Basic information
- Standard SMILES
CC(=O)Nc1ccccc1C- InChIKey
BPEXTIMJLDWDTL-UHFFFAOYSA-N- Molecular formula
- C9H11NO
- Average molar mass
- 149.19 g/mol
- Monoisotopic mass
- 149.08406397
Overview
O-acetotoluidide appears as colorless crystals. Insoluble in water. (NTP, 1992)
Names & identifiers
- Preferred name
- N-acetyl-o-toluidine
- IUPAC
- N-(2-methylphenyl)acetamide
- English name
- 2-Methylacetanilide
- Molecular formula
- C9H11NO
- Molecular weight
- 149.19
Names & synonyms
120-66-1o-AcetotoluidideN-(2-Methylphenyl)acetamide2'-Methylacetanilideo-AcetotoluideN-ACETYL-O-TOLUIDINEo-MethylacetanilideAcetyl-o-toluidineN-o-TolylacetamideAcetamide, N-(2-methylphenyl)-N-Acetyl-2-toluidineN-Acetyl-o-toludine
Show more names
2-MethylacetanilineAcet-o-toluidideO-TOLYLACETAMIDEO-ACETOTOLUIDINE2-ACETOTOLUIDINE2-ACETAMIDOTOLUENE
2`-MethylacetanilideN-Acetoxy-2-toluidineNSC 3365CCRIS 1237DTXSID1024413HSDB 4256EINECS 204-414-4AI3-03946
Database identifiers
- CAS
120-66-1- PubChem CID
- 8443
- DTXSID
DTXSID1024413- ChEMBL
CHEMBL1568309- ChEBI
CHEBI:189137- UNII
- 425I3L2A81
- EC Number
- 204-414-4
- Nikkaji
- J5.330I
Properties
Computed structural properties
- XLogP
- 0.9
- 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
- 144
Experimental & physicochemical properties
Chemical Classes
Nitrogen Compounds -> Other Aromatics (Nitrogen)
Dye
SpringerMaterials PropertiesBoiling point
Density
1.168 (NTP, 1992) - Denser than water; will sink
1.168 @ 15 °C
Color/Form
CRYSTALS
COLORLESS
Solubility
Insoluble (NTP, 1992)
SLIGHTLY SOL IN WATER; SOL IN ALC, CHLOROFORM, ETHER
SOL IN BENZENE, GLACIAL ACETIC ACID
INSOL IN HOT WATER
Boiling Point
565 °F at 760 mmHg (NTP, 1992)
296 °C
Melting Point
230 °F (NTP, 1992)
110 °C
Vapor Pressure0.000183 [mmHg]
Physical Description
O-acetotoluidide appears as colorless crystals. Insoluble in water. (NTP, 1992)
Colorless solid; [HSDB] Colorless crystalline powder; [Alfa Aesar MSDS]
Other Experimental Properties
UV: 831 (Sadtler Research Laboratories Spectral Collection) /3-Methylacetanilide/
UV: 2664 (Absorption Spectra in the UV and visible Regions, Academic Press, New York) /4-Methylacetanilide/
Physicochemical properties
- Melting point
- 109 · 109-112 °C
- Boiling point
- 296 °C · 296 °C
- Density
- 1.16 · 1.16
- refractive index
- 1.5279 · 1.5279 (estimate)
- Flash point
- 296 °C · 296°C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- It is slightly soluble in acetone, chloroform, toluene, benzene.
