chloroacetamide
{{Chembox
| ImageFile = 2-chloroacetamide 200.svg
| PIN = 2-Chloroacetamide
| OtherNames =
|Section1={{Chembox Identifiers
| Abbreviations =
| CASNo = 79-07-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2R97846T1L
| EINECS = 201-174-2
| PubChem = 6580
| ChemSpiderID = 6332
| SMILES = ClCC(=O)N
| InChI = InChI=1S/C2H4ClNO/c3-1-2(4)5/h1H2,(H2,4,5)
| InChIKey = VXIVSQZSERGHQP-UHFFFAOYAM
| StdInChI = 1S/C2H4ClNO/c3-1-2(4)5/h1H2,(H2,4,5)
| StdInChIKey = VXIVSQZSERGHQP-UHFFFAOYSA-N
| RTECS =
| MeSHName =
| ChEBI = 361034
| KEGG =
}}
|Section2={{Chembox Properties
| Formula = {{chem2|ClCH2CONH2}}
| C=2 | H=4 | Cl=1 | N=1 | O=1
| Appearance = Colorless crystals or white fine powder (yellow if impure)
| Density = 1.58 g/cm3 at 20 °C
| Odor = Characteristic
| MeltingPtC = 120
| MeltingPt_notes =
| BoilingPt =
| BoilingPt_notes =
| Solubility = {{ubl|52.5 g/l at 20 °C|90 g/L at 25 °C}}
| SolubleOther =
| Solvent =
| LogP =
| VaporPressure = 0.07 hPa at 20 °C
| HenryConstant =
| AtmosphericOHRateConstant =
| pKa =
| pKb =
}}
| Section7 = {{Chembox Hazards
| Hazards_ref =
| ExternalSDS = https://www.sigmaaldrich.cn/CN/en/sds/mm/8.02412?userType=anonymous
| GHSPictograms = {{GHS06}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|H301|H317|H361|H402}}
| PPhrases = {{P-phrases|P201|P202|P261|P264|P270|P272|P273|P280|P301+P310+P330|P302+P352|P308+P313|P333+P313|P405|P501}}
| MainHazards = Very toxic. It is suspected of reproductive toxicity and teratogenicity.
| IngestionHazard = Very toxic
| InhalationHazard = Very toxic
| EyeHazard = Irritation
| SkinHazard = Irritation
| FlashPtC = 170
| LD50 = 138 mg/kg (oral, rat)
>2000 mg/kg (skin, rat)
| LDLo =
| LC50 = 19.8 mg/l, 96 h (Carassius auratus (goldfish))
}}
|Section8={{Chembox Related
| OtherCompounds = {{ubl|Fluoroacetamide|Bromoacetamide|Iodoacetamide|Chloroacetic acid|Acetamide|Dichloroacetamide|N-Chlorosuccinimide}}
}}
}}
Chloroacetamide (2-chloroacetamide) is a chlorinated organic compound with the molecular formula {{chem2|ClCH2CONH2|auto=1}}. It is a colorless solid although older samples appear yellow. It has a characteristic odor and is readily soluble in water.[http://www.inchem.org/documents/icsc/icsc/eics0640.htm 2-Chloroacetamide] It has the structure {{chem2|Cl\sCH2\sC(\dO)\sNH2}}.
Production
Chloroacetamide is produced by ammonolysis of esters of chloroacetic acid:{{Ullmann |author = Koenig, G. |author2 = Lohmar, E. |author3 = Rupprich, N. |title = Chloroacetic Acids |doi = 10.1002/14356007.a06_537}}{{cite journal |first1=W. A.|last1=Jacobs|first2=M. |last2=Heidelberger|doi=10.15227/orgsyn.007.0016|title=Chloroacetamide|journal=Organic Syntheses|year=1927|volume=7|page=16}}
:{{chem2|ClCH2CO2CH3 + NH3 → ClCH2C(O)NH2 + CH3OH}}
Uses
Chloroacetamide has been used as an herbicide,[http://www.epochem.com/products/agroHerbicides.htm Herbicides - Epochem] {{webarchive|url=https://web.archive.org/web/20080520105742/http://www.epochem.com/products/agroHerbicides.htm |date=2008-05-20}} preservative.[http://www.chemicalsubstanceschimiques.gc.ca/challenge-defi/batch-lot-5/79-07-2_e.html Acetamide, 2-chloro- - Government of Canada] {{webarchive|url=https://web.archive.org/web/20090131112114/http://chemicalsubstanceschimiques.gc.ca/challenge-defi/batch-lot-5/79-07-2_e.html |date=2009-01-31}} and in the manufacturing of pharmaceuticals.
Hazards
Chloroacetamide is toxic, irritates eyes and skin, and may cause an allergic reaction. It is suspected of reproductive toxicity and teratogenicity.{{cite web | url = http://ansm.sante.fr/content/download/41931/545388/version/1/file/dps-120625-Chloroacetamide-du-14062012.pdf | publisher = Agence Nationale de Sécurité du Médicament et des Produits de Santé | language = fr | title = Decisiondu 14 juin 2012 | access-date = 2012-07-03 | archive-date = 2013-05-23 | archive-url = https://web.archive.org/web/20130523054342/http://ansm.sante.fr/content/download/41931/545388/version/1/file/dps-120625-Chloroacetamide-du-14062012.pdf | url-status = dead}}
See also
- Novosphingobium chloroacetimidivorans, a bacterium named after its ability to degrade chloroacetamide