1-Methyl-1H-1,2,3-triazole-5-carbaldehyde

1-Methyl-1H-1,2,3-triazole-5-carbaldehyde Property

Boiling point:

253.5±32.0 °C(Predicted)

Density 

1.31±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.22±0.10(Predicted)

Appearance

Colorless to off-white Solid-Liquid Mixture

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

1-Methyl-1H-1,2,3-triazole-5-carbaldehyde Chemical Properties,Usage,Production

Synthesis

1.6 M n-butyllithium (0.9 mL, 1.4 mmol) was added slowly and dropwise to a tetrahydrofuran (THF, 10 mL) solution of 1-methyl-1H-1,2,3-triazole (32.0 mg, 1.2 mmol) at -78 °C, ensuring that the reaction temperature was maintained below -60 °C. After the reaction mixture was stirred continuously at -78 °C for 30 min, N,N-dimethylformamide (0.14 mL, 1.8 mmol) was added. Subsequently, the reaction system was slowly warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate (3 × 10 mL). The organic phases were combined, washed with water (3 x 10 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with an eluent ratio of 95:5 to 100:0 dichloromethane to methanol, resulting in 1-methyl-1H-1,2,3-triazole-5-carboxaldehyde as a yellow oil (40 mg, 30% yield).1H NMR (CDCl3) data: δ 4.10 (s, 3H), 7.88 (s, 1H), 9.55 (s, 1H). 1H).

References

[1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 6, p. 650 - 654
[2] Patent: WO2008/135826, 2008, A2. Location in patent: Page/Page column 157; 158
[3] Patent: US2014/107094, 2014, A1. Location in patent: Paragraph 0625; 0626
[4] Patent: US2015/105372, 2015, A1. Location in patent: Paragraph 0304; 0305
[5] Patent: WO2015/57206, 2015, A1. Location in patent: Page/Page column 74; 75