2-Chloropropionic acid

Description

2-Chloropropionic acid is a colorless to white crystalline solid or liquid that is denser than water; therefore, can sink and mix with water. It has a slight odor and is the simplest chiral chlorocarboxylic aid.

Preparation

2-Chloropropionic acid is prepared from diazotization of L-alanine in hydrochloric acid.

Application

2-Chloropropionic acid is employed in the production of propargyl 2-chloropropionate (PCP), which is an atom transfer radical polymerization (ATRP) initiator, by the esterification of propargyl alcohol.

The chemical is also used in the synthesis of benzimidazole derivatives when treated with o-phenylenediamine phosphate.

It can also be used in the preparation of biologically active chitin derivative (1-carboxyethyl) chitosan.

It is used as a building block for the preparation of herbicides, dyestuffs, pesticides, as well as forestand agro-chemicals.

Biochemical Action

2-Chloropropionic acid induces necrosis of granule cell layer of rat cerebellum when administered orally.

Safety

2-Chloropropionic acid is a neurotoxin, as such it should be handled with utmost care. When inhaled, the chemical can irritate the nose, throat, and lungs, causing wheezing and coughing.

The chemical is a corrosive substance, which may occur by ingestion. Contact of the chemical with the eyes and skin may cause pain, irritation, redness, and severe burns.

Chemical Properties

colourless liquid

Uses

Intermediate for weed killers.

Uses

• 2-Chloropropionic acid is used in the preparation of propargyl 2-chloropropionate (PCP), an atom transfer radical polymerization (ATRP) initiator, by the esterification of propargyl alcohol.
• It can be employed in the synthesis of a biologically active chitin derivative, (1-carboxyethyl) chitosan.
• It can be treated with o-phenylenediamine phosphate to synthesize benzimidazole derivatives.

General Description

A pale liquid with a slight odor. Sinks in and mixes with water. Only aluminum, stainless steel or steel covered with a protective lining or coating may contact the liquid or vapor.

Air & Water Reactions

Water soluble.

Reactivity Profile

2-Chloropropionic acid is neutralized in exothermic reactions by all bases. Reacts with aqueous solutions containing a chemical base and dissolves if neutralization generates a soluble salt. May react with active metals to form gaseous hydrogen and a metal salt. May corrode or dissolve iron, steel, and aluminum parts and containers. Reacts with cyanide salts to generate gaseous hydrogen cyanide. Reacts with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides to generate flammable and/or toxic gases and heat. Reacts with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Reacts with carbonates and bicarbonates to generate a harmless gas (carbon dioxide) but some heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. May initiate polymerization reactions or catalyze other chemical reactions. Fire produces highly toxic chloride fumes [USCG, 1999].

Hazard

Combustible. Toxic by skin contact. Male reproductive damage.

Health Hazard

Harmful if inhaled. Irritating to throat. May cause severe skin and eye burns. Harmful if absorbed through skin.

Flammability and Explosibility

Non flammable

Biochem/physiol Actions

2-Chloropropionic acid on oral administration induces necrosis of granule cell layer of rat cerebellum.

Safety Profile

Poison by skin contact. A corrosive. Combustible when exposed to heat or flame. To fight fire, use water, foam, alcohol foam. When heated to decomposition it emits toxic fumes of Cl-. See also 3-CHLOROPROPIONIC ACID.

Purification Methods

Dry it with P2O5 and fractionally distil it under vacuum. [Beilstein 2 IV 745.]