20511-12-0

Basic information

• Product Name: 2-Amino-5-iodopyridine
• Synonyms: ASISCHEM U79390;BUTTPARK 153\33-57;2-AMINO-5-IODOPYRIDINE;2-PYRIDINAMINE, 5-IODO-;5-IODOPYRIDIN-2-AMINE;5-IODO-PYRIDIN-2-YLAMINE;5-IODO-2-PYRIDINAMINE;AKOS BB-8250
• CAS NO: 20511-12-0
• Molecular Formula: C₅H₅IN₂
• Molecular Weight: 220.01
• EINECS: -0
• Product Categories: Amines;blocks;Iodides;Pyridines;Pyridine series;pyridine derivative;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine;Pyridines derivates;Heterocyclic Compounds;Anilines, Amides & Amines;Iodine Compounds;Miscellaneous Compounds;Halopyridines;Iodopyridines;Heterocycles;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Amino-pyridine series
• Mol File: 20511-12-0.mol
• Article Data: 48

Chemical Properties

• Melting Point: 128-131 °C(lit.)
• Boiling Point: 293.8 °C at 760 mmHg
• Flash Point: 131.5 °C
• Appearance: light yellow needles
• Density: 2.055 g/cm³
• Vapor Pressure: 0.00169mmHg at 25°C
• Storage Temp.: 0-10°C
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 4.91±0.13(Predicted)
• Water Solubility: Insoluble
• Sensitive: Light Sensitive
• BRN: 108738
• CAS DataBase Reference: 2-Amino-5-iodopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-iodopyridine(20511-12-0)
• EPA Substance Registry System: 2-Amino-5-iodopyridine(20511-12-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 20511-12-0(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow needles

InChI:InChI=1/C5H5IN2/c6-4-1-2-5(7)8-3-4/h1-3H,(H2,7,8)/p+1

Upstream product

• 504-29-0 2-aminopyridine 
• 7553-56-2 iodine 
• 110-86-1 pyridine 
• 46224-49-1 (pyridin-1-iumyl)[(pyridin-2-yl)aminide] 
• 1072-97-5 5-bromo-2-pyridylamine 
• 1600-27-7 mercury(II) diacetate 
• 157020-27-4 pyridinium N-<2'-(5'-iodopyridyl)>aminide 
• 148292-02-8 pyridinium N-<2'-(3',5'-diiodopyridyl)>aminide 

Downstream Products

• 166266-23-5 2-(N-Benzoylamino)-5-iodopyridine 
• 69045-79-0 2-choro-5-iodopyridine 
• 474012-75-4 4-(6-iodo-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine 
• 270925-65-0 [(2R,5R)-5-(6-Amino-pyridin-3-yl)-3-(tert-butyl-diphenyl-silanyloxy)-2,5-dihydro-furan-2-yl]-methanol 
• 477889-91-1 1-(5-iodopyridin-2-yl)-2,5-dimethyl-1H-pyrrole 
• 885275-91-2 2-(chloromethyl)-6-iodoimidazo[1,2-a]pyridine 
• 71167-00-5 5-(ethylthio)pyridin-2-amine 
• 39771-08-9 2-(2,4,6-trinitrophenylamino)-3,5-dinitropyridine 
• 74477-06-8 2-(N-picrylamino)-5-nitropyridine 
• 57187-81-2 3-tert. butyl-5-nitro-N-(5'-iodopyrid-2'-yl)salicylamide 
• 1186121-27-6 C₁₈H₁₉IN₂O₅ 
• 54818-84-7 N-(5-chloropyridin-2-yl)-4-methylbenzenesulfonamide 
• 31860-60-3 2,3’-bipyridin-6’-amine 
• 1147548-93-3 2-(4'-hydroxy-3'-methoxyphenyl)-6-iodoimidazo[1,2-a]pyridine 

Relevant articles and documents

Synthesis of 2,3-Disubstituted 5-Iodo-1H-Pyrrolo[2,3-b]pyridines via Fischer Cyclization

A simple and convenient procedure for the preparation of some unknown 2,3-disubstituted 5-iodo-1H-pyrrolo[2,3-b]pyridines from readily available starting materials by Fischer indole cyclization in polyphosphoric acid is described. The present methodology provides an alternative synthetic approach to the synthesis of 5-iodo-7-azaindole scaffold. All synthesized compounds were characterized by IR, MS, 1H and 13C NMR, and elemental analysis.

NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl

In situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system has been developed. The NCBSI reagent requires no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge density on nitrogen. The system is adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide can be recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.

Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes

Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.

