide In 1,4-dioxane at 80℃; for 8h;A 11%
B 86%
With ammonium metavanadate; aluminum tri-bromide; oxygen In 1,4-dioxane at 80℃; for 8h;A 11%
B 86%
With perchloric acid; C12H18MoN2O5; dihydrogen peroxide; potassium bromide In methanol; water at 24.84℃; for 0.25h; Catalytic behavior;
With perchloric acid; dihydrogen peroxide; potassium bromide In water at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent;
4-bromo-2-[1,3]dithiolan-2-yl-phenol

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

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With β‐cyclodextrin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetone at 20℃; for 3h;85%
4-bromo-2-[1,3]oxathiolan-2-yl-phenol

4-bromo-2-[1,3]oxathiolan-2-yl-phenol

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; β‐cyclodextrin In water; acetone at 20℃; for 0.416667h;85%
2-hydroxy-5-bromobenzaldehyde oxime
82486-43-9

2-hydroxy-5-bromobenzaldehyde oxime

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With 1H-imidazole; [bis(acetoxy)iodo]benzene; Cu(AAOPD) In acetonitrile at 20℃; for 0.2h;85%
5-bromosalicylaldehyde dimethyl acetal
501085-54-7

5-bromosalicylaldehyde dimethyl acetal

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With β‐cyclodextrin In methanol; water at 50℃; for 10h;80%
salicylaldehyde
90-02-8

salicylaldehyde

A

3,5-Dibromosalicylaldehyde
90-59-5

3,5-Dibromosalicylaldehyde

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With perchloric acid; C72H100N4O7V2; dihydrogen peroxide; potassium bromide In tetrahydrofuran; methanol; water at 25℃; for 12h; Kinetics; Catalytic behavior; Time; Reagent/catalyst; Solvent;A 13%
B 77%
With perchloric acid; C74H104N4O7V2; dihydrogen peroxide; potassium bromide In tetrahydrofuran; methanol; water at 25℃; for 12h; Catalytic behavior; Reagent/catalyst; Time;A n/a
B 74%
With dihydrogen peroxide; sodium bromide In acetic acid at 20℃; Green chemistry;A 40%
B 60%
6-bromo-2,2-dimethylbenzo[1,3]dioxin-4-one
82944-17-0

6-bromo-2,2-dimethylbenzo[1,3]dioxin-4-one

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h;75%
ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate
954374-78-8

ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate

4-amino-phenol
123-30-8

4-amino-phenol

A

C28H28NO8Br

C28H28NO8Br

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid In acetone at 20℃; for 12h;A 75%
B n/a
ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate
954374-78-8

ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate

sulfanilamide
63-74-1

sulfanilamide

A

C28H29N2O9BrS

C28H29N2O9BrS

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;A 75%
B n/a
salicylaldehyde
90-02-8

salicylaldehyde

A

3,5-Dibromosalicylaldehyde
90-59-5

3,5-Dibromosalicylaldehyde

B

2,3,5-tribromo-6-hydroxybenzaldehyde

2,3,5-tribromo-6-hydroxybenzaldehyde

C

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With perchloric acid; C36H50ClN2O3V; dihydrogen peroxide; potassium bromide In tetrahydrofuran; methanol; water at 25℃; for 12h; Kinetics; Catalytic behavior; Time; Reagent/catalyst; Solvent;A 8%
B n/a
C 73%
2-benzyloxy-5-bromobenzaldehyde
121124-94-5

2-benzyloxy-5-bromobenzaldehyde

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃; for 1h;70%
salicylaldehyde
90-02-8

salicylaldehyde

A

2-bromo-6-hydroxybenzaldehyde
22532-61-2

2-bromo-6-hydroxybenzaldehyde

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With trimethylsilyl bromide; bis(4-chlorophenyl)sulfoxide In acetonitrile at 25℃; for 6h; Inert atmosphere; regioselective reaction;A n/a
B 70%
2-hydroxy-5-bromobenzaldehyde oxime
82486-43-9

