ChemicalBook--->CAS DataBase List--->42122-75-8

42122-75-8

42122-75-8 Structure

42122-75-8 Structure
IdentificationBack Directory
[Name]

Methyl-5-amino-2-chlorobenzoate
[CAS]

42122-75-8
[Synonyms]

OTAVA-BB 7020693933
TIMTEC-BB SBB013130
Methyl-5-amino-2-chlorobenzoate
Methyl 3-amino-6-chlorobenzoate
METHYL 2-CHLORO-5-AMINOBENZOATE
Methyl 2-chloro-5-aminobenzoate 95+%
2-Chloro-5-aMinobenzoic acid Methyl ester
5-Amino-2-chlorobenzoic acid methyl ester
BENZOIC ACID, 5-AMINO-2-CHLORO-, METHYL ESTER
methyl 5-amino-2-chlorobenzoate(SALTDATA: HCl)
[Molecular Formula]

C8H8ClNO2
[MDL Number]

MFCD07800315
[MOL File]

42122-75-8.mol
[Molecular Weight]

185.608
Chemical PropertiesBack Directory
[Melting point ]

68-70℃
[Boiling point ]

320℃
[density ]

1.311
[Fp ]

147℃
[storage temp. ]

under inert gas (nitrogen or Argon) at 2–8 °C
[solubility ]

soluble in Methanol
[form ]

powder to lump
[pka]

2.81±0.10(Predicted)
[color ]

White to Yellow to Orange
[InChI]

InChI=1S/C8H8ClNO2/c1-12-8(11)6-4-5(10)2-3-7(6)9/h2-4H,10H2,1H3
[InChIKey]

LBNPBOFVHYOPIB-UHFFFAOYSA-N
[SMILES]

C(OC)(=O)C1=CC(N)=CC=C1Cl
Safety DataBack Directory
[HS Code ]

2916399090
Hazard InformationBack Directory
[Chemical Properties]

Pale yellow crystal
[Uses]

Methyl 5-amino-2-chlorobenzoate
[Synthesis]

Methanol

67-56-1

5-Amino-2-chlorobenzoic acid

89-54-3

Methyl-5-amino-2-chlorobenzoate

42122-75-8

The general procedure for the synthesis of methyl 2-chloro-5-aminobenzoate from methanol and 5-amino-2-chlorobenzoic acid was as follows: to a stirred solution of 5-amino-2-chlorobenzoic acid (50 g, 291 mmol) in methanol (300 mL) was added chloromethane (45 mL, 605 mmol) dropwise at 0 °C. The reaction mixture was refluxed for 12 hours and then cooled to room temperature. Subsequently, the reaction mixture was concentrated under vacuum and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate (3 x 100 mL), dried over anhydrous sodium sulfate and concentrated again under vacuum to give methyl 5-amino-2-chlorobenzoate as a light white solid (54 g, quantitative yield).LC/MS analysis: m/e Calculated value C8H8ClNO2 (M +H)+: 186.61, measured value: 185.9.

[References]

[1] Patent: WO2011/128251, 2011, A1. Location in patent: Page/Page column 180-181
[2] Patent: US2011/257151, 2011, A1. Location in patent: Page/Page column 67
[3] Patent: WO2007/60026, 2007, A1. Location in patent: Page/Page column 48-49
[4] Patent: EP1746099, 2007, A1. Location in patent: Page/Page column 18-19
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2465 - 2481
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl-5-amino-2-chlorobenzoate(42122-75-8)1HNMR
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