3-Hydroxyacetanilide

HCID 12124CAS 621-42-1

Basic information

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

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 · 3 items

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)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
Chloroform (Slightly), DMSO (Slightly), Methanol

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

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 · 1 item

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).

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Safety data

F
1-8
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
AE4100000
ridadr
2811

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
杭州创引化工科技有限公司0571-87086220 13516718938 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海凌富药物研究有限公司+86(21)5895 0110 19945755304 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]

Additional notes

DefinitionChEBI: A derivative of phenol which has an acetamido substituent located meta to the phenolic -OH group. It is a non-toxic regioisomer of paracetamol with analgesic properties, but has never been marketed as a drug.

Related reactions

161 records

Linked notes

Loading…