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Phenacetin

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Identification
Molecular formula
C10H13NO2
CAS number
62-44-2
IUPAC name
N-(4-ethoxyphenyl)acetamide
State
State
Solid at room temperature. Phenacetin remains stable as a crystalline powder under standard conditions, making it easy to handle and store.
Melting point (Celsius)
134.00
Melting point (Kelvin)
407.20
Boiling point (Celsius)
515.30
Boiling point (Kelvin)
788.50
General information
Molecular weight
179.22g/mol
Molar mass
179.2170g/mol
Density
1.0990g/cm3
Appearence

Phenacetin appears as a white, crystalline solid with a slightly bitter taste. It is typically odorless and has a polished appearance under light due to its crystal-like structure.

Comment on solubility

Solubility of N-(4-ethoxyphenyl)acetamide

N-(4-ethoxyphenyl)acetamide, with the chemical formula C10H13NO2, exhibits specific solubility characteristics that are important to consider in various applications. This compound is primarily known for its moderate to low solubility in water, which can be attributed to the presence of the ethoxy group and the amide functional group in its structure. Here are some key points regarding its solubility:

  • Water solubility: Generally poor, due to its hydrophobic segments.
  • Solvents: It tends to dissolve more readily in organic solvents such as ethanol, methanol, and dichloromethane.
  • Temperature dependence: Increased temperature can enhance solubility in organic solvents, a common trait among organic compounds.
  • pH effects: Changes in pH can also influence the degree of ionization and thus solubility, especially for amides which may engage in hydrogen bonding.

In summary, while N-(4-ethoxyphenyl)acetamide does not readily dissolve in water, its solubility in organic solvents makes it suitable for various applications in organic synthesis and pharmaceutical formulations. As stated: "Understanding the solubility principles of compounds is essential in predicting their behavior in different environments."

Interesting facts

Interesting Facts About N-(4-ethoxyphenyl)acetamide

N-(4-ethoxyphenyl)acetamide, often simply referred to as an amide, holds a significant place in the realm of organic chemistry due to its unique properties and versatile applications. This compound is classified as an aromatic amide, and its structure is characterized by an ethoxy group linked to a phenyl ring, which is directly attached to the acetamide functional group. Here are some fascinating aspects about N-(4-ethoxyphenyl)acetamide:

  • Biological Significance: Compounds of this class have been of interest in pharmaceuticals due to their potential biological activities. Some derivatives exhibit anti-inflammatory properties, making them attractive candidates for drug development.
  • Industrial Use: The synthesis of amides like N-(4-ethoxyphenyl)acetamide plays a crucial role in the production of agrochemicals and polymers. Their versatility allows them to be utilized as intermediates in the manufacturing of other complex compounds.
  • Aromaticity: The presence of the phenyl group enhances the stability and reactivity of the compound. This aromatic stability is a key factor in many chemical reactions, contributing to its behavior during synthesis.
  • Synthesis Routes: Common synthesis techniques involve the acetylation of amines or through the reaction of ethoxybenzoyl chloride with amines. This showcases the breadth of organic reactions that can produce such compounds.
  • Research & Development: Ongoing research is focused on understanding the biological mechanisms of amides like N-(4-ethoxyphenyl)acetamide. This research is vital as it can lead to the development of novel therapeutic agents.

In conclusion, N-(4-ethoxyphenyl)acetamide serves as an excellent example of how simple organic compounds can have wide-ranging implications in both scientific research and industrial applications. Its synthesis and study continue to be an exciting endeavor for chemists seeking to uncover new properties and functionalities.

