5-Formylsalicylic acid supplier

Name
5-Formylsalicylic acid
EINECS 210-492-0
CAS No. 616-76-2
Article Data20
CAS DataBase
Density 1.482 g/cm³
Solubility
Melting Point 250 °C (dec.)(lit.)
Formula C₈H₆O₄
Boiling Point 361.2 °C at 760 mmHg
Molecular Weight 166.133
Flash Point 186.5 °C
Transport Information
Appearance light beige fine crystalline powder
Safety 22-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms 5-formyl-2-hydroxy-benzoic acid;5-formyl-2-hydroxy-benzoate;5-Formylsalicy Acid;
PSA 74.60000
LogP 0.90290

Synthetic route

: 89-56-5
5-Methylsalicylic acid

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

Conditions

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;

: 619-21-6
m-formylphenyl benzoic acid

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

Conditions

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%

: 100-97-0
hexamethylenetetramine

: 69-72-7
salicylic acid

A: 610-04-8
3-formylsalicylic acid

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

Conditions

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;

...Expand

: 100-97-0
hexamethylenetetramine

: 69-72-7
salicylic acid

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

Conditions

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

: 100-97-0
hexamethylenetetramine

: 64-19-7
acetic acid

: 69-72-7
salicylic acid

A: 610-04-8
3-formylsalicylic acid

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

Conditions

Conditions	Yield
anschliessendes Behandeln mit wss. Salzsaeure;

...Expand

: 636-46-4
4-hydroxyisophthalic acid

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

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

Conditions

Conditions	Yield
With potassium hydroxide; chloroform; water

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

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

Conditions

Conditions	Yield
With potassium hydroxide
With sulfuric acid

: 50-00-0
formaldehyd

: 69-72-7
salicylic acid

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

Conditions

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

: 67-66-3
chloroform

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

: 69-72-7
salicylic acid

A: 610-04-8
3-formylsalicylic acid

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

Conditions

Conditions	Yield
Product distribution;

...Expand

: 67-66-3
chloroform

: 69-72-7
salicylic acid

A: 610-04-8
3-formylsalicylic acid

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

Conditions

Conditions	Yield
With sodium hydroxide

...Expand

: 75-25-2
Bromoform

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

: 69-72-7
salicylic acid

A: 610-04-8
3-formylsalicylic acid

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

Conditions

Conditions	Yield
Product distribution;

...Expand

: 50-00-0
formaldehyd

: 7732-18-5
water

: 69-72-7
salicylic acid

hydroxylamino-benzenesulfonic acid: hydroxylamino-benzenesulfonic acid

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

Conditions

Conditions	Yield
Zersetzung des Produktes mit Salzsaeure;

...Expand

: 100-97-0
hexamethylenetetramine

: 7732-18-5
water

: 69-72-7
salicylic acid

A: 610-04-8
3-formylsalicylic acid

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

Conditions

Conditions	Yield
anschliessendes Behandeln mit wss. Salzsaeure;

...Expand

: 67-66-3
chloroform

: 69-72-7
salicylic acid

NaOH/KOH: NaOH/KOH

A: 610-04-8
3-formylsalicylic acid

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

...Expand

: 7664-93-9
sulfuric acid

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

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

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

methanol. KOH-solution: methanol. KOH-solution

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

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

potassium dichromate: potassium dichromate

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

: 69-72-7
salicylic acid

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

Conditions

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

: 298-14-6
potassium hydrogencarbonate

: 123-08-0
4-hydroxy-benzaldehyde

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

Conditions

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;

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

: 100-39-0
benzyl bromide

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

Conditions

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%

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

: 2746-25-0
p-Methoxybenzyl bromide

: 1251530-68-3
C16H14O5

Conditions

Conditions	Yield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;	100%

: 67-56-1
methanol

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

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

Conditions

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%

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

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

Conditions

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

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

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

Conditions

Conditions	Yield
With thionyl chloride at 85℃;	99%

: 5805-39-0
2-(aminophenyl)benzimidazole

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

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

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 8h; Pictet-Spengler Synthesis; Sonication;	99%

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

: 5080-22-8
N-isopropylhydroxyamine

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

Conditions

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%

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

: 100-39-0
benzyl bromide

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

Conditions

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%

: 75-52-5
nitromethane

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

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

Conditions

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%

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

: 75-65-0
tert-butyl alcohol

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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran	93%
With dicyclohexyl-carbodiimide for 3h; Reflux;	75%

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

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

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

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

Conditions

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%

...Expand

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

: γ-benzyl L-glutamate hydrochloride

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

Conditions

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%

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

: 110-58-7
1-pentanamine

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

Conditions

Conditions	Yield
With benzotriazol-1-ol; dacarbazine In dichloromethane	88%

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

: 2462-34-2
L-valine benzyl ester hydrochloride

: 5-formyl-2-hydroxy-benzoylvaline benzyl ester

Conditions

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%

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

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

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

Conditions

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%

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

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

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 0℃; for 3h;	86.6%
With sulfuric acid; nitric acid at -10 - -5℃;

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

: 15035-17-3
tyrosine benzyl ester hydrochloride

: 5-formyl-2-hydroxy-benzoyltyrosine benzyl ester

Conditions

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%

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

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

: 5-formyl-2-hydroxy-benzoylproline benzyl ester

Conditions

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%

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

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

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

Conditions

Conditions	Yield
In ethanol for 6h; Reflux;	84%

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

: 3-bromo-5-formylsalicylic acid

Conditions

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%

: 6272-26-0
6-hydroxybenzofuran-3-one

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

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

Conditions

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 80℃; for 16h;	84%

: methionine benzyl ester hydrochloride

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

: 5-formyl-2-hydroxy-benzoylmethionine benzyl ester

Conditions

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%

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

: L-threonine benzyl ester hydrochloride

: 5-formyl-2-hydroxy-benzoylthreonine benzyl ester

Conditions

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%

: 885518-50-3
4-amino-6-bromo-1H-indazole

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

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

Conditions

Conditions	Yield
With 1,4-dihydropyridine; trifluoroacetic acid In dichloromethane at 40℃; for 12h; Inert atmosphere; Molecular sieve;	82%

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

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

: 5-formyl-2-hydroxy-benzoylalanine benzyl ester

Conditions

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%

: 7169-34-8
3-oxo-2,3-dihydrobenzo[b]furan

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

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

Conditions

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 80℃;	82%

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

: 2462-35-3
L-leucine benzyl ester hydrochloride

: 5-formyl-2-hydroxy-benzoylleucine benzyl ester

Conditions

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%

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

: 103310-88-9
L-isoleucine benzyl ester hydrochloride

: 5-formyl-2-hydroxy-benzoylisoleucine benzyl ester

Conditions

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%

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

: 60022-62-0
L-serine benzyl ester hydrochloride

: 5-formyl-2-hydroxy-benzoylserine benzyl ester

Conditions

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%

5-Formylsalicylic acid Specification

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

Product Name

5-Formylsalicylic acid

Synthetic route

5-Formylsalicylic acid Specification

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