Chloroacetamide

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Chloroacetamide
Chloroacetamide structure image.png
Structure of chloroacetamide
Names
IUPAC name
2-Chloroacetamide
Other names
Chloracetamide
Chlorocetamide
Properties
C2H4ClNO
Molar mass 93.51 g/mol
Appearance Colorless or pale yellow solid
Melting point 120 °C (248 °F; 393 K)
Boiling point 225 °C (437 °F; 498 K) (decomposition)[1]
9.8 g/100 ml (20 °C)
9.0 g/100 ml (25 °C)
Solubility Soluble in ethanol, methanol
Insoluble in diethyl ether
Vapor pressure 0.05 mmHg (20 °C)
Hazards
Safety data sheet Sigma-Aldrich
Flash point 170 °C (338 °F; 443 K)
Lethal dose or concentration (LD, LC):
138 mg/kg (rat, oral)
Related compounds
Related compounds
Acetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Chloroacetamide or 2-chloroacetamide is a chlorinated organic compound with the molecular formula C2H4ClNO or ClCH2CONH2. It is used in the manufacturing of herbicides.

Properties

Chemical

Chloroacetamide is used to add an acetamide functional group to organic compounds.

Phosphorus pentoxide will dehydrate chloroacetamide to chloroacetonitrile.[2]

Addition of a strong base, like NaOH, will produce glycolic acid derivates.

Physical

Chloroacetamide is a colorless solid although older samples appear yellow. It has a characteristic odor and is readily soluble in water and in some organic solvents.

Availability

Chloroacetamide is sold by chemical suppliers.

Some herbicides contain chloroacetamide.

Preparation

Chloroacetamide is produced by ammonolysis of esters of chloroacetic acid. For example, by stirring ethyl chloroacetate with aq. ammonia at low temperatures (0–5°), as higher temperatures favor the replacement of the chlorine, forming glycine and its esters, which lowers the yield.[3]

ClCH2CO2CH2CH3 + NH3 → ClCH2C(O)NH2 + CH3CH2OH
ClCH2CO2CH2CH3 + 2 NH3 → H2NCH2COOH + NH4Cl + CH3CH2OH

A less known route involves the reaction of ethenone with nitrogen trichloride at -60 °C, in anhydrous conditions.[4]

Projects

  • Preparation of chloroacetonitrile
  • Synthesis of Modafinil
  • Make herbicides

Handling

Safety

Chloroacetamide is toxic, irritates eyes and skin, and may cause an allergic reaction. It is suspected of reproductive toxicity and teratogenicity.

Storage

Should be kept in airtight glass of plastic bottles, away from light, moisture or air.

Disposal

Can be neutralized with a solution of NaOH or KOH to less harmful products, diluted and poured down the drain.

References

  1. Bisschopinck; Chemische Berichte; vol. 6; (1873); p. 734
  2. http://orgsyn.org/demo.aspx?prep=CV4P0144
  3. http://orgsyn.org/demo.aspx?prep=cv1p0153
  4. Coleman; Peterson; Goheen; Journal of the American Chemical Society; vol. 58; (1936); p. 1876

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