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Oxetan-3-yl Methanesulfonate, with the chemical formula C5H10O3S, is an organic sulfonate ester that serves as a reagent in organic synthesis and as a protecting group for alcohols and amines. It is recognized for its selective protection of hydroxyl groups in the presence of other functional groups, which makes it a valuable asset in organic chemistry. Its versatile reactivity and stability contribute to its significance as a building block in the synthesis of complex organic molecules, particularly in drug discovery and various industrial applications.

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  • 148430-81-3 Structure
  • Basic information

    1. Product Name: Oxetan-3-yl Methanesulfonate
    2. Synonyms: Oxetan-3-yl Methanesulfonate;3-Oxetanol 3-Methanesulfonate
    3. CAS NO:148430-81-3
    4. Molecular Formula: C4H8O4S
    5. Molecular Weight: 152.16892
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 148430-81-3.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 308.9±31.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.38±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    8. Solubility: N/A
    9. CAS DataBase Reference: Oxetan-3-yl Methanesulfonate(CAS DataBase Reference)
    10. NIST Chemistry Reference: Oxetan-3-yl Methanesulfonate(148430-81-3)
    11. EPA Substance Registry System: Oxetan-3-yl Methanesulfonate(148430-81-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 148430-81-3(Hazardous Substances Data)

148430-81-3 Usage

Uses

Used in Organic Synthesis:
Oxetan-3-yl Methanesulfonate is used as a reagent for the synthesis of complex organic molecules, leveraging its versatile reactivity and stability to facilitate the creation of a wide range of compounds.
Used in Drug Discovery:
In the pharmaceutical industry, Oxetan-3-yl Methanesulfonate is utilized as a protecting group for hydroxyl groups during the synthesis of drug candidates, ensuring the selective protection of these groups and enabling the development of more sophisticated and effective medicinal compounds.
Used as a Protecting Group in Organic Chemistry:
Oxetan-3-yl Methanesulfonate is employed as a protecting group for alcohols and amines, allowing chemists to selectively shield hydroxyl groups from unwanted reactions, which is crucial for the synthesis of complex organic molecules with multiple functional groups. This selective protection is particularly valuable in the synthesis of intricate organic structures where precise control over the reaction is necessary.

Check Digit Verification of cas no

The CAS Registry Mumber 148430-81-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,8,4,3 and 0 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 148430-81:
(8*1)+(7*4)+(6*8)+(5*4)+(4*3)+(3*0)+(2*8)+(1*1)=133
133 % 10 = 3
So 148430-81-3 is a valid CAS Registry Number.

148430-81-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Oxetan-3-yl methanesulfonate

1.2 Other means of identification

Product number -
Other names oxetan-3-yl methanesulfonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:148430-81-3 SDS

148430-81-3Relevant articles and documents

Mild C–C Bond Formation via Lewis Acid Catalyzed Oxetane Ring Opening with Soft Carbon Nucleophiles

Huang, Hai,Zhang, Tianyu,Sun, Jianwei

supporting information, p. 2668 - 2673 (2020/12/07)

Mild oxetane opening by soft carbon nucleophiles has been developed for efficient C?C bond formation. In the presence of LiNTf2 or TBSNTf2 as catalyst, silyl ketene acetals were found to be effective nucleophiles to generate a wide range of highly oxygenated molecules, which are key substructure in natural products like polyketides. Furthermore, intramolecular oxetane opening by a styrene-based carbon nucleophile via a Prins-type process was also achieved with Sc(OTf)3 as catalyst, leading to efficient formation of the useful 2,3-dihydrobenzo[b]oxepine skeleton.

