N-(4-Methoxyphenyl)-3-oxobutanamide

Base Information

• Chemical Name: N-(4-Methoxyphenyl)-3-oxobutanamide
• CAS No.: 5437-98-9
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Hs Code.: 2924299090
• European Community (EC) Number: 226-615-6
• NSC Number: 116392,216130,16508
• UNII: YCG3918U16
• DSSTox Substance ID: DTXSID7044689
• Nikkaji Number: J86.303C
• Wikidata: Q27294450
• ChEMBL ID: CHEMBL3185475
• Mol file: 5437-98-9.mol

Synonyms:5437-98-9;N-(4-Methoxyphenyl)-3-oxobutanamide;4'-Methoxyacetoacetanilide;p-ACETOACETANISIDIDE;Butanamide, N-(4-methoxyphenyl)-3-oxo-;N-(4-methoxyphenyl)-3-oxo-butyramide;Acetoacet-p-anisidide;p-Acetoacetanisidine;para-Acetoacetanisidide;N-(4-Methoxyphenyl)acetoacetamide;p-Acetoacetaniside;NSC 16508;Acetoacetanilide, 4'-methoxy-;Butanamide, N-(4-methoxyphenyl)-oxo-;NSC 116392;NSC 216130;p-Methoxyacetoacetanilide;EINECS 226-615-6;BRN 2213866;UNII-YCG3918U16;AI3-52429;DTXSID7044689;YCG3918U16;N-(4-Methoxyphenyl)acetylacetamide;NSC-16508;NSC-116392;NSC-216130;EC 226-615-6;Maybridge1_001183;N-Acetoacetyl-p-anisidine;4/'-Methoxyacetoacetanilide;4\'-Methoxyacetoacetanilide;N-Acetoacetyl-4-methoxyaniline;SCHEMBL1117828;CHEMBL3185475;DTXCID5024689;HMS544N17;ACETOACETIC ACID P-ANISIDIDE;NSC16508;Tox21_301481;CCG-52405;MFCD00008783;NSC116392;NSC216130;STK397314;AKOS000120070;DS-1122;N-(4-Methoxy-phenyl)-3-oxo-butyramide;N-(4-Methoxyphenyl)-3-oxobutanamide #;NCGC00256049-01;Butanamide, 3-oxo-N-(4-methoxyphenyl)-;CAS-5437-98-9;A1307;CS-0155065;FT-0621789;EN300-17092;D70282;10D-068;A830140;SR-01000641644-1;W-105635;Q27294450;Z56876415

Chemical Property of N-(4-Methoxyphenyl)-3-oxobutanamide

Chemical Property:

• Appearance/Colour: off-white crystalline flake powder
• Vapor Pressure: 6.28E-07mmHg at 25°C
• Melting Point: 115-118 °C
• Refractive Index: 1.552
• Boiling Point: 409.9 °C at 760 mmHg
• PKA: 11.35±0.46(Predicted)
• Flash Point: 201.7 °C
• PSA: 55.40000
• Density: 1.173 g/cm³
• LogP: 1.68580
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

N-(4-Methoxyphenyl)-3-oxobutanamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)NC1=CC=C(C=C1)OC
• Uses: N-(4-Methoxyphenyl)-3-oxobutanamide is an intermediate in the synthesis of Tafenoquine-d3 Succinate is the labelled analog of Tatenoquine (T004760), a new 8-aminoquinoline with an improved therapeutic index and safety profile as compared to primaquine (P733500).Tafenoquine has the potential to become a widely used drug in the prevention and treatment of malaria infection and could replace some currently used drugs as resistant strains of Plasmodium species increase.

Technology Process of N-(4-Methoxyphenyl)-3-oxobutanamide

There total 9 articles about N-(4-Methoxyphenyl)-3-oxobutanamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) + 4-methoxy-aniline (104-94-9) → 4'-methoxyacetoacetanilide (5437-98-9)

Guidance literature:

In water; for 2.5h; Reflux; Green chemistry;

DOI:10.1039/c5ra14355a

Reference yield: 93.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + 4-methoxy-aniline (104-94-9) → 4'-methoxyacetoacetanilide (5437-98-9)

Guidance literature:

In benzene; at 65 ℃; for 2h;

DOI:10.1007/s00044-012-0157-0

Reference yield: 93.0%

ethyl acetoacetate (141-97-9) + 4-methoxy-aniline (104-94-9) → 4'-methoxyacetoacetanilide (5437-98-9)

Guidance literature:

With 1,1,1,3',3',3'-hexafluoro-propanol; In acetonitrile; at 80 ℃; for 12h; Sealed tube; Green chemistry;

DOI:10.1016/j.tetlet.2020.152535

upstream raw materials:

4-methyleneoxetan-2-one

4-methoxy-aniline

ethyl acetoacetate

2,2,6-trimethyl-4H-1,3-dioxin-4-one

Downstream raw materials:

2-hydroxy-4-methyl-6-methoxyquinoline

3-amino-crotonic acid p-anisidide

2-Acetyl-monothiomalonsaeure-bis-<4-methoxy-anilid>

2-Butyl-acetoacet-p-anisid

Refernces

• 1、 Kabi, Arup K.,Gujjarappa, Raghuram,Vodnala, Nagaraju,Kaldhi, Dhananjaya,Tyagi, Ujjawal,Mukherjee, Kalisadhan,Malakar, Chandi C.. "HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst". supporting information. . Retrieved 2020/10/20.
• 2、 Tang, Jing,Huber, Andrew D.,Pineda, Dallas L.,Boschert, Kelsey N.,Wolf, Jennifer J.,Kankanala, Jayakanth,Xie, Jiashu,Sarafianos, Stefan G.,Wang, Zhengqiang. "5-Aminothiophene-2,4-dicarboxamide analogues as hepatitis B virus capsid assembly effectors". supporting information. p. 179 - 192. Retrieved 2019/01/04.