N-Methylbenzamid

Bezeichnung:N-Methylbenzamid

CAS-Nr613-93-4

Englisch Name:N-Methylbenzamide

CBNumberCB0273752

SummenformelC8H9NO

Molgewicht135.16

MOL-Datei613-93-4.mol

Synonyma

N-Methylbenzamid

N-Methylbenzamid physikalisch-chemischer Eigenschaften

Schmelzpunkt	76-78 °C (lit.)
Siedepunkt	167 °C/11 mmHg (lit.)
Dichte	1.1031 (rough estimate)
Brechungsindex	1.5589 (estimate)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	ethanol: soluble50mg/mL, clear, yellow-green
pka	15.00±0.46(Predicted)
Wasserlöslichkeit	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 Datenbank	613-93-4(CAS DataBase Reference)
EPA chemische Informationen	N-Methylbenzamide (613-93-4)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22-22
S-Sätze:	24/25
WGK Germany	1
RTECS-Nr.	CV5570000
TSCA	Yes
HS Code	29242990

Gefahreninformationscode (GHS)

N-Methylbenzamide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
N-methylbenzamide is an off-white crystalline solid.
Verwenden
N-Methylbenzamide is an important pesticide intermediate. It acts as a potent PDE10A (phosphodiesterase with a remarkable localization as the protein is abundant only in brain tissue) inhibitor.
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
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
N-METHYLBENZAMIDE 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).
Brandgefahr
Flash point data concerning N-METHYLBENZAMIDE are not available, however, N-METHYLBENZAMIDE is probably combustible.
Synthese
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

N-Methylbenzamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

613-93-4, N-Methylbenzamide Verwandte Suche:

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