16063-69-7

Basic information

• Product Name: 2,4,6-Trichloropyridine
• Synonyms: 2 4 6-TRICHLOROPYRIDINE 97;2,4,6-trichloro-pyridin;2,4,6-Trichloropyridine;Pyridine,2,4,6-trichloro-;2,4,6-Trichloropyridine,98%
• CAS NO: 16063-69-7
• Molecular Formula: C₅H₂Cl₃N
• Molecular Weight: 182.44
• Product Categories: Pyridine series;Pyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyridine series
• Mol File: 16063-69-7.mol

Chemical Properties

• Melting Point: 33-37 °C(lit.)
• Boiling Point: 212.5 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: Yellow to yellow-brown/Crystalline Powder
• Density: 1.539 g/cm³
• Vapor Pressure: 0.251mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C
• PKA: -2.93±0.10(Predicted)
• Water Solubility: Sparingly soluble in water. (0.113 mm Hg at 25°C)
• CAS DataBase Reference: 2,4,6-Trichloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trichloropyridine(16063-69-7)
• EPA Substance Registry System: 2,4,6-Trichloropyridine(16063-69-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-41-43
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• RTECS: UU0875000
• Hazardous Substances Data: 16063-69-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4,6-Trichloropyridine is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique chemical structure allows it to be a key component in the development of new pharmaceutical compounds, contributing to the advancement of medical treatments.
Used in Chemical Synthesis:
In addition to its pharmaceutical applications, 2,4,6-Trichloropyridine is also utilized as an intermediate in the synthesis of other chemicals. Its reactivity and stability make it a valuable building block for creating a wide range of chemical products, further expanding its utility across different industries.

InChI:InChI=1/C5H2Cl3N/c6-3-1-4(7)9-5(8)2-3/h1-2H

Upstream product

• 2587-02-2 2,6-dichloro-[4]pyridylamine 
• 116632-24-7 2-amino-4,6-dichloropyridine 
• 2587-00-0 2,6-dichloropyridine N-oxide 
• 98027-84-0 2,6-dichloro-4-iodopyridine 
• 2402-78-0 2,6-dichloropyridine 

Downstream Products

• 175461-34-4 2,6-dichloro-N,N-dimethylpyridin-4-amine 
• 1262133-23-2 tert-butyl 4-(benzyloxy)-2-chloro-6-phenethylnicotinate 
• 1262133-21-0 tert-butyl 4-(benzyloxy)-2,6-dichloronicotinate 
• 1262133-20-9 4-(benzyloxy)-2,6-dichloropyridine 
• 1218994-35-4 methyl 2,4,6-trichloronicotinate 
• 852333-59-6 4-(4,6-dichloropyridin-2-yl)morpholine 
• 175461-33-3 2,6-dichloro-N-methylpyridine-4-amine 
• 767334-78-1 2,4-dichloro-6-(5-chloro-2-methoxy-phenyl)-pyridine 
• 2412-97-7 3,5-dichloro-2,4,6-trimethoxypyridine 
• 14121-36-9 2,3,4,6-Tetrachloropyridine 
• 874491-78-8 2,3,6-trichloro-[4]pyridylamine 
• 108279-31-8 2-benzyloxy-4,6-dimethoxypyridine 
• 108279-65-8 6-chloro-4-methoxypyridine-2(1H)-one 
• 1027502-01-7 (6R-trans)-3-(chloromethyl)-7-[[[(2,6-dichloro-4-pyridinyl)thio]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0.]oct-2-ene-2-carboxylic acid, diphenylmethyl ester 

Relevant articles and documents

Stereo- and Regioselective Alkyne Hydrometallation with Gold(III) Hydrides

The hydroauration of internal and terminal alkynes by gold(III) hydride complexes [(C^N^C)AuH] was found to be mediated by radicals and proceeds by an unexpected binuclear outer-sphere mechanism to cleanly form trans-insertion products. Radical precursors such as azobisisobutyronitrile lead to a drastic rate enhancement. DFT calculations support the proposed radical mechanism, with very low activation barriers, and rule out mononuclear mechanistic alternatives. These alkyne hydroaurations are highly regio- and stereospecific for the formation of Z-vinyl isomers, with Z/E ratios of >99:1 in most cases.