2-hydroxy-5-bromobenzaldehyde oxime

A

5-bromosalicyclic acid
89-55-4

5-bromosalicyclic acid

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With calcium hypochlorite; montmorillonite K-10 In chloroform at 20℃; for 4h;A 2.5%
B 69%
4-bromo-phenol
106-41-2

4-bromo-phenol

chloroform
67-66-3

chloroform

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 0.0666667h; Reimer-Tiemann reaction; Irradiation;60%
With pyridine; sodium hydroxide at 50 - 60℃; zuletzt bei 100grad;
With potassium hydroxide at 25℃; for 15h; Irradiation; or with pyridine;17.57 % Chromat.
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With palladium diacetate; toluene-4-sulfonic acid; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate; acetic acid; 2-Amino-4-chlorobenzoic acid at 90℃; for 24h; Sealed tube;56%
ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate
954374-78-8

ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate

benzaldehyde
100-52-7

benzaldehyde

p-toluidine
106-49-0

p-toluidine

A

C29H30NO7Br
954374-96-0

C29H30NO7Br

B

diethyl 1-(4-methylphenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
136886-13-0

diethyl 1-(4-methylphenyl)-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate

C

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 3h;A 55%
B 40%
C n/a
ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate
954374-78-8

ethyl (E)-3-(4-bromo-2-formylphenoxy)acrylate

p-aminoethylbenzoate
94-09-7

p-aminoethylbenzoate

A

C31H32NO9Br

C31H32NO9Br

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;A 50%
B n/a
4-bromo-phenol
106-41-2

4-bromo-phenol

hexamethylenetetramine
100-97-0

hexamethylenetetramine

A

2,6-diformyl-4-bromophenol
109517-99-9

2,6-diformyl-4-bromophenol

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid at 100℃; for 24h; Duff Aldehyde Synthesis; Inert atmosphere;A 35%
B 25%
6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine
252-72-2

6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With bromine
5-bromosalicyclic acid
89-55-4

5-bromosalicyclic acid

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

Conditions
ConditionsYield
With sodium amalgam; boric acid; sodium sulfite
Multi-step reaction with 2 steps
1: trifluoroacetic anhydride; trifluoroacetic acid / 48 h / 20 °C
2: 75 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C
View Scheme
2-Acetoxy-benzoic acid 4-bromo-2-formyl-phenyl ester

2-Acetoxy-benzoic acid 4-bromo-2-formyl-phenyl ester

A

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

B

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With hydroxide In 1,4-dioxane; water at 37℃; Rate constant; Thermodynamic data; var. temp., ΔH(excit.), ΔS)(excit.);
6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine
252-72-2

6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine

bromine
7726-95-6

bromine

acetic acid
64-19-7

acetic acid

A

3,5-Dibromosalicylaldehyde
90-59-5

3,5-Dibromosalicylaldehyde

B

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

C

anhydro-bis-<5-bromo-salicylaldehyde >

anhydro-bis-<5-bromo-salicylaldehyde >

ethyl acetoacetate
141-97-9

ethyl acetoacetate

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

3-Acetyl-6-bromo-chromen-2-one
2199-93-1

3-Acetyl-6-bromo-chromen-2-one

Conditions
ConditionsYield
With piperidine In ethanol at 80℃; for 0.0166667h; Knoevenagel Condensation; Microwave irradiation; Green chemistry;100%
With zinc oxide nanoparticle at 120℃; under 7200.72 Torr; for 0.1h; Knoevenagel condensation; Microwave irradiation; Neat (no solvent);95%
With piperidine In acetonitrile at 20℃; for 4h; Knoevenagel Condensation;94.1%
5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-hydroxybenzyl alcohol
2316-64-5

5-bromo-2-hydroxybenzyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran100%
With sodium tetrahydroborate; Dowex1-x8 In tetrahydrofuran at 20℃; for 0.01h;98%
With sodium tetrahydroborate; ethanol at 0 - 5℃; for 2h; Reagent/catalyst;98%
allyl bromide
106-95-6

allyl bromide

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

2-allyloxy-5-bromobenzaldehyde
40359-62-4

2-allyloxy-5-bromobenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;100%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 2h;99%
With potassium carbonate In N,N-dimethyl-formamide97%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

