BIS(2-CYANOETHYL)-N,N-DIISOPROPYL PHOSPHORAMIDITE

Base Information

• Chemical Name: BIS(2-CYANOETHYL)-N,N-DIISOPROPYL PHOSPHORAMIDITE
• CAS No.: 102690-88-0
• Molecular Formula: C12H22N3O2P
• Molecular Weight: 271.299
• Hs Code.: 2931900090
• European Community (EC) Number: 802-449-5
• DSSTox Substance ID: DTXSID80394434
• Nikkaji Number: J1.140.744G
• Wikidata: Q72444768
• Mol file: 102690-88-0.mol

Synonyms:Phosphoramidousacid, bis(1-methylethyl)-, bis(2-cyanoethyl) ester (9CI);Bis(2-cyanoethoxy)(diisopropylamino)phosphine;Bis(2-cyanoethoxy)-N, N-diisopropylaminophosphine;

Chemical Property of BIS(2-CYANOETHYL)-N,N-DIISOPROPYL PHOSPHORAMIDITE

Chemical Property:

• Vapor Pressure: 0.000121mmHg at 25°C
• Refractive Index: n20/D1.465
• Boiling Point: 335.3 °C at 760 mmHg
• PKA: 3.11±0.70(Predicted)
• Flash Point: 156.6 °C
• PSA: 82.87000
• Density: 1.039 g/mL at 25 °C
• LogP: 3.19266
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 271.14496395
• Heavy Atom Count: 18
• Complexity: 286

Purity/Quality:

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

Bis(2-cyanoethyl)-N,N-diisopropylPhosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 23-24-25-36-38
• Safety Statements: 26-36-37-39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCCC#N)OCCC#N
• Uses: Bis(2-cyanoethyl)-N,N-diisopropyl Phosphoramidite is a useful phosphorylating reagent.

Technology Process of BIS(2-CYANOETHYL)-N,N-DIISOPROPYL PHOSPHORAMIDITE

There total 10 articles about BIS(2-CYANOETHYL)-N,N-DIISOPROPYL PHOSPHORAMIDITE 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: 81.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 3-Hydroxypropionitrile (109-78-4) → bis(2-cyanoethyl) diisopropylamidophosphite (102690-88-0)

Guidance literature:

With N,N-diisopropylamine tetrazolide; In dichloromethane; for 2h;

DOI:10.1002/hlca.19870700122

Reference yield: 74.0%

N,N-diisopropylphosphoramidite + 3-Hydroxypropionitrile (109-78-4) → bis(2-cyanoethyl) diisopropylamidophosphite (102690-88-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In benzene; at 0 - 20 ℃; for 1h; Inert atmosphere; Cooling with ice;

DOI:10.1016/j.bmcl.2012.03.008

Reference yield: 65.0%

N,N-diisopropylphosphoramide dichloride (921-26-6) + 3-Hydroxypropionitrile (109-78-4) → bis(2-cyanoethyl) diisopropylamidophosphite (102690-88-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -78 - 20 ℃; for 3h;

DOI:10.1021/ja512528p

upstream raw materials:

N,N-diisopropylphosphoramide dichloride

3-Hydroxypropionitrile

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

Downstream raw materials:

Phosphorous acid bis-(2-cyano-ethyl) ester (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester

phosphorous acid 4-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanyl]-butyl ester bis-(2-cyano-ethyl) ester

phosphoric acid 4-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanyl]-butyl ester bis-(2-cyano-ethyl) ester

C₂₇H₂₁ClFN₆O₅P

Refernces

• 1、 Heeb, Norbert V.,Nambiar, Krishnan P.. "Synthesis of (R)-lysothiophosphatidic acid and (R)-thiophosphatidic acid". . p. 6193 - 6196. Retrieved 1993.
• 2、 Gendaszewska-Darmach, Edyta,Laska, Edyta,Rytczak, Przemys?aw,Okruszek, Andrzej. "The chemical synthesis of metabolically stabilized 2-OMe-LPA analogues and preliminary studies of their inhibitory activity toward autotaxin". supporting