Synthesis and evaluation of novel imidazo[4,5-: C] pyridine derivatives as antimycobacterial agents against Mycobacterium tuberculosis

The current study involves the synthesis of novel imidazo[4,5-c]pyridine derivatives (IPD) containing amide/urea/sulfonamide. The synthesized compounds were evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis. The pharmacological activities were determined by the objective to better understand their structure-activity relationship (SAR) for their in vitro antimycobacterial activity against M. tuberculosis. Some synthesized compounds showed significant activity against M. tuberculosis based on the agar dilution method. Among the forty-one compounds screened, compounds 21, 22 and 23 were found to be the most active compounds against M. tuberculosis. In the in vivo animal model, 21, 22 and 23 decreased the bacterial load in lung and spleen tissues at the dose of 50 mg kg-1 body weight.

The discovery of novel diarylpyri(mi)dine derivatives with high level activity against a wide variety of HIV-1 strains as well as against HIV-2

By means of structure-based molecular hybridization strategy, a series of novel diarylpyri(mi)dine derivatives targeting the entrance channel of HIV-1 reverse transcriptase (RT) were designed, synthesized and evaluated as potent non-nucleoside reverse transcriptase inhibitors (NNRTIs). Encouragingly, all the tested compounds showed good activities against wild-type (WT) HIV-1 (IIIB) with EC50 in the range of 1.36 nM–29 nM, which is much better than those of nevirapine (NVP, EC50 = 125.42 nM) and azidothymidine (AZT, EC50 = 11.36 nM). Remarkably, these compounds also displayed effective activity against the most of the single and double-mutated HIV-1 strains with low EC50 values, which is comparable to the control drugs. Besides, these compounds were also exhibited favorable enzymatic inhibitory activity. Moreover, preliminary structure-activity relationships (SARs) and molecular modeling study were investigated and discussed in detail. Unexpectedly, four diarylpyrimidines yielded moderate anti-HIV-2 activities. To our knowledge, this is rarely reported that diarylpyrimidine-based NNRTIs have potent activity against both HIV-1 and HIV-2 in cell culture.

Design, synthesis and anti-HIV evaluation of novel diarylpyridine derivatives targeting the entrance channel of NNRTI binding pocket

The development of novel NNRTIs with activity against variants of HIV-1RT is crucial for overcoming treatment failure. In the present study, a series of novel 6-substituted diarylpyridine derivatives targeting the entrance channel of the NNIBP of RT were designed through a molecular hybridization strategy. Encouragingly, these new diarylpyridine derivatives were found to be active against wild-type (WT) HIV-1 with an EC50 values ranging from 0.035 μM to 1.99 μM. Nearly half of them exhibited more potent inhibitory activities in cellular assays than the control drug nevirapine (NVP). Notably, three most promising compounds If (EC50 = 35 nM), Ia (EC50 = 43 nM) and IIa (EC50 = 41 nM) showed high potency against WT and were comparable to the reference drug delavirdine (DLV) (EC50 = 33 nM). Moreover, compounds Ib, IIb and IIh displayed effective activity against the most common clinically observed single and double-mutated HIV-1 strains in micromolar concentrations. In particular, the inhibition of IIb against the K103N mutation (EC50 = 49 nM), which confers resistance to a wide variety of NNRTIs, was about 140 times more effective than NVP (EC50 = 6.78 μM), 50 times more than DLV (EC50 = 2.48 μM) and about 3 times more than EFV (EC50 = 0.12 μM), indicating that the newly designed compounds have great potential to be further developed as new anti-HIV-1 agents. Preliminary structure-activity relationships (SARs) and molecular modeling of the new diarylpyridine derivatives were discussed in detail.