- form
- Solid
- pka
- 15.13 · 15.13±0.70(Predicted)
- color
- Needles
- Merck
- 14 · 14,74
- BRN
- 2207054 · 2207054
- InChI
- InChI=1S/C9H11NO/c1-7-5-3-4-6-9(7)10-8(2)11/h3-6H,1-2H3,(H,10,11)
- InChIKey
- BPEXTIMJLDWDTL-UHFFFAOYSA-N
- SMILES
- C(NC1=CC=CC=C1C)(=O)C
- CAS DataBase Reference
- 120 · 120-66-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 425 I3L2A81 · 425I3L2A81
- EPA Substance Registry System
- o-Acetotoluidide (120-66-1)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 264 · P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- Hazard Codes
- Xn
- Risk Statements
- 36 · 36/37/38-22
- Safety Statements
- 37 · 37/39-26-36-36/37
- RTECS
- 2900000 · AN2900000
- Hazard Note
- Harmful
- TSCA
- TSCA listed
- HS Code
- 29242990 · 29242990
- Hazardous Substances Data
- 120 · 120-66-1(Hazardous Substances Data)
- Toxicity
- 1 mg/plate · mma-sat 1 mg/plate NTPTB* JAN 82
Safety & regulation
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 543 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: Acetamide, N-(2-methylphenyl)-
Health HazardsACUTE/CHRONIC HAZARDS: Toxic. Hazardous decomposition products. (NTP, 1992)
Hazards SummaryEnlarged livers with severe hydropic swelling and fatty changes observed in rats at high doses (44-fold excess molar dose); [HSDB] A skin and strong eye irritant; [Alfa Aesar MSDS]
Reactive GroupAmides and Imides
Reactivity Profile
O-ACETOTOLUIDIDE is an amide. Amides react with azo and diazo compounds to generate toxic gases. 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.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
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: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong 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.
Toxicology
InteractionsO-ACETOTOLUIDIDE WAS, AMONG ISOMERS, THAT PREVENTED DEATH OF RATS DUE TO TOXICITY OF 300 PPM OF N-2-FLUORENYLACETAMIDE.
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Non-Human Toxicity ExcerptsA 44-FOLD MOLAR EXCESS DOSE OF O-ACETOTOLUIDIDE PRODUCED IN RATS ENLARGED LIVERS WITH MARKED HYDROPIC SWELLING & FATTY CHANGES.
Safety data
- tsca
- TSCA listed
- rtecs
- AN2900000
- hs_code
- 29242990
- Toxicity
- mma-sat 1 mg/plate NTPTB* JAN 82
- risk_code
- 36/37/38-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- hazard_note
- Harmful
- safety_code
- 37/39-26-36-36/37
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- Hazardous Substances Data
- 120-66-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
YIELDS N-ACETYLANTHRANILIC ACID IN RABBIT; BRAY, HG, & THORPE, WV, BIOCHEM J, 43, 211 (1948). /FROM TABLE/
FOLLOWING SINGLE DOSE (400 MG/KG SUBCUTANEOUS) OF O-(METHYL-(14)C)TOLUIDINE TO MALE F344 RAS, N-ACETYL-O-TOLUIDINE WAS PRODUCED AS A METABOLITE.
Absorption, Distribution and ExcretionAFTER 48 HR FOLLOWING SC INJECTION OF 400 MG/KG OF O-(METHYL-(14)C)TOLUIDINE TO MALE RATS, 83.9% APPEARED IN URINE, 3.3% IN FECES & 1.4% WAS EXHALED.
Uses & manufacturing
Uses
Used to make dyes; [HSDB]
CHEM INT FOR DYES, EG, C.I. SULFUR YELLOW 12
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) No Data
(1979) No Data
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
Methods of ManufacturingREACTION OF GLACIAL ACETIC ACID WITH O-TOLUIDINE
Formulations/PreparationsGRADE: TECHNICAL.
General Manufacturing InformationAcetamide, N-(2-methylphenyl)-: ACTIVE
Applications
Useso-Methylacetanilide is a substituted acetanilide that is used as precursor for various pharmaceuticals including their intermediates.
UsesAcetanilide is used as an inhibitor of peroxides andstabilizer for cellulose ester varnishes.It is used as an intermediate for the synthesis ofrubber accelerators, dyes and dye intermediate and camphor. It is used as a precursor in penicillin synthesis and other pharmaceuticals including painkillers and intermediates.
General DescriptionColorless crystals. Insoluble in water.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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Additional notes
DefinitionChEBI: 2`-Methylacetanilide is a member of toluenes.
Related reactions
16 records
Linked notes
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