Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
salicylic acid
A
3-formylsalicylic acid
B
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
acetic acid
salicylic acid
A
3-formylsalicylic acid
B
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
anschliessendes Behandeln mit wss. Salzsaeure; |
4-hydroxyisophthalic acid
A
2-hydroxy-5-formylbenzoic acid
B
5-formyl-4-hydroxy-isophthalic acid
Conditions | Yield |
---|---|
With potassium hydroxide; chloroform; water |
2-hydroxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide | |
With sulfuric acid |
Conditions | Yield |
---|---|
With sodium hydroxide anschliessendes Erhitzen mit Natrium-<3-nitro-benzolsulfonat>; | |
in Gegenwart einer aromatischen Hydroxylaminverbindung und Zersetzung des Reaktionsproduktes; |
chloroform
salicylic acid
A
3-formylsalicylic acid
B
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
Product distribution; |
chloroform
salicylic acid
A
3-formylsalicylic acid
B
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
Bromoform
salicylic acid
A
3-formylsalicylic acid
B
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
Product distribution; |
Conditions | Yield |
---|---|
Zersetzung des Produktes mit Salzsaeure; |
hexamethylenetetramine
water
salicylic acid
A
3-formylsalicylic acid
B
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
anschliessendes Behandeln mit wss. Salzsaeure; |
chloroform
salicylic acid
A
3-formylsalicylic acid
B
2-hydroxy-5-formylbenzoic acid
sulfuric acid
2-hydroxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid
2-hydroxy-5-formylbenzoic acid
2-hydroxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
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
4-hydroxy-benzaldehyde
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
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
benzyl bromide
benzyl 2-hydroxy-5-formylbenzoate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h; | 100% |
methanol
2-hydroxy-5-formylbenzoic acid
methyl-5-formyl-2-hydroxybenzoate
Conditions | Yield |
---|---|
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
5-cyano-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
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
5-Formyl-2-hydroxy-benzoyl chloride
Conditions | Yield |
---|---|
With thionyl chloride at 85℃; | 99% |
Conditions | Yield |
---|---|
With acetic acid In ethanol at 20℃; for 8h; Pictet-Spengler Synthesis; Sonication; | 99% |
Conditions | Yield |
---|---|
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
benzyl bromide
benzyl 5-formyl-2-(benzyloxy)benzoate
Conditions | Yield |
---|---|
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-formamide | 77% |
nitromethane
2-hydroxy-5-formylbenzoic acid
2-hydroxy-5-(2-nitroethenyl)benzoic acid
Conditions | Yield |
---|---|
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
tert-butyl alcohol
tert-butyl 5-formyl-2-hydroxybenzoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran | 93% |
With dicyclohexyl-carbodiimide for 3h; Reflux; | 75% |
2-hydroxy-5-formylbenzoic acid
terbium(III) acetate tetrahydrate
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
1-pentanamine
5-formyl-2-hydroxy-N-pentyl-benzamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dacarbazine In dichloromethane | 88% |
Conditions | Yield |
---|---|
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% |
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 0℃; for 3h; | 86.6% |
With sulfuric acid; nitric acid at -10 - -5℃; |
2-hydroxy-5-formylbenzoic acid
tyrosine benzyl ester hydrochloride
Conditions | Yield |
---|---|
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
benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride
Conditions | Yield |
---|---|
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
1,2-diamino-benzene
5-(1H-benzimidazol-3-ium-2-yl)-2-hydroxybenzoate
Conditions | Yield |
---|---|
In ethanol for 6h; Reflux; | 84% |
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at 80℃; for 16h; | 84% |
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
2-hydroxy-5-formylbenzoic acid
Conditions | Yield |
---|---|
With 1,4-dihydropyridine; trifluoroacetic acid In dichloromethane at 40℃; for 12h; Inert atmosphere; Molecular sieve; | 82% |
2-hydroxy-5-formylbenzoic acid
L-alanine benzyl ester hydrochloride
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at 80℃; | 82% |
Conditions | Yield |
---|---|
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
L-isoleucine benzyl ester hydrochloride
Conditions | Yield |
---|---|
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
L-serine benzyl ester hydrochloride
Conditions | Yield |
---|---|
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% |
The 5-Formylsalicylic acid , with cas registry number of 616-76-2, belongs to categories of Intermediates of Dyes and Pigments; Acids and Derivatives; Carbonyl Compounds; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzene derivatives. With appearance of light beige fine crystalline powder, it is also known as 2-Hydroxy-5-formylbenzoic acid . Both systematic name and IUPAC name are called the same which is 5-formyl-2-hydroxybenzoic acid .
Physical properties about this chemical are: (1) ACD/LogP: 2.25 ; (2) # of Rule of 5 Violations: 0 ; (3) ACD/LogD (pH 5.5): -0.82 ; (4) ACD/LogD (pH 7.4): -0.9 ; (5) ACD/BCF (pH 5.5): 1 ; (6) ACD/BCF (pH 7.4): 1 ; (7) ACD/KOC (pH 5.5): 1 ; (8) ACD/KOC (pH 7.4): 1 ; (9) #H bond acceptors: 4 ; (10) #H bond donors: 2 ; (11) #Freely Rotating Bonds: 3 ; (12) Index of Refraction: 1.669 ; (13) Molar Refractivity: 41.81 cm3 ; (14) Molar Volume: 112 cm3 ; (15) Surface Tension: 74.7 dyne/cm ; (16) Density: 1.482 g/cm3 ; (17) Flash Point: 186.5 °C ; (18) Enthalpy of Vaporization: 64.05 kJ/mol ; (19) Boiling Point: 361.2 °C at 760 mmHg ; (20) Vapour Pressure: 7.53E-06 mmHg at 25°C.
Uses of 5-Formylsalicylic acid : this chemical can react with nitromethane to give 5-(2-Nitroethenyl)salicylic acid .
This reaction will need reagent n-butylamine , solvent Acetic acid and other conditions like heating. The reaction time is about 3 hours. The yield is 48%.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. So when you are using it, avoid contact with skin and eyes. And do not breathe dust.
You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)c1cc(ccc1O)C=O ;
(2)InChI:InChI=1/C8H6O4/c9-4-5-1-2-7(10)6(3-5)8(11)12/h1-4,10H,(H,11,12);
(3)InChIKey:UTCFOFWMEPQCSR-UHFFFAOYAO
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