CAS RN: 229625-50-7 | Product Number: D5835
Di-tert-butyl Chloromethyl Phosphate
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|Purity / Analysis Method||>97.0%(T)|
|Molecular Formula / Molecular Weight||C__9H__2__0ClO__4P = 258.68|
|Physical State (20 deg.C)||Liquid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Moisture Sensitive,Heat Sensitive|
|Reaxys Registry Number||8406856|
|Appearance||Colorless to Light yellow clear liquid|
|Purity(Precipitation Titration)||min. 97.0 %|
|Flash point||139 °C|
|Hazard Statements||H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
H341 : Suspected of causing genetic defects.
|Precautionary Statements||P501 : Dispose of contents/ container to an approved waste disposal plant.
P201 : Obtain special instructions before use.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P308 + P313 : IF exposed or concerned: Get medical advice/ attention.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
To a solution of 4-hydroxybenzaldehyde (0.25 g, 2.0 mmol) in DMF (5 mL) was added sodium hydride (60%, dispersion in paraffin liquid) (0.12 g, 3.1 mmol) and the mixture was stirred at ambient temperature for 0.5 hour. The suspension was added di-tert-butyl chloromethyl phosphate (0.58 g, 2.3 mmol) and potassium iodide (1.0 g, 6.1 mmol), and stirred for 25 hours. The suspension was poured into water (20 mL) and cooled with an ice bath. Then saturated ammonium chloride aqueous solution (5 mL) was added. The mixture was extracted with diethyl ether and the organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The given residue was purified by column chromatography (ethyl acetate:hexane = 1:4 - 2:3 on silica gel) to give compound 1 (0.27 g, 38%) as a colorless oil.
The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.33).
1H NMR (400 MHz, CDCl3); δ 9.92 (1H, s), 7.87 (2H, d, J = 8.4 Hz), 7.20 (2H, d, J = 8.4 Hz), 5.70 (2H, d, J = 12.0 Hz), 1.46 (18H, s).
- Synthesis and Characterization of a Phosphate Prodrug of Isoliquiritigenin
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