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616-76-2

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616-76-2 Usage

Chemical Properties

light beige fine crystalline powder

Uses

5-Formylsalicylic Acid is used as a selective phase for the extraction of iron(III) in silica gel. It is also used in preparation of styrylquinolines as potent HIV-1 integrase inhibitors that block HIV-1 replication in CEM cells.

Check Digit Verification of cas no

The CAS Registry Mumber 616-76-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 6 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 616-76:
(5*6)+(4*1)+(3*6)+(2*7)+(1*6)=72
72 % 10 = 2
So 616-76-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O4/c9-4-5-1-2-7(10)6(3-5)8(11)12/h1-4,10H,(H,11,12)/p-1

616-76-2SDS

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 5-Formylsalicylic acid

1.2 Other means of identification

Product number -
Other names 5-formyl-2-hydroxybenzoic acid

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:616-76-2 SDS

616-76-2Synthetic route

5-Methylsalicylic acid
89-56-5

5-Methylsalicylic acid

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
With oxygen; cobalt(II) diacetate tetrahydrate; sodium hydroxide In ethylene glycol at 80℃; under 760.051 Torr; for 8h;89%
With oxygen; sodium hydroxide In 2-methoxy-ethanol at 80℃; for 7h; chemoselective reaction;
m-formylphenyl benzoic acid
619-21-6

m-formylphenyl benzoic acid

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
With oxygen; potassium acetate; palladium diacetate; C19H24N2O; p-benzoquinone In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 24h; regioselective reaction;73%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

salicylic acid
69-72-7

salicylic acid

A

3-formylsalicylic acid
610-04-8

3-formylsalicylic acid

B

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
Stage #1: hexamethylenetetramine; salicylic acid With copper(I) oxide In trifluoroacetic acid for 5h; Duff Aldehyde Synthesis; Reflux;
Stage #2: With hydrogenchloride In water at 20℃; for 1h; Concentration; Reagent/catalyst; regioselective reaction;
A 55.7%
B 24.3%
Stage #1: hexamethylenetetramine; salicylic acid With acetic acid for 2h; Reflux;
Stage #2: With sulfuric acid for 1h; Reflux;
With acetic acid for 8h; Reflux;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

salicylic acid
69-72-7

salicylic acid

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
With acetic acid for 8h; Temperature; Reflux;16%
With water for 16h; Heating;12%
In water at 100℃; for 16h;2.2 g
In water at 100℃; for 16h;2.2 g
hexamethylenetetramine
100-97-0

hexamethylenetetramine

acetic acid
64-19-7

acetic acid

salicylic acid
69-72-7

salicylic acid

A

3-formylsalicylic acid
610-04-8

3-formylsalicylic acid

B

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
anschliessendes Behandeln mit wss. Salzsaeure;
4-hydroxyisophthalic acid
636-46-4

4-hydroxyisophthalic acid

A

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

B

5-formyl-4-hydroxy-isophthalic acid
855641-74-6

5-formyl-4-hydroxy-isophthalic acid

Conditions
ConditionsYield
With potassium hydroxide; chloroform; water
2-hydroxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid
85392-08-1

2-hydroxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
With potassium hydroxide
With sulfuric acid
formaldehyd
50-00-0

formaldehyd

salicylic acid
69-72-7

salicylic acid

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
With sodium hydroxide anschliessendes Erhitzen mit Natrium-<3-nitro-benzolsulfonat>;
in Gegenwart einer aromatischen Hydroxylaminverbindung und Zersetzung des Reaktionsproduktes;
chloroform
67-66-3

chloroform

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

salicylic acid
69-72-7

salicylic acid

A

3-formylsalicylic acid
610-04-8

3-formylsalicylic acid

B

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
Product distribution;
chloroform
67-66-3

chloroform

salicylic acid
69-72-7

salicylic acid

A

3-formylsalicylic acid
610-04-8

3-formylsalicylic acid

B

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
With sodium hydroxide
Bromoform
75-25-2