6-substitute diaryl pyridine derivative and preparing method and application thereof

The invention discloses a 6-substitute diaryl pyridine derivative and a preparing method and application thereof. The compound has a structure shown in a formula I. The invention further relates to a drug composition containing the compound with the structure in the formula I and provides application of the compound to preparation of anti-HIV drugs.

Structural optimization of pyridine-type DAPY derivatives to exploit the tolerant regions of the NNRTI binding pocket

Based on the crystallographic studies of diarylpyrimidines (DAPYs), we embarked on incorporating the hydrophilic piperidyl or morpholinyl group into the known DAPY derivatives bearing the pyridine moiety as a core structure, with the double aim to exploit additional interactions with the HIV-1 NNRTI binding pocket (NNIBP), as well as to improve the compound solubility. The antiviral evaluation result show that the most potent compounds I-8b2, I-8b3, I-8b4 and I-8c3 exhibited anti-HIV-1 (IIIB) strain activity ranging from 7.4 nM to 9.4 nM (SI = 168-1283), superior to FDA-approved drugs of nevirapine (NVP), lamivudine (3TC) and delavirdine (DLV), and comparable to etravirine (ETV), zidovudine (AZT) and efavirenz (EFV). Additionally, compounds I-8c2 and I-8c3 showed moderate activity against NNRTI resistant strains baring mutations K103N and Y181C with EC50 values of 6.2 mM and 6.8 mM, respectively. Preliminary structure-activity relationships (SARs), reverse transcriptase inhibition efficacy and molecular modeling of selected compounds are also presented. These outcomes support our design hypothesis and demonstrate that the piperidyl group modified pyridine-typed DAPY derivatives are highly potent NNRTIs with improved water solubility.

Discovery of 2-pyridone derivatives as potent HIV-1 NNRTIs using molecular hybridization based on crystallographic overlays

Based on crystallographic overlays of the known inhibitors TMC125 and R221239 complexed in RT, we designed a novel series of 4-phenoxy-6-(phenylamino) pyridin-2(1H)-one derivatives as HIV NNRTIs by molecular hybridization approach. The biological testing results indicated that 2-pyridone scaffold of these inhibitors was indispensable for their anti-HIV-1 activity, and substitution of halogen at the 3-position of the 2-pyridone ring would decrease the anti-HIV activity. Four most potent compounds had anti-HIV-1 IIIB activities at low micromolar concentrations (EC50 = 0.15-0.84 μM), comparable to that of nevirapine and delavidine. Some compounds were selected to test their anti-HIV-1 RT inhibitory action and to perform molecular modeling studies to predict the binding mode of these 2-pyridone derivatives.

BICYCLIC INHIBITORS OF ALK

The present invention relates to compounds of formula (1) or pharmaceutical acceptable salts, Formula (1) wherein R1, R2, R3, X, Y, Z, A, B, G1, m, and n are defined in the description. The present invention relates also to compositions containing said compounds which are useful for inhibiting kinases such as ALK and methods of treating diseases such as cancer.

BICYCLIC INHIBITORS OF ALK

The present invention relates to compounds of formula (1) or pharmaceutical acceptable salts, wherein R1, X, Y, Z, A, B, G1, and n are defined in the description. The present invention relates also to compositions containing said compounds which are useful for inhibiting kinases such as ALK and methods of treating diseases such as cancer.

BICYCLIC INHIBITORS OF ANAPHASTIC LYMPHOMA KINASE

Disclosed are compounds of formula (Ⅰ) and their pharmaceutical acceptable salts, wherein R1, R2, R3, X, Y, Z, A, B, G1, m and n are defined in the description. The compositions containing the said compounds used for inhibiting kinases such as anaphastic lymphoma kinase (ALK) and methods of treating diseases such as cancer are disclosed.