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(S)-(-)-2-METHOXYPROPIONIC ACID
  • (S)-(-)-2-METHOXYPROPIONIC ACID(S)-(-)-2-METHOXYPROPIONIC ACID

(S)-(-)-2-METHOXYPROPIONIC ACID

This molecule looks simple: C₄H₈O₃, molecular weight just 104.1. But don’t let its size fool you. (S)-(-)-2-Methoxypropionic acid carries a single chiral center at the α‑carbon (the carbon bearing both the methoxy and the carboxylic acid groups). The specific rotation is negative, and its enantiopurity is what gives this compound value as a chiral reagent in asymmetric transformations. The structure consists of a propionic acid backbone with a methoxy substituent at the 2‑position, locked into the S configuration. It appears as a transparent, slightly yellow liquid, with a boiling point of 99 °C at 20 mmHg and a refractive index range of 1.4132–1.4152. While most simple carboxylic acids are solids or liquids at room temperature, this one is a low‑viscosity liquid that is freely soluble in common organic solvents such as chloroform, ethyl acetate, and methanol.

(S)-(-)-2-Methoxypropionic Acid (CAS: 23943-97-7) is the enantiomeric counterpart to its (R)-(+)-form, offering complementary stereochemistry for asymmetric synthesis. (S)-(-)-2-Methoxypropionic Acid features a single chiral center with a negative optical rotation, making it an essential building block for the preparation of enantiomerically pure pharmaceuticals and agrochemicals. As a compact, polar carboxylic acid, (S)-(-)-2-Methoxypropionic Acid can be readily derivatized via esterification, amidation, or reduction without the need for protecting groups. Whether you need a reference standard for chiral method development or a versatile intermediate for drug discovery, (S)-(-)-2-Methoxypropionic Acid delivers consistent quality and reliable performance.


Product Parameters

Parameter

Specification

CAS Number

23953-00-6

IUPAC Name

(2S)-2-methoxypropanoic acid

Molecular Formula

C₄H₈O₃

Molecular Weight

104.10 g/mol

Melting Point

124–125 °C (note: literature sometimes reports as liquid; value based on given data)

Boiling Point

99 °C / 20 mmHg

Density

1.1141 g/cm³ (rough estimate)

Refractive Index

1.4132 – 1.4152

pKa

3.59 ± 0.10

Appearance

Transparent, slightly yellow liquid

Solubility

Soluble in chloroform, ethyl acetate, methanol

Storage

Refrigerator (2–8 °C), under inert atmosphere recommended

Storage Class

10 – Flammable liquids

Hazard Symbols

Xi (Irritant)

WGK Germany

WGK 3 (water hazard class 3 – highly hazardous to water)


What Makes This Compound a Useful Chiral Reagent?

The carboxylic acid group can be activated to form amides or esters with prochiral or chiral amines/alcohols. Its small size and defined absolute configuration (S) make it an excellent candidate for:

● Chiral derivatizing agent (CDA) for determining enantiomeric excess of chiral amines and alcohols by ¹H NMR. The methoxy group gives a distinct chemical shift difference in diastereomers.

● Chiral resolving agent – the acid can form diastereomeric salts with racemic amines, allowing separation by crystallization.

● Building block for chiral pharmaceuticals – the 2‑methoxypropionyl group appears in various drug candidates as a fragment that improves metabolic stability compared to the unsubstituted propionyl.

● Asymmetric synthesis – can be reduced to the corresponding chiral alcohol ((S)-2‑methoxypropanol) or converted to the acid chloride for Friedel‑Crafts type introductions.


Safety and Handling

This compound is classified as a flammable liquid (storage class 10) and poses a serious risk of eye damage (Category 1) . It is also irritating to the respiratory system and skin (R36/37/38). Follow these precautions:

● Eye protection: Wear chemical safety goggles or a face shield (safety statement 39).

● Gloves: Use chemical‑resistant gloves (e.g., nitrile) – safety statement 37.

● Ventilation: Handle in a fume hood to avoid inhalation of vapors.

● First aid: In case of eye contact, rinse immediately with plenty of water for at least 15 minutes and seek medical advice (safety statement 26). For skin contact, wash with soap and water.

● Storage: Keep in a refrigerator (2–8 °C), away from sources of ignition, oxidizers, and heat. The container should be tightly sealed and stored under inert atmosphere if possible.

● Disposal: Follow local regulations for flammable organic acids. Do not release into the environment – WGK 3 indicates high water hazard.


Frequently Asked Questions (FAQ)

Q1: How do I determine the enantiomeric purity of this compound?

A: Enantiomeric purity can be assessed by chiral GC (using a cyclodextrin column) or by converting the acid to a methyl ester with (R)- or (S)-1‑phenylethylamine and analyzing the diastereomers by NMR or HPLC. Cosperpharm provides the specific rotation value on each COA as a batch‑specific quality attribute.


Q2: Is this compound water‑soluble?

A: The free acid has limited water solubility but is miscible with many polar organic solvents (chloroform, ethyl acetate, methanol). For reactions in aqueous media, the sodium salt (S)-2‑methoxypropionate is water‑soluble.


Contact us

Have a project that needs a reliable source of (S)-(-)-2-methoxypropionic acid? Drop us a note – whether you need a small bottle for method development or a larger volume for scale‑up, Cosperpharm is ready to help. We’ll reply with a quote, a sample request form, or just a friendly answer to your technical question. No pushy sales pitch – just honest support for your research.


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