Bromoform

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

salicylic acid
69-72-7

salicylic acid

A

3-formylsalicylic acid
610-04-8

3-formylsalicylic acid

B

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
Product distribution;
formaldehyd
50-00-0

formaldehyd

water
7732-18-5

water

salicylic acid
69-72-7

salicylic acid

hydroxylamino-benzenesulfonic acid

hydroxylamino-benzenesulfonic acid

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
Zersetzung des Produktes mit Salzsaeure;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

water
7732-18-5

water

salicylic acid
69-72-7

salicylic acid

A

3-formylsalicylic acid
610-04-8

3-formylsalicylic acid

B

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
anschliessendes Behandeln mit wss. Salzsaeure;
chloroform
67-66-3

chloroform

salicylic acid
69-72-7

salicylic acid

NaOH/KOH

NaOH/KOH

A

3-formylsalicylic acid
610-04-8

3-formylsalicylic acid

B

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

sulfuric acid
7664-93-9

sulfuric acid

2-hydroxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid
85392-08-1

2-hydroxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

2-hydroxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid
85392-08-1

2-hydroxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid

methanol. KOH-solution

methanol. KOH-solution

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

2-hydroxy-5-(hydroxymethyl)benzoic acid
7437-20-9

2-hydroxy-5-(hydroxymethyl)benzoic acid

potassium dichromate

potassium dichromate

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

salicylic acid
69-72-7

salicylic acid

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid
2: sulfuric acid
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / Erwaermen des Reaktionsprodukts mit Chlorwasserstoff enthaltendem Methanol
2: sulfuric acid
View Scheme
potassium hydrogencarbonate
298-14-6

potassium hydrogencarbonate

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

Conditions
ConditionsYield
With Lyophilized E. coli whole cells overexpressed Aspergillus oryzae 2,3-dihydroxybenzoic acid decarboxylase In methanol; aq. phosphate buffer at 30℃; pH=8.5; Enzymatic reaction; regioselective reaction;
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl 2-hydroxy-5-formylbenzoate
176047-66-8

benzyl 2-hydroxy-5-formylbenzoate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;100%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;100%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20 - 25℃; for 24h; Inert atmosphere;90%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

p-Methoxybenzyl bromide
2746-25-0

p-Methoxybenzyl bromide

C16H14O5
1251530-68-3

C16H14O5

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;100%
methanol
67-56-1

methanol

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

methyl-5-formyl-2-hydroxybenzoate
41489-76-3

methyl-5-formyl-2-hydroxybenzoate

Conditions
ConditionsYield
With sulfuric acid for 24h; Heating / reflux;99%
With sulfuric acid at 90℃; for 5h;99.98%
With sulfuric acid for 48h; Reflux;96%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

5-cyano-2-hydroxybenzoic acid
10435-57-1

5-cyano-2-hydroxybenzoic acid

Conditions
ConditionsYield
With formic acid; hydroxyammonium sulfate; sodium formate at 80℃; for 6h;99%
Multi-step reaction with 3 steps
1: potassium carbonate / butanone / 8 h / Heating / reflux
2: hydroxylamine hydrochloride / 1-methyl-pyrrolidin-2-one / 4 h / 115 °C
3: hydrogen / 5%-palladium/activated carbon / tetrahydrofuran; ethanol / 2 h / 20 °C
View Scheme
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

5-Formyl-2-hydroxy-benzoyl chloride
138851-41-9

5-Formyl-2-hydroxy-benzoyl chloride

Conditions
ConditionsYield
With thionyl chloride at 85℃;99%
2-(aminophenyl)benzimidazole
5805-39-0

2-(aminophenyl)benzimidazole

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

5-(5,6-dihydrobenzimidazolo[1,2-c]-quinazolin-6-yl)salicylic acid

5-(5,6-dihydrobenzimidazolo[1,2-c]-quinazolin-6-yl)salicylic acid

Conditions
ConditionsYield
With acetic acid In ethanol at 20℃; for 8h; Pictet-Spengler Synthesis; Sonication;99%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

N-isopropylhydroxyamine
5080-22-8

N-isopropylhydroxyamine

sodium (Z)-2-hydroxy-5-((isopropyloxidoimino)methyl)benzoate

sodium (Z)-2-hydroxy-5-((isopropyloxidoimino)methyl)benzoate

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid; N-isopropylhydroxyamine In methanol at 20℃;
Stage #2: With sodium hydroxide In methanol; water at 20℃;
96%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl 5-formyl-2-(benzyloxy)benzoate
150258-60-9

benzyl 5-formyl-2-(benzyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 16h;95%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 20h;85%
With caesium carbonate In ethyl acetate; N,N-dimethyl-formamide77%
nitromethane
75-52-5

nitromethane

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

2-hydroxy-5-(2-nitroethenyl)benzoic acid
42571-07-3

2-hydroxy-5-(2-nitroethenyl)benzoic acid

Conditions
ConditionsYield
With ammonium acetate In ethanol at 60℃; for 1h;93%
With ammonium acetate In ethanol at 60℃; for 1h;93%
With ammonium acetate In ethanol at 60℃; for 1h;93%
With N-butylamine In acetic acid for 3h; Heating;48%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-butyl 5-formyl-2-hydroxybenzoate
431049-86-4