Synonyms
phenacetin
62-44-2
N-(4-Ethoxyphenyl)acetamide
Acetophenetidin
Acetphenetidin
Acetophenetidine
Acetophenetin
p-Acetophenetidide
Phenacetine
4'-Ethoxyacetanilide
Phenazetin
Phenacetinum
Fenidina
Kalmin
Achrocidin
Codempiral
Commotional
Contradol
Contradouleur
Fenacetina
4-Ethoxyacetanilide
p-Acetophenetidine
Pertonal
Phenacet
Phenacitin
Phenedina
Phenidin
Pyraphen
Fenina
Phenin
p-Ethoxyacetanilide
p-Acetophenetide
p-Acetphenetidin
Acetamide, N-(4-ethoxyphenyl)-
Clistanol
Coricidin
Coriforte
Daprisal
Dolostop
Emprazil
Fortacyl
Gelonida
Helvagit
Hocophen
Melaforte
Paramette
Paratodol
Phenazetina
Pyrroxate
Quadronal
Salgydal
Sanalgine
Stellacyl
Synalogos
Tetracydin
Anapac
Dasikon
Edrisal
Empiral
Epragen
Gewodin
Pamprin
Seranex
Sinedal
Sinubid
Sinutab
Treupel
Acetylphenetidin
Fenia
Malex
Tacol
Viden
Xaril
Kafa
para-Phenacetin
Phenaphen plus
Bromo seltzer
Robaxisal-ph
Citra-fort
Aceto-4-phenetidine
Dasin ch
Emprazil-C
Paracetophenetidin
Acet-p-phenalide
Coryban-D
Hjorton'S powder
Acet-p-phenetidin
Thephorin A-C
Buff-A-Comp
Para-acetphenetidin
Melabon
N-Acetyl-p-phenetidine
Phenodyne
Saridon
Sinutabs
Veganine
1-Acetamido-4-ethoxybenzene
Aceto-para-phenalide
para-Acetophenetidide
Super Anahist
Acetanilide, 4'-ethoxy-
Aceto-para-phenetidide
p-Phenetidine, N-acetyl-
Fenacetin
Fiorinal
para-Acetophenetidine
Rcra waste number U187
para-Ethoxyacetanilide
Fenacetin [Czech]
Acetamide, N-(4-ethoxyphenol)-
N-para-Ethoxyphenylacetamide
CCRIS 496
4-(Acetylamino)phenetole
N-Acetyl-4-ethoxyaniline
N-Acetyl-para-phenetidine
Fenacetina [INN-Spanish]
HSDB 3152
p-Ethoxyanilid kyseliny octove
BRN 1869238
Acetic acid amide, N-(4-ethoxyphenyl)-
Phenacetin Melting Point Standard
AI3-00783
UNII-ER0CTH01H9
NSC 7651
NSC-7651
EINECS 200-533-0
ER0CTH01H9
4-Ethoxy-1-acetylaminobenzene
p-Ethoxyanilid kyseliny octove [Czech]
CHEBI:8050
DTXSID1021116
Phenacetin (Standard)
1-Acetyl-p-phenetidin
N-Acetyl-p-ethoxyaniline
MFCD00009094
DTXCID001116
N-[4-(ethyloxy)phenyl]acetamide
NSC7651
CAS-62-44-2
NCGC00016281-06
PHENACETIN (IARC)
PHENACETIN [IARC]
PHENACETIN (MART.)
PHENACETIN [MART.]
PHENACETIN (USP-RS)
PHENACETIN [USP-RS]
Phenacetin (p-Acetophenetidide)
paracetophentidin
Phenacetine [INN-French]
Phenacetinum [INN-Latin]
40674-52-0
SMR000752916
SR-01000787183
RCRA waste no. U187
Terracydin
Phenacetin [USP:INN:JAN]
N-(4-ethoxyphenyl)-acetamide
Acetamide,N-(4-ethoxyphenyl)-
Zactirin compound
p-Acetophenetitide
Prestwick_862
Phenacetin, 97%
4-Ethoxy-acetanilid
N-acetylphenetylamine
para Acetylphenetidin
FENEDINA
4-Ethoxy-acetanilide
4-Ethoxy Acetanilide
ASA COMPOUND
Butigetic (Salt/Mix)
Spectrum_000782
Acetanilide, p-ethoxy-