4-bromo-2-[(5-methyl-3-isoxazolyl)imino]methylphenol
88812-68-4

4-bromo-2-[(5-methyl-3-isoxazolyl)imino]methylphenol

Conditions
ConditionsYield
Reflux;100%
In ethanol for 2h; Reflux;95%
In ethanol Heating;
ethyl bromoacetate
105-36-2

ethyl bromoacetate

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

methyl (4-bromo-2-formylphenoxy)acetate
24581-99-5

methyl (4-bromo-2-formylphenoxy)acetate

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide for 15h; Ambient temperature;100%
benzyl bromide
100-39-0

benzyl bromide

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

2-benzyloxy-5-bromobenzaldehyde
121124-94-5

2-benzyloxy-5-bromobenzaldehyde

Conditions
ConditionsYield
Stage #1: 5-bromosalicyclaldehyde With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 4h;
100%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 4h;100%
With potassium carbonate In N,N-dimethyl-formamide for 18h; Inert atmosphere;99%
1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-((4-chlorobenzyl)oxy)benzaldehyde
428482-55-7

5-bromo-2-((4-chlorobenzyl)oxy)benzaldehyde

Conditions
ConditionsYield
Stage #1: 5-bromosalicyclaldehyde With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h;
Stage #2: 1-Chloro-4-(chloromethyl)benzene In DMF (N,N-dimethyl-formamide) at 65℃;
100%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 4h;98%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;98.9%
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 2h;
1,2-diaminopropan
78-90-0, 10424-38-1

1,2-diaminopropan

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

C17H16Br2N2O2

C17H16Br2N2O2

Conditions
ConditionsYield
In ethanol for 3h; Heating;100%
p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

3-bromo-6-((4-methoxybenzyl)oxy)benzaldehyde
325457-67-8

3-bromo-6-((4-methoxybenzyl)oxy)benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 3h;100%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;83%
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 2h;
With potassium carbonate In N,N-dimethyl-formamide at 60℃;
Stage #1: 5-bromosalicyclaldehyde With sodium hydride In dichloromethane at 20℃; for 0.5h;
Stage #2: p-methoxybenzyl chloride In dichloromethane at 20℃; for 16h;
5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

2-(bromomethyl)-1,3,5-trifluorobenzene
151411-98-2

2-(bromomethyl)-1,3,5-trifluorobenzene

5-bromo-2-(2,4,6-trifluorobenzyloxy)-benzaldehyde
632626-99-4

5-bromo-2-(2,4,6-trifluorobenzyloxy)-benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 55℃;100%
methanol
67-56-1

methanol

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromosalicylaldehyde dimethyl acetal
501085-54-7

5-bromosalicylaldehyde dimethyl acetal

Conditions
ConditionsYield
With sodium tetrahydroborate at 0 - 20℃; for 1h;100%
propyl bromide
106-94-5

propyl bromide

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-propoxybenzaldehyde
61564-89-4

5-bromo-2-propoxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;93%
With potassium carbonate In water; N,N-dimethyl-formamide
5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

5-bromosalicylaldehyde dimethyl acetal
501085-54-7

5-bromosalicylaldehyde dimethyl acetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 20℃; for 1h;100%
With toluene-4-sulfonic acid for 24h; Heating / reflux;89%
With Amberlyst 15 resin In methanol at 20℃; for 20h; Inert atmosphere;
With Amberlyst 15 In methanol at 20℃; for 20h;
2-(tert-butyldimethylsilyloxy)ethyl bromide
86864-60-0

2-(tert-butyldimethylsilyloxy)ethyl bromide

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-(2-(tert-butyldimethylsilyloxy)ethoxy)benzaldehyde
949027-49-0

5-bromo-2-(2-(tert-butyldimethylsilyloxy)ethoxy)benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h;100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 20h; Inert atmosphere;73%
2-methylpropylmagnesium chloride
5674-02-2

