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N-(2-Hydroxyphenyl)acetamide

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Identification
Molecular formula
C8H9NO2
CAS number
614-80-2
IUPAC name
N-(2-hydroxyphenyl)acetamide
State
State

The compound is typically found as a solid at room temperature.

Melting point (Celsius)
153.00
Melting point (Kelvin)
426.15
Boiling point (Celsius)
310.00
Boiling point (Kelvin)
583.15
General information
Molecular weight
151.17g/mol
Molar mass
151.1650g/mol
Density
1.2257g/cm3
Appearence

N-(2-Hydroxyphenyl)acetamide appears as a white crystalline solid. It is often in the form of a fine powder or crystalline flakes, depending on the purity and processing of the sample.

Comment on solubility

Solubility of N-(2-hydroxyphenyl)acetamide

N-(2-hydroxyphenyl)acetamide, also known as 2-hydroxyacetanilide, displays interesting solubility characteristics that merit discussion:

  • Solvent Compatibility: This compound is generally soluble in polar solvents such as water, ethanol, and methanol, thanks to its ability to form hydrogen bonds.
  • Water Solubility: The presence of the -OH group contributes to its hydrophilicity, allowing it to dissolve effectively in aqueous solutions.
  • Solubility Trends: As a rule of thumb, compounds with functional groups that can engage in hydrogen bonding typically exhibit greater solubility in water.

It's important to note that the specific solubility can vary depending on the temperature and the pH of the solution. For instance, Declan notes that "the interaction of solute and solvent is crucial in determining solubility," which is particularly relevant for this compound.

Overall, the solubility of N-(2-hydroxyphenyl)acetamide is favorable for applications in various fields, making it a compound of interest for further exploration.

Interesting facts

Interesting Facts About N-(2-hydroxyphenyl)acetamide

N-(2-hydroxyphenyl)acetamide, also known as paracetamol or acetaminophen, is a widely used medication that is particularly famous for its analgesic (pain relief) and antipyretic (fever reduction) properties. Some notable aspects of this compound include:

  • Pain Relief: Paracetamol is commonly utilized to alleviate headaches, muscle aches, arthritis, backaches, toothaches, colds, and fevers. It is often considered a first-line treatment due to its efficacy and low side effect profile.
  • Mechanism of Action: While the exact mechanism remains somewhat unclear, it is believed to inhibit the enzyme cyclooxygenase (COX), which is involved in the synthesis of prostaglandins—components that mediate pain and inflammation.
  • Comparison with NSAIDs: Unlike non-steroidal anti-inflammatory drugs (NSAIDs), paracetamol does not significantly affect inflammation and has a lower risk of gastrointestinal side effects, making it a safer alternative for many patients.
  • Hepatic Metabolism: It is metabolized in the liver, primarily through conjugation with sulfate and glucuronide, as well as through the cytochrome P450 pathway—a small fraction producing a toxic metabolite that can lead to liver damage in cases of overdose.
  • Common Formulations: Paracetamol can be found in various formulations, such as tablets, capsules, liquid suspensions, and even intravascular injections, catering to different patient needs and enhancing its usability.
  • Global Reach: This compound is one of the most frequently used pharmaceuticals worldwide, often recommended as an over-the-counter remedy for mild to moderate pain and fever.

Despite its safety record, it is essential to use paracetamol responsibly, as exceeding the recommended dosage can lead to severe hepatic complications. As a compound, N-(2-hydroxyphenyl)acetamide is a prime example of how a simple molecule can have a profound impact on public health.

Synonyms
2-Acetamidophenol
N-(2-Hydroxyphenyl)acetamide
614-80-2
o-Hydroxyacetanilide
2'-Hydroxyacetanilide
2-Hydroxyacetanilide
2-Acetaminophenol
o-Acetamidophenol
o-(Acetylamino)phenol
2-(Acetylamino)phenol
o-Acetaminophenol
N-Acetyl-o-aminophenol
N-Acetyl-2-aminophenol
Acet-o-aminofenol
Acetanilide, 2'-hydroxy-
Acetamide, N-(2-hydroxyphenyl)-
o-Acetylaminofenol
Phenol, 2-acetamido-
NSC 3989
Acet-o-aminofenol [Czech]
o-Acetylaminofenol [Czech]
2-Hydroxyanilid kyseliny octove
2-(N-ACETYLAMINO)PHENOL
EINECS 210-396-9
BRN 0607592
4AS8989RNI
2-Hydroxyanilid kyseliny octove [Czech]
DTXSID8022082
AI3-01928
NSC-3989
HYDROXYACETANILIDE, O-
DTXCID402082
ACETANILIDE, O-HYDROXY-
CHEBI:143107
3-13-00-00778 (Beilstein Handbook Reference)
PARACETAMOL IMPURITY A [EP IMPURITY]
PARACETAMOL IMPURITY A (EP IMPURITY)
210-396-9
inchi=1/c8h9no2/c1-6(10)9-7-4-2-3-5-8(7)11/h2-5,11h,1h3,(h,9,10
MFCD00002181
MLS000069599
SMR000059037
N-(2-hydroxyphenyl)ethanamide
CHEBI:88870
N-(2-Hydroxyphenyl)acetamide (2-Acetamidophenol)
57047-65-1
Acetylaminophenol
N-Phenylglycolamide
ar-Hydroxyacetanilide
Glycolic acid anilide
Paracetamol Impurity A
UNII-4AS8989RNI
Orthocetamol
2-acetamido-phenol
9KS
NSC 99271
BRN 1210581
Opera_ID_1257
2-Acetamidophenol, 97%
2-(N-acetylamino)-phenol
WLN: QR BMV1
SCHEMBL79487
2-Acetamidophenol (Standard)
cid_11972
MLS001066417
Acetamide, N-(hydroxyphenyl)-
CHEMBL1456301
BDBM60355
N-(2-Hydroxyphenyl)acetamide #
NSC3989
HMS1715J07
HMS2235M05
HMS3370F05
HY-W015600R
Tox21_302185
STL182726
AKOS000319633
AB00212
CS-W016316
FA16942
HY-W015600
NCGC00257536-01
AC-13288
AS-15275
CAS-614-80-2
SY004721
DB-002416
H0189
NS00006277
EN300-17802
O11987
4-12-00-00879 (Beilstein Handbook Reference)
AG-996/01589028
Q27160885
Z57040482
F1962-0202
N-(2-Hydroxyphenyl)acetamide;2'-Hydroxyacetanilide;2-(Acetylamino)phenol
2-Acetamidophenol, Pharmaceutical Secondary Standard; Certified Reference Material