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N-ethyl-N-phenylacetamide

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Identification
Molecular formula
C10H13NO
CAS number
92-91-1
IUPAC name
N-ethyl-N-phenyl-acetamide
State
State

At room temperature, N-ethyl-N-phenylacetamide is typically a solid.

Melting point (Celsius)
73.00
Melting point (Kelvin)
346.15
Boiling point (Celsius)
319.30
Boiling point (Kelvin)
592.45
General information
Molecular weight
163.22g/mol
Molar mass
163.2130g/mol
Density
1.0300g/cm3
Appearence

N-ethyl-N-phenylacetamide appears as a solid, usually in the form of white to off-white crystals or crystalline powder. The appearance can vary slightly depending on the purity and specific synthesis method used.

Comment on solubility

Solubility of N-ethyl-N-phenyl-acetamide

N-ethyl-N-phenyl-acetamide, with the chemical formula C11H15NO, exhibits unique solubility characteristics that are worthwhile to explore. This compound is notably a member of the amide family, which often influences its interactions with solvents.

Solubility Remarks:

  • Polar Solvents: N-ethyl-N-phenyl-acetamide tends to have moderate solubility in polar solvents such as water, typically due to the presence of the amide functional group which can engage in hydrogen bonding.
  • Non-Polar Solvents: Conversely, it is more soluble in non-polar solvents like ether and chloroform. This is a result of its hydrophobic ethyl and phenyl groups.
  • Miscibility: The compound is generally not completely miscible with water, indicating limited solubility, yet it shows better solubility in organic solvents, making it versatile in various chemical applications.

Overall, the solubility of N-ethyl-N-phenyl-acetamide demonstrates the delicate balance between its polar and non-polar characteristics. As stated in chemistry, “like dissolves like” — one should consider the polarity of both the solvent and solute for successful dissolving outcomes.

Interesting facts

Interesting Facts about N-Ethyl-N-phenyl-acetamide

N-Ethyl-N-phenyl-acetamide, also known as phenacetin, is a notable compound that has played a significant role in the history of medicinal chemistry. Here are some intriguing details about this compound:

  • Historical Usage: Phenacetin was widely used as an analgesic and antipyretic in the early 20th century, providing relief from pain and fever. Its popularity declined due to safety concerns, especially regarding its potential to cause kidney damage.
  • Chemical Structure: The compound features a unique combination of an ethyl group and a phenyl group attached to an acetamide, giving it interesting properties that influence its biological activity.
  • Metabolic Pathways: In biological systems, phenacetin is metabolized to paracetamol (acetaminophen), which is still a commonly used pain reliever today. The understanding of its metabolism has provided valuable insights into drug interactions and pharmacodynamics.
  • Research Applications: Despite its decline in medical use, phenacetin remains an important compound in laboratory research, particularly in studying mechanisms of pain relief and drug metabolism.
  • Regulatory Status: Given its history and side effects, the use of phenacetin has been banned in many countries. This underlines the importance of safety in pharmaceuticals and the ongoing evaluation of drug safety profiles.

Overall, N-ethyl-N-phenyl-acetamide serves as an essential case study in the evolution of drug safety regulations and the dynamic nature of medicinal chemistry.

Synonyms
N-Ethylacetanilide
N-Ethyl-N-phenylacetamide
Mannol
Ethylacetanilide
Acetamide, N-ethyl-N-phenyl-
Acetethylanilide
ACETANILIDE, N-ETHYL-
NSC 8737
EINECS 208-466-9
BRN 2208178
AI3-05523
DTXSID1060186
FSSVIYSWRLKICW-UHFFFAOYSA-
DTXCID8041321
208-466-9
4-12-00-00379 (beilstein handbook reference)
fssviyswrlkicw-uhfffaoysa-n
inchi=1/c10h13no/c1-3-11(9(2)12)10-7-5-4-6-8-10/h4-8h,3h2,1-2h3
529-65-7
ACETYL-N-ETHYLANILIDE
N-ethyl-acetanilide
N-ethyl-N-phenyl-acetamide
WLN: 2NR&V1
SCHEMBL1333185
NSC8737
NSC-8737
AKOS003277540
HS-6387
DB-052224
CS-0258619
NS00032627
EN300-706202
G32390
Z58324632