2433-17-2

Basic information

• Product Name: 2-(2-PYRIDYL)THIAZOLE
• Synonyms: 2-(2-PYRIDYL)THIAZOLE;PYRIDINE, 2-(2-THIAZOLYL)-;2-(thiazol-2-yl)pyridine;2-(2-Thiazolyl)pyridine;2-(Pyridin-2-yl)thiazole
• CAS NO: 2433-17-2
• Molecular Formula: C₈H₆N₂S
• Molecular Weight: 162.21
• Mol File: 2433-17-2.mol

Chemical Properties

• Melting Point: 46-46.3 °C
• Boiling Point: 137-139 °C(Press: 5 Torr)
• Appearance: /
• Density: 1.241±0.06 g/cm3(Predicted)
• PKA: 1.58±0.10(Predicted)
• CAS DataBase Reference: 2-(2-PYRIDYL)THIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-PYRIDYL)THIAZOLE(2433-17-2)
• EPA Substance Registry System: 2-(2-PYRIDYL)THIAZOLE(2433-17-2)

Safety Data

• Hazardous Substances Data: 2433-17-2(Hazardous Substances Data)

Upstream product

• 3034-53-5 2-bromo-1,3-thiazole 
• 17997-47-6 2-tri-n-butylstannylpyridine 
• 109-04-6 2-bromo-pyridine 
• 24244-60-8 2-(phenylsulfonyl)pyridine 
• 106736-33-8 2-(pyridine-2-yl)-4,5-dihydro-1,3-thiazole 
• 100-70-9 2-Cyanopyridine 
• 288-47-1 1,3-thiazole 
• 110-86-1 pyridine 
• 93472-27-6 2-Thiazol-2-yl-2H-pyridine-1-carboxylic acid ethyl ester 
• 5346-38-3 pyridine-2-carbothioamide 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 623-46-1 1,2-dichloro-2-ethoxyethane 
• 107-20-0 2-chloroethanal 

Downstream Products

• 14485-00-8 1-(2-oxo-2-phenyl-ethyl)-2-thiazol-2-yl-pyridinium; bromide 

Relevant articles and documents

ADDITION OF 2-SILYLAZOLES TO HETEROARYL CATIONS. SYNTHESIS OF UNSYMMETRICAL AZADIARYLS

Thiazole, pyridine and some of their benzoderivatives react via their N-ethoxycarbonyl chlorides with 2-trimethylsilylthiazole (1a) and 4-methyl-2-trimethylsilyloxazole (1b) to give the corresponding adducts at Cα which by oxidative deacylation afford azadiaryls.

Convergent and Practical Synthesis of Fluorescent Triphenylamine Derivatives and Their Localization in Living Cells

In the search for new fluorescent triphenylamine (TP) derivatives, we studied the influence of the position and substitution of diverse heterocyclic substituents. A library of 10 fluorescent triphenylamines bearing either oxazoles or thiazoles and pyridiniums, substituted at different positions has been developed. The approach is based on a convergent C?H activation reaction between pyridine-oxazoles or pyridine-thiazoles and di-iodo triphenylamine. We showed that the nature and substitution pattern of the 5-membered- (oxazole, thiazole) or 6-membered heterocycle (pyridine) has a strong influence on their fluorescence properties and on their localization in living cells as they stain either the nucleus or mitochondria.

Sulfur(IV)-Mediated Unsymmetrical Heterocycle Cross-Couplings

Despite the tremendous utilities of metal-mediated cross-couplings in modern organic chemistry, coupling reactions involving nitrogenous heteroarenes remain a challenging undertaking – coordination of Lewis basic atoms into metal centers often necessitate elevated temperature, high catalyst loading, etc. Herein, we report a sulfur (IV) mediated cross-coupling amendable for the efficient synthesis of heteroaromatic substrates. Addition of heteroaryl nucleophiles to a simple, readily-accessible alkyl sulfinyl (IV) chloride allows formation of a trigonal bipyramidal sulfurane intermediate. Reductive elimination therefrom provides bis-heteroaryl products in a practical and efficient fashion.

