Methyl-3-methylanthranilat

Bezeichnung:Methyl-3-methylanthranilat

CAS-Nr22223-49-0

Englisch Name:Methyl 2-amino-3-methylbenzoate

CBNumberCB9773134

SummenformelC9H11NO2

Molgewicht165.19

MOL-Datei22223-49-0.mol

Synonyma

Methyl-3-methylanthranilat

Methyl-3-methylanthranilat physikalisch-chemischer Eigenschaften

Schmelzpunkt	115-117°C
Siedepunkt	153℃/23mm
Dichte	1.132±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	2.05±0.10(Predicted)
Farbe	Pink
FreezingPoint	25.0 to 29.0 ℃
InChI	1S/C9H11NO2/c1-6-4-3-5-7(8(6)10)9(11)12-2/h3-5H,10H2,1-2H3
InChIKey	VSFYTPXXMLJNAU-UHFFFAOYSA-N
SMILES	O=C(OC)C1=C(N)C(C)=CC=C1
CAS Datenbank	22223-49-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39
WGK Germany	WGK 3
HazardClass	IRRITANT
HS Code	2922498590
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral

Gefahreninformationscode (GHS)

Methyl 2-amino-3-methylbenzoate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Pale brown liquid
Verwenden
2-Amino-3-methylbenzoic Acid Methyl Ester is the methyl ester derivative of 2-Amino-3-methylbenzoic Acid (A612150); a metabolite of Lidocaine (L397800) with potential herbicidal activity. 2-Amino-3-methylbenzoic Acid Methyl Ester is also used as the starting material in the synthesis of N-(2-Methoxyacetate)-N-(2-carboxy-6-methylphenyl)-alanine (M260810); a metabolite of Metalaxyl (M258740) which is an agricultural fungicide.
Synthese

5471-82-9

22223-49-0

The general steps for synthesizing methyl 2-amino-3-methylbenzoate from methyl 3-methyl-2-nitrobenzoate are as follows: Step A: Preparation of methyl 2-amino-3-methylbenzoate Methyl 3-methyl-2-nitrobenzoate (98.5 g, 505 mmol), 5% Pd/C (Degussa CE 105 XRCAV, 1.0 g) and acetonitrile (300 mL) were mixed in a 600 mL pressure vessel. The mixture was heated to 70°C and hydrogenated at 65 psi (450 kPa) under hydrogen pressure for 8 hours. Subsequently, 5% Pd/C (1.0 g) was added supplementally and hydrogenation was continued for 8.5 hours at 100 psi (690 kPa) hydrogen pressure. Upon completion of the reaction, the reaction mixture was cooled to room temperature, the hydrogen in the reactor was replaced with nitrogen, and then filtered through a Celite diatomaceous earth filter aid. The filter cake was washed with acetonitrile (3 x 25 mL). The combined filtrates were concentrated to about 160 g, and then the total weight was adjusted with acetonitrile to 200 g. The amount of the title compound in solution was measured to be 40.3 wt%, or 80.6 g, in 97.5% yield by quantitative HPLC analysis.
Einzelnachweise
[1] Tetrahedron, 2013, vol. 69, # 32, p. 6679 - 6686
[2] Patent: WO2006/62978, 2006, A1. Location in patent: Page/Page column 23
[3] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 1921 - 1930
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5629 - 5633
[5] Chemische Berichte, 1907, vol. 40, p. 4413

Methyl 2-amino-3-methylbenzoate Upstream-Materialien And Downstream Produkte

Methyl-3-methylanthranilat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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