ChemicalBook--->CAS DataBase List--->20191-76-8

20191-76-8

20191-76-8 Structure

20191-76-8 Structure
IdentificationBack Directory
[Name]

1-Amino-2,4-dibromonaphthalene
[CAS]

20191-76-8
[Synonyms]

2,4-Dibromo-1-naphtylamine
2,4-Dibromo-1-naphthalenamine
2,4-dibromonaphthalen-1-amine
1-Amino-2,4-dibromonaphthalene
2,4-Dibromonaphthalene-1-amine
1-Naphthalenamine, 2,4-dibromo-
[Molecular Formula]

C10H7Br2N
[MDL Number]

MFCD00155345
[MOL File]

20191-76-8.mol
[Molecular Weight]

300.98
Chemical PropertiesBack Directory
[Melting point ]

115 °C
[Boiling point ]

369.7±27.0 °C(Predicted)
[density ]

1.902±0.06 g/cm3(Predicted)
[storage temp. ]

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

-0.22±0.10(Predicted)
[Appearance]

Yellow to brown Solid
Safety DataBack Directory
[Symbol(GHS) ]

GHS hazard pictograms
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P280-P301+P312-P302+P352-P305+P351+P338
[HS Code ]

2921599090
Hazard InformationBack Directory
[Uses]

2,4-Dibromonaphthalen-1-amine is used as a reactant in the preparation of pyrazoles as inhibitors of macrophage migration inhibitory factor.
[Synthesis]

1-Naphthylamine

134-32-7

1-Amino-2,4-dibromonaphthalene

20191-76-8

General procedure for the synthesis of 2,4-dibromo-1-aminonaphthalene from 1-naphthylamine: a mixture of 1-naphthylamine (286 mg, 2 mmol), potassium bromide (309 mg, 2.6 mmol), acetic acid (9 mL), water (1 mL), and dichloromethane (5 mL) was added sequentially to a three-necked flask equipped with a condenser and a thermometer. ZnAl-BrO3-LDHs (3.6 g, 3.6 mmol) was slowly added over 15 min in a thermostatically heated magnetic stirring water bath. The reaction temperature was controlled to be 25 °C for 5 h. The reaction was carried out at a constant temperature with magnetic stirring. After completion of the reaction, the reaction mixture was washed with sodium sulfite solution. It was subsequently extracted with dichloromethane (3 × 10 mL), the organic phases were combined and silica gel (200-300 mesh) was added to the organic phase. The organic solvent was removed by distillation under reduced pressure and the residue was purified by column chromatography (eluent was petroleum ether: ethyl acetate = 13:1) to afford 566 mg of the target product 2,4-dibromo-1-aminonaphthalene as a reddish brown solid in 94% yield.

[References]

[1] Canadian Journal of Chemistry, 2005, vol. 83, # 2, p. 146 - 149
[2] Patent: CN107417543, 2017, A. Location in patent: Paragraph 0056-0058; 0062
[3] Patent: WO2017/201161, 2017, A1. Location in patent: Paragraph 0215; 0246
[4] Synthetic Communications, 2004, vol. 34, # 24, p. 4597 - 4604
[5] ChemMedChem, 2018, vol. 13, # 11, p. 1092 - 1097
Spectrum DetailBack Directory
[Spectrum Detail]

1-Amino-2,4-dibromonaphthalene(20191-76-8)MS
1-Amino-2,4-dibromonaphthalene(20191-76-8)1HNMR
1-Amino-2,4-dibromonaphthalene(20191-76-8)IR1
1-Amino-2,4-dibromonaphthalene(20191-76-8)IR2
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