tert-Butyl diethylphosphonoacetate

Base Information

• Chemical Name: tert-Butyl diethylphosphonoacetate
• CAS No.: 27784-76-5
• Molecular Formula: C10H21O5P
• Molecular Weight: 252.247
• Hs Code.: 29319090
• European Community (EC) Number: 678-186-3,695-158-6
• DSSTox Substance ID: DTXSID40378639
• Nikkaji Number: J449.954I
• Wikidata: Q72502923
• Mol file: 27784-76-5.mol

Synonyms:27784-76-5;tert-Butyl diethylphosphonoacetate;tert-butyl 2-(diethoxyphosphoryl)acetate;tert-butyl 2-diethoxyphosphorylacetate;(Diethoxy-phosphoryl)-acetic acid tert-butyl ester;MFCD00075414;tert-butyl (diethoxyphosphoryl)acetate;tert-Butyl 2-(diethylphosphono)acetate;tert-butyl 2-(diethyl phosphono)acetate;Acetic acid, (diethoxyphosphinyl)-, 1,1-dimethylethyl ester;Diethylphosphonoacetic Acid tert-Butyl Ester;Diethyl (Boc-methyl)phosphonate;t-butyl diethylphosphonoacetate;Tert-butyl diehylphosphonoacetate;t-butyldiethylphosphonoacetate;SCHEMBL234057;DTXSID40378639;NFEGNISFSSLEGU-UHFFFAOYSA-N;t-butyl (diethoxyphosphoryl)acetate;tert-butyl diethoxyphosphorylacetate;AMY11206;BCP24438;tert-butyl(diethoxyphosphoryl)acetate;AKOS015915427;AB02873;CS-W002322;DS-2306;T-BUTYL DIETHYL PHOSPHONOACETATE;tert-Butyl (diethoxyphosphinyl)acetate,;tert-butyl2-(diethoxyphosphoryl)acetate;tert-Butyl diethylphosphonoacetate, 95%;SY005984;B2814;FT-0647778;Diethyl (tert-Butoxycarbonylmethyl)phosphonate;EN300-140859;(Diethoxyphosphinyl)acetic acid tert-butyl ester;A819192;J-016883;J-524780;DIETHYL (PHOSPHONOACETIC ACID TERT-BUTYL ESTER);(DIETHOXYPHOSPHINYL)ACETIC ACID 1,1-DIMETHYLETHYL ESTER;ACETIC ACID, 2-(DIETHOXYPHOSPHINYL)-, 1,1-DIMETHYLETHYL ESTER

Chemical Property of tert-Butyl diethylphosphonoacetate

Chemical Property:

• Appearance/Colour: Colorless transparent liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 100-103 °C1.5 mm Hg(lit.)
• Refractive Index: n20/D 1.431(lit.)
• Boiling Point: 274.7 °C at 760 mmHg
• Flash Point: 155.1 °C
• PSA: 71.64000
• Density: 1.077 g/cmH³
• LogP: 2.59420
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 252.11266076
• Heavy Atom Count: 16
• Complexity: 259

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl2-(diethylphosphono)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/38:Irritating to eyes and skin.
• Hazard Codes: R36/38:Irritating to eyes and skin.
• Statements: 36/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOP(=O)(CC(=O)OC(C)(C)C)OCC
• 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

Technology Process of tert-Butyl diethylphosphonoacetate

There total 7 articles about tert-Butyl diethylphosphonoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

bromoacetic acid tert-butyl ester (5292-43-3) + triethyl phosphite (122-52-1) → tert-butyl diethylphosphonoacetate (27784-76-5)

Guidance literature:

at 65 ℃; for 2h;

DOI:10.1002/(sici)1521-3765(19990401)5:4<1218::aid-chem1218>3.3.co;2-o

Reference yield: 100.0%

diethylphosphonoacetic acid (3095-95-2) + tert-butyl alcohol (75-65-0) → tert-butyl diethylphosphonoacetate (27784-76-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 0.25h;

DOI:10.1021/ol0166855

Reference yield: 70.0%

tert-Butyl chloroacetate (107-59-5) + phosphonic acid diethyl ester (762-04-9) → tert-butyl diethylphosphonoacetate (27784-76-5)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; at 0 - 5 ℃; for 0.833333h;

DOI:10.1055/s-1985-31418

upstream raw materials:

acetic acid tert-butyl ester

diethyl chlorophosphate

tert-Butyl chloroacetate

phosphonic acid diethyl ester

Downstream raw materials:

5-phenyl-2(E)-pentenoic acid tert-butyl ester

3-[2-(2-t-butoxycarbonylmethyl-1-cycloheptenyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

trans-3,5-dichlorocinnamic acid tert-butyl ester

tert-butyl (E)-3-(3-fluoro-4-methylphenyl)acrylate

Refernces

• 1、 Righi, Giuliana,Bovicelli, Paolo,Tirotta, Ilaria,Sappino, Carla,Mandic’, Emanuela. "Double Stereodifferentiation in the Asymmetric Dihydroxylation of Optically Active Olefins". . p. 387 - 393. Retrieved 2016.
• 2、 Zimmermann, Birte M.,Kobosil, Sarah C. K.,Teichert, Johannes F.. "Catalytic hydrogenation of α,β-unsaturated carboxylic acid derivatives using copper(i)/N-heterocyclic carbene complexes". supporting information. p. 2293 - 2296. Retrieved 2019/02/27.
• 3、 Yamamoto, Daisuke,Ansai, Hiromasa,Hoshino, Junichi,Makino, Kazuishi. "Manganese-catalyzed oxophosphorylation reaction of carbon–carbon double bonds using molecular oxygen in air". . p. 873 - 879. Retrieved 2018/09/10.