2-methoxypropionic acid

2-methoxypropionic acid Property

Melting point:

128.5 °C

Boiling point:

199℃

Density 

1.085

Flash point:

87℃

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

pka

3.59±0.10(Predicted)

color 

Colorless

InChI

InChI=1S/C4H8O3/c1-3(7-2)4(5)6/h3H,1-2H3,(H,5,6)

InChIKey

ICPWFHKNYYRBSZ-UHFFFAOYSA-N

SMILES

C(O)(=O)C(OC)C

Safety

HazardClass 

IRRITANT

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..…

2-methoxypropionic acid Chemical Properties,Usage,Production

Synthesis

A methanolic solution of 25% sodium methanolate (16 mL) was slowly added dropwise to a stirring solution of 2-bromopropionic acid (19.6 mmol) in methanol (5 mL) under nitrogen protection. The reaction mixture was heated and reacted at 50 °C overnight while continuously protected by the passage of nitrogen. Upon completion of the reaction, the reaction solution was concentrated under reduced pressure by rotary evaporator. The residue was adjusted to pH 1 with aqueous 1N hydrochloric acid, followed by three extractions with ethyl acetate (70 mL, 25 mL, 10 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated again under reduced pressure to afford 2-methoxypropionic acid as a colorless oil in the yield of 2.04 g (99% yield), which was pure enough to be used directly in the subsequent reaction without further purification. The product was characterized by 1H NMR (CD3OD): δ 3.67 (q, 1H), 3.33 (s, 3H), 1.33 ppm (d, 3H).

References

[1] Patent: WO2006/96338, 2006, A1. Location in patent: Page/Page column 41
[2] Patent: WO2006/133006, 2006, A2. Location in patent: Page/Page column 46-47
[3] Australian Journal of Chemistry, 1980, vol. 33, # 4, p. 809 - 821
[4] Organic Letters, 2018, vol. 20, # 16, p. 4867 - 4870
[5] Patent: KR2015/128789, 2015, A. Location in patent: Paragraph 0896; 0898; 0899