ChemicalBook--->CAS DataBase List--->52833-94-0

52833-94-0

52833-94-0 Structure

52833-94-0 Structure
IdentificationMore
[Name]

2-Amino-5-bromonicotinic acid
[CAS]

52833-94-0
[Synonyms]

2-AMINO-5-BROMONICOTINIC ACID
2-AMINO-5-BROMOPYRIDINE-3-CARBOXYLIC ACID
5-Bromo-2-Amino Nicotinic Acid
2-Amino-5-bromonicotinic acid 95%
2-Amino-5-bromonicotinic acid ,97%
[Molecular Formula]

C6H5BrN2O2
[MDL Number]

MFCD01860227
[Molecular Weight]

217.02
[MOL File]

52833-94-0.mol
Questions And AnswerBack Directory
[Synthesis]

Synthesis of 52833-94-0

In a 500mL three-necked flask equipped with a stirrer and a reflux condenser, 20.7g (0.15mol) of 2-aminonicotinic acid and 80mL of acetic acid were added. The mixture was stirred at room temperature. A mixture of 40mL of acetic acid and 4.1mL of bromine (0.08mol) was added dropwise using a constant-pressure dropping funnel. Stirring continued for 4-5 hours after the addition was complete. The mixture was filtered, washed with acetic acid, dried, and the solid was heated under reflux with 100mL of methanol for 10 minutes, then allowed to stand at room temperature, filtered, and dried. 31.2g of a white solid, 2-amino-5-bromonicotinic acid, was obtained, with a yield of 96%.

1H NMR (400MHz, DMSO-d6)δ12.72(s,1H),9.05(d,J=2.4Hz,1H),8.63(d,J=2.4Hz,1H),8.36(s,1H).MS: m/z(ESI+)228.3[M+H]+.

[Uses]

2-Amino-5-bromonicotinic acid is an organic intermediate that can be prepared by brominating 2-aminonicotinic acid. Literature reports that 2-amino-5-bromonicotinic acid can be used to prepare 6-pyrazole-substituted quinazoline compounds and their derivatives. These compounds exhibit high tyrosine kinase inhibitory activity and strong inhibitory activity against human breast cancer cells and lung adenocarcinoma cells.
Chemical PropertiesBack Directory
[Appearance]

Light yellow powder
[Melting point ]

253-255°C
[Boiling point ]

350.4±42.0 °C(Predicted)
[density ]

1.909
[refractive index ]

1.5150 (estimate)
[storage temp. ]

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

powder
[pka]

2.55±0.10(Predicted)
[color ]

Pale yellow
[Detection Methods]

HPLC
[CAS DataBase Reference]

52833-94-0(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

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

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

UN2811
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

29333990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Methanol-->Acetic acid-->Petroleum ether-->Chloroform-->Bromine-->Acetic anhydride-->Ammonium hydroxide-->Chlorine-->Zinc chloride-->Malononitrile-->1,1,3,3-Tetramethoxypropane
Hazard InformationBack Directory
[Chemical Properties]

Light yellow powder
[References]

[1] Patent: US6369056, 2002, B1
[2] Patent: US6399593, 2002, B1
[3] Patent: US2006/30583, 2006, A1. Location in patent: Page/Page column 113
[4] Patent: CN106565684, 2017, A. Location in patent: Paragraph 0177; 0178; 0179; 0180
[5] Patent: WO2014/209727, 2014, A1. Location in patent: Page/Page column 60-61
Spectrum DetailBack Directory
[Spectrum Detail]

2-Amino-5-bromonicotinic acid(52833-94-0)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2-Amino-5-bromonicotinic acid, 95%(52833-94-0)
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