3-Hydroxyacetanilide
Basic information
- CAS
621-42-1- Standard SMILES
CC(=O)Nc1cccc(O)c1- InChIKey
QLNWXBAGRTUKKI-UHFFFAOYSA-N- Molecular formula
- C8H9NO2
- Average molar mass
- 151.16 g/mol
- Monoisotopic mass
- 151.06332853
Overview
N-acetyl-m-aminophenol is a light gray solid. (NTP, 1992)
Names & identifiers
- Preferred name
- 3-Hydroxyacetanilide
- IUPAC
- N-(3-hydroxyphenyl)acetamide
- English name
- 3-ACETAMIDOPHENOL
- Molecular formula
- C8H9NO2
- Molecular weight
- 151.16
Names & synonyms
3-Hydroxyacetanilideacetyl-m-aminophenolRefChem:8111923-AcetamidophenolMetacetamolN-(3-Hydroxyphenyl)acetamide621-42-13'-Hydroxyacetanilidem-AcetamidophenolN-Acetyl-m-aminophenolPeditussAcetamide, N-(3-hydroxyphenyl)-
Show more names
Nebsbs479BS 479
MetalidPyrapapRystal3-(Acetylamino)phenolM-HYDROXYACETANILIDEm-(Acetylamino)phenolBS 749Metacetamolum
Database identifiers
- CAS
621-42-1- PubChem CID
- 12124
- DTXSID
DTXSID3022089- ChEMBL
CHEMBL9419- ChEBI
CHEBI:76987- UNII
- V942ZCN81H
- EC Number
- 210-687-0
- Nikkaji
- J6.832B
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 147
Experimental & physicochemical properties
DrugsPharmaceutical
LogP0.73
Solubilityless than 1 mg/mL at 72 °F (NTP, 1992)
Melting Point406 °F (NTP, 1992)
Physical DescriptionN-acetyl-m-aminophenol is a light gray solid. (NTP, 1992)
Collision Cross Section
129.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
137.29 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
130.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 145 · 145-148 °C(lit.)
- Boiling point
- 273.17 °C · 273.17°C (rough estimate)
- Density
- 1.249 · 1.249
- refractive index
- 1.581 · 1.5810 (estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Commission Regulation No 844/2012
3-Acetamidophenol: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelPoison
Fire HazardsFlash point data for this compound are not available. It is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes.
Reactive GroupAmides and Imides
Reactivity Profile
Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has pKa = 9.88). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds capable of relieving pain without the loss of CONSCIOUSNESS.
Uses & manufacturing
General Manufacturing InformationAcetamide, N-(3-hydroxyphenyl)-: ACTIVE
Applications
Uses3-Acetamidophenol is the ortho-regioisomer of Acetaminophen (A161220), an over-the-counter analgesic and antipyretic agent (1,2).
General DescriptionLight gray solid.
Preparation methods
PreparationIt can be obtained by acetylation, alkylation, hydrolysis, and neutralization of m-aminophenol.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
161 records
Compound notes
Loading…