Quinoline-5-carboxylic acid Chemical Properties

Melting point:

>300°C

Boiling point:

386.5±15.0 °C(Predicted)

Density 

1.339±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

0.97±0.10(Predicted)

color 

White to Gray to Red

Water Solubility 

Slightly soluble in water.

BRN 

129178

InChI

InChI=1S/C10H7NO2/c12-10(13)8-3-1-5-9-7(8)4-2-6-11-9/h1-6H,(H,12,13)

InChIKey

RAYMXZBXQCGRGX-UHFFFAOYSA-N

SMILES

N1C2C(=C(C(O)=O)C=CC=2)C=CC=1

CAS DataBase Reference

7250-53-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36/38-22

Safety Statements 

26-36-37/39-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29334900

Storage Class

11 - Combustible Solids

MSDS

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Quinoline-5-carboxylic acid Usage And Synthesis

Uses

Quinoline-5-carboxylic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Application

Quinoline-5-carboxylic acid could synthesize a thermally stable microporous metal-organic framework (MOF Ni-Qc-5) to enhance the separation of CH4 against N2. The highest adsorption CH4 uptake (1.3 mmol/g) was achieved compared to N2 (0.28 mmol/g). Compared with other MOF materials, Ni-Qc-5 possessed very low adsorption energy and high selectivity at low pressure of 0.1 bar[1].

Synthesis

Synthesis of methyl quinoline-5-carboxylate (Intermediate-97):

A 500 mL RB flask equipped with a magnetic stirrer was charged with m-aminobenzoic acid (60 g, 435 mmol), glycerol (168 g, 1824 mmol) in 90 mL of concentrated H25O4. RB flask equipped with a magnetic stirrer was charged with m-aminobenzoic acid (60 g, 435 mmol), glycerol (168 g, 1824 mmol), 3-nitrobenzoic acid (30 g, 179 mmol) in 90 mL of concentrated H25O4. The reaction mixture was heated at 150 ??C for 7 h. After the reaction was cooled to room temperature MeOH (600 mL) was added and refluxed for 12 hours. It was then cooled to 0??C, burst with ice and concentrated. The crude reaction mixture was alkalized with NaHCO3, extracted with DCM and concentrated. The resulting crude material was purified by silica gel column chromatography using petroleum ether (60-80), ethyl acetate and 0.5% triethylamine as eluents. A product (Intermediate-97) was obtained as a brown liquid (21 g).

Synthesis of quinoline-5-carboxylic acid (Intermediate-98):

To a stirred solution of Intermediate-97 (21 g, 112 mmol) in THF:MeOH mixture (25 mL:200 mL) at 0 ??C, LiOH (10.75 g, 448 mmol) in water (25 mL) was added. The resulting reaction mixture was stirred at room temperature for 3 hours. After the reaction (monitored by TLC), it was concentrated and acidified with 1N.HCl (pH = 5). The resulting precipitate was filtered and dried to yield intermediate-98 (19 g).

References

[1] Salman Qadir. “A thermally stable isoquinoline based ultra-microporous metal-organic framework for CH4 separation from coal mine methane.” Chemical Engineering Journal 51 1 (1900): 131136.

Quinoline-5-carboxylic acid(7250-53-5)Related Product Information

• 3,5-Dihydroxybenzoic acid
• Isoquinoline
• Quinclorac
• Quinaldic acid
• Quinhydrone
• Quinoline
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 6-Hydroxy-2(1H)-3,4-dihydroquinolinone
• 5,6,7,8-TETRAHYDROISOQUINOLINE
• QUINOLINE-4-CARBOXYLIC ACID
• Ethoxyquin
• 6-Quinolinecarboxylic acid
• 3-Quinolinecarboxylic acid
• 3-Quinolineboronic acid
• quinoline-6-carbonitrile
• 5-HYDROXYMETHYLQUINOLINE
• Quinoline-5-carboxaldehyde