3-((Bis(diisopropylamino)phosphino)oxy)propanenitrile

Base Information

• Chemical Name: 3-((Bis(diisopropylamino)phosphino)oxy)propanenitrile
• CAS No.: 102691-36-1
• Molecular Formula: C15H32N3OP
• Molecular Weight: 301.412
• Hs Code.: 29299000
• European Community (EC) Number: 600-337-9
• UNII: 8P2H5F3TEA
• DSSTox Substance ID: DTXSID8075176
• Nikkaji Number: J738.473D
• Wikidata: Q72458191
• Mol file: 102691-36-1.mol

Synonyms:2-cyanoethyl-N,N,N',N'-tetraisopropylphosphorodiamidite;CETIPD

Chemical Property of 3-((Bis(diisopropylamino)phosphino)oxy)propanenitrile

Chemical Property:

• Appearance/Colour: Clear to cloudy colourless liquid
• Refractive Index: n20/D 1.470(lit.)
• Boiling Point: 298.1 °C at 760 mmHg
• PKA: 6.78±0.70(Predicted)
• Flash Point: 177.9 °C
• PSA: 53.09000
• Density: 0.949 g/mL at 25 °C(lit.)
• LogP: 4.38118
• Storage Temp.: 2-8°C
• Sensitive.: moisture sensitive, store cold
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 301.22829965
• Heavy Atom Count: 20
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

2-CyanoethylN,N,N’,N’-Tetraisopropylphosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 5-36/37/38-42/43-36/38
• Safety Statements: 3-26-36-24/25-23-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(N(C(C)C)C(C)C)OCCC#N
• Uses: Reagent for synthesizing phosphitylated nucleotides.1 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite was used:in preparation of prosphoramidite reagent, required for synthesis of 12-mer oligodeoxynucleotideas phosphorylating agent in synthesis of 1,2-diacyl-sn-glycerophosphatidylserinein situ preparation of deoxyribonucleoside phosphoramiditesin preparation of 2′-deoxy-2′-fluoro-3′-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-5′-O-(4-methoxytrityl)-4′-thio-β-D-arabinouridine and 1-(3-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-2-deoxy-2-fluoro-5-O-(4,4′-dimethoxytrityl)-4-thio-β-D-arabinofuranosyl)-thymineas reagent for synthesizing phosphitylated nucleotides

Technology Process of 3-((Bis(diisopropylamino)phosphino)oxy)propanenitrile

There total 7 articles about 3-((Bis(diisopropylamino)phosphino)oxy)propanenitrile 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%

→ N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1)

Guidance literature:

Reference yield: 88.5%

2-cyanoethyl phosphorodichloridite (76101-30-9) + diisopropylamine (108-18-9) → N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1)

Guidance literature:

In tetrahydrofuran; at -10 - 20 ℃; for 73.5h;

Reference yield: 42.0%

diisopropylamine (108-18-9) + 3-Hydroxypropionitrile (109-78-4) → N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1)

Guidance literature:

diisopropylamine; With phosphorus trichloride; In acetonitrile; for 1h; Inert atmosphere;

3-Hydroxypropionitrile; In hexane; acetonitrile; for 1.5h; Inert atmosphere;

DOI:10.1007/s00706-010-0318-0

upstream raw materials:

5'-amino-5'-deoxythymidine

2-cyanoethyl phosphorodichloridite

diisopropylamine

3-Hydroxypropionitrile

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-N-dimethyl-formamidine-2'-deoxyguanosine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite

Benzoic acid 1-{2-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-1-octadecanoylamino-ethyl}-hexadecyl ester

2',3'-O-dibenzoyl-3-undecyluridine 5'-<(2-cyanoethyl) diisopropylamino phosphite>

2',3'-O-dibenzoyl-3-<11-<(4-monomethoxytrityl)thio>undecyl>uridine 5'-<(2-cyanoethyl) diisopropylamino phosphite>

Refernces

Versatile strategy for oligonucleotide derivatization. Introduction of lanthanide(III) chelates to oligonucleotides

10.1021/ol016093m

2'-Deoxy-5'-O-(4,4'-dimethoxytrityl)uridine (1) is a protected nucleoside, specifically a protected deoxyuridine. The 5'-hydroxyl group is protected with a 4,4'-dimethoxytrityl (DMT) group, which is commonly used in solid phase oligonucleotide synthesis to prevent unwanted reactions at the 5' position. It serves as a starting material for the synthesis of nucleoside phosphoramidite building blocks. The DMT group can be removed later in the synthesis to allow for further functionalization. 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphoramidite is a phosphoramidite reagent used in the phosphorylation step of nucleoside phosphoramidite synthesis. It is used to convert nucleoside derivatives (2a-d) into the desired phosphoramidites (3a-d) which are then used in machine-assisted DNA synthesis. Succinic anhydride, a cyclic anhydride used for alcohol esterification, was used to convert the nucleoside derivative 2a to the corresponding succinate ester (17), which was then immobilized on a long-chain alkylamine CPG polymer support.