INHIBITORS OF COLLAGEN PROLYL 4-HYDROXYLASE

Biheteroaryl dicarboxylates and esters, and salts thereof which are useful as modulators of CP4H activity and more particularly as inhibitors of CP4H. Compounds of formula: and salts thereof where: X is S, O, NH, or NR, where R is an alkyl group having 1-3 carbon atoms; R1 and R2 independently are —OR7, or —NHSO2R8, where R7 is selected from: hydrogen, alkyl, alkenyl, alkoxyalkyl, —R′—CO—R″, —R′—CO—O—R″, —CO—R″, —R′—O—CO—R″, —R′—CO—NR″, —CO—NR″, or —R′—O—CO—NR″, and R8 is selected from hydrogen, alkyl, aryl, arylalkyl; R3, R4 and R6 independently are hydrogen, alkyl, alkoxy, alkenyl, alkenoxy, halo alkyl, haloalkenyl, halogen, hydroxyl, hydroxyalkyl, hydroxyalkenyl, aryl, aryloxy, arylalkyl or arylalkyloxy; R5 is hydrogen, halogen, alkyl having 1-3 carbon atoms, or alkoxy having 1-3 carbon atoms; —R′— is a divalent straight chain or branched alkylene, and —R″ is an alkyl, alkenyl, arylalkyl, or aryl group. Methods for inhibition of CP4H in vivo and in vitro.

DDQ-induced dehydrogenation of heterocycles for c-c double bond formation: Synthesis of 2-thiazoles and 2-oxazoles

Strong as an Ox: 2-Thiazoles and 2-oxazoles are formed by oxidation of 2-thiazolines and 2-oxazolines without requiring substituents at the C4 and C5 positions. DDQ plays an important role as the oxidant in this transformation and metal is unnecessary. This general procedure shows good functional group tolerance and provides a wide variety of 2-thiazoles and 2-oxazoles in moderate to excellent yields.

Negishi coupling of 2-pyridylzinc bromide-paradigm shift in cross-coupling chemistry?

The efficient cross-coupling of 2-pyridylzinc bromide with functionalized aryl halides has been accomplished by a simple and highly efficient protocol. To the best of our knowledge, we report the first shelf life study of 2-pyridylzinc bromide which confirms the excellent stability of this compound and underlines the synthetic value of organozinc reagents in the cross-coupling reactions of sensitive heterocyclic nucleophiles on academic and commercial scale.

PROCESS FOR PRODUCING 2-SUBSTITUTED PYRIDINE DERIVATIVE

The present invention provides a method of producing a pyridine derivative having a substituent at the 2-position of a heterocyclic structure conveniently and with fine selectivity. The present invention relates to a production method of a pyridine derivative having a substituent at the 2-position of a heterocyclic structure, which is represented by the formula (III), which includes reacting a 2-sulfonylpyridine derivative of the formula (I) with an organometallic compound of the formula (II) and the like, and the like: wherein each symbol is as defined in the Description.

Preparation of 2- and 5-aryl substituted thiazoles via palladium-catalyzed Negishi cross-coupling

2-Aryl substituted thiazoles 3a-k were prepared by oxidative insertion of zinc into 2-bromothiazole (1) followed by palladium(0)-catalyzed Negishi cross-coupling in a one-pot procedure. 5-Aryl substituted thiazoles 6a-i were prepared by regioselective C-5 lithiation of 2-(trimethylsilyl)thiazole (4) followed by transmetalation with zinc chloride and palladium(0)-catalyzed Negishi cross-coupling in a one-pot procedure. The synthetic sequences were combined to give 2,5-diaryl substituted thiazoles 8a,b and 10 via stepwise C-2 and C-5 arylation and vice versa.

The effect of some additives on the Stille Pd0-catalyzed cross-coupling reaction

It has been found that the addition of cupric oxide to the cross-coupling reaction (Stille reaction) of 2-tributylstannylpyridine with various halobenzenes and heterocyclic halides leads to a much faster reaction and higher yields. This is also the case for the formation of thieno-1,6-naphthyridine from 2-(2-trimethylstannyl-3-pyridyl)-1,3-dioxolane and t-butyl-N-(2-bromo-3-thienyl)carbamate.

Palladium-Catalyzed Coupling of Heteroaryl Alkylstannanes with Heteroaryl Halides in the Presence of Silver(I) oxide

The Pd-catalyzed coupling of heteroaryl trialkylstannanes with a variety of heteroaryl halides has been shown to be greatly promoted by silver(I) oxide.