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Cas Database

131986-28-2

131986-28-2

Identification

  • Product Name:Pyridine,3-(4-chloro-1,2,5-thiadiazol-3-yl)-

  • CAS Number: 131986-28-2

  • EINECS:

  • Molecular Weight:197.648

  • Molecular Formula: C7H4ClN3S

  • HS Code:2934999090

  • Mol File:131986-28-2.mol

Synonyms:3-CHLORO-4-(PYRIDIN-3-YL)-1,2,5-THIADIAZOLE;3-(4-CHLORO-1,2,5-THIADIAZOL-3-YL)PYRIDINE;3-Chloro-4-(3-pyridyl)-1,2,5-thiadiazole, 95%

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole
  • Packaging:500mg
  • Price:$ 170
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole 95%
  • Packaging:500mg
  • Price:$ 98
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole 95%
  • Packaging:250mg
  • Price:$ 62
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  • Manufacture/Brand:J&W Pharmlab
  • Product Description:3-(4-Chloro-[1,2,5]thiadiazol-3-yl)-pyridine 97%
  • Packaging:1g
  • Price:$ 398
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  • Manufacture/Brand:J&W Pharmlab
  • Product Description:3-(4-Chloro-[1,2,5]thiadiazol-3-yl)-pyridine 97%
  • Packaging:5g
  • Price:$ 1390
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  • Manufacture/Brand:Crysdot
  • Product Description:3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole 95+%
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  • Price:$ 420
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  • Manufacture/Brand:Crysdot
  • Product Description:3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole 95+%
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  • Manufacture/Brand:Chemenu
  • Product Description:3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole 95%
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  • Manufacture/Brand:Axon Medchem
  • Product Description:3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole 99%
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3-CHLORO-4-(PYRIDIN-3-YL)-1,2,5-THIADIAZOLE 95.00%
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Relevant articles and documentsAll total 14 Articles be found

Muscarinic agonists with antipsychotic-like activity: Structure-activity relationships of 1,2,5-thiadiazole analogues with functional dopamine antagonist activity

Sauerberg, Per,Jeppesen, Lone,Olesen, Preben H.,Rasmussen, Th?ger,Swedberg, Michael D. B.,Sheardown, Malcolm J.,Fink-Jensen, Anders,Thomsen, Christian,Th?gersen, Henning,Rimvall, Karin,Ward, John S.,Calligaro, David O.,DeLapp, Neil W.,Bymaster, Frank P.,Shannon, Harlan E.

, p. 4378 - 4384 (1998)

Muscarinic agonists were tested in two models indicative of clinical antipsychotic activity: conditioned avoidance responding (CAR) in rats and inhibition of apomorphine-induced climbing in mice. The standard muscarinic agonists oxotremorine and pilocarpine were both active in these tests but showed little separation between efficacy and cholinergic side effects. Structure-activity relationships of the alkylthio-1,2,5-thiadiazole azacyclic type muscarinic partial agonists are shown, revealing the exo-6-(3- propyl/butylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane analogues (4a,b and 9a,b) to be the most potent antipsychotic agents with large separation between efficacy and cholinergic side effects. The lack of enantiomeric selectivity suggests the pharmacophoric elements are in the mirror plane of the compounds. A model explaining the potency differences of closely related compounds is offered. The data suggest that muscarinic agonists act as functional dopamine antagonists and that they could become a novel treatment of psychotic patients.

The palladium-catalyzed cross-coupling reactions of 3-chloro-4-halogeno-1,2,5-thiadiazoles

Merschaert, Alain,Gorissen, Hugo J.

, p. 29 - 45 (2003)

3,4-Dichloro- and 3-chloro-4-halogeno-1,2,5-thiadiazoles (halogeno-: bromo- and iodo-) are involved in Pd-catalyzed cross-coupling reactions under Stille and Suzuki conditions. As a result, by using the commercially available 3,4-dichloro-1,2,5-thiadiazole as substrate, several 3-alkyl-, 3-alkenyl-, 3-alkynyl-and 3-aryl-4-chloro-1,2,5-thiadiazoles can easily be prepared. However, these reactions through direct desymmetrization of the 3,4-dichloro-1,2,5-thiadiazole always occur with side-reactions resulting from the concurrent decomposition of the heterocyclic ring of the starting material. These problems are resolved by involving, in these Pd-catalyzed cross-coupling reactions, the more reactive and selective 3-bromo-4-chloro- and 3-chloro-4-iodo-1,2,5-thiadiazole. These new dihalogeno-1,2,5-thiadiazoles can easily be prepared, via diazotization reaction followed by halogen substitution, from the 3-amino-4-chloro-1,2,5-thiadiazole.

