Acetoacetanilide
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 591704

CAS#: 102-01-2

Description: Acetoacetanilide is an organic compound with the formula CH₃CCH₂CNHC₆H₅. It is the acetoacetamide derivative of aniline. It is a white solid that is poorly soluble in water.


Chemical Structure

img
Acetoacetanilide
CAS# 102-01-2

Theoretical Analysis

MedKoo Cat#: 591704
Name: Acetoacetanilide
CAS#: 102-01-2
Chemical Formula: C10H11NO2
Exact Mass: 177.079
Molecular Weight: 177.2
Elemental Analysis: C, 67.78; H, 6.26; N, 7.90; O, 18.06

Price and Availability

Size Price Availability Quantity
500.0g USD 230.0 2 Weeks
Bulk inquiry

Synonym: Acetoacetanilide; NSC 2656; NSC-2656; NSC2656

IUPAC/Chemical Name: Butanamide, 3-oxo-N-phenyl-

InChi Key: DYRDKSSFIWVSNM-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H11NO2/c1-8(12)7-10(13)11-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,11,13)

SMILES Code: CC(CC(NC1=CC=CC=C1)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 177.2 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Mousavi SR. Claisen-Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives with different substituents in H(2) O/EtOH. Chirality. 2016 Nov;28(11):728-736. doi: 10.1002/chir.22653. PubMed PMID: 27791320.

2: Gholami A, Mohsenikia A, Masoum S. Determination of Very Low Level of Free Formaldehyde in Liquid Detergents and Cosmetic Products Using Photoluminescence Method. J Anal Methods Chem. 2016;2016:1720530. doi: 10.1155/2016/1720530. Epub 2016 Aug 21. PubMed PMID: 27635279; PubMed Central PMCID: PMC5011240.

3: Joseph J, Janaki GB. Copper complexes bearing 2-aminobenzothiazole derivatives as potential antioxidant: Synthesis, characterization. J Photochem Photobiol B. 2016 Sep;162:86-92. doi: 10.1016/j.jphotobiol.2016.06.030. Epub 2016 Jun 23. PubMed PMID: 27344637.

4: Priya NP, Firdous AP, Jeevana R, Aravindakshan KK. Cytotoxic and Antitumour Studies of Acetoacetanilide N(4)-methyl(phenyl)thiosemicarbazone and its Transition Metal Complexes. Indian J Pharm Sci. 2015 Nov-Dec;77(6):655-60. PubMed PMID: 26997691; PubMed Central PMCID: PMC4778223.

5: Azzam RA, Mohareb RM. Multicomponent Reactions of Acetoacetanilide Derivatives with Aromatic Aldehydes and Cyanomethylene Reagents to Produce 4H-Pyran and 1,4-Dihydropyridine Derivatives with Antitumor Activities. Chem Pharm Bull (Tokyo). 2015;63(12):1055-64. doi: 10.1248/cpb.c15-00685. PubMed PMID: 26633027.

6: Chen K, Prabel J, Dutton J, Gotoda M, Asai Y, Grobin A. Trans-3,4-dideoxyglucone-3-ene (trans-3,4-DGE), a most reactive glucose degradation product in freshly heat sterilized glucose solutions. Carbohydr Res. 2015 Dec 11;418:57-64. doi: 10.1016/j.carres.2015.10.003. Epub 2015 Oct 19. PubMed PMID: 26546740.

7: Chandrasekaran D, Vandarkuzhali SA, Sridharan G, Natarajan R, Brindha P. Comparative in vitro Cytotoxic Studies of Novel 8-(4'/2'-Methoxy/Unsubstituted phenylcarbamoyl)bicyclo[3.3.1]nonane Derivatives on Ehrlich Ascites Carcinoma Cell Line. Indian J Pharm Sci. 2014 Jul;76(4):370-4. PubMed PMID: 25284936; PubMed Central PMCID: PMC4171875.

8: Mousavi MR, Maghsoodlou MT, Habibi-Khorassani SM. One-pot diastreoselective synthesis of highly functionalized cyclohexenones: 2-oxo-N,4,6-triarylcyclohex-3-enecarboxamides. Mol Divers. 2014 Nov;18(4):821-8. doi: 10.1007/s11030-014-9541-7. Epub 2014 Aug 6. PubMed PMID: 25096399.

9: Ghosh S, Khamarui S, Gayen KS, Maiti DK. ArCH(OMe)₂--a Pt(IV)-catalyst originator for diverse annulation catalysis. Sci Rep. 2013 Oct 18;3:2987. doi: 10.1038/srep02987. PubMed PMID: 24136161; PubMed Central PMCID: PMC3798883.

