13534-98-0

Basic information

• Product Name: 4-Amino-3-bromopyridine
• Synonyms: IFLAB-BB F3250-0675;AKOS BBS-00005959;AKOS PAO-0460;1H-PYRAZOLE-5-CARBOXYLIC ACID;4-AMINO-3-BROMOPYRIDINE;3-Bromo-4-aminopyridine;3-Bromo-4-pyridinamine;3-Bromo-4-aminopyridine, 3-Bromo-4-pyridinamine
• CAS NO: 13534-98-0
• Molecular Formula: C₅H₅BrN₂
• Molecular Weight: 173.01
• EINECS: -0
• Product Categories: Pyridine;Amines;Pyridines
• Mol File: 13534-98-0.mol

Chemical Properties

• Melting Point: 65-67°C
• Boiling Point: 275.83 °C at 760 mmHg
• Flash Point: 120.6 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.6065 (rough estimate)
• Vapor Pressure: 0.00498mmHg at 25°C
• Refractive Index: 1.5182 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: pK1: 7.04(+1) (20°C)
• BRN: 110183
• CAS DataBase Reference: 4-Amino-3-bromopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-3-bromopyridine(13534-98-0)
• EPA Substance Registry System: 4-Amino-3-bromopyridine(13534-98-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-37/39-39
• WGK Germany: 3
• HazardClass: IRRITANT, AIR SENSITIVE
• Hazardous Substances Data: 13534-98-0(Hazardous Substances Data)

Usage

Chemical Properties

yellow Cryst

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

Upstream product

• 13534-90-2 dibromo-3,4 pyridine 
• 1678-49-5 3-Bromo-4-nitropyridine N-oxide 
• 504-24-5 4-aminopyridine 
• 130671-16-8 4-Amino-3-bromo-1-(2-cyano-ethyl)-pyridinium; bromide 
• 135041-83-7 4-Amino-3-bromo-1-[2-(4-nitro-phenyl)-ethyl]-pyridinium; bromide 
• 141375-53-3 4-Amino-3-bromo-1-(3-oxo-propyl)-pyridinium 
• 141375-60-2 4-Amino-3-bromo-1-(3-oxo-butyl)-pyridinium 
• 141375-76-0 4-Amino-3-bromo-1-(2-carbamoyl-ethyl)-pyridinium 
• 114080-98-7 3-Bromo-N-hydroxy-isonicotinamide 
• 239137-59-8 3-Bromo-4-(2,2-dimethylpropanoylamino)pyridine 
• 36953-42-1 3-bromo-4-chloropyridine 
• 70298-89-4 4-N-pivaloylaminopyridine 
• 110-86-1 pyridine 
• 141375-68-0 4-Amino-3-bromo-1-(2-methanesulfonyl-ethyl)-pyridinium 

Downstream Products

• 13535-03-0 N-(3-bromopyridin-4-yl)acetamide 
• 100953-53-5 N-benzyl-3-bromopyridin-4-amine 
• 104830-01-5 ethyl 4-amino-3-pyridineacrylate 
• 239137-42-9 3-bromo-N-phenylpyridin-4-amine 
• 239137-46-3 3-Bromo-4-(2-bromoanilino)pyridine 
• 20350-26-9 2,4-dinitrophenolate 
• 14609-74-6 p-nitrophenolate 
• 449173-31-3 4-amino-3-(2-phenylethynyl)pyridine 
• 1849-36-1 para-nitrobenzenethiol 
• 855749-05-2 4-methyl-N-(3-phenylethynyl-pyridin-4-yl)-benzenesulfonamide 
• 239137-50-9 3-Bromo-4-[2-bromo-N-(methylsulfonyl)anilino]pyridine 
• 271-34-1 5-azaindole 
• 23616-29-7 1,6-naphthyridin-2(1H)-one 

Relevant articles and documents

Synthesis of N-Heterocycles-Fused Azasilines by Palladium-Catalyzed Si-Si Bond Activation

Azasilines fused nitrogen heterocycles are prepared in excellent yields (from 74 to 98 % according to the structures) for the first time in one operation with high regio- and stereoselectivities. The key step consists of an intramolecular palladium-cataly

Preparation method of pyridine derivative (by machine translation)

To the method, piperidine-4-one hydrochloride is used as a raw material, and a series of pyridine derivatives are obtained through halogenation reaction and elimination reaction. The reaction is eliminated by reacting piperidine-4-one hydrochloride with a specific amount of the 3,5 - halogenating agent in a halogenation 3, 3, 5 - reaction with a halogen-3, 3, 5, 5 - based reaction, followed by reaction with a pyridine derivative of a hydroxyl group, an amino group 4 - or a dimethylamino group, respectively, by eliminating the reaction with a different kind of basic agent. The method is simple and convenient to operate, mild in condition, short in technological process, low in waste water yield, environment-friendly, low in cost and beneficial to green industrial production of the pyridine derivative. (by machine translation)

