13534-99-1

Basic information

• Product Name: 3-Bromo-2-pyridinamine
• Synonyms: 3-BROMO-2-PYRIDINAMINE;3-BROMOPYRIDIN-2-AMINE;3-BROMO-PYRIDIN-2-YLAMINE;2-AMINO-3-BROMOPYRIDINE;IFLAB-BB F1371-0194;TIMTEC-BB SBB005538;2-Pyridinamine, 3-bromo-;2-AMINO-3-BROMOPYRIDINE 97%
• CAS NO: 13534-99-1
• Molecular Formula: C₅H₅BrN₂
• Molecular Weight: 173.01
• EINECS: -0
• Product Categories: Pyridine;pharmacetical;Pyridine series;Pyridines;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 13534-99-1.mol

Chemical Properties

• Melting Point: 63-67 °C
• Boiling Point: 232 °C at 760 mmHg
• Flash Point: 94.1 °C
• Appearance: Gray to brown/Powder
• Density: 1.6065 (rough estimate)
• Vapor Pressure: 0.0604mmHg at 25°C
• Refractive Index: 1.5182 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.14±0.36(Predicted)
• BRN: 109867
• CAS DataBase Reference: 3-Bromo-2-pyridinamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-2-pyridinamine(13534-99-1)
• EPA Substance Registry System: 3-Bromo-2-pyridinamine(13534-99-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: II
• Hazardous Substances Data: 13534-99-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-2-pyridinamine is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its application reason is due to its ability to undergo multiple chemical reactions, leading to the formation of a wide range of bioactive molecules.
Used in Chemical Synthesis:
3-Bromo-2-pyridinamine is used as a building block for the synthesis of various organic compounds, such as:
2-acylamido-3-bromopyridines for their potential applications in medicinal chemistry.
2-anilino-3-bromopyridine as a precursor to other pyridine-based compounds.
3-[(2-methoxyphenyl)ethynyl]pyridin-2-amine and 3-[(4-methoxyphenyl)ethynyl]pyridin-2-amine for their potential use in the development of novel materials and pharmaceuticals.
N-(bromopyridyl)amidines, carbolines, and nitro-substituted N,N′-dipyridinylamines through palladium-catalyzed reactions, which are important in the synthesis of complex organic molecules.
2-amino-3-cyanopyridine via palladium-catalyzed cyanation reaction, which can be further utilized in the synthesis of various heterocyclic compounds.
2-amino-3-iodopyridine through a reaction with sodium iodide, which can be used as a starting material for the synthesis of other pyridine derivatives.
The versatility of 3-Bromo-2-pyridinamine in chemical synthesis makes it a valuable compound for researchers and chemists working in various fields, including pharmaceuticals, materials science, and organic chemistry.

InChI:InChI=1/C5H5BrN2/c6-4-2-1-3-8-5(4)7/h1-3H,(H2,7,8)/p+1

Upstream product

• 13534-89-9 2,3-dibromopyridine 
• 504-29-0 2-aminopyridine 
• 36178-05-9 3-bromo-2-fluoropyridine 
• 697300-73-5 2-amino-3-bromo-5-iodopyridine 
• 149489-04-3 tert-butyl N-(3-bromo-2-pyridyl)-carbamate 
• 110-86-1 pyridine 
• 86847-59-8 2-(pivaloylamino)pyridine 
• 239137-57-6 N-(3-bromopyridin-2-yl)-2,2-dimethylpropanamide 
• 114080-99-8 3-Bromo-pyridine-2-carboxylic acid hydroxyamide 
• 54231-33-3 3-bromo-2-nitropyridine 