A GAP Replacement: Improved Synthesis of 3-Azidooxetane and Its Homopolymer Based on Sulfonic Acid Esters of Oxetan-3-ol

Born, Max,Karaghiosoff, Konstantin,Klap?tke, Thomas M.

supporting information, p. 12607 - 12614 (2021/09/18)

In the field of energetic binders, only hydroxy-terminated glycidyl azide polymer (GAP) has found widespread application and prevailed in the market. However, oxiranes such as glycidyl azide (GA) allow two ring-opening modes during polymerization and thus

N-(AZAARYL)CYCLOLACTAM-1-CARBOXAMIDE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF

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Paragraph 0143; 0162; 0163, (2020/03/23)

An N-(azaaryl)cyclolactam-1-carboxamide derivative having a structure of formula (I), a preparation method therefor, and a use thereof are disclosed in the application. Each substituent are defined in the specification and claims. The series of compounds of the application can be widely applied in the preparation of drugs for treating cancer, tumor, autoimmune disease, metabolic disease or metastatic disease, particularly for treating ovarian cancer, pancreatic cancer, prostate cancer, breast cancer, cervical cancer, glioblastoma, multiple myeloma, metabolic disease, neurodegenerative disease, primary tumor site metastasis or osseous metastasis cancer, and are expected to be developed into a new generation of CSF-1R inhibitor drugs.

Optimizing Pyrazolopyrimidine Inhibitors of Calcium Dependent Protein Kinase 1 for Treatment of Acute and Chronic Toxoplasmosis

Janetka, James W.,Hopper, Allen T.,Yang, Ziping,Barks, Jennifer,Dhason, Mary Savari,Wang, Qiuling,Sibley, L. David

supporting information, p. 6144 - 6163 (2020/07/10)

Calcium dependent protein kinase 1 (CDPK1) is an essential Ser/Thr kinase that controls invasion and egress by the protozoan parasite Toxoplasma gondii. The Gly gatekeeper of CDPK1 makes it exquisitely sensitive to inhibition by small molecule 1H-pyrazolo

Discovery of Novel 1-Cyclopentenyl-3-phenylureas as Selective, Brain Penetrant, and Orally Bioavailable CXCR2 Antagonists

Lu, Hongfu,Yang, Ting,Xu, Zhongmiao,Lin, Xichen,Ding, Qian,Zhang, Yueting,Cai, Xin,Dong, Kelly,Gong, Sophie,Zhang, Wei,Patel, Metul,Copley, Royston C. B.,Xiang, Jianing,Guan, Xiaoming,Wren, Paul,Ren, Feng

supporting information, p. 2518 - 2532 (2018/03/26)

CXCR2 has emerged as a therapeutic target for not only peripheral inflammatory diseases but also neurological abnormalities in the central nervous system (CNS). Herein, we describe the discovery of a novel 1-cyclopentenyl-3-phenylurea series as potent and CNS penetrant CXCR2 antagonists. Extensive SAR studies, wherein molecules' property forecast index (PFI) was carefully optimized for overall balanced developability profiles, led to the discovery of the advanced lead compound 68 with a desirable PFI. Compound 68 demonstrated good in vitro pharmacology with excellent selectivity over CXCR1 and other chemokine receptors. Rat and dog pharmacokinetics (PK) revealed good oral bioavailability, high oral exposure, and desirable elimination half-life of the compound in both species. In addition, the compound demonstrated dose-dependent efficacy in the in vivo pharmacology neutrophil infiltration "air pouch" model in rodents after oral administration. Further, compound 68 is a CNS penetrant molecule with high unbound fraction in brain tissue.

Amino 6-membered ring derivative and pharmaceutical applications thereof including the use for manufacturing dipeptidyl peptidase-4(IDPP-IV) inhibitor

-

Page/Page column 98; 99, (2017/07/31)

The present invention relates to an amino 6-membered ring derivative and pharmaceutical applications thereof, which specifically relates to the amino 6-membered ring derivative represented by the general formula (I) or stereoisomers thereof, pharmaceutically acceptable salts thereof, a prodrug, a pharmaceutical composition comprising the derivative, and the pharmaceutical use for manufacturing dipeptidyl peptidase-4(IDPP-IV) inhibitor, wherein the definition of each substituent in the general formula (I) is the same as described in the specification.

