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
Show more names
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
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)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol
- pka
- 9.5 · 9.50±0.10(Predicted)
- form
- Crystals, Crystalline Powder or Needles
- color
- 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 DataBase Reference
- 621 · 621-42-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 942 ZCN81H · V942ZCN81H
- EPA Substance Registry System
- 3 · 3'-Hydroxyacetanilide (621-42-1)
- UNSPSC Code
- 77101502 · 77101502
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- RIDADR
- 2811 · 2811
- WGK Germany
- 2 · 2
- RTECS
- 4100000 · AE4100000
- F
- 1 · 1-8
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 29242995 · 29242995
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2
- Toxicity
- 50 intraperitoneal · LD50 intraperitoneal in mouse: 1025mg/kg
Safety & regulation
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
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).
Safety & protection
First Aid
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
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.
Personal Protective Equipment (PPE)
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
- hs_code
- 29242995
- Toxicity
- LD50 intraperitoneal in mouse: 1025mg/kg
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
- 26-36
- hazard_class
- 6.1(b)
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H315-H319
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Chemistry & industry
Pharmacology
Uses & manufacturing
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
Suppliers50 total
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
Linked notes
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