Description

tert-Butyl Dimethylphosphonoacetate (CAS No. 62327-21-3) is a high-purity organophosphorus compound with the molecular formula C₈H₁₇O₅P. Also known as tert-butyl 2-dimethoxyphosphorylacetate, this versatile reagent is widely used in organic synthesis, particularly in Horner-Wadsworth-Emmons (HWE) reactions for the preparation of α,β-unsaturated esters. Its stable tert-butyl ester group and reactive phosphonate moiety make it an excellent building block for constructing complex molecular architectures. This product is rigorously tested for purity and consistency, ensuring optimal performance in sensitive applications. Packaged under inert gas to maintain stability, it is ideal for researchers in pharmaceuticals, agrochemicals, and materials science.

Properties

• CAS Number: 62327-21-3
• Complexity: 235
• IUPAC Name: tert-butyl 2-dimethoxyphosphorylacetate
• InChI: InChI=1S/C8H17O5P/c1-8(2,3)13-7(9)6-14(10,11-4)12-5/h6H2,1-5H3
• InChI Key: SAZYDWOWLRDDRQ-UHFFFAOYSA-N
• Exact Mass: 224.08136064
• Molecular Formula: C8H17O5P
• Molecular Weight: 224.19
• SMILES: CC(C)(C)OC(=O)CP(=O)(OC)OC
• Topological: 61.8
• Monoisotopic Mass: 224.08136064
• Synonyms: tert-butyl dimethylphosphonoacetate, 629-650-9, 62327-21-3, tert-Butyl 2-(dimethoxyphosphoryl)acetate, tert-Butyl O,O-dimethylphosphonoacetate, tert-Butyl P,P-dimethylphosphonoacetate, Tert-butyl 2-dimethoxyphosphorylacetate, MFCD00042939, dimethylphosphonoacetic acid tert-butyl ester, tert-Butyl (dimethoxyphosphinyl)acetate, Acetic acid, (dimethoxyphosphinyl)-, 1,1-dimethylethyl ester, SCHEMBL421908, t-Butyl dimethylphosphonoacetate, Dimethyl (Boc-methyl)phosphonate, SCHEMBL10398858, tert-butyldimethylphosphonoacetate, DTXSID00404307, SAZYDWOWLRDDRQ-UHFFFAOYSA-N, BCP24437, tert-butyl dimethoxyphosphorylacetate, tert-butyl(dimethoxyphosphoryl)acetate, AKOS015900253, CS-W019393, Tert-butyl (dimethoxyphosphoryl)acetate, tert-butyl P,P-Dimethyl phosphonoacetate, AS-64884, dimethyl t-butoxycarbonyl-methylphosphonate, SY045276, DB-092180, B5094, Dimethyl (tert-Butoxycarbonylmethyl)phosphonate, O12106, Dimethyl [(tert-Butoxycarbonyl)methyl]phosphonate, tert-Butyl P,P-dimethylphosphonoacetate, >=97.0% (GC)

Application

tert-Butyl Dimethylphosphonoacetate is primarily employed in the Horner-Wadsworth-Emmons reaction to generate α,β-unsaturated esters, key intermediates in fine chemical synthesis. It is also used in the preparation of phosphonate-based ligands for catalysis and as a precursor for modified peptides and bioactive molecules. Its stability and reactivity make it valuable in medicinal chemistry for drug discovery and development.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (66.7%)

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