tert-Butyl diethylphosphonoacetate Chemical Properties

Boiling point:

100-103 °C/1.5 mmHg (lit.)

Density 

1.074 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.431(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Liquid

Specific Gravity

1.074

color 

Clear colorless

Water Solubility 

Not miscible or difficult to mix in water.

BRN 

2050126

InChI

InChI=1S/C10H21O5P/c1-6-13-16(12,14-7-2)8-9(11)15-10(3,4)5/h6-8H2,1-5H3

InChIKey

NFEGNISFSSLEGU-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)CP(OCC)(OCC)=O

CAS DataBase Reference

27784-76-5(CAS DataBase Reference)

Safety Information

Risk Statements 

36/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

tert-Butyl diethylphosphonoacetate Usage And Synthesis

Chemical Properties

Clear colorless liquid

Uses

tert-Butyl diethylphosphonoacetate is used as a reactant for preparation of hydroxymethylated dihydroxyvitamin D3 analogs via Wittig-Horner approach, as potential antitumor agents, synthesis of phosphopeptide mimetic prodrugs targeted to Src homology 2 (SH2) domain of signal transducer and activator of transcription 3 (Stat 3) and bicyclic triaminophosphine-promoted stereoselective synthesis of a,?-unsaturated esters, fluorides, and nitriles from aldehydes and ketones using Wadsworth-Emmons phosphonates

Application

tert-Butyl diethylphosphonoacetate serves as an important intermediate in the synthesis of phosphonate derivatives, which are widely used in agrochemicals, pharmaceuticals, and materials science.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Triethyl phosphite (485 g) is warmed up to 90°C under N2 atmosphere in a three-necked round-bottomed flask, and /-butyl bromoacetate (541 g) is added dropwise into the system within 2 h. Then, the mixture is stirred at 90°C for around 4 hours and cooled to room temperature. The obtained mixture is distilled under vacuo to remove compounds with low boiling points, and the residue is collected as a colorless liquid tert-butyl diethylphosphonoacetate in 97 percent yield (680 g).

References

[1] Chemistry - A European Journal, 1999, vol. 5, # 4, p. 1218 - 1225
[2] Tetrahedron, 2009, vol. 65, # 49, p. 10192 - 10213
[3] Patent: WO2015/101554, 2015, A1. Location in patent: Page/Page column 17
[4] Patent: US2015/183764, 2015, A1. Location in patent: Paragraph 0039
[5] Journal of the American Chemical Society, 2007, vol. 129, # 47, p. 14818 - 14825

tert-Butyl diethylphosphonoacetate(27784-76-5)Related Product Information

• tert-Butyl carbazate
• tert-Butyl bromoacetate
• TERT-BUTYL ISOCYANIDE
• Isobutyl acetate
• 2-Butoxyethanol
• Cyhalofop-butyl
• Diethyl carbonate
• Diethyl malonate
• Diethylene glycol monobutyl ether
• tert-Butanol
• Buprofezin
• tert-Butylisocyanate
• tert-Butyl acetate
• tert-Butyl chloroacetate
• Diethyl phthalate
• Butyl acetate
• Mefenpyr-diethyl
• Butyl acrylate