| Identification | More | [Name]
N-METHYLBENZAMIDE | [CAS]
613-93-4 | [Synonyms]
N-METHYLBENZAMIDE
n-methyl-benzamid
N-Methylbenzenamide
n-methylbenzenecarboxamide
N-METHYLBENZAMIDE, 99+%
Benzamide, N-methyl-(6CI,7CI,8CI,9CI) | [EINECS(EC#)]
210-362-3 | [Molecular Formula]
C8H9NO | [MDL Number]
MFCD00011642 | [Molecular Weight]
135.16 | [MOL File]
613-93-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystals or crystalline powder | [Melting point ]
76-78 °C (lit.) | [Boiling point ]
167 °C/11 mmHg (lit.) | [density ]
1.1031 (rough estimate) | [refractive index ]
1.5589 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
ethanol: soluble50mg/mL, clear, yellow-green | [form ]
Solid | [pka]
15.00±0.46(Predicted) | [color ]
White to off-white | [Water Solubility ]
Insoluble in water. | [InChI]
InChI=1S/C8H9NO/c1-9-8(10)7-5-3-2-4-6-7/h2-6H,1H3,(H,9,10) | [InChIKey]
NCCHARWOCKOHIH-UHFFFAOYSA-N | [SMILES]
C(NC)(=O)C1=CC=CC=C1 | [CAS DataBase Reference]
613-93-4(CAS DataBase Reference) | [EPA Substance Registry System]
N-Methylbenzamide (613-93-4) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
1
| [RTECS ]
CV5570000
| [TSCA ]
Yes | [HS Code ]
29242990 |
| Hazard Information | Back Directory | [General Description]
Off-white crystalline solid. | [Reactivity Profile]
N-METHYLBENZAMIDE(613-93-4) is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides 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 & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data concerning this compound are not available, however, N-METHYLBENZAMIDE is probably combustible. | [Chemical Properties]
white crystals or crystalline powder | [Uses]
It acts as a potent PDE10A (phosphodiesterase with a remarkable localization as the protein is abundant only in brain tissue) inhibitor. It is also employed as a pharmaceutical intermediate. | [Synthesis Reference(s)]
Synthetic Communications, 7, p. 549, 1977 DOI: 10.1080/00397917709409275
Tetrahedron Letters, 30, p. 451, 1989 DOI: 10.1016/S0040-4039(00)95225-0 | [Synthesis]
Add benzoic acid (977 mg, 8 mmol), dry DCM (20 mL) and catalytic amount of DMF in a 100 mL round-bottom flask. Cool the reaction mixture to 0°C and stir for 5 minutes. Add (COCl)2 (0.89 mL, 1.3 equiv.) dropwise to the reaction mixture and stir at room temperature for 4 hours. Concentrate the resulting mixture under reduced pressure to obtain acid chloride. Add catalytic amount of 4-dimethylaminopyridine, dry DCM (15 mL), MeNH2 (2 (M) in THF) (5.19 mL, 1.3 equiv.) and Et3N (1.56 mL, 1.4 equiv.) to the mixture in a 100 mL round-bottom flask. Cool the reaction mixture to 0°C. Add acid chloride (1.0 equiv.) dropwise at 0°C. Stir the reaction mixture at room temperature for 12 hours. Add water (40 mL) and seperate the organic layer. Extract the aqueous layer with DCM (3 x 30 mL). Wash the combined organic layer with saturated aqueous NaHCO3 (30 mL) solution followed by water (30 mL). Dry the organic layer over Na2SO4 and concentrated under reduced pressure. Purify the crude mass by silica gel column chromatography (20% ethyl acetate in hexane as eluent) to obtain N-methylbenzamide. DOI: 10.1002/anie.202203539
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