2-methylpropylmagnesium chloride

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

4-bromo-2-(1-hydroxy-2-methylpropyl)phenol
1029529-29-0

4-bromo-2-(1-hydroxy-2-methylpropyl)phenol

Conditions
ConditionsYield
Stage #1: 2-methylpropylmagnesium chloride; 5-bromosalicyclaldehyde In tetrahydrofuran; diethyl ether at 20℃; for 0.25h;
Stage #2: With hydrogenchloride; water; ammonium chloride In tetrahydrofuran; methanol; diethyl ether
100%
propargyl bromide
106-96-7

propargyl bromide

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-prop-2-ynyloxy-benzaldehyde
122835-14-7

5-bromo-2-prop-2-ynyloxy-benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;100%
Stage #1: 5-bromosalicyclaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃;
97%
With potassium carbonate In acetonitrile at 20℃; for 24h;95%
methanol
67-56-1

methanol

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

5-bromosalicylaldehyde dimethyl acetal
501085-54-7

5-bromosalicylaldehyde dimethyl acetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 1h;100%
5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

cyanomethyl bromide
590-17-0

cyanomethyl bromide

2-(4-bromo-2-formylphenoxy)acetonitrile
125418-95-3

2-(4-bromo-2-formylphenoxy)acetonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;100%
Stage #1: 5-bromosalicyclaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere;
Stage #2: cyanomethyl bromide In N,N-dimethyl-formamide Inert atmosphere;
82%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 8h;73%
Stage #1: 5-bromosalicyclaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere;
Stage #2: cyanomethyl bromide In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;
Stage #1: 5-bromosalicyclaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere;
Stage #2: cyanomethyl bromide In N,N-dimethyl-formamide at 20℃;
1-(2-chloroethyl)pyrrolidine hydrochloride
7250-67-1

1-(2-chloroethyl)pyrrolidine hydrochloride

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-(2-(pyrrolidin-1-yl)ethoxy)benzaldehyde
866930-38-3

5-bromo-2-(2-(pyrrolidin-1-yl)ethoxy)benzaldehyde

Conditions
ConditionsYield
Stage #1: 5-bromosalicyclaldehyde With potassium carbonate In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: 1-(2-chloroethyl)pyrrolidine hydrochloride In tetrahydrofuran at 80℃; for 12h;
100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;22%
5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

methyl iodide
74-88-4

methyl iodide

5-bromo-2-methoxybenzaldehyde
25016-01-7

5-bromo-2-methoxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
Stage #1: 5-bromosalicyclaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 21℃; Inert atmosphere;
98%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 15h;98%
3-bromo-2-phenylprop-1-ene
3360-54-1

3-bromo-2-phenylprop-1-ene

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-(2-phenylallyloxy)benzaldehyde
1310930-86-9

5-bromo-2-(2-phenylallyloxy)benzaldehyde

Conditions
ConditionsYield
With (Z)-β-bromo-α-methylstyrene; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 13h; Inert atmosphere;100%
2-amino-1-benzylamine
4403-69-4

2-amino-1-benzylamine

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

4-bromo-2-[2-(5-bromo-2-hydroxybenzylideneaminomethyl)phenyliminomethyl]phenol
501447-01-4

4-bromo-2-[2-(5-bromo-2-hydroxybenzylideneaminomethyl)phenyliminomethyl]phenol

Conditions
ConditionsYield
In methanol Warming;100%
In methanol Reflux;87.9%
N-isopropylethane-1,2-diamine
19522-67-9

N-isopropylethane-1,2-diamine

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

4-bromo-2-[(2-isopropylaminoethylimino)methyl]phenol
1266680-11-8

4-bromo-2-[(2-isopropylaminoethylimino)methyl]phenol

Conditions
ConditionsYield
In methanol100%
In methanol at 20℃; for 0.166667h;95%
2-cyano-N-cyclohexylacetamide
15029-38-6