PHENACETIN [MI]
Phenacetin (JAN/INN)
PHENACETIN [INN]
PHENACETIN [JAN]
Prestwick0_000533
Prestwick1_000533
Prestwick2_000533
Prestwick3_000533
Spectrum2_001940
Spectrum3_001404
Spectrum4_000515
Spectrum5_001902
PARA-ACETOPHENETIDE
PHENACETIN [HSDB]
4'ETHOXYACETANILIDE
ACET-PARA-PHENALIDE
p-Acetophenetidide (8CI)
PARA-ACETOPHENETIDIN
PHENACETIN [VANDF]
PHENACETINUM [HPUS]
WLN: 2OR DMV1
N-(4-ethoxyphenol)acetamide
PHENACETIN [WHO-DD]
SCHEMBL23280
BSPBio_000545
BSPBio_003048
KBioGR_001089
KBioSS_001262
N-(4-ethoxyphenyl)ethanamide
PARA-ETHOXY-ACETANILID
MLS001304971
MLS002153862
MLS002303055
aniline, N-acetyl-4-ethoxy-
CHEMBL16073
DivK1c_000580
P-A-C Compound (Salt/Mix)
SPECTRUM1500642
SPBio_001979
SPBio_002466
BPBio1_000601
GTPL7402
ACETANILIDE,4'-ETHOXY-
P-PHENETIDINE, N-ACETYL
SCHEMBL20476396
HMS501M22
HY-B0476R
KBio1_000580
KBio2_001262
KBio2_003830
KBio2_006398
KBio3_002268
N02BE03
NINDS_000580
HMS1569L07
HMS1921M21
HMS2092E14
HMS2096L07
HMS2234P11
HMS3373I02
HMS3651N07
HMS3713L07
HMS3884H10
Pharmakon1600-01500642
BCP09084
HY-B0476
KCA90227
Phenacetin, >=98.0% (HPLC)
N-PARA-ETHOXYPHENYL-ACETAMIDE
Tox21_110347
Tox21_201926
Tox21_302895
BDBM50420191
CCG-39439
NSC757401
STK011463
AKOS000370201
Phenacetin 1.0 mg/ml in Acetonitrile
Tox21_110347_1
DB03783
FA26860
NSC-757401
IDI1_000580
Acetamide, N-(4-ethoxyphenyl)- (9CI)
NCGC00016281-01
NCGC00016281-02
NCGC00016281-03
NCGC00016281-04
NCGC00016281-05
NCGC00016281-07
NCGC00016281-08
NCGC00016281-11
NCGC00091376-01
NCGC00091376-02
NCGC00091376-03
NCGC00091376-04
NCGC00091376-05
NCGC00256345-01
NCGC00259475-01
1ST10057
AC-28909
AS-87619
SBI-0051571.P002
DB-054164
Phenacetin, Vetec(TM) reagent grade, 98%
AB00052135
Acetamide, N-[4-(ethoxy-1-13C)phenyl]-
CS-0694917
NS00006373
P1669
S2577
SW196989-3
BIM-0051571.0001
C07591
D00569
D84419
EN300-178258
AB00052135_10
AB00052135_11
ACETIC ACID, AMIDE, N(4-ETHOXYPHENYL)-
A833774
AE-848/04969036
Q419175
Phenacetin (136 degrees C) Melting Point Standard
Phenacetin (p-Acetophenetidide), 1mg/ml in Methanol
SR-01000787183-2
SR-01000787183-3
BRD-K38323065-001-05-8
BRD-K38323065-001-09-0
BRD-K38323065-001-18-1
BRD-K38323065-001-19-9
Z27807932
Acetophenetidine Acetophenidin Acetylphenetidine Phenacetin
Phenacetin, United States Pharmacopeia (USP) Reference Standard
N-(4-Ethoxyphenyl)acetamide;Phenacetin;4-Acetophenetidine;4'-Ethoxyacetanilide
Phenacetin Melting Point Standard, United States Pharmacopeia (USP) Reference Standard
200-533-0
InChI=1/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12
N4E
Phenacetin melting point standard, Pharmaceutical Secondary Standard; Certified Reference Material