Tacrine-xanomeline and tacrine-iperoxo hybrid ligands: Synthesis and biological evaluation at acetylcholinesterase and M1 muscarinic acetylcholine receptors

Cirillo, Davide,Dallanoce, Clelia,De Amici, Marco,Holzgrabe, Ulrike,Maspero, Marco,Messerer, Regina,Sotriffer, Christoph,Volpato, Daniela,Yuan Chen, Natalia

, (2020/02/11)

We synthesized a set of new hybrid derivatives (7-C8, 7-C10, 7-C12 and 8-C8, 8-C10, 8-C12), in which a polymethylene spacer chain of variable length connected the pharmacophoric moiety of xanomeline, an M1/M4-preferring orthosteric muscarinic agonist, with that of tacrine, a well-known acetylcholinesterase (AChE) inhibitor able to allosterically modulate muscarinic acetylcholine receptors (mAChRs). When tested in vitro in a colorimetric assay for their ability to inhibit AChE, the new compounds showed higher or similar potency compared to that of tacrine. Docking analyses were performed on the most potent inhibitors in the series (8-C8, 8-C10, 8-C12) to rationalize their experimental inhibitory power against AChE. Next, we evaluated the signaling cascade at M1 mAChRs by exploring the interaction of Gαq-PLC-β3 proteins through split luciferase assays and the myo-Inositol 1 phosphate (IP1) accumulation in cells. The results were compared with those obtained on the known derivatives 6-C7 and 6-C10, two quite potent AChE inhibitors in which tacrine is linked to iperoxo, an exceptionally potent muscarinic orthosteric activator. Interestingly, we found that 6-C7 and 6-C10 behaved as partial agonists of the M1 mAChR, at variance with hybrids 7-Cn and 8-Cn containing xanomeline as the orthosteric molecular fragment, which were all unable to activate the receptor subtype response.

Hybrid molecules from xanomeline and tacrine: Enhanced tacrine actions on cholinesterases and muscarinic M1 receptors

Fang, Lei,Jumpertz, Sabine,Zhang, Yihua,Appenroth, Dorothea,Fleck, Christian,Mohr, Klaus,Tr?nkle, Christian,Decker, Michael

scheme or table, p. 2094 - 2103 (2010/08/19)

A set of amide- and amine-linked hybrid molecules comprising moieties of the orthosteric M1 muscarinic receptor agonist xanomeline and the Cholinesterase inhibitor and allosteric receptor modulator tacrine were prepared with varying spacer length of 10-17 atoms. The hybrids inhibited acetylcholinesterase with similar or higher potency compared to tacrine. M 1 receptor binding affinity was similar or higher relative to xanomeline and far higher relative to tacrine. Affinities hardly changed when the receptors' orthosteric site was occupied by an inverse agonist ligand. When occupied by the orthosteric activator acetylcholine, affinity for the hybrids declined to unmeasureably low levels. Hybrids did not activate M1 receptors. In vivo studies assaying cognition impairment in rats induced by scopolamine revealed pronounced enhancement of scopolamine action. Taken together, instead of dualsteric (simultaneous allosteric/orthosteric) binding, the hybrids seem to prefer purely allosteric binding at the inactive M 1 receptor.

Synthesis and evaluation of xanomeline analogs-Probing the wash-resistant phenomenon at the M1 muscarinic acetylcholine receptor

Kane, Brian E.,Grant, Marianne K.O.,El-Fakahany, Esam E.,Ferguson, David M.

, p. 1376 - 1392 (2008/09/18)

A series of xanomeline analogs were synthesized and evaluated for binding at the M1 muscarinic acetylcholine receptor (M1 receptor). Specifically, compounds that substitute the O-hexyl chain of xanomeline with polar, ionizable, or conformationally restricted moieties were assessed for their ability to bind to the M1 receptor in a wash-resistant manner (persistent binding). From our screen, several novel ligands that persistently bind to the M1 receptor with greater affinity than xanomeline were discovered. Results indicate that persistent binding may arise not only from hydrophobic interactions but also from ionic interactions with a secondary M1 receptor binding site. Herein, a qualitative model that accounts for both binding scenarios is proposed and applied to understand the structural basis to wash-resistant binding and long-acting effects of xanomeline-based compounds.

PESTICIDAL SUBSTITUTED 1,2,5,-THIADIAZOLE DERIVATIVES

-

Page/Page column 32-33, (2008/06/13)

Insecticidal and acaricidal compositions comprising an insecticidally or acaricidally effective amount of a 1,2,5-thiadiazole of the formula (I); wherein R, Q and m are as defined in admixture with at least one agriculturally acceptable extender or adjuvant are disclosed. In addition, methods of controlling insects and acarids comprising applying said compositions to a locus of crops where control is desired are disclosed.

Palladium-catalyzed cross-coupling chemistry on 3-chloro-4-halo-1,2,5-thiadiazole

-

, (2008/06/13)

The present invention relates to 3-chloro-4-halo-1,2,5-thiadiazole compounds, a method of producing novel mono- and di-substituted-1,2,5-thiadiazoles therefrom, as well as mono- and di-substituted -1,2,5-thiadiazoles.