2-cyano-N-cyclohexylacetamide

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

6-bromo-N-cyclohexyl-2-imino-2H-chromene-3-carboxamide
891583-06-5

6-bromo-N-cyclohexyl-2-imino-2H-chromene-3-carboxamide

Conditions
ConditionsYield
With sodium carbonate In water at 20℃;100%
With 42H3N*42H(1+)*72Mo(6+)*60Mo(5+)*372O(2-)*72H2O*30C2H3O2(1-) In neat (no solvent) at 110℃; for 0.166667h; Green chemistry;90%
2-(2-Aminoethylamino)ethanol
111-41-1

2-(2-Aminoethylamino)ethanol

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

4-bromo-2-[(2-(2-hydroxyethylamino)ethylimino)methyl]phenol
1395880-19-9

4-bromo-2-[(2-(2-hydroxyethylamino)ethylimino)methyl]phenol

Conditions
ConditionsYield
In methanol100%
N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

2-(2-(diethylamino)ethyliminomethyl)-4-bromophenol
333752-77-5

2-(2-(diethylamino)ethyliminomethyl)-4-bromophenol

Conditions
ConditionsYield
In methanol100%
In methanol for 1h; Reflux;
In acetonitrile for 1h;
cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-(cyclopropylmethoxy)benzaldehyde
1156170-18-1

5-bromo-2-(cyclopropylmethoxy)benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
With potassium carbonate In tetrahydrofuran at 70℃; for 40h; Inert atmosphere; Reflux;83%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

5-bromo-2-[(tert-butyldimethylsilyl)oxy]benzaldehyde

5-bromo-2-[(tert-butyldimethylsilyl)oxy]benzaldehyde

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃;100%
With 1H-imidazole In dichloromethane at 20℃; Schlenk technique;
With 1H-imidazole In dichloromethane at 0℃; Sealed tube;
ethylenediamine
107-15-3

ethylenediamine

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

2-[(2-aminoethylimino)methyl]-4-bromophenol
1447755-14-7

2-[(2-aminoethylimino)methyl]-4-bromophenol

Conditions
ConditionsYield
In methanol for 0.5h;100%

1761-61-1Relevant articles and documents

Vanadium(V) complexes of some bidentate hydrazone ligands and their bromoperoxidase activity

Adak, Piyali,Ghosh, Bipinbihari,Pakhira, Bholanath,Sekiya, Ryo,Kuroda, Reiko,Chattopadhyay, Shyamal Kumar

, p. 135 - 143 (2017)

Dinuclear methoxy bridged complexes of vanadium, [VO(μ-OMe)(OMe)(L)]2(1–3) have been synthesized from the reaction of VOSO4·H2O with triethylamine and the respective hydrazone ligand. The compounds have been characterized by spectroscopic methods and determination of single crystal X-ray structure of one of them (1). DFT and TD-DFT calculations were used to understand the electronic structures of the complexes and their electronic spectra respectively. Though the dimeric complexes are stable in the solid state, the ESI-MS spectra as well as1H NMR spectra of the complexes suggest that in solution the monomeric forms of the complexes are the major species. The V(V) complexes in DMF were used to catalyze the oxidative bromination of salicylaldehyde, in aqueous H2O2/KBr in the presence of HClO4at room temperature. The complexes show exceptionally high bromoperoxidase activity with salicylaldehyde as a model substrate to produce 5-bromo salicylaldehyde in good yield and high TOF and TON. Therefore, these complexes behave as functional models of vanadate dependent bromoperoxidase enzyme.

-

Barker et al.

, p. 1327 (1966)

-

Efficient one-pot synthesis of ethyl [2-(2H-Chromene-3yl)-4-oxo-L,3- thiazolidin-3-yl]acetates

Reddy, S. Satyanarayana,Krupadanam, G. L. David

, p. 1305 - 1311 (2010)

Ethyl [2-(2H-chromene-3yl)-4-oxo-1,3-thiazolidin-3yl]acetates (6a-e) were synthesized in a single pot by the reaction of 2H-3-chromenecarbaldehydes (3a-e), glycine ethyl ester hydrochloride (4), and mercaptoacetic acid (5) in diisopropylethylamine/benzene under refluxing conditions in a Dean-Stark trap.

