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ChemicalBook--->CAS DataBase List--->22223-49-0

22223-49-0

22223-49-0 Structure

22223-49-0 Structure
IdentificationMore
[Name]

Methyl 2-amino-3-methylbenzoate
[CAS]

22223-49-0
[Synonyms]

2-amino-3-methylbenzoic acid methyl ester
METHYL 2-AMINO-3-METHYLBENZENECARBOXYLATE
METHYL 2-AMINO-3-METHYLBENZOATE
Methyl 3-methyl-2-aminobenzoate
methyl 3-methylanthranilate
2-Amino-m-toluicacidmethylester(COOCH3=1)
[EINECS(EC#)]

244-847-6
[Molecular Formula]

C9H11NO2
[MDL Number]

MFCD06200918
[Molecular Weight]

165.19
[MOL File]

22223-49-0.mol
Chemical PropertiesBack Directory
[Melting point ]

115-117°C
[Boiling point ]

153℃/23mm
[density ]

1.132±0.06 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Sealed in dry,Room Temperature
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

2.05±0.10(Predicted)
[color ]

Pink
[FreezingPoint ]

25.0 to 29.0 ℃
[CAS DataBase Reference]

22223-49-0(CAS DataBase Reference)
Questions And AnswerBack Directory
[Synthesis]

Methyl 3-methyl-2-nitrobenzoate

5471-82-9

Methyl 2-amino-3-methylbenzoate

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.

references:

[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

Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
[HazardClass ]

IRRITANT
[HS Code ]

2922498590
Hazard InformationBack Directory
[Chemical Properties]

Pale brown liquid
[Uses]

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.
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl 2-amino-3-methylbenzoate(22223-49-0)1HNMR
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