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Metacetamol

3-Hydroxyacetanilide

HCID 12124
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Grundinformationen

CAS
621-42-1
Standard-SMILES
CC(=O)Nc1cccc(O)c1
InChIKey
QLNWXBAGRTUKKI-UHFFFAOYSA-N
Summenformel
C8H9NO2
Durchschnittliche Molmasse
151,16 g/mol
Monoisotopische Masse
151,06332853

Überblick

N-acetyl-m-aminophenol is a light gray solid. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
3-Hydroxyacetanilide
IUPAC
N-(3-hydroxyphenyl)acetamide
Lokaler Name
Metacetamol
Englischer Name
3-ACETAMIDOPHENOL
Summenformel
C8H9NO2
Molmasse
151.16

Namen und Synonyme

3-Hydroxyacetanilideacetyl-m-aminophenolRefChem:8111923-AcetamidophenolMetacetamolN-(3-Hydroxyphenyl)acetamide621-42-13'-Hydroxyacetanilidem-AcetamidophenolN-Acetyl-m-aminophenolPeditussAcetamide, N-(3-hydroxyphenyl)-
Weitere Namen anzeigen
Nebsbs479BS 479
MetalidPyrapapRystal3-(Acetylamino)phenolM-HYDROXYACETANILIDEm-(Acetylamino)phenolBS 749Metacetamolum

Datenbank-Bezeichner

CAS
621-42-1
PubChem CID
12124
DTXSID
DTXSID3022089
ChEMBL
CHEMBL9419
ChEBI
CHEBI:76987
UNII
V942ZCN81H
EC Number
210-687-0
Nikkaji
J6.832B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,7
Polarare Oberfläche (TPSA)
49,3 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
11
Formalladung
0
Komplexität
147

Experimentelle und physikochemische Eigenschaften

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 Einträge

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]

Physikochemische Eigenschaften

Schmelzpunkt
145 · 145-148 °C(lit.)
Siedepunkt
273.17 °C · 273.17°C (rough estimate)
Dichte
1.249 · 1.249
Brechungsindex

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 2 Einträge

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 Eintrag

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).

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological ClassificationCompounds capable of relieving pain without the loss of CONSCIOUSNESS.

Verwendung und Herstellung

General Manufacturing InformationAcetamide, N-(3-hydroxyphenyl)-: ACTIVE

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

3-acetaMidophenyl acetate3-HydroxyphenylacetyleneAcetonitril3-Aminophenol3-Aminoacetanilid3'-HydroxyacetophenonEssigsäureanhydridEssigsure

Nachgelagerte Produkte

m-Phenetidin2-Amino-4-methoxy-benzoic acid3-Amino-4-nitrophenol5-AMino-2,4-di-tert-butylphenolN-(3-Hydroxy-4-nitrosophenyl)acetamide

Zugehörige Reaktionen

161
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HRID 1826als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 1829
HRID 1829als Eduktuspto-grants-1998_03
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HRID 16284als Eduktuspto-grants-2010_06
Reaktionsgleichung von HRID 26671
HRID 26671als Eduktuspto-grants-1979_04
Reaktionsgleichung von HRID 29028
HRID 29028als Eduktuspto-grants-2008_09
Reaktionsgleichung von HRID 35418
HRID 35418als Produktuspto-grants-1988_08
Reaktionsgleichung von HRID 44641
HRID 44641als Eduktuspto-grants-2013_09
Reaktionsgleichung von HRID 55605
HRID 55605als Eduktuspto-grants-1997_04
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1.581 · 1.5810 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
Chloroform (Slightly), DMSO (Slightly), Methanol
pka
9.5 · 9.50±0.10(Predicted)
Aggregatzustand
Crystals, Crystalline Powder or Needles
Farbe
Off-white to tan or light gray
PH
6 · 6-7 (H2O)(saturated solution)
BRN
907998 · 907998
InChI
1S/C8H9NO2/c1-6(10)9-7-3-2-4-8(11)5-7/h2-5,11H,1H3,(H,9,10)
InChIKey
QLNWXBAGRTUKKI-UHFFFAOYSA-N
SMILES
CC(=O)Nc1cccc(O)c1
CAS Datenbank
621 · 621-42-1(CAS DataBase Reference)
EPA chemische Informationen
3 · 3'-Hydroxyacetanilide (621-42-1)
Air and Water ReactionsWater insoluble.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheit und Schutzausrüstung

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

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 Eintrag

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 Eintrag

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)

Sicherheitsdaten

F
1-8
wgk
2
tsca
TSCA listed
ridadr
2811
hs_code
2924299090
RTECS-Nr.
AE4100000
risk_code
36/37/38
Toxizität
LD50 intraperitoneal in mouse: 1025mg/kg
hazard_code
Xi,Xn
hazard_note
Irritant
safety_code
26-36
hazard_class
6.1(b)
packing_group
III
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2

Ergänzende Hinweise

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.