10: Pagadala R, Maddila S, Jonnalagadda SB. Eco-efficient ultrasonic responsive synthesis of pyrimidines/pyridines. Ultrason Sonochem. 2014 Mar;21(2):472-7. doi: 10.1016/j.ultsonch.2013.08.024. Epub 2013 Sep 8. PubMed PMID: 24063995.

11: Arjunan V, Kalaivani M, Senthilkumari S, Mohan S. Vibrational, NMR and quantum chemical investigations of acetoacetanilde, 2-chloroacetoacetanilide and 2-methylacetoacetanilide. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Nov;115:154-74. doi: 10.1016/j.saa.2013.06.003. Epub 2013 Jun 20. PubMed PMID: 23832223.

12: Al-Adiwish WM, Tahir MI, Siti-Noor-Adnalizawati A, Hashim SF, Ibrahim N, Yaacob WA. Synthesis, antibacterial activity and cytotoxicity of new fused pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c][1,2,4]triazine derivatives from new 5-aminopyrazoles. Eur J Med Chem. 2013 Jun;64:464-76. doi: 10.1016/j.ejmech.2013.04.029. Epub 2013 Apr 23. PubMed PMID: 23669354.

13: Souza ER, Zulato CH, Mazali IO, Sigoli FA. Synthesis and photoluminescent properties of lanthanides acetoacetanilide complexes. J Fluoresc. 2013 Sep;23(5):939-46. doi: 10.1007/s10895-013-1219-5. Epub 2013 May 2. PubMed PMID: 23636353.

14: Vijayan N, Rani N, Bhagavannarayana G, Haranath D, Jayabharathi J, Wahab MA, Das S. Optical, elemental and structural analyses of acetoacetanilide single crystals for nonlinear optical applications. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Jul;93:75-80. doi: 10.1016/j.saa.2012.02.077. Epub 2012 Mar 2. PubMed PMID: 22465771.

15: Sengupta T, Gayen KS, Pandit P, Maiti DK. FeCl3⋅6H2O-catalyzed intermolecular-cascade cyclization of acetoacetanilide: aldehyde-tuned synthesis to valuable 2-pyridone analogues. Chemistry. 2012 Feb 13;18(7):1905-9. doi: 10.1002/chem.201103354. Epub 2012 Jan 20. PubMed PMID: 22266708.

16: Hu Y, Fu X, Barry BD, Bi X, Dong D. Regiospecific β-lactam ring-opening/recyclization reactions of N-aryl-3-spirocyclic-β-lactams catalyzed by a Lewis-Brønsted acids combined superacid catalyst system: a new entry to 3-spirocyclicquinolin-4(1H)-ones. Chem Commun (Camb). 2012 Jan 18;48(5):690-2. doi: 10.1039/c1cc15881c. Epub 2011 Dec 1. PubMed PMID: 22134176.

17: Wei Y, Liu J, Lin S, Ding H, Liang F, Zhao B. Acetoacetanilides as masked isocyanates: facile and efficient synthesis of unsymmetrically substituted ureas. Org Lett. 2010 Oct 1;12(19):4220-3. doi: 10.1021/ol101474f. PubMed PMID: 20809613.

18: Gopalakrishnan S, Joseph J. Antifungal Activities of Copper(II) with Biosensitive Macrocyclic Schiff Base Ligands Derived from 4-Aminoantipyrine Derivatives. Mycobiology. 2009 Jun;37(2):141-6. doi: 10.4489/MYCO.2009.37.2.141. Epub 2009 Jun 30. PubMed PMID: 23983523; PubMed Central PMCID: PMC3749404.

19: Priya NP, Arunachalam S, Manimaran A, Muthupriya D, Jayabalakrishnan C. Mononuclear Ru(III) Schiff base complexes: synthesis, spectral, redox, catalytic and biological activity studies. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Apr;72(3):670-6. doi: 10.1016/j.saa.2008.10.028. Epub 2008 Oct 31. PubMed PMID: 19081293.

20: Lee JT, Mah H, Nam KD, Shin D, Ha DC, Hahn HG. Syntheses of 1,3-imidazolin-2-ones and 1,3-imidazolin-2-thiones from new building blocks, gamma-aminoacetoacetanilides. J Comb Chem. 2008 Nov-Dec;10(6):803-6. doi: 10.1021/cc8000713. Epub 2008 Sep 26. PubMed PMID: 18817450.