Methyl 2-amino-5-chlorobenzoate
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Methyl 2-amino-5-chlorobenzoate
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CAS No:
5202-89-1
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Formula:
C8H8ClNO2
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Chemical Name:
Methyl 2-amino-5-chlorobenzoate
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Synonyms:
Benzoic acid,2-amino-5-chloro-,methyl ester;Anthranilic acid,5-chloro-,methyl ester;Methyl 5-chloroanthranilate;Methyl 2-amino-5-chlorobenzoate;5-Chloroanthranilic acid methyl ester;2-Amino-5-chlorobenzoic acid methyl ester;4-Chloro-2-carbomethoxyaniline;5-Chloro anthranilate methyl
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CAS No:
Methyl 2-amino-5-chlorobenzoate Basic Attributes
185.61
185.61
1072894
225-992-4
DTXSID90199992
2922499990
Characteristics
52.3
3.3
Cream to beige-brown Crystals or Crystal Powder
1.3±0.1 g/cm3
66-68 °C
168-170 °C
168-170°C/1mm
1.581
Safety Information
NONH for all modes of transport
3
36/37/38
26-37/39
Xi
Irritant
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Methyl 2-amino-5-chlorobenzoate Use and Manufacturing
To a stirred solution of 2-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropwise at 0 °C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3 x 100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-amino-5-chloro- benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for CTo a stirred solution of 2-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropwise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3.x.100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-amino-5-chloro-benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C(109-8) (109-8) Reference General procedure: B(C6F5)3 (1 mol percent) was added to a stirringsolution of aldehyde (1 mmol) in MeOH (6 mL). After 15 min., 5.5 M TBHP indecane (3 mmol) was added slowly and reaction mixture was refluxed untilthe complete conversion of starting material (monitored by TLC). Aftercompletion of reaction, the methanol was evaporated in vacuo. Later, thereaction mixture was diluted with water (20 mL) and extracted with ethylacetate (3 15 mL). The organic layer was washed with cold saturated sodiumbicarbonate solution (2 20 mL) followed by brine. The organic layer wasdried over MgSO4 and concentrated under reduced pressure and products werepurified over silica gel column chromatography in ethyl acetate/hexane. Allcompounds were characterized and confirmed by comparison of their spectraldata and physical properties with reported literature.
Used as pesticide and pharmaceutical intermediate
Computed Properties
Molecular Weight:185.61
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:185.0243562
Monoisotopic Mass:185.0243562
Topological Polar Surface Area:52.3
Heavy Atom Count:12
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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