Di-tert-butyl N,N-diethylphosphoramidite

Base Information

• Chemical Name: Di-tert-butyl N,N-diethylphosphoramidite
• CAS No.: 117924-33-1
• Molecular Formula: C12H28NO2P
• Molecular Weight: 249.334
• Hs Code.: 29319090
• European Community (EC) Number: 627-954-6
• DSSTox Substance ID: DTXSID10401241
• Nikkaji Number: J1.433.907H
• Wikidata: Q72470008
• Mol file: 117924-33-1.mol

Synonyms:di-tert-butyl diethylphosphoramidite

Chemical Property of Di-tert-butyl N,N-diethylphosphoramidite

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Vapor Pressure: 0.104mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Boiling Point: 221.963 °C at 760 mmHg
• PKA: 4.41±0.70(Predicted)
• Flash Point: 78.333 °C
• PSA: 35.29000
• Density: 0.896 g/mL at 25 °C(lit.)
• LogP: 4.18530
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: Hydrolyzes in water. Soluble in chloroform and methanol.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 249.18576613
• Heavy Atom Count: 16
• Complexity: 176

Purity/Quality:

98%,99%, ^*data from raw suppliers

Di-t-butylN,N-Diethylphosphoramidite(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)P(OC(C)(C)C)OC(C)(C)C
• Uses: A useful reagent for the efficient phosphorylative conversion of alcohols into their corresponding dibenzylphosphorotriesters. It is applied as a phosphitylating agent in water-soluble phosphate prodrugs of 1-propargyl-8-styrylxanthine derivatives, a2a-selective adenosine receptor antagonists. Di-tert-butyl N,N-diethylphosphoramidite is a useful reagent for the efficient phosphorylative conversion of alcohols into their corresponding dibenzylphosphorotriesters.

Technology Process of Di-tert-butyl N,N-diethylphosphoramidite

There total 6 articles about Di-tert-butyl N,N-diethylphosphoramidite 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: 63.0%

diethylphosphoramidous dichloride (1069-08-5) + tert-butyl alcohol (75-65-0) → di-tert-butyl N,N-diethylphosphoramidite (117924-33-1)

Guidance literature:

With triethylamine; In diethyl ether; at 20 ℃; for 2h;

Reference yield: 55.0%

→ di-tert-butyl N,N-diethylphosphoramidite (117924-33-1)

Guidance literature:

Reference yield:

tri(tert-butyl)phosphite (15205-62-6) → di-tert-butyl N,N-diethylphosphoramidite (117924-33-1)

Guidance literature:

Multi-step reaction with 2 steps

1: PCl₃ / Heating

2: diethyl ether / 20 °C

With phosphorus trichloride; In diethyl ether;

DOI:10.1080/10426500008045253

upstream raw materials:

tetraethyldiamidophosphorous acid tert-butyl ester

tert-butyl diethylphosphoramidochloridite

diethylphosphoramidous dichloride

tert-butyl alcohol

Refernces

• 1、 -. "Synthesis of combretastatin A-4 prodrugs and trans-isomers thereof". Page/Page column 9. . Retrieved 2008/06/13.
• 2、 Gazizov, T. Kh.,Sal'keeva, L. K.. "REACTION OF tert-BUTYL(TETRAETHYLDIAMIDO)PHOSPHITE". . p. 299 - 302. Retrieved 2007/10/02.