N-(3-Acetyl-4-(oxiran-2-ylmethoxy)phenyl)butanamide

Base Information

• Chemical Name: N-(3-Acetyl-4-(oxiran-2-ylmethoxy)phenyl)butanamide
• CAS No.: 28197-66-2
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• European Community (EC) Number: 248-893-8
• UNII: IYI0EW471K
• DSSTox Substance ID: DTXSID10865420
• Nikkaji Number: J250.671H
• Wikidata: Q27280954
• Mol file: 28197-66-2.mol

Synonyms:28197-66-2;N-(3-Acetyl-4-(oxiran-2-ylmethoxy)phenyl)butanamide;N-(3-ACETYL-4-(OXIRAN-2-YLMETHOXY)PHENYL)BUTYRAMIDE;N-[3-acetyl-4-(oxiran-2-ylmethoxy)phenyl]butanamide;N-(3-ACETYL-4-(2,3-EPOXYPROPOXY)PHENYL)BUTYRAMIDE;EINECS 248-893-8;UNII-IYI0EW471K;IYI0EW471K;3'-ACETYL-4'-(2,3-EPOXYPROPOXY)-BUTYRANILIDE;N-[3-Acetyl-4-(oxiranylmethoxy)phenyl]butyramide;N-(3-Acetyl-4-(oxiran-2-yLmethoxy)-phenyl)butyramide;N-(3-Acetyl-4-(oxiranylmethoxy)phenyl)butyramide;3'-Acetyl-4'-(2,3-epoxypropoxy-d5)-butyranilide;Butanamide, N-(3-acetyl-4-(oxiranylmethoxy)phenyl)-;N-[3-Acetyl-4-[(2RS)-oxiran-2-ylmethoxy]phenyl]butanamide;3'-Acetyl-4'-(2,3-epoxypropoxy)butyranilide;SCHEMBL10594486;DTXSID10865420;AKOS015967256;AB44817;N-(4-Glycidyloxy-3-acetylphenyl)butanamide;FT-0661227;A913507;J-003349;W-110720;Q27280954;ACEBUTOLOL HYDROCHLORIDE IMPURITY A [EP IMPURITY];N-{3-Acetyl-4-[(oxiran-2-yl)methoxy]phenyl}butanamide;BUTYRANILIDE, 3'-ACETYL-4'-(2,3-EPOXYPROPOXY)-;BUTANAMIDE, N-(3-ACETYL-4-(2-OXIRANYLMETHOXY)PHENYL)-;N-(3-ACETYL-4-(OXIRAN-2-YLMETHOXY)PHENYL)BUTANAMIDE, (+/-)-;N-(3-ACETYL-4-(OXIRAN-2-YLMETHOXY)PHENYL)BUTANAMIDE, (2RS)-;3 inverted exclamation mark -Acetyl-4 inverted exclamation mark -(2,3-epoxypropoxy)butyranilide

Chemical Property of N-(3-Acetyl-4-(oxiran-2-ylmethoxy)phenyl)butanamide

Chemical Property:

• Melting Point: 126-128 °C(Solv: toluene (108-88-3))
• Boiling Point: 496.5 °C at 760 mmHg
• PKA: 14.13±0.70(Predicted)
• Flash Point: 254.1 °C
• PSA: 67.93000
• Density: 1.198 g/cm³
• LogP: 2.47840
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 277.13140809
• Heavy Atom Count: 20
• Complexity: 358

Purity/Quality:

99.9% ^*data from raw suppliers

3’-Acetyl-4’-(2,3-epoxypropoxy)butyranilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)NC1=CC(=C(C=C1)OCC2CO2)C(=O)C
• Uses: Intermediate in the preparation of Acebutolol

Technology Process of N-(3-Acetyl-4-(oxiran-2-ylmethoxy)phenyl)butanamide

There total 3 articles about N-(3-Acetyl-4-(oxiran-2-ylmethoxy)phenyl)butanamide 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: 84.0%

(S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + N-(3-acetyl-4-hydroxyphenyl)butanamide (40188-45-2) → (S)-N-(3-acetyl-4-(oxiran-2-ylmethoxy)phenyl)butyramide (28197-66-2)

Guidance literature:

With potassium carbonate; In acetonitrile; Reflux;

DOI:10.1002/chir.22444

Reference yield: 82.0%

N-(3-acetyl-4-hydroxyphenyl)butanamide (40188-45-2) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → (RS)-N-(3-acetyl-4-(oxiran-2-ylmethoxy)phenyl)butyramide (28197-66-2)

Guidance literature:

With potassium carbonate; In acetonitrile; Reflux;

DOI:10.1002/chir.22444

Reference yield: 81.0%

(R)-(-)-epichlorohydrin (51594-55-9,24969-06-0,13403-37-7) + N-(3-acetyl-4-hydroxyphenyl)butanamide (40188-45-2) → (R)-N-(3-acetyl-4-(oxiran-2-ylmethoxy)phenyl)butyramide (28197-66-2)

Guidance literature:

With potassium carbonate; In acetonitrile; Reflux;

DOI:10.1002/chir.22444

upstream raw materials:

N-(3-acetyl-4-hydroxyphenyl)butanamide

epichlorohydrin

(R)-(-)-epichlorohydrin

(S)-epichlorohydrin

Downstream raw materials:

(R)-acebutolol