Basic information
- CAS
103-89-9- Standard SMILES
CC(=O)Nc1ccc(C)cc1- InChIKey
YICAMJWHIUMFDI-UHFFFAOYSA-N- Molecular formula
- C9H11NO
- Average molar mass
- 149.19 g/mol
- Monoisotopic mass
- 149.08406397
Overview
N-acetyl-p-toluidine appears as colorless needles. (NTP, 1992)
Names & identifiers
- Preferred name
- 4-Methylacetanilide
- IUPAC
- N-(4-methylphenyl)acetamide
- English name
- p-Acetotoluidide
- Molecular formula
- C9H11NO
- Molecular weight
- 149.19
Names & synonyms
4-MethylacetanilideRefChem:8579664'-Methylacetanilide103-89-9p-AcetotoluidideN-(4-Methylphenyl)acetamideP-AcetotoluideN-ACETYL-P-TOLUIDINEp-Acetotoluidine4-AcetotoluideAcetyl-p-toluidinep-Methylacetanilide
Show more names
NSC 7644p-TolyacetamideP-TOLYLACETAMIDE
Acetamide, N-(4-methylphenyl)-p-Acetamidotoluene4-(Acetylamino)toluene1-Acetamido-4-methylbenzene4-AcetotoluidideN-Acetyl-p-toluidideN-(p-tolyl)acetamideN-p-tolylacetamide
Database identifiers
- CAS
103-89-9- PubChem CID
- 7684
- DTXSID
DTXSID6024414- ChEMBL
CHEMBL1604472- ChEBI
CHEBI:143108- UNII
- N36D4JN82T
- EC Number
- 203-155-4
- Nikkaji
- J4.024J
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 29.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 136
Experimental & physicochemical properties
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP1.4
Density1.212 at 59 °F (NTP, 1992) - Denser than water; will sink
Solubilityless than 1 mg/mL at 70 °F (NTP, 1992)
Flash Point335 °F (NTP, 1992)
Boiling Point585 °F at 760 mmHg (sublimes) (NTP, 1992)
Melting Point307 °F (NTP, 1992)
Vapor Density5.14 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Physical DescriptionN-acetyl-p-toluidine appears as colorless needles. (NTP, 1992)
Physicochemical properties
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
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Acetamide, N-(4-methylphenyl)-
Acetamide, N-(4-methylphenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)
Reactive GroupAmides and Imides
Reactivity Profile
N-ACETYL-P-TOLUIDINE is an amide. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. 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).
Air and Water ReactionsWater insoluble.
Chemistry & industry
Pharmacology
Metabolism/Metabolites4'-Methylacetanilide is a known human metabolite of p-Toluidine.
Uses & manufacturing
General Manufacturing InformationAcetamide, N-(4-methylphenyl)-: ACTIVE
Applications
Descriptionp-Acetotoluidide is an off-white to brown flake, odourless, solid or crystalline powder (pure form), which is soluble in hot water, alcohol, ether, chloroform, acetone, glycerol, and benzene. It is combustible and undergoes self-ignition (at 5450°C) but is otherwise stable under most conditions. p-Acetanilide on decomposition releases carbon monoxide, oxides of nitrogen, carbon dioxide, and toxic fumes. p-Acetanilide is used as an inhibitor of peroxides and stabiliser for cellulose ester varnishes. It is used as an intermediate for the synthesis of rubber accelerators, dyes and dye intermediate, and camphor. It is also used as a precursor in penicillin synthesis and other pharmaceuticals including painkillers and intermediates. Phenylacetamide structure shows analgesic and antipyretic effects. But acetanilide is not used directly for this application due to causing methemoglobinemia (the presence of excessive methemoglobin which does not function reversibly as an oxygen carrier in the blood).
Uses4′-Methylacetanilide was used in the synthesis of stable crystalline phosphorus ylides.
General DescriptionColorless needles.
Upstream & downstream products
Downstream products
Related reactions
4 records
Compound notes
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