Di-tert-butyl N,N-diisopropylphosphoramidite

Base Information

• Chemical Name: Di-tert-butyl N,N-diisopropylphosphoramidite
• CAS No.: 137348-86-8
• Molecular Formula: C14H32NO2P
• Molecular Weight: 277.387
• Hs Code.: 29349990
• European Community (EC) Number: 627-964-0
• DSSTox Substance ID: DTXSID00357384
• Nikkaji Number: J986.171H
• Wikidata: Q72470011
• Mol file: 137348-86-8.mol

Synonyms:137348-86-8;di-tert-butyl diisopropylphosphoramidite;Di-tert-butyl N,N-diisopropylphosphoramidite;Di-t-butyl N,N-diisopropylphosphoramidite;N-[bis[(2-methylpropan-2-yl)oxy]phosphanyl]-N-propan-2-ylpropan-2-amine;MFCD00153506;N-Di-tert-butoxyphosphanyl-N-isopropyl-propan-2-amine;Phosphoramidous acid, bis(1-methylethyl)-, bis(1,1-dimethylethyl) ester;C14H32NO2P;Di-tert-butoxy(diisopropylamino)phosphine;di-tert-butyl-N,N-diisopropylphosphoramidite;SCHEMBL5930;DTXSID00357384;YGFLCNPXEPDANQ-UHFFFAOYSA-N;BBL102757;GEO-03953;STL556563;AKOS015915662;CS-W010070;di-tertbutyl diisopropyl-phosphoramidite;AS-66083;di-t-butyl-N,N-diisopropylphosphoramidite;SY052611;di-tert-butyl dipropan-2-ylphosphoramidoite;D4211;FT-0625354;A21062;H11363;Di-tert-butyl N,N-dipropan-2-ylphosphoramidoite;[bis(tert-butoxy)phosphanyl]bis(propan-2-yl)amine;Di-tert-butyl N,N-diisopropylphosphoramidite, 95%;Diisopropyl-phosphoramidous acid di-tert-butyl ester;J-007006;Di-tert-butyl N,N-diisopropylphosphoramidite, technical, ~90% (GC/31P-NMR)

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

Chemical Property:

• Appearance/Colour: Clear Colourless Liquid
• Vapor Pressure: 0.0195mmHg at 25°C
• Melting Point: 85-90 °C 0.2 mm Hg(lit.)
• Refractive Index: n20/D 1.444(lit.)
• Boiling Point: 252.2 °C at 760 mmHg
• PKA: 4.90±0.70(Predicted)
• Flash Point: 106.4 °C
• PSA: 35.29000
• Density: 0.879 g/cm³
• LogP: 4.96230
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 277.21706626
• Heavy Atom Count: 18
• Complexity: 217

Purity/Quality:

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

Di-t-butylN,N-Diisopropylphosphoramidite ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OC(C)(C)C)OC(C)(C)C
• Uses: Di-tert-butyl N,N-diisopropylphosphoramidite is a general reagent to introduce tert-butyl-protected phosphate groups. It is commonly used in phosphorylation of biomolecules. It can also be used in the synthesis of phosphoramidate-linked glycoconjugates. A phosphinane derivative with immunomodulating activity.

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

There total 4 articles about Di-tert-butyl N,N-diisopropylphosphoramidite 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%

N,N-diisopropylphosphoramide dichloride (921-26-6) + tert-butyl alcohol (75-65-0) → di-tert-butyl diisopropylphosphoramide (137348-86-8)

Guidance literature:

With triethylamine; In diethyl ether; at 0 - 20 ℃; for 3.25h;

Reference yield: 58.0%

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane (137348-88-0) + tert-butyl alcohol (75-65-0) → di-tert-butyl diisopropylphosphoramide (137348-86-8)

Guidance literature:

With N,N-diisopropylamine tetrazolide; for 3h;

DOI:10.1002/hlca.19910740621

Reference yield:

diisopropylamine (108-18-9) → di-tert-butyl diisopropylphosphoramide (137348-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: PCl₃ / diethyl ether / 3 h / 20 °C

2: Et₃N / diethyl ether / 20 °C

With triethylamine; phosphorus trichloride; In diethyl ether;

DOI:10.1080/10426500008045253

upstream raw materials:

[tert-butyloxy]bis(N,N-diisopropylamino)phosphane

tert-butyl alcohol

N,N-diisopropylphosphoramide dichloride

diisopropylamine

Downstream raw materials:

4-(4-((di(tert-butoxy)phosphoryl)oxy)benzoyl)phenyl hexanoate

4-(4-((di(tert-butoxy)phosphoryl)oxy)benzoyl)phenyl octanoate

4-(4-((di(tert-butoxy)phosphoryl)oxy)benzoyl)phenyl decanoate

4-(4-((di(tert-butoxy)phosphoryl)oxy)benzoyl)phenyl laurate

Refernces

• 1、 Chen, Shui-Bing,Li, Yan-Mei,Luo, Shi-Zhong,Zhao, Gang,Tan, Bo,Zhao, Yu-Fen. "The study of phosphoramidite as O-phosphitylation agent and its reactivity". . p. 277 - 291. Retrieved 2007/10/03.
• 2、 Kitas, Eric A.,Knorr, Reinhard,Trzeciak, Arnold,Bannwarth, Willi. "Alternative Strategies for the Fmoc Solid-Phase Synthesis of O4-Phospho-L-tyrosine-Containing Peptides". . p. 1314 - 1328. Retrieved 2007/10/02.