Process route upstream and downstream products

Process route

2-amino-2-(pyridin-3-yl)acetonitrile
131988-63-1

2-amino-2-(pyridin-3-yl)acetonitrile

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

Conditions
Conditions Yield
With disulfur dichloride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;
79%
2-amino-2-(pyridin-3-yl)acetonitrile; With disulfur dichloride; In DMF (N,N-dimethyl-formamide); dichloromethane; at 0 - 20 ℃; for 48h;
With potassium carbonate; In water;
76.6%
With sulfur monochloride; In N,N-dimethyl-formamide; at 0 ℃; for 0.75h;
58%
With disulfur dichloride; sodium hydroxide; Yield given. Multistep reaction; 1.) DMF, 5 deg C, 30 min, 2.) 5 deg C;
With disulfur dichloride; In N,N-dimethyl-formamide;
With disulfur dichloride; In N,N-dimethyl-formamide; at 10 ℃; for 1.5h;
3-Diethylboranylpyridine
89878-14-8

3-Diethylboranylpyridine

3,4-dichloro-1,2,5-thiadiazole
5728-20-1

3,4-dichloro-1,2,5-thiadiazole

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

Conditions
Conditions Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 24h; Heating;
18%
With potassium carbonate; tetrakis(triphenylphosphine)palladium (0); In toluene;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: aq. NH4Cl, NH3
2: S2Cl2 / dimethylformamide
With disulfur dichloride; ammonia; ammonium chloride; In N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: acetic acid / water / 23 h / 0 - 20 °C
2: ammonium chloride; ammonium hydroxide / water / 22 h / 20 °C
3: disulfur dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C
With disulfur dichloride; ammonium hydroxide; ammonium chloride; acetic acid; In water; N,N-dimethyl-formamide;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: AcOH / H2O / 18 h / Ambient temperature
2: aq. NH4Cl, 25percent aq. NH3 / 18 h / Ambient temperature
3: 1.) S2Cl2, 2.) aq. NaOH / 1.) DMF, 5 deg C, 30 min, 2.) 5 deg C
With disulfur dichloride; ammonium hydroxide; sodium hydroxide; ammonium chloride; acetic acid; In water;
2-hydroxy-2-(pyridin-3-yl)acetonitrile
17604-74-9,107986-64-1

2-hydroxy-2-(pyridin-3-yl)acetonitrile

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: aq. NH4Cl, 25percent aq. NH3 / 18 h / Ambient temperature
2: 1.) S2Cl2, 2.) aq. NaOH / 1.) DMF, 5 deg C, 30 min, 2.) 5 deg C
With disulfur dichloride; ammonium hydroxide; sodium hydroxide; ammonium chloride;
Multi-step reaction with 2 steps
1: ammonium chloride; ammonium hydroxide / water / 22 h / 20 °C
2: disulfur dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C
With disulfur dichloride; ammonium hydroxide; ammonium chloride; In water; N,N-dimethyl-formamide;
3-(tributylstannyl)pyridine
59020-10-9

3-(tributylstannyl)pyridine

3,4-dichloro-1,2,5-thiadiazole
5728-20-1

3,4-dichloro-1,2,5-thiadiazole

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

Conditions
Conditions Yield
tetratrifurylphosphinepalladium; In toluene; Heating;
25%
3-(tributylstannyl)pyridine
59020-10-9

3-(tributylstannyl)pyridine

3-bromo-4-chloro-1,2,5-thiadiazole
537706-13-1

3-bromo-4-chloro-1,2,5-thiadiazole

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

Conditions
Conditions Yield
tetratrifurylphosphinepalladium; In toluene; Heating;
51 % Chromat.
3-(tributylstannyl)pyridine
59020-10-9

3-(tributylstannyl)pyridine

3-chloro-4-iodo-1,2,5-thiadiazole
537706-14-2

3-chloro-4-iodo-1,2,5-thiadiazole

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

Conditions
Conditions Yield
tris-(dibenzylideneacetone)dipalladium(0); In toluene; for 2h; Heating;
76 % Chromat.
3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

Conditions
Conditions Yield
76%
45%
45%
45%
45%
28%
N-tert-butoxycarbonyl-3-aminopropanol
58885-58-8

N-tert-butoxycarbonyl-3-aminopropanol

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine
131986-28-2

3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine

3-(3-(3-(tert-butoxycarbonylamino)propoxy)-1,2,5-thiadiazol-4-yl)pyridine
1018846-18-8

3-(3-(3-(tert-butoxycarbonylamino)propoxy)-1,2,5-thiadiazol-4-yl)pyridine

Conditions
Conditions Yield
With sodium hydride; In tetrahydrofuran; at 20 ℃; for 18h;
50%

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