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ChemicalBook--->CAS DataBase List--->104670-74-8

104670-74-8

104670-74-8 Structure

104670-74-8 Structure
IdentificationBack Directory
[Name]

Benzoic acid, 2-amino-3-bromo-, methyl ester
[CAS]

104670-74-8
[Synonyms]

2-amino-3-bromo-
Ethyl 3-bromo-2-aminobenzoate
2-Amino-3-Bromo-, Methyl Ester
Methyl 2-aMino-3-broMobenzoate
3-Bromoanthranilic acid methyl ester
Benzoic acid, 2-amino-3-bromo-, methyl ester
[EINECS(EC#)]

200-158-5
[Molecular Formula]

C8H8BrNO2
[MDL Number]

MFCD11042862
[MOL File]

104670-74-8.mol
[Molecular Weight]

230.06
Chemical PropertiesBack Directory
[Melting point ]

47-48℃
[Boiling point ]

287.2±20.0 °C(Predicted)
[density ]

1.578±0.06 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Inert atmosphere,Room temperature
[form ]

solid
[pka]

0.13±0.10(Predicted)
[color ]

Light brown
[InChI]

InChI=1S/C8H8BrNO2/c1-12-8(11)5-3-2-4-6(9)7(5)10/h2-4H,10H2,1H3
[InChIKey]

FGSIUBWPZRBMOC-UHFFFAOYSA-N
[SMILES]

C(OC)(=O)C1=CC=CC(Br)=C1N
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H227
[Precautionary statements ]

P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235
[HS Code ]

2922498590
Spectrum DetailBack Directory
[Spectrum Detail]

Benzoic acid, 2-amino-3-bromo-, methyl ester(104670-74-8)1HNMR
Hazard InformationBack Directory
[Synthesis]

Methanol

67-56-1

2-AMINO-3-BROMOBENZOIC ACID

20776-51-6

Benzoic acid, 2-amino-3-bromo-, methyl ester

104670-74-8

Example 1: Synthesis of 3-(3-methylaminosulfonyl-phenylethynyl)-2-pyrrol-1-yl-benzoic acid 2-amino-3-bromo-benzoic acid methyl ester: 2-amino-3-bromo-benzoic acid (5 g, 23 mmol) was dissolved in methanol (30 mL) and concentrated sulfuric acid (1 mL) was added slowly and dropwise. The reaction mixture was refluxed at 80 °C for 24 h and subsequently cooled to room temperature. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. The residue was diluted with distilled water (10 mL) and the pH was adjusted to alkaline with saturated sodium bicarbonate solution. Extraction was performed using ethyl acetate (20 mL x 3) and the organic layers were combined. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated. Purification was carried out by silica gel column chromatography (80 g) with ethyl acetate/hexane (10%) as eluent to give the colorless oily product methyl 2-amino-3-bromo-benzoate (5 g, 95% yield).

[References]

[1] Patent: WO2015/73864, 2015, A1. Location in patent: Paragraph 0253-0254; 0413
[2] Patent: WO2011/25859, 2011, A1. Location in patent: Page/Page column 59
[3] Patent: US2011/71136, 2011, A1. Location in patent: Page/Page column 31
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2781 - 2787
[5] Patent: US2009/239859, 2009, A1. Location in patent: Page/Page column 298
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