Pivaloyloxymethyl chloride
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Pivaloyloxymethyl chloride is an organic intermediate used to introduce the pivaloyloxymethyl (POM) protecting group, and it can be prepared from trimethylacetic acid and chloromethyl chlorosulfonate as raw materials. Pivaloyloxymethyl chloride is an alkylating reagent for the synthesis of phosphonic acid prodrugs; the introduction of the hydrophobic POM group enhances the lipid solubility and membrane permeability of molecules. Pivaloyloxymethyl chloride can be used in the synthesis of tetrakis (pivaloyloxymethyl) methylenebisphosphonate, which is a precursor of the pivaloyloxymethyl clodronate prodrug. Pivaloyloxymethyl chloridecan support the synthesis of aryl/pivaloyloxymethyl mixed phosphonate prodrugs of butyrophilin 3A1 ligands.
For research use only. We do not sell to patients.
- Purity: 99.98%
- CAS No.: 18997-19-8
- Formula: C6H11ClO2
- Molecular Weight:150.60
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Storage:Pure form -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Pivaloyloxymethyl chloride (POMCl) reacts with esters 6a and 6b under reflux in acetonitrile for 24 h to produce a racemic mixture of diesters[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 18997-19-8
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Appearance Liquid (Density: 1.056±0.06 g/cm3)
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Molecular Weight 150.60
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Formula C6H11ClO2
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Color Colorless to light yellow
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SMILES
CC(C)(C)C(OCCl)=O
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Pure form -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvent & Solubility
DMSO : 200 mg/mL (1328.02 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (270 KB)
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SDS (605 KB)
- English - EN (605 KB)
- Français - FR (605 KB)
- Deutsch - DE (605 KB)
- Norwegian - NO (605 KB)
- Español - ES (605 KB)
- Swedish - SV (605 KB)
- Italian - IT (605 KB)
- Korean - KR (605 KB)
- Portuguese - PT (605 KB)
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Handling Instructions (2659 KB)
References
[1]. Foust BJ, Poe MM, Lentini NA, et al.. Mixed Aryl Phosphonate Prodrugs of a Butyrophilin Ligand. ACS medicinal chemistry letters. 2017 Sep 14;8(9):914-918. [Content Brief]
[2]. Niemi R, Vepsäläinen J, Taipale H and, et al.. Bisphosphonate prodrugs: synthesis and in vitro evaluation of novel acyloxyalkyl esters of clodronic acid. Journal of medicinal chemistry. 1999 Dec 02;42(24):5053-8. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
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| DMSO | 1 mM | 6.6401 mL | 33.2005 mL | 66.4011 mL | 166.0026 mL |
| 5 mM | 1.3280 mL | 6.6401 mL | 13.2802 mL | 33.2005 mL | |
| 10 mM | 0.6640 mL | 3.3201 mL | 6.6401 mL | 16.6003 mL | |
| 15 mM | 0.4427 mL | 2.2134 mL | 4.4267 mL | 11.0668 mL | |
| 20 mM | 0.3320 mL | 1.6600 mL | 3.3201 mL | 8.3001 mL | |
| 25 mM | 0.2656 mL | 1.3280 mL | 2.6560 mL | 6.6401 mL | |
| 30 mM | 0.2213 mL | 1.1067 mL | 2.2134 mL | 5.5334 mL | |
| 40 mM | 0.1660 mL | 0.8300 mL | 1.6600 mL | 4.1501 mL | |
| 50 mM | 0.1328 mL | 0.6640 mL | 1.3280 mL | 3.3201 mL | |
| 60 mM | 0.1107 mL | 0.5533 mL | 1.1067 mL | 2.7667 mL | |
| 80 mM | 0.0830 mL | 0.4150 mL | 0.8300 mL | 2.0750 mL | |
| 100 mM | 0.0664 mL | 0.3320 mL | 0.6640 mL | 1.6600 mL |
Pivaloyloxymethyl chloride Related Classifications
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