1-Methylindole-2-carboxylic acid Chemical Properties

Melting point:

212-213 °C (dec.) (lit.)

Boiling point:

389.0±15.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

4.19±0.30(Predicted)

color 

Beige

CAS DataBase Reference

16136-58-6(CAS DataBase Reference)

NIST Chemistry Reference

1-Methylindole-2-carboxylic acid(16136-58-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

RTECS 

NL6012400

HazardClass 

IRRITANT

HS Code 

29339980

MSDS

• Language:English Provider:SigmaAldrich

1-Methylindole-2-carboxylic acid Usage And Synthesis

Chemical Properties

Beige crystalline powder

Uses

• ;Reactant for preparation of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors1• ;Reactant for synthesis of fenbufen and ethacrynic acid derivatives as potential antitumor agents via amide coupling reactions2• ;Reactant for diastereoselective synthesis of vinylated heterocycles via ruthenium-catalyzed oxidative vinylation with alkenes3• ;Reactant for synthesis of 2,3-dihalo indoles via hypervalent iodine mediated decarboxylative halogenation4• ;Reactant for preparation of α-ketoamides as cathepsin S inhibitors with potential applications ag

Uses

• Reactant for preparation of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors
• Reactant for synthesis of fenbufen and ethacrynic acid derivatives as potential antitumor agents via amide coupling reactions
• Reactant for diastereoselective synthesis of vinylated heterocycles via ruthenium-catalyzed oxidative vinylation with alkenes
• Reactant for synthesis of 2,3-dihalo indoles via hypervalent iodine mediated decarboxylative halogenation
• Reactant for preparation of α-ketoamides as cathepsin S inhibitors with potential applications against tumor invasion and angiogenesis
• Reactant for preparation of anthranilic acid mimics as bacterial translation inhibitors

General Description

1-Methylindole-2-carboxylic acid reacts with thionyl chloride to yield sulfinyl chlorides.

Synthesis

The general procedure for the synthesis of 1-methylindole-2-carboxylic acid from methyl 1-methyl-1H-indole-2-carboxylate was as follows: to a mixed solution of THF/H2O (2:1, 15 mL) of methyl 1-methyl-1H-indole-2-carboxylate (250 mg, 1.32 mmol) at 23 °C, LiOH-H2O (291 mg, 6.94 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent and subsequently partitioned between H2O (100 mL) and ether (100 mL). The aqueous layer was adjusted to pH 2-3 with 1.0 N HCl and then extracted with ethyl acetate (2 x 100 mL). The organic layers were combined, dried over anhydrous MgSO4, filtered and concentrated to give 1-methyl-1H-indole-2-carboxylic acid (210 mg, 91% yield).

References

[1] Tetrahedron, 2004, vol. 60, # 44, p. 10039 - 10047
[2] Journal of Organic Chemistry, 2016, vol. 81, # 16, p. 7288 - 7300
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2093 - 2100
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5298 - 5310
[5] Patent: US2006/211603, 2006, A1. Location in patent: Page/Page column 71

1-Methylindole-2-carboxylic acid(16136-58-6)Related Product Information

• Phthalic acid
• Methyl formate
• Benzyl benzoate
• Methyl salicylate
• Benzoic acid
• Bensulfuron methyl
• 4-Methyl-2-pentanol
• 2-Methylindole
• Calcium formate
• Ethyl 2-(Chlorosulfonyl)acetate
• Indole
• Ethyl formate
• Folic acid
• Indole-2-carboxylic acid
• Retinoic acid
• 1-Methylindole
• Thiophanate-methyl
• Citric acid