tert-Butyl 2-(dimethoxyphosphoryl)acetate (CAS 62327-21-3) is a functionalized phosphonate ester that combines a tert‑butyl ester protecting group with a dimethyl phosphonate moiety. The molecular formula is C₈H₁₇O₅P, and the molecular weight is 224.19 g/mol. The molecule features a central acetate backbone bearing a dimethylphosphoryl group (−P(=O)(OCH₃)₂) at the α‑position and a tert‑butyl ester at the carboxyl terminus.
tert-Butyl 2-(dimethoxyphosphoryl)acetate is a versatile Horner‑Wadsworth‑Emmons reagent widely employed in organic synthesis for the stereoselective construction of α,β‑unsaturated esters. The key structural feature of tert-Butyl 2-(dimethoxyphosphoryl)acetate is the dimethyl phosphonate group, which after deprotonation reacts with aldehydes and ketones to form α,β‑unsaturated esters with predictable (E)‑selectivity. tert-Butyl 2-(dimethoxyphosphoryl)acetate offers distinct advantages over the corresponding ethyl or methyl esters, as the tert‑butyl protecting group can be cleaved under mild acidic conditions to liberate the free carboxylic acid without affecting the phosphonate functionality. Additionally, tert-Butyl 2-(dimethoxyphosphoryl)acetate has been utilized as a reactant in the preparation of phosphonate‑terminated dendrimers with anti‑HIV‑1 activity, in the synthesis of myxopyronin B analogs with antibacterial activity, and in allylation/ring‑closing metathesis sequences. The compound is also known as tert‑butyl dimethylphosphonoacetate and is classified as a C‑C bond formation reagent.
Product Parameters
Parameter
Specification
Product Name
tert-Butyl 2-(dimethoxyphosphoryl)acetate
CAS Number
62327-21-3
Molecular Formula
C₈H₁₇O₅P
Molecular Weight
224.19 g/mol
Boiling Point
86–87 °C/0.02 mmHg
Density
1.131 g/mL at 20 °C
Flash Point
110 °C
Physical Form
Clear liquid
Appearance
Colorless to almost colorless
Storage Condition
Under inert gas (nitrogen or argon) at 2–8 °C
Application
tert-Butyl 2-(dimethoxyphosphoryl)acetate can be used as an organic synthesis intermediate or pharmaceutical intermediate compound, which is used to synthesize a variety of compounds with specific functions. For example, in drug synthesis, it can serve as a building block for drug molecules and participate in the synthesis of drugs with specific pharmacological activities. In addition, it can also be used in the fields of pesticides, dyes, etc. Moreover, tert-Butyl 2-(dimethoxyphosphoryl)acetate can also act as a catalyst or additive for certain reactions, which can alter the reaction pathway and improve the reaction efficiency.
Hazard
tert-Butyl 2-(dimethoxyphosphoryl)acetate is somewhat toxic to the human body. Contact with or ingestion of this compound carries the risk of irritating the eyes, respiratory system and skin. Therefore, special attention should be paid to safety protection measures during use to avoid direct contact with the skin, eyes, etc. In addition, it may also have a certain impact on the environment. If discharged into the environment without proper treatment, it may cause pollution to water bodies, soil, etc. Therefore, during use and storage, it is necessary to strictly abide by the relevant environmental protection regulations to ensure that no adverse impact is caused to the environment.
Product Quality Assurance
Cosperpharm maintains a comprehensive quality management system for tert-Butyl 2-(dimethoxyphosphoryl)acetate. Each batch undergoes GC purity verification (≥97%) and physical property testing including density and refractive index confirmation. Full batch traceability from synthesis through final packaging is maintained. Every shipment includes a Certificate of Analysis and Safety Data Sheet.
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