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553719

Sigma-Aldrich

2-Amino-3-bromopyridine

97%

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About This Item

Empirical Formula (Hill Notation):
C5H5BrN2
CAS Number:
13534-99-1
Molecular Weight:
173.01
MDL number:
MFCD03095187
UNSPSC Code:
12352100
PubChem Substance ID:
24879347
NACRES:
NA.22

Assay

97%

form

solid

mp

63-67 °C

SMILES string

Nc1ncccc1Br

InChI

1S/C5H5BrN2/c6-4-2-1-3-8-5(4)7/h1-3H,(H2,7,8)

InChI key

RBCARPJOEUEZLS-UHFFFAOYSA-N

Related Categories

Application

2-Amino-3-bromopyridine may be used to synthesize:
  • 2-acylamido-3-bromopyridines
  • 2-anilino-3-bromopyridine
  • 3-[(2-methoxyphenyl)ethynyl]pyridin-2-amine
  • 3-[(4-methoxyphenyl)ethynyl]pyridin-2-amine
  • N-(bromopyridyl)amidines
  • carbolines via palladium catalyzed arylation followed by palladium catalyzed amination reaction
  • 2-amino-3-cyanopyridine via palladium catalyzed cyanation reaction with potassium ferro-cyanide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene [DBU]
  • nitro-substituted N,N′-dipyridinylamines via palladium catalyzed coupling reaction with 2-chloro-3-nitropyridine in the presence of Xantphos ligand
  • 2-amino-3-iodopyridine via reaction with sodium iodide in the presence of copper(I)iodide and trans-N,N′-dimethylcyclohexane-1,2-diamine

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction.
Iwaki T, et al.
Journal of the Chemical Society. Perkin Transactions 1, 11, 1505-1510 (1999)
Phosphonylation of 2-Amino-and 2-Amido-3-bromopyridines and 2-Amino-3-chloroquinoxalines with Triethyl Phosphite.
Adam M, et al.
European Journal of Organic Chemistry, 27, 4655-4665 (2009)
"Smiles Rearrangement as a Tool for the Preparation of Dihydrodipyridopyrazines"
Patriciu I-O, et al.
Organic Letters, 11(23), 5502-5505 (2009)
Synthesis of pyridopyrimidines by palladium-catalyzed isocyanide insertion.
Este'vez V, et al.
ACS Catalysis, 4(1), 40-43 (2013)
"Syntheses of pyrido [1, 2-a][1, 3, 5] triazin-4-one C-deoxyribonucleosides"
Oda H, et al.
Tetrahedron, 64(45), 11021-11029 (2007)
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