3D Mol Similar

5-Methylnicotinic acid

Iupac Name：5-methylpyridine-3-carboxylic acid

CAS No.: 3222-49-9

Molecular Weight：137.138

Modify Date.: 2022-11-29 11:01

Introduction:

Is an intermediate of the anti-allergic drug rupatadine

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1. Names and Identifiers

1.1 Name: 5-Methylnicotinic acid
1.2 Synonyms: 3-Pyridinecarboxylic acid, 5-methyl- 5-Methyl-3-pyridinecarboxylic acid 5-Methylnicotinicacid 5-Methyl-nicotinsaeure 5-methyl-nikotinsaeure 5-Methylpyridine-3-carboxylic acid MFCD00829036 T6NJ CVQ E1

1.3 CAS No.: 3222-49-9

1.4 CID: 256208

1.5 EINECS(EC#): 608-720-2

1.6 Molecular Formula: C7H7NO2 (isomer)

1.7 Inchi: InChI=1S/C7H7NO2/c1-5-2-6(7(9)10)4-8-3-5/h2-4H,1H3,(H,9,10)

1.8 InChkey: DJDHHXDFKSLEQY-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=CC(=CN=C1)C(=O)O

1.10 Isomers Smiles: CC1=CC(=CN=C1)C(=O)O

2. Properties

2.1 Density: 1.23

2.1 Melting point: 210-212oC

2.1 Boiling point: 303.9 °C at 760 mmHg

2.1 Refractive index: 1.561?

2.1 Flash Point: 137.6 °C

2.1 Precise Quality: 137.04800

2.1 PSA: 50.19000

2.1 logP: 1.08820

2.1 Solubility: Sparingly soluble (0.083 g/L at 25°C).

2.2 Appearance: Not Available

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: Solid 5-Methylnicotinic acidSupplier

2.5 pKa: 2.27±0.10(Predicted)

2.6 Water Solubility: Sparingly soluble (0.083 g/L at 25°C).

2.7 StorageTemp: Room temperature.

3. Use and Manufacturing

3.1 Methods of Manufacturing: Step 1. To a solution of KMnO4 in water (1.1 L) was added lutidine (25.0 g, 0.233 mmol) and the mixture was stirred mechanically at 45 C. overnight. The reaction mixture was cooled and filtered through Celite to remove MnO2. The filtrate was concentrated to about 150 mL and acidified with a 2N HCl Solution. White solid precipitated and was removed by filtration and washed with water (2*50 mL). The filtrate and washing were evaporated to dryness. The residue was boiled with ethanol (200 mL) and filtered repeatedly. The combined filtrate was concentrated to give of 5-methylnicotinic acid as a white solid (14.8 g, 46%): mp 213-215 C.General procedure: General Experimental Procedures:[0423]To the flask was added 9 (57 mg, 0.2 mmol) , R-COOH (1.2 eq, 0.24 mmol) , EDCI (58 mg, 0.3 mmol) , DMAP (5 mg, 0.04 mmol) in DCM (5 mL) successively, followed by DIPEA (77 mg, 0.6 mmol) with stirring. The resulting mixture was stirred at room temperature for overnight, and purified by column chromatography to give product.

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S36

4.1 Hazard Declaration: H315-H319-H335

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261-P305 + P351 + P338

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

3222-49-9Total: 6 Synthesis Route

591-22-0 98 Suppliers

3222-49-9 159 Suppliers

Literatures:
Pfizer Inc. Patent: US2009/54395 A1, 2009 ; Location in patent: Page/Page column 42 ;
Yield: ~59%

612-58-8 77 Suppliers

3222-49-9 159 Suppliers

Literatures:
Chemische Berichte, , vol. 66, p. 1338,1341, 1342
Yield: null

591-22-0 98 Suppliers

3222-49-9 159 Suppliers

499-81-0 157 Suppliers

Literatures:
Kyba, Evan P.; Liu, Shiuh-Tzung; Chockalingam, Kannappan; Reddy, B. Raghava Journal of Organic Chemistry, 1988 , vol. 53, # 15 p. 3513 - 3521
Yield: null

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8. Precursor and Product

precursor:

612-58-8

591-22-0

7732-18-5

42972-46-3

112945-08-1

product :

402-66-4

455-70-9

39891-04-8

20970-77-8

158876-82-5

884494-95-5

102074-19-1

20826-02-2

70-57-5

29681-45-6

100910-66-5

407-21-6

9. Other Information

9.0 用途

9.1 Usage: 5-Methylnicotinic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

9.2 Storage Conditions: Step 1. To a solution of KMnO4 in water (1.1 L) was added lutidine (25.0 g, 0.233 mmol) and the mixture was stirred mechanically at 45 C. overnight. The reaction mixture was cooled and filtered through Celite to remove MnO2. The filtrate was concentrated to about 150 mL and acidified with a 2N HCl Solution. White solid precipitated and was removed by filtration and washed with water (2*50 mL). The filtrate and washing were evaporated to dryness. The residue was boiled with ethanol (200 mL) and filtered repeatedly. The combined filtrate was concentrated to give of 5-methylnicotinic acid as a white solid (14.8 g, 46%): mp 213-215 C.General procedure: General Experimental Procedures:[0423]To the flask was added 9 (57 mg, 0.2 mmol) , R-COOH (1.2 eq, 0.24 mmol) , EDCI (58 mg, 0.3 mmol) , DMAP (5 mg, 0.04 mmol) in DCM (5 mL) successively, followed by DIPEA (77 mg, 0.6 mmol) with stirring. The resulting mixture was stirred at room temperature for overnight, and purified by column chromatography to give product.

10. Computational chemical data

Molecular Weight: 137.138g/mol
Molecular Formula: C₇H₇NO₂
Compound Is Canonicalized: True
XLogP3-AA: 0.7
Exact Mass: 137.047678466
Monoisotopic Mass: 137.047678466
Complexity: 136
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 50.2
Heavy Atom Count: 10
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBiMAAAAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHgAACAAADADBmgQ+iJIIEgCoAjD3TACCgCA1ACAA2CEoTNgIJvrAlZGEcYhmwAHI2caYEQIMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==