Copper(II) N, N, O-Chelating Complexes as Potential Anticancer Agents

Pe?a, Quim,Sciortino, Giuseppe,Maréchal, Jean-Didier,Bertaina, Sylvain,Simaan, A. Jalila,Lorenzo, Julia,Capdevila, Mercè,Bayón, Pau,Iranzo, Olga,Palacios, òscar

, p. 2939 - 2952 (2021)

Three novel dinuclear Cu(II) complexes based on a N,N,O-chelating salphen-like ligand scaffold and bearing varying aromatic substituents (-H, -Cl, and -Br) have been synthesized and characterized. The experimental and computational data obtained suggest that all three complexes exist in the dimeric form in the solid state and adopt the same conformation. The mass spectrometry and electron paramagnetic resonance results indicate that the dimeric structure coexists with the monomeric form in solution upon solvent (dimethyl sulfoxide and water) coordination. The three synthesized Cu(II) complexes exhibit high potentiality as ROS generators, with the Cu(II)/Cu(I) redox potential inside the biological redox window, and thus being able to biologically undergo Cu(II)/Cu(I) redox cycling. The formation of ROS is one of the most promising reported cell death mechanisms for metal complexes to offer an inherent selectivity to cancer cells. In vitro cytotoxic studies in two different cancer cell lines (HeLa and MCF7) and in a normal fibroblast cell line show promising selective cytotoxicity for cancer cells (IC50 about 25 μM in HeLa cells, which is in the range of cisplatin and improved with respect to carboplatin), hence placing this N,N,O-chelating salphen-like metallic core as a promising scaffold to be explored in the design of future tailor-made Cu(II) cytotoxic compounds.

Syntheses and characterization of monobasic tridentate Cu(II) Schiff-base complexes for efficient oxidation of 3,5-di-: tert -butylcatechol and oxidative bromination of organic substrates

Kumari, Sweta,Mahato, Arun Kumar,Maurya, Abhishek,Singh, Vijay Kumar,Kesharwani, Neha,Kachhap, Payal,Koshevoy, Igor O.,Haldar, Chanchal

, p. 13625 - 13646 (2017)

Two monomeric copper complexes [CuII(sal-ppzH)Cl2] (1) and [CuII(hyap-ppzH)Cl2] (2) were synthesized by reacting CuCl2·2H2O with the monobasic tridentate Schiff-base ligands [Hsal-ppz] (I) and [Hyap-ppz] (II) (derived by reacting 1-(2-aminoethyl) piperazine with salicylaldehyde and 2-hydroxyacetophenone) respectively. Elemental analysis, IR, UV-Vis, 1H NMR and 13C NMR data confirm the structures of the ligands and those of the complexes. Both complexes are monomeric in nature in the solid state and in solution as well. Single crystal XRD data suggest a distorted square pyramidal geometry for 1 crystallized in the P1 space group. DFT studies established a similar molecular structure for 2. The synthesized metal complexes [CuII(sal-ppzH)Cl2] (1) and [CuII(hyap-ppzH)Cl2] (2) successfully catalyzed the oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC) in methanol in the presence of H2O2 with high Kcat values of 1.182 × 104 mmol h-1 and 2.880 × 104 mmol h-1, respectively. [CuII(sal-ppzH)Cl2] (1) and [CuII(hyap-ppzH)Cl2] (2) were also anchored into the polymeric matrix of chloromethylated polystyrene and were analyzed by TGA, atomic absorption spectroscopy (AAS), EPR, scanning electron microscopy (SEM) as well as energy dispersive X-ray (EDX) analysis. The polymer grafted metal complexes were used as catalyst precursors in the oxidative bromination of salicylaldehyde in the presence of H2O2, KBr and HClO4. Under optimized reaction conditions, both catalysts show nearly quantitative oxidative bromination of salicylaldehyde, with the order of % products formed being 5-bromosalicylaldehyde > 3,5-dibromosalicylaldehyde > 3-bromosalicylaldehyde. Plausible reactive species involved in the catalytic cycle are identified by UV-Vis spectroscopy, pH metric titration, ESI-MS, EPR and DFT studies.

