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Propanamide

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Propanamide
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name Propanamide
Other names n-propylamide
Propionamide
Propylamide
Propionic amide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.066 Edit this at Wikidata
EC Number
  • 201-182-6
MeSH C034666
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H7NO/c1-2-3(4)5/h2H2,1H3,(H2,4,5)Key: QLNJFJADRCOGBJ-UHFFFAOYSA-N
  • InChI=1/C3H7NO/c1-2-3(4)5/h2H2,1H3,(H2,4,5)Key: QLNJFJADRCOGBJ-UHFFFAOYAE
SMILES
  • CCC(=O)N
Properties
Chemical formula C3H7NO
Molar mass 73.095 g·mol
Appearance liquid , yellow
Density 1.042 g/mL
Melting point 80 °C (176 °F; 353 K)
Boiling point 213 °C (415 °F; 486 K)
Solubility in water very soluble in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Propanamide has the chemical formula CH3CH2C=O(NH2). It is the amide of propanoic acid.

This organic compound is a mono-substituted amide. Organic compounds of the amide group can react in many different organic processes to form other useful compounds for synthesis.

Preparation

Propanamide can be prepared by the condensation reaction between urea and propanoic acid:

( NH 2 ) 2 CO + 2 CH 3 CH 2 COOH ⟶ CH 3 CH 2 CO ( NH 2 ) + H 2 O + CO 2 {\displaystyle {\ce {(NH2)2CO + 2CH3CH2COOH -> CH3CH2CO(NH2) + H2O + CO2}}}

or by the dehydration of ammonium propionate:

( NH 4 ) CH 3 CH 2 COO ⟶ CH 3 CH 2 CONH 2 + H 2 O {\displaystyle {\ce {(NH4)CH3CH2COO -> CH3CH2CONH2 + H2O}}}

Reactions

Propanamide being an amide can participate in a Hofmann rearrangement to produce ethylamine gas.

References

  1. Ramazani, Ali; Rouhani, Morteza; Joo, Sang Woo (2016-01-01). "Catalyst-free sonosynthesis of highly substituted propanamide derivatives in water". Ultrasonics Sonochemistry. 28: 393–399. doi:10.1016/j.ultsonch.2015.08.019. ISSN 1350-4177. PMID 26384923.
  2. Ye, Xuewei; Chai, Weiyun; Lian, Xiao-Yuan; Zhang, Zhizhen (2017-06-18). "Novel propanamide analogue and antiproliferative diketopiperazines from mangrove Streptomyces sp. Q24". Natural Product Research. 31 (12): 1390–1396. doi:10.1080/14786419.2016.1253079. ISSN 1478-6419. PMID 27806640. S2CID 24563632.
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