30165-97-0

Basic information

• Product Name: 4-MORPHOLIN-4-YL-1,2,5-THIADIAZOL-3-OL
• Synonyms: 4-MORPHOLIN-4-YL-1,2,5-THIADIAZOL-3-OL;4-Morpholin-4-yl-1,2,5-thiadiazol-3-ol 97%;3-Hydroxy-4-morpholino-1,2,5-thiazole;4-morpholino-1,2,5-thiadiazol-3-ol;3-Hydroxy-4-(morpholin-4-yl)-1,2,5-thiadiazole 97%;3-Hydroxy-4-(morpholin-4-yl)-1,2,5-thiadiazole;4-(Morpholin-4-yl)-1,2,5-thiadiazol-3-ol, 4-(3-Hydroxy-1,2,5-thiadiazol-4-yl)morpholine;1,2,5-Thiadiazol-3(2H)-one, 4-(4-Morpholinyl)-
• CAS NO: 30165-97-0
• Molecular Formula: C₆H₉N₃O₂S
• Molecular Weight: 187.22
• EINECS: 608-450-5
• Product Categories: Oxadiazoles & Thiadiazoles;Oxadiazoles & Thiadiazoles;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 30165-97-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 200-204 °C
• Boiling Point: 336.6 °C at 760 mmHg
• Flash Point: 157.3 °C
• Appearance: /
• Density: 1.69 g/cm³
• Vapor Pressure: 5.7E-05mmHg at 25°C
• Refractive Index: 1.753
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated and Sonicated)
• PKA: 6.20±0.40(Predicted)
• CAS DataBase Reference: 4-MORPHOLIN-4-YL-1,2,5-THIADIAZOL-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-MORPHOLIN-4-YL-1,2,5-THIADIAZOL-3-OL(30165-97-0)
• EPA Substance Registry System: 4-MORPHOLIN-4-YL-1,2,5-THIADIAZOL-3-OL(30165-97-0)

Safety Data

• Hazardous Substances Data: 30165-97-0(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 30165-97-0 differently. You can refer to the following data:
1. 3-Hydroxy-4-morpholino-1,2,5-thiazole (Timolol EP Impurity D; Timolol BP Impurity D; Timolol USP Related Compound D) is an intermediate for the preparation of Timolol.
2. An intermediate for the preparation of Timolol

InChI:InChI=1/C6H9N3O2S/c10-6-5(7-12-8-6)9-1-3-11-4-2-9/h1-4H2,(H,8,10)

Upstream product

• 26839-75-8 timolol 
• 30165-96-9 3-Morpholino-4-chloro-1,2,5-thiadiazole 

Downstream Products

• 26839-75-8 timolol 
• 69500-53-4 4-{4-[(2S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine 
• 741719-53-9 4-{4-[(2R)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine 
• 26839-76-9 R-(+)-1-tert-butylamino-3-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]-2-propanol 
• 26921-17-5 timolol maleate 
• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 
• 110638-00-1 3-chloro-1-<(4-morpholino-1,2,5-thidiazol-3-yl)oxy>-2-propanol 
• 57519-99-0 d,l-3-<4-(4-Morpholinyl)-1.2.5-thiadiazol-3-yloxy>-milchsaeure 

Relevant articles and documents

Preparation method of timolol impurity

The invention discloses a timolol impurity preparation method, and belongs to the technical field of timolol impurity synthesis. 3-halo-4-morpholinyl-1,2,5-thiadiazole is used as an initial raw material to prepare an intermediate M1 through alkaline hydrolysis and acid treatment, potassium ethyl malonate and tert-butyl amine are subjected to a condensation reaction to prepare an intermediate M2, the intermediate M2 and liquid bromine are subjected to a substitution reaction to prepare an intermediate M3, the intermediate M3 and the intermediate M1 are subjected to a nucleophilic substitution reaction to prepare an intermediate M4, and the intermediate M4 is subjected to a reduction reaction and alkaline hydrolysis to prepare a target product. The method has the characteristics of reasonable synthetic route, easily available raw materials, simple and easy operation, high yield and high purity. The prepared timolol can be used as a reference substance for qualitative and quantitative research of impurities in timolol quality research, the content of related substances in bulk drugs is controlled, and the quality of the bulk drugs is guaranteed.

Optimization of 1,2,5-thiadiazole carbamates as potent and selective ABHD6 inhibitors

At present, inhibitors of α/β-hydrolase domain 6 (ABHD6) are viewed as a promising approach to treat inflammation and metabolic disorders. This article describes the development of 1,2,5-thiadiazole carbamates as ABHD6 inhibitors. Altogether, 34 compounds were synthesized, and their inhibitory activity was tested using lysates of HEK293 cells transiently expressing human ABHD6 (hABHD6). Among the compound series, 4-morpholino-1,2,5-thiadiazol-3-yl cyclooctyl(methyl)carbamate (JZP-430) potently and irreversibly inhibited hABHD6 (IC50 = 44 nM) and showed ～ 230-fold selectivity over fatty acid amide hydrolase (FAAH) and lysosomal acid lipase (LAL), the main off-targets of related compounds. Additionally, activity-based protein profiling indicated that JZP-430 displays good selectivity among the serine hydrolases of the mouse brain membrane proteome. JZP-430 has been identified as a highly selective, irreversible inhibitor of hABHD6, which may provide a novel approach in the treatment of obesity and type II diabetes.

Thiadiazole carbamates: Potent inhibitors of lysosomal acid lipase and potential niemann-pick type C disease therapeutics

Niemann-Pick type C (NPC) disease is a lysosomal storage disorder characterized at the cellular level by abnormal accumulation of cholesterol and other lipids in lysosomal storage organelles. Lysosomal acid lipase (LAL) has been recently identified as a potential therapeutic target for NPC. LAL can be specifically inhibited by a variety of 3,4-disubstituted thiadiazole carbamates. An efficient synthesis of the C(3) oxygenated/C(4) aminated analogues has been developed that furnishes the products in high yields and high degrees of purity. Common intermediates can also be used for the synthesis of the C(3) carbon substituted derivatives. Herein we tested various thiadiazole carbamates, amides, esters, and ketones for inhibition of LAL. In addition, we tested a diverse selection of commercially available non-thiadiazole carbamates. Our studies show that, among the compounds examined herein, only thiadiazole carbamates are effective inhibitors of LAL. We present a mechanism for LAL inhibition by these compounds whereby LAL transiently carbamoylates the enzyme similarly to previously described inhibition of acetylcholinesterase by rivastigmine and other carbamates as well as acylation of various lipases by orlistat.