Diethyl N-(tert-Butoxycarbonyl)phosphoramidate

Base Information

• Chemical Name: Diethyl N-(tert-Butoxycarbonyl)phosphoramidate
• CAS No.: 85232-02-6
• Molecular Formula: C9H20 N O5 P
• Molecular Weight: 253.235
• Hs Code.: 2931900090
• European Community (EC) Number: 678-028-3
• DSSTox Substance ID: DTXSID80431616
• Nikkaji Number: J1.629.959F
• Wikidata: Q82245546
• Mol file: 85232-02-6.mol

Synonyms:85232-02-6;Diethyl N-(tert-Butoxycarbonyl)phosphoramidate;N-(tert-Butoxycarbonyl)phosphoramidic Acid Diethyl Ester;Tert-butyl N-diethoxyphosphorylcarbamate;N-Boc-phosphoramidic Acid Diethyl Ester;Diethyl N-Boc-phosphoramidate;tert-Butyl diethoxyphosphorylcarbamate;CS-WAA0080;SCHEMBL14819108;DTXSID80431616;MFCD00015667;AKOS015838165;tert-Butyl (diethoxyphosphoryl)carbamate;AS-69055;tert-butyl N-(diethoxyphosphoryl)carbamate;diethyl-N-(t-butoxycarbonyl)phosphoramidate;B1734;CS-0035353;FT-0702094;(Diethoxyphosphinyl)carbamic acid tert-butyl ester

Chemical Property of Diethyl N-(tert-Butoxycarbonyl)phosphoramidate

Chemical Property:

• Melting Point: 70 °C
• Refractive Index: 1.438
• PKA: 8.30±0.46(Predicted)
• PSA: 83.67000
• Density: 1.119g/cm³
• LogP: 3.08310
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 253.10790974
• Heavy Atom Count: 16
• Complexity: 264

Purity/Quality:

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

Diethyl N-(tert-Butoxycarbonyl)phosphoramidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diethyl N-(tert-Butoxycarbonyl)phosphoramidate

There total 4 articles about Diethyl N-(tert-Butoxycarbonyl)phosphoramidate 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%

diethoxyphosphoryl isocyanate (20039-33-2) + tert-butyl alcohol (75-65-0) → diethyl N-tert-butyloxycarbonylphosphoramidate (85232-02-6)

Guidance literature:

In tetrachloromethane; for 1h; Ambient temperature;

DOI:10.1055/s-1982-29997

Reference yield:

diethyl [2-tert-butoxycarbonylamino-1-(diethoxyphosphoryl)-2-phenylethyl]phosphonate (1011258-60-8) → diethyl (E)-(2-phenylethenyl)phosphonate (20408-33-7) + diethyl N-tert-butyloxycarbonylphosphoramidate (85232-02-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 12h; Title compound not separated from byproducts.;

DOI:10.1016/j.tet.2007.11.072

Reference yield:

2-bromo-pentanoic acid ethyl ester (615-83-8) + Diethyl N-sodio-N-(tert-butoxycarbonyl)phosphoramidate (85232-03-7) → diethyl N-tert-butyloxycarbonylphosphoramidate (85232-02-6) + C16H32NO7P (85232-01-5)

Guidance literature:

tetrabutylammomium bromide; In acetonitrile; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1055/s-1982-29997

upstream raw materials:

2-bromo-pentanoic acid ethyl ester

Diethyl N-sodio-N-(tert-butoxycarbonyl)phosphoramidate

diethoxyphosphoryl isocyanate

tert-butyl alcohol

Downstream raw materials:

C₁₄H₃₀NO₆P

C₁₈H₂₈NO₅P

diethyl N-(tert-butoxycarbonyl)aminomethylphosphonate

C₁₇H₂₆NO₆P

Refernces

• 1、 Zwierzak, Andrzej,Pilichowska, Slawomira. "Diethyl N-(t-Butoxycarbonyl)-phosphoramidate: A New, Useful Substitute of Phthalimide in Gabriel-Type Syntheses of Primary Amines". . p. 922 - 924. Retrieved 2007/10/02.