| Identification | More | [Name]
tert-Butyl diethylphosphonoacetate | [CAS]
27784-76-5 | [Synonyms]
(DIETHOXYPHOSPHORYL)ACETIC ACID TERT-BUTYL ESTER
DIETHYL(2-TERT-BUTOXYCARBONYLMETHYL)PHOSPHONATE
DIETHYL (BOC-METHYL)PHOSPHONATE
DIETHYLPHOSPHONOACETIC ACID TERT-BUTYL ESTER
DIETHYL (TERT-BUTOXYCARBONYLMETHYL)PHOSPHONATE
T-BUTYL DIETHYL PHOSPHONOACETATE
TERT-BUTYL DIETHYLPHOSPHONOACETATE
Tert-buty diethylphosphonoacetate
tert-Butyl diethylphosphonoacetate, 98 %
Tert-Butyl p,p-diethylphosphonoacetate
ACETIC ACID, 2-(DIETHOXYPHOSPHINYL)-, 1,1-DIMETHYLETHYL ESTER | [EINECS(EC#)]
-0 | [Molecular Formula]
C10H21O5P | [MDL Number]
MFCD00075414 | [Molecular Weight]
252.24 | [MOL File]
27784-76-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless liquid | [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.)
| [Fp ]
>230 °F
| [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Liquid | [color ]
Clear colorless | [Specific Gravity]
1.074 | [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 Data | Back Directory | [Risk Statements ]
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29319090 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [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 |
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