4-METHYLAMINO BUTANOL

4-METHYLAMINO BUTANOL Property

Boiling point:

87 °C(Press: 9 Torr)

Density 

0.9184 g/cm3

storage temp. 

2-8°C(protect from light)

pka

15.14±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C5H13NO/c1-6-4-2-3-5-7/h6-7H,2-5H2,1H3

InChIKey

DBKSSENEKWOVKL-UHFFFAOYSA-N

SMILES

C(O)CCCNC

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..…

4-METHYLAMINO BUTANOL Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 4-(methylamino)butan-1-ol from 4-amino-1-butanol and ethyl formate: ethyl formate (5.86 mL, 75.5 mmol) was added to a stirred ethanol (50 mL) solution of 4-amino-1-butanol (4.31 g, 48.4 mmol) and the mixture was stirred at reflux for 18 h under nitrogen protection. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the resulting crude product was used directly in the next step of the reaction. The crude product was dissolved in tetrahydrofuran (25 mL) and slowly added dropwise to a suspension of lithium aluminum hydride (5.50 g, 145 mmol) in tetrahydrofuran (50 mL) under the protection of a drying tube. The reaction mixture was refluxed and the progress of the reaction was monitored by thin-layer chromatography (20% ethanol/80% chloroform) and nuclear magnetic resonance hydrogen spectroscopy (CDCl3).After 2 h, the feedstock was completely consumed, the reaction mixture was cooled, and water (4.16 mL), 4 M sodium hydroxide solution (4.16 mL) and water (12.5 mL) were added sequentially with vigorous stirring. Subsequently, the precipitate was removed by filtration and the filtrate was concentrated under vacuum. The residue was redissolved in chloroform, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 4-(methylamino)butan-1-ol as a colorless oil (2.76 g, 56% yield). NMR hydrogen spectral (CDCl3) data: δ 3.74 (broad peak, 2H), 3.57 (triple peak, 2H), 2.62 (triple peak, 2H), 2.43 (single peak, 3H), 1.50-1.75 (multiple peaks, 4H).

References

[1] Patent: WO2013/148230, 2013, A1. Location in patent: Page/Page column 29; 30