2-METHYL-1H-PYRROLE-3-CARBOXYLIC ACID

2-METHYL-1H-PYRROLE-3-CARBOXYLIC ACID Property

Melting point:

178-179℃

Boiling point:

322.4±22.0 °C(Predicted)

Density 

1.295

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

5.60±0.50(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C6H7NO2/c1-4-5(6(8)9)2-3-7-4/h2-3,7H,1H3,(H,8,9)

InChIKey

YBJBJOLFTYIFKP-UHFFFAOYSA-N

SMILES

N1C=CC(C(O)=O)=C1C

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-METHYL-1H-PYRROLE-3-CARBOXYLIC ACID Chemical Properties,Usage,Production

Uses

2-Methyl-1H-Pyrrole-3-carboxylic acid was examined for its inhibitory properties of BET bromodomains. 2-Methyl-1H-Pyrrole-3-carboxylic acid is also patented as a plant-growth regulator.

Synthesis

Example 149a Synthesis of 2-methyl-1H-pyrrole-3-carboxylic acid: an aqueous solution (20 mL) of lithium hydroxide (1.563 g, 65.3 mmol) was added to a solution of dioxane (20 mL) containing ethyl 2-methyl-1H-pyrrole-3-carboxylate (2.0 g, 13.06 mmol). The reaction mixture was heated under reflux conditions for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently extracted by partitioning with ethyl acetate and 1 M hydrochloric acid. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target compound 2-methyl-1H-pyrrole-3-carboxylic acid (1.513 g, 93% yield).

References

[1] Patent: US2014/275079, 2014, A1. Location in patent: Paragraph 0604
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 29, p. 7911 - 7914
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 10, p. 2225 - 2233
[4] Chemische Berichte, 1911, vol. 44, p. 490
[5] Chemische Berichte, 1918, vol. 51, p. 569