Methyl 2-(hydroxymethyl)nicotinate Property

Boiling point:

300.6±32.0 °C(Predicted)

Density 

1.244±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.96±0.10(Predicted)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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.

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

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

Methyl 2-(hydroxymethyl)nicotinate Chemical Properties,Usage,Production

Uses

Methyl 2-(hydroxymethyl)nicotinate can be used as pharmaceutical intermediate for laboratory research.

Description

Methyl 2-(hydroxymethyl)nicotinate is a derivative of methyl nicotinate, which is used in the preparation of a novel glycosidase inhibitor, 1-azasugars. Methyl 2-(hydroxymethyl)nicotinate and its derivatives are used in the preparation of haemoglobin modulators^[1].

Synthesis

To a solution of methyl 2-(acetoxymethyl)nicotinate (7.90 g, 37.76 mmol, 1.0 equiv), in MeOH (80 mL) was added acetyl chloride (3.60 g, 45.86 mmol, 1.2 equiv). The reaction solution was stirred overnight at room temperature; then, the solvent was removed under reduced pressure, and the resulting residue was dissolved in water (20 mL). The pH was adjusted to 8 with NaHCO 3 solid and extracted with ethyl acetate (30 mL*3). The combined organic phase was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated in vacuum. The residue was puri - fied by silica gel column with ethyl acetate/petroleum ether (1/1), giving Methyl 2-(hydroxymethyl)nicotinate. LCMS (ES) [M+1] + m/z: 168.

References

[1] GUOHUA ZHAO; Bruce G; Urmila C Deo. Selective Fowler Reductions: Asymmetric Total Syntheses of Isofagomine and Other 1-Azasugars from Methyl Nicotinate[J]. Organic Letters, 2000. DOI:10.1021/ol006810x.