Acetoacetamide

Acetoacetamide
Names
Other names
3-oxobutanamide, 3-oxobutyramide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.025.250 Edit this at Wikidata
EC Number
  • 227-774-4
KEGG
  • InChI=1S/C4H7NO2/c1-3(6)2-4(5)7/h2H2,1H3,(H2,5,7)
    Key: GCPWJFKTWGFEHH-UHFFFAOYSA-N
  • CC(=O)CC(=O)N
Properties
C4H7NO2
Molar mass 101.105 g·mol−1
Appearance white solid
Melting point 53-56
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Acetoacetamide is an organic compound with the formula CH3COCH2CONH2. It is the amide of acetoacetic acid. It is produced by treating diketene with aqueous ammonia[1]

It results from degradation of the sweetner acesulfame potassium.[2]

Acetoacetanilide (CH3COCH2CONH2) is the N-phenyl derivative of acetoacetamide. It is also prepared from diketene.[3] It and various derivatives are used in the production of organic pigments called arylide yellows, one example being Pigment Yellow 74. Many analogues have been prepared.[4] To make the dyes, acetoacetanilides are coupled to diazonium salts, "azo coupling".[5]

Acetoacetylation with diketene followed by diazo coupling. The ketohydrazone tautomer is shown.

References

  1. ^ Miller, Raimund; Abaecherli, Claudio; Said, Adel; Jackson, Barry (2001). "Ketenes". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a15_063. ISBN 978-3-527-30385-4.
  2. ^ George, V.; Arora, S.; Wadhwa, B. K.; Singh, A. K. (August 2010). "Analysis of multiple sweeteners and their degradation products in lassi by HPLC and HPTLC plates". Journal of Food Science and Technology. 47 (4): 408–413. doi:10.1007/s13197-010-0067-4. ISSN 0022-1155. PMC 3551007. PMID 23572661.
  3. ^ Williams, Jonathan W.; Krynitsky, John A. (1941). "Acetoacetanilide". Organic Syntheses. 21: 4. doi:10.15227/orgsyn.021.0004.
  4. ^ Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3.
  5. ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371


Stub icon

This article about an organic compound is a stub. You can help Wikipedia by adding missing information.

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.