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5-Formylsalicylic acid

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Name

5-Formylsalicylic acid

EINECS 210-492-0
CAS No. 616-76-2 Density 1.482 g/cm3
PSA 74.60000 LogP 0.90290
Solubility N/A 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 N/A Appearance light beige fine crystalline powder
Safety 22-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 616-76-2 (5-Formylsalicylic acid) Hazard Symbols N/A
Synonyms

5-formyl-2-hydroxy-benzoic acid;5-formyl-2-hydroxy-benzoate;5-Formylsalicy Acid;

Article Data 20

5-Formylsalicylic acid Synthetic route

89-56-5

5-Methylsalicylic 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;
619-21-6

m-formylphenyl benzoic 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%
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
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;
100-97-0

hexamethylenetetramine

69-72-7

salicylic 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
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
ConditionsYield
anschliessendes Behandeln mit wss. Salzsaeure;
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
ConditionsYield
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
ConditionsYield
With potassium hydroxide
With sulfuric acid
50-00-0

formaldehyd

69-72-7

salicylic 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;
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
ConditionsYield
Product distribution;
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
ConditionsYield
With sodium hydroxide

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

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