tert-butyl 5-formyl-2-hydroxybenzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran93%
With dicyclohexyl-carbodiimide for 3h; Reflux;75%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

terbium(III) acetate tetrahydrate
15280-54-3, 85077-88-9, 100587-92-6

terbium(III) acetate tetrahydrate

tetrasodium ethylenediamine-N,N,N',N'-tetraacetate

tetrasodium ethylenediamine-N,N,N',N'-tetraacetate

C18H16N2O12Tb(3-)*3Na(1+)*4H2O

C18H16N2O12Tb(3-)*3Na(1+)*4H2O

Conditions
ConditionsYield
Stage #1: terbium(III) acetate tetrahydrate; tetrasodium ethylenediamine-N,N,N',N'-tetraacetate With sodium hydroxide In ethanol; water at 60℃; for 1h;
Stage #2: 2-hydroxy-5-formylbenzoic acid In ethanol; water at 60℃; for 1h; Quantum yield;
89%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

γ-benzyl L-glutamate hydrochloride

γ-benzyl L-glutamate hydrochloride

5-formyl-2-hydroxy-benzoylglutamic acid dibenzyl ester

5-formyl-2-hydroxy-benzoylglutamic acid dibenzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: γ-benzyl L-glutamate hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
88.4%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

1-pentanamine
110-58-7

1-pentanamine

5-formyl-2-hydroxy-N-pentyl-benzamide
369366-12-1

5-formyl-2-hydroxy-N-pentyl-benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dacarbazine In dichloromethane88%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

L-valine benzyl ester hydrochloride
2462-34-2

L-valine benzyl ester hydrochloride

5-formyl-2-hydroxy-benzoylvaline benzyl ester

5-formyl-2-hydroxy-benzoylvaline benzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: L-valine benzyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
87.3%
(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid hydrochloride

(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid hydrochloride

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

5-formyl-2-hydroxy-benzoylaspartic acid dibenzyl ester

5-formyl-2-hydroxy-benzoylaspartic acid dibenzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: (S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
86.9%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

5-formyl-2-hydroxy-3-nitro-benzoic acid

5-formyl-2-hydroxy-3-nitro-benzoic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0℃; for 3h;86.6%
With sulfuric acid; nitric acid at -10 - -5℃;
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

tyrosine benzyl ester hydrochloride
15035-17-3

tyrosine benzyl ester hydrochloride

5-formyl-2-hydroxy-benzoyltyrosine benzyl ester

5-formyl-2-hydroxy-benzoyltyrosine benzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: tyrosine benzyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
85.7%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride
16652-71-4

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

5-formyl-2-hydroxy-benzoylproline benzyl ester

5-formyl-2-hydroxy-benzoylproline benzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
84.2%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

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

1,2-diamino-benzene

5-(1H-benzimidazol-3-ium-2-yl)-2-hydroxybenzoate
1297611-18-7

5-(1H-benzimidazol-3-ium-2-yl)-2-hydroxybenzoate

Conditions
ConditionsYield
In ethanol for 6h; Reflux;84%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

3-bromo-5-formylsalicylic acid

3-bromo-5-formylsalicylic acid

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 70℃; for 3h; Inert atmosphere;84%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 70℃; for 3h; Inert atmosphere;84%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 70℃; for 3h; Inert atmosphere;84%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 70℃; for 3h; Inert atmosphere;84%
6-hydroxybenzofuran-3-one
6272-26-0

6-hydroxybenzofuran-3-one

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

2-hydroxy-5-{[(2Z)-6-hydroxy-3-oxo-benzofuran-2-ylidene]methyl}benzoic acid

2-hydroxy-5-{[(2Z)-6-hydroxy-3-oxo-benzofuran-2-ylidene]methyl}benzoic acid

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 80℃; for 16h;84%
methionine benzyl ester hydrochloride

methionine benzyl ester hydrochloride

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

5-formyl-2-hydroxy-benzoylmethionine benzyl ester

5-formyl-2-hydroxy-benzoylmethionine benzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: methionine benzyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
83.7%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

L-threonine benzyl ester hydrochloride

L-threonine benzyl ester hydrochloride

5-formyl-2-hydroxy-benzoylthreonine benzyl ester

5-formyl-2-hydroxy-benzoylthreonine benzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: L-threonine benzyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
83.7%
4-amino-6-bromo-1H-indazole
885518-50-3

4-amino-6-bromo-1H-indazole

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

5-(((6-bromo-1H-indazol-4-yl)amino)methyl)-2-hydroxybenzoic acid

5-(((6-bromo-1H-indazol-4-yl)amino)methyl)-2-hydroxybenzoic acid

Conditions
ConditionsYield
With 1,4-dihydropyridine; trifluoroacetic acid In dichloromethane at 40℃; for 12h; Inert atmosphere; Molecular sieve;82%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