Discovery of a Potent, Selective T-type Calcium Channel Blocker as a Drug Candidate for the Treatment of Generalized Epilepsies

Bezen?on, Olivier,Heidmann, Bibia,Siegrist, Romain,Stamm, Simon,Richard, Sylvia,Pozzi, Davide,Corminboeuf, Olivier,Roch, Catherine,Kessler, Melanie,Ertel, Eric A.,Reymond, Isabelle,Pfeifer, Thomas,De Kanter, Ruben,Toeroek-Schafroth, Michael,Moccia, Luca G.,Mawet, Jacques,Moon, Richard,Rey, Markus,Capeleto, Bruno,Fournier, Elvire

supporting information, p. 9769 - 9789 (2017/12/26)

We report here the discovery and pharmacological characterization of N-(1-benzyl-1H-pyrazol-3-yl)-2-phenylacetamide derivatives as potent, selective, brain-penetrating T-type calcium channel blockers. Optimization focused mainly on solubility, brain penetration, and the search for an aminopyrazole metabolite that would be negative in an Ames test. This resulted in the preparation and complete characterization of compound 66b (ACT-709478), which has been selected as a clinical candidate.

1 -(CYCLOPENT-2-EN-1 -YL)-3-(2-HYDROXY-3-(ARYLSULFONYL)PHENYL)UREA DERIVATIVES AS CXCR2 INHIBITORS

-

Page/Page column 169, (2015/12/18)

The invention relates to 1-(3-sulfonylphenyl)-3-(cyclopent-2-en-1-yl)urea derivatives, and their use in treating or preventing diseases and conditions mediated by the CXCR2 receptor. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.

MODULATORS OF THE GPR119 RECEPTOR AND THE TREATMENT OF DISORDERS RELATED THERETO

-

Page/Page column 124; 125, (2013/04/25)

The present invention relates to compounds of Formula (I) and pharmaceutically acceptable salts, solvates, hydrates, and N-oxides thereof,that are useful as single pharmaceutical agents or in combination with one or more additional pharmaceutical agents, such as, an inhibitor of DPP-IV, a biguanide, an alpha-glucosidase inhibitor, an insulin analogue, a sulfonylurea, an SGLT2 inhibitor, a meglitinide, a thiazolidinedione, or an anti-diabetic peptide analogue, in the treatment of, for example, a disorder selected from: a GPR119-receptor-related disorder; a condition ameliorated by increasing secretion of an incretin; a condition ameliorated by increasing a blood incretin level; a condition characterized by low bone mass; a neurological disorder; a metabolic-related disorder; type 2 diabetes; obesity; and complications related thereto.

Herbicidal oxetane and thiaetane derivatives

-

, (2008/06/13)

Oxetane and thiaetane derivatives of the formula I in which, Q is oxygen, sulfur, -COO-, -Z-CH(R3)-COO-, or CO-Y4-CH(R10)-COO-;, W is and R1 is hydrogen or fluorine; R2 is halogen or cyano; R3 and R10 independently of one another are hydrogen or C1-C3alkyl; R4 is hydrogen, fluorine, chlorine, bromine, C1-C4alkyl or trifluoromethyl; R5 and R7 independently of one another are C1-C4alkyl; R6 and R8 independently of one another are hydrogen or C1-C4alkyl; R9 is hydrogen, C1-C6alkyl, C3-C7cycloalkyl, C1-C4alkoxy-C1-C4alkyl or C1-C7haloalkyl; X is oxygen or sulfur; Y1, Y2, Y3, Y4, Y5 and Y6 independently of one another are oxygen or sulfur; Z is oxygen or sulfur; n is 0; 1, 2, 3 or 4; and q is 1 or 2, have good selective herbicidal properties when used pre- or post-emergence.

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