Synthesis of pyrrolo[1,2-a]naphthyridines by Lewis acid mediated cycloisomerization

Pyrrolo[1,2-a]naphthyridines were synthesized from 3-alkynyl-2-([1H]-pyrrol-1-yl)pyridines and 3-alkynyl-4-([1H]-pyrrol-1-yl)pyridines by cycloisomerization. The reactions are performed by application of the Lewis acids PtCl2 or Bi(OTf)3 without the need of further additives. With the described methods a number of derivatives containing a variety of functional groups have been synthesized in up to 78% yield.

Synthesis and biological evaluation of 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives as potential c-met inhibitors

Six series of novel 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives conjugated with aza-aryl formamide/amine scaffords were designed and synthesized through a structure-based molecular hybridization approach. The target compounds were evaluated for c-Met kinase inhibitory activities and cytotoxicity against four cancer cell lines (HT-29, A549, MKN-45 and MDA-MB-231) in vitro. Most compounds exhibited moderate to excellent potency, and the most promising candidate 26c (c-Met kinase IC50 = 8.2 nM) showed a 4.7-fold increase in cytotoxicity against c-Met-addicted MKN-45 cell line in vitro (IC50 = 3 nM), superior to that of Foretinib (IC50 = 23 nM). The preliminary structure-activity relationship indicated that a 1H-benzo [e] [1,3,4]thiadiazine-3-carboxamide-4,4-dioxide moiety as linker contributed to the antitumor potency.

Enantioselective halocyclization using reagents tailored for chiral anion phase-transfer catalysis

A chiral anion phase-transfer system for enantioselective halogenation is described. Highly insoluble, ionic reagents were developed as electrophilic bromine and iodine sources, and application of this system to o-anilidostyrenes afforded halogenated 4H-3,1-benzoxazines with excellent yield and enantioselectivity.

Compounds and their use

This invention relates to compounds, pharmaceutical compositions, and methods of using the disclosed compounds for inhibiting PARP.

Mild regioselective halogenation of activated pyridines with N-bromosuccinimide

Regioselective mono and dihalogenations of amino, hydroxy and methoxy pyridines (2-, 3-, and 4-substituted) as well as 2,6-dimethoxy pyridine with N-bromosuccinimide in different solvents have been studied. Reactivity of the substrates decreases in the order amino>hydroxy>methoxy and regioselectivity depends on the position of the substituent (2-substituted > 3-substituted). In most of the cases we obtained monobrominated derivatives regioselectively and in high yields. Hydroxy and amino pyridines can also be dibrominated in almost quantitative yield with 2 equivalents of NBS.

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.

Rate-Determining Steps in Michael-Type Additions and E1cb Reactions in Aqueous Solution

Rates of equilibration of a series of 10 substituted pyridines and five Michael acceptors (CH2=CHZ, Z = CHO, COCH3, SO2CH3, CN and CONH2) with the corresponding N(ZCH2CH2) pyridinium cations have been measured in aqueous solution at ionic strength 0.1 and 25 deg C.Analysis of the dependence of the pseudo-first-order rate constants for equilibration as a function of acceptor concentration and of pH allows the evaluation of the second-order rate constants (kNu) for the nucleophilic attack of each of these pyridines upon each of these acceptors and also the second-order rate constants (kOH) for the hydroxide ion catalyzed E1cb elimination reaction which is the microscopic reverse of each of these Michael-type addition reactions.Broensted-type plots for each of these processes as a function of the basicity of the substituted pyridine are concave down for each of Z = CHO, COCH3, and CN and are consistent with a change from rate-determining nucleophilic attack for the more basic pyridines to rate-determining protonation of the carbanionic intermediate by a water molecule for less basic pyridines and the corresponding microscopic reverse processes in the elimination reactions.The "break" in these Broensted-type plots is shown to occur at a pyridine basicity that is a function of the Z-activating substituent.Broensted β1g and βnuc are evaluated for each rate-determining step (wherever accessible); these two parameters are shown to pass through minima as a function of reactivity. βeq is shown to be a simple linear function of reactivity (as log kNu) for nucleophilic addition to the acceptor species, although Keq is relatively insensitive to the nature of the Z-activating substituent.

CONDENSED HETEROAROMATIC RING SYSTEMS. XXII. SIMPLE AND GENERAL SYNTHESIS OF 1H-PYRROLOPYRIDINES

Four kinds of 1H-pyrrolopyridines having no substituent were simply and easily synthesized by the palladium-catalyzed reaction of easily available nitropyridine derivatives with (Z)-1-ethoxy-2-tributylstannylethene as a key reaction.