Method for preparing 4 - (6 -aminopyridine -3 -yl) piperazine -1 - carboxylic acid tert-butyl ester

The invention discloses a method for preparing 4 - (6 - aminopyrid -3 -yl) piperazine -1 - carboxylic acid tert-butyl ester, which comprises the following steps of: reacting 2 - aminopyridine with iodine to generate 2 - amino -5 -iodopyridine. Step II: 2 - amino -5 -iodopyridine was subjected to a coupling reaction to obtain 4 - (6 - aminopyrid -3 -yl) piperazine -1 -carboxylic acid tert-butyl ester. The method has the advantages of short synthetic route, high target product yield and low cost.

BICYCLIC KINASE INHIBITORS AND USES THEREOF

The invention relates to kinase inhibitors, in particular inhibitors of protein kinases including the SIK-family, CSF1R, HCK, TEK-family, BRK, ABL, KIT and/or their mutants. Although structurally similar to other bicyclic kinase inhibitors, the kinase inhibitors of the invention are distinctive; possessing a particular class of heterocyclic moiety. Such kinase inhibitors can display one or more certain properties distinct to their structurally similar kinase inhibitors. The kinase inhibitors of the invention or pharmaceutical compositions comprising them may be used in the treatment of a disorder or condition, such as a proliferative disorder, for example, a leukaemia or solid tumour. In particular, these and other structurally related kinase inhibitors may be used in the treatment of a proliferative disorder - such as a mixed phenotype acute leukaemia (MPAL) - characterised by (inter-alia) the presence of MEF2C protein, a human chromosomal translocation at 11q23, and/or a KMT2A fusion oncoprotein. The kinase inhibitors or pharmaceutical compositions of the invention may be used topically to modulate skin pigmentation in a subject, for example to impart UV protection and reduce skin cancer risk.

CN-Modified Imidazopyridine as a New Electron Accepting Unit of Thermally Activated Delayed Fluorescent Emitters

Two efficient thermally activated delayed fluorescent (TADF) emitters were developed by utilizing CN-modified imidazopyridine as an acceptor unit. The CN-modified imidazopyridine acceptor was combined with either an acridine donor or a phenoxazine donor through a phenyl linker to produce two TADF emitters, Ac-CNImPy and PXZ-CNImPy. The acridine-based Ac-CNImPy emitter exhibited sky-blue emission with a CIE coordinate of (0.18, 0.38), whereas the phenoxazine-donor-based PXZ-CNImPy showed greenish-yellow emission with a CIE coordinate of (0.32, 0.58). A high photoluminescence quantum yield of 80 % was observed for the PXZ-CNImPy emitter compared with 40 % for the Ac-CNImPy emitter. Organic light-emitting diodes based on the PXZ-CNImPy emitter demonstrated high external quantum efficiency of 17.0 %. Hence, the CN-modified imidazopyridine unit can be considered as a useful electron acceptor for the future design of highly efficient TADF emitters.

2-amino-5-iodopyridine synthesis method

The invention discloses a 2-amino-5-iodopyridine synthesis method, which comprises: (1) dissolving 2-aminopyridine in water; (2) adding iodine in 3-5 batches while stirring, and keeping the temperature for 2 h after the iodine is added; (3) after thermal insulation is finished, adding hydrogen peroxide in a dropwise manner, and continuously carrying out thermal insulation for 2-3 h after the adding; and (4) after the reaction is finished, carrying out heating reflux for 20-30 min, cooling and filtering, rinsing a filter cake with ice water, and drying to obtain the 2-amino-5-iodopyridine. According to the present invention, water is used as the solvent for synthesis, and no organic solvent is used, such that the reaction process is safe and free of pollution.

BICYCLIC COMPOUND AND USE THEREOF FOR INHIBITING SUV39H2

The present invention directs to a compound represented by formula (I).

Self-assembly of heteroleptic dinuclear metallosupramolecular kites from multivalent ligands via social self-sorting

A Tr?ger's base-derived racemic bis(1,10-phenanthroline) ligand (rac)-1 and a bis(2,2′-bipyridine) ligand with a central 1,3-diethynylbenzene unit 2 were synthesized. Each of these ligands acts as a multivalent entity for the binding of two copper(I) ions. Upon coordination to the metal ions these two ligands undergo selective self-assembly into heteroleptic dinuclear metallosupramolecular kites in a high-fidelity social self-sorting manner as evidenced by NMR spectroscopy and mass spectrometry.

Ionic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes

Hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), an ionic liquid iodinating reagent, have been prepared and characterized. Its ability to perform iodination reactions with a variety of substrates has been explored. In general, iodination reactions of aromatic and heteroaromatic amines proceed with good yields in the absence of solvent. Reactions of terminal alkynes in the presence of 1,8-diazabicyclo [5.4.O] undec-7-ene and tetrahydrofuran have been investigated as well.