Synthesis and characterization of Azo schiff bases and their β-lactam derivatives

Shinde, Anil H.,Patil

, p. 1520 - 1524 (2020)

Azo salicylaldehyde (I5) was synthesized by reaction of 5-bromo-salicylaldehyde with diazonium salt of 4-nitroaniline by diazotization method. Thus, synthesized azoaldehyde was treated with variable 2-aminobenzothiazoles (I6a-f) to synthesize the Schiff bases (I7a-f). The β-lactam derivatives (I8a-f) were also synthesized. All the newly synthesized compounds were characterized by TLC, UV-visible and FT-IR techniques.

Design and synthesis of novel Vitamin D-coumarin hybrids using microwave irradiation

Zhang, Hengrui,Fang, Zhijie

, p. 684 - 687 (2017)

A series of novel vitamin D-coumarin hybrids were synthesised by esterification of the corresponding coumarin-3-carboxylic acids and vitamin D or vitamin D CD-ring alcohol in CH2Cl2 under microwave irradiation. They were obtained in higher yields (from 64-81% up to 79-87%) and shorter reaction time (from 3 h down to 15 min), compared with earlier conventional methodologies. The structures of all the target compounds were confirmed by 1H NMR, 13C NMR and HRMS. This provides an attractive and alternative method for the preparation of high-value vitamin D-coumarin hybrids.

Synthesis, characterization, reactivity, and catalytic studies of heterobimetallic vanadium(V) complexes containing hydrazone ligands

Borthakur, Rosmita,Dhanpat, Shobha A.,Kumar, Arvind,Kurbah, Sunshine D.,Lal, Ram A.,Syiemlieh, Ibanphylla

supporting information, (2020/10/21)

Six heterobimetallic alkali metal dioxidovanadium(V) coordination polymer complexes {[M6{VO(μ-O)}2(μ-OH)4(μ4-slox/nph)].n DMF}∞ where M = Na, K, and Cs; n = 1 for (1), 0 for (2)-(6) of two dihydrazone ligands, disalicylaldehydeoxaloyldihydrazone (H4slox) and bis(2-hydroxy-1-naphthaldehyde)oxaloyldihydrazone (H4nph) are reported. All the complexes have been characterized by various physicochemical techniques such as elemental analyses, molar conductance, IR, NMR, UV–vis, and cyclic voltammetry. The IR, 1HNMR, and 13CNMR spectral data suggest that the dihydrazones are coordinated through phenolate/naphtholate oxygen, enolate oxygen, and azine nitrogen atoms to the metal centres. The structure of complex {[Na6{VO(μ-O)}2(μ-OH)4(μ4-slox)].DMF}∞ (1) is also determined by single-crystal X-ray data, which revealed that the H4slox coordinated via all possible dative sites to metal centres as tetrabasic octadentate ligand. The vanadium metal centres adopted distorted square-pyramidal coordination geometries, and the sodium atoms are also in five coordination atmospheres. The electronic spectra of the complexes showed LMCT bands in addition to intra-ligand π → π* and n → π* transitions. As evident from the cyclic voltammetry, the complexes showed two metal-centred electron transfer reactions {[(VVVV(slox)2?/VVVIV(slox)3?] and [(VVVIV(slox)3?/VVVIV(slox)4?]}, in addition to the ligand centred electron transfer reactions. Further, bovine serum albumin (BSA interaction studies of the complexes {[Na6{VO(μ-O)}2(μ-OH)4(μ4-slox)].DMF}∞ (1) and [Na6{VO(μ-O)}2(μ-OH)4(μ4-nph)]∞ (4) revealed strong binding affinity. Moreover, the catalytic studies of the complexes (1) and (4) were found to be effective for the oxidation of alcohols into their corresponding aldehydes and ketones and bromination of some organic substrates in the presence of H2O2 as an oxidizing agent.

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