L-alanine benzyl ester hydrochloride
5557-81-3, 5557-83-5, 34404-37-0

L-alanine benzyl ester hydrochloride

5-formyl-2-hydroxy-benzoylalanine benzyl ester

5-formyl-2-hydroxy-benzoylalanine benzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: L-alanine benzyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
82%
3-oxo-2,3-dihydrobenzo[b]furan
7169-34-8

3-oxo-2,3-dihydrobenzo[b]furan

2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

2-hydroxy-5-{[(2Z)-3-oxobenzofuran-2-ylidene]methyl}benzoic acid

2-hydroxy-5-{[(2Z)-3-oxobenzofuran-2-ylidene]methyl}benzoic acid

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 80℃;82%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

L-leucine benzyl ester hydrochloride
2462-35-3

L-leucine benzyl ester hydrochloride

5-formyl-2-hydroxy-benzoylleucine benzyl ester

5-formyl-2-hydroxy-benzoylleucine benzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: L-leucine benzyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
81.8%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

L-isoleucine benzyl ester hydrochloride
103310-88-9

L-isoleucine benzyl ester hydrochloride

5-formyl-2-hydroxy-benzoylisoleucine benzyl ester

5-formyl-2-hydroxy-benzoylisoleucine benzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: L-isoleucine benzyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
81.7%
2-hydroxy-5-formylbenzoic acid
616-76-2

2-hydroxy-5-formylbenzoic acid

L-serine benzyl ester hydrochloride
60022-62-0

L-serine benzyl ester hydrochloride

5-formyl-2-hydroxy-benzoylserine benzyl ester

5-formyl-2-hydroxy-benzoylserine benzyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-5-formylbenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: L-serine benzyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran for 8h; pH=9;
81.4%

616-76-2Relevant articles and documents

Helicity induction in hydrogen-bonding-driven zinc porphyrin foldamers by chiral C60-incorporating histidines

Hou, Jun-Li,Yi, Hui-Ping,Shao, Xue-Bin,Li, Chuang,Wu, Zong-Quan,Jiang, Xi-Kui,Wu, Li-Zhu,Tung, Chen-Ho,Li, Zhan-Ting

, p. 796 - 800 (2006)

(Chemical Equation Presented) High chiral amplification is exhibited by a new series of zinc porphyrin appended, hydrogen-bonded foldamers on binding with C60-incorporating chiral histidines as a result of the cooperation of two discrete noncovalent interactions: zinc porphyrin/ imidazole coordination and zinc porphyrin/C6 π-π stacking (see picture).

Magnetic nano-structured cobalt-cobalt oxide/nitrogen-doped carbon material as an efficient catalyst for aerobic oxidation of p-cresols

Liang, Cheng,Li, Xuefeng,Su, Diefeng,Ma, Qiyi,Mao, Jianyong,Chen, Zhirong,Wang, Yong,Yao, Jia,Li, Haoran

, p. 121 - 131 (2018/05/22)

Efficient aerobic oxidation has been developed for the selective preparation of a sequence of valuable p-hydroxybenzaldehydes from corresponding p-cresols, using a new magnetically separable catalyst of nano-structured cobalt-cobalt oxide/nitrogen-doped carbon (CoOx@CN) material. CoOx@CN showed high activity for the 2-methoxy-4-cresol oxidation to vanillin, giving great yield (90%) and with good turnover number (210), as well as other p-cresols in good to great yields. The catalytic performance was investigated and related to the structural, chemical and magnetic properties which determined by scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Fourier-transform infrared spectroscopy (FT-IR) and vibrating sample magnetometer (VSM). The effects of base to substrate molar ratio, catalyst concentration, temperature, and solvent on the conversion and selectivity patterns also have been studied. The investigation revealed that remarkable catalytic properties of CoOx@CN could be ascribed to the active species cobalt oxide, doped nitrogen and porous carbon with large surface area. The size of the catalyst is a key factor for catalyst performance. The ferromagnetic property of catalyst enables to recycle easily by an external magnetic field and reuse six successive times without significant activity loss.

Synthesis of salicylaldehydes from phenols via copper-mediated duff reaction

Fu, Xue-Wen,Pu, Wen-Chen,Zhang, Guo-Lin,Wang, Chun

, p. 8147 - 8158 (2015/02/19)

A copper-mediated Duff reaction for ortho-selective formylation of phenols has been developed. In the presence of copper species, significant improvements of yield and ortho-selectivity of the Duff formylation were achieved, which provides an easy access to salicylaldehydes from phenols.

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