Downstream Products

• 35486-42-1 2-amino-3,5-dibromopyridine 
• 99516-14-0 3-bromo-2-{[(N,N-dimethylamino)ethyl]amino}pyridine 
• 868603-37-6 3-bromo-2-(benzylamino)pyridine 
• 64064-61-5 2-amino-3-(phenylthio)pyridine 
• 53439-81-9 benzo[c][1,8]naphthyridin-6(5H)-one 
• 1216772-15-4 methyl 4-(2-aminopyridin-3-yl)benzoate 
• 1216771-53-7 4-(2-aminopyridin-3-yl)benzamide 
• 86847-74-7 2-t-Butyl<1H>-pyrrolo<2,3-b>pyridine 
• 1236979-36-4 2-(4-isopropylphenyl)-1H-pyrrolo[2,3-b]pyridine 
• 7076-11-1 5,6,7,8-tetrahydro-9H-pyrido<2,3-b>indole 
• 947017-94-9 2-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine 
• 10586-52-4 2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 139962-68-8 2-(4-Methoxyphenyl)<1H>-pyrrolo<2,3-b>pyridine 
• 1236979-34-2 2-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

3-Substituted 2-isocyanopyridines as versatile convertible isocyanides for peptidomimetic design

We report the use of 3-substituted 2-isocyanopyridines as convertible isocyanides in Ugi four-component reactions. TheN-(3-substituted pyridin-2-yl)amide Ugi products can be cleaved by amines, alcohols, and water with Zn(OAc)2as a catalyst. In addition, the applicability of the method was demonstrated in constrained di-/tripeptides bearing acid and base sensitive protective groups obtainedviaUgi-4CR post-condensation modifications.

Selectfluor-promoted regioselective chlorination/bromination of 2-aminopyridines and 2-aminodiazines using LiCl/LiBr

Using LiCl as a chlorine source, the chlorination of 2-aminopyridines or 2-aminodiazines in the presence of Selectfluor and DMF is established under mild conditions. This method gives chlorinated pyridines or diazines in good to high yields with high regioselectivities. Also, this method is extended to the bromination of 2-aminopyridines or 2-aminodiazines by using LiBr. The regioselectivity of the chlorination reaction is strongly dependent upon the substituent pattern in either the 2-aminopyridines or 2-aminodiazines. The synthesis of Buparlisib from chlorinated pyridines was explored. A study of the mechanism revealed that this chlorination occurs via either a pyridine or diazine radical process.

Preparation method of 2-amino substituted six-membered nitrogen-containing heterocycle complex

The invention discloses a preparation method of a 2-amino substituted six-membered nitrogen-containing heterocycle complex. The preparation method comprises the following steps: mix 2-fluorine substituted six-membered nitrogen-containing heterocycle complex and amidine hydrochloride salt compound, and then react under the action of a alkaline substance to obtain a 2-amino substituted six-memberednitrogen-containing heterocycle complex. Preferably, the 2-amino substituted six-membered nitrogen-containing heterocycle complex is a 2-amino pyridine compound, a 2-aminopyrimidine compound or a 2-aminopyrazine compound. Compared with the prior art, the method has the advantages of simple synthesis conditions, less reaction steps, mild reaction conditions, low cost of the catalyst used, less waste discharge and good functional group tolerance.

Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride

Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products.

Preparation method of intermediate 3-bromopyridine-2-amine

The invention relates to the field of medicinal chemistry, in particular to a preparation method of a phosphatidylinositol 3-kinase inhibitor intermediate. The preparation method of 3-bromopyridine-2-amine provided by the invention includes: taking 3-bromo-5-iodopyridine-2-amine as the starting raw material, carrying out halogen-metal exchange reaction, and conducting 5-position deiodination to obtain 3-bromopyridine-2-amine. The synthesis route of 3-bromopyridine-2-amine provided by the invention is different from the existing routes, and also has high yield of the product 3-bromopyridine-2-amine, thus being suitable for industrial production.

A quick, mild and efficient bromination using a CFBSA/KBr system

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Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction

Four parent carbolines and the corresponding 5- or 9-methylsulfonyl derivatives were synthesized by the palladium-catalyzed intramolecular arylation reaction of ortho-bromo-substituted anilinopyridines which were prepared by the palladium-catalyzed amination reaction of iodobenzenes with aminopyridines. Carbazole and its 9-methylsulfonyl derivative were also synthesized by the same method.

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