5-CYANOINDOLE-3-CARBOXALDEHYDE

5-CYANOINDOLE-3-CARBOXALDEHYDE Property

Melting point:

248-253 °C

Boiling point:

429.6±25.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Solid

pka

14.12±0.30(Predicted)

Appearance

Brown to reddish brown Solid

CAS DataBase Reference

17380-18-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-43

Safety Statements 

26-36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

5-CYANOINDOLE-3-CARBOXALDEHYDE Chemical Properties,Usage,Production

Uses

• ;Reactant for synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators1• ;Reactant for enantioselective preparation of antifungal agents2• ;Reactant for synthesis of indole- and 7-azaindole-1,3-dicarboxamide hydroxyethylamine inhibitors of BACE-13• ;Reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents4• ;Reactant for preparation of indolecarboxamide derivatives as antitumor agents5• ;Reactant for synthesis of a selective serotonin reuptake inhibitor6

Uses

• Reactant for synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators
• Reactant for enantioselective preparation of antifungal agents
• Reactant for synthesis of indole- and 7-azaindole-1,3-dicarboxamide hydroxyethylamine inhibitors of BACE-1
• Reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents
• Reactant for preparation of indolecarboxamide derivatives as antitumor agents
• Reactant for synthesis of a selective serotonin reuptake inhibitor

Synthesis

General procedure for the synthesis of 5-cyanoindole-3-carboxaldehyde from 5-cyanoindole: Phosphoryl chloride (4.24 mL, 45.48 mmol) was slowly added dropwise to dimethylformamide (3.52 mL, 45.48 mmol), and stirred at room temperature for 30 min. Subsequently, a solution of 1H-indole-5-carbonitrile (5.39 g, 37.9 mmol) in dimethylformamide (10 mL) was added dropwise. To promote stirring, solid precipitated dimethylformamide (10 mL) was added and the reaction mixture continued to be stirred for 3 hours at room temperature. Upon completion of the reaction, the reaction mixture was quenched by the addition of water and stirring was continued for 18 hours. Stirring was stopped and the reaction mixture was allowed to stand for 24 h. A pink solid precipitated from the organic layer. The layers were separated, the organic layer was filtered, washed with water and dried to afford the target product 5-cyanoindole-3-carbaldehyde (5.44 g, 84% yield). The product was characterized by 1H NMR (DMSO): δ 7.60-7.80 (m, 2H), 8.20-8.30 (m, 2H), 10.00 (s, 1H), 12.20-12.35 (s, br, 1H).

References

[1] Patent: EP997474, 2000, A1
[2] Patent: US6180627, 2001, B2
[3] Patent: US2003/73849, 2003, A1
[4] Organic Process Research and Development, 2008, vol. 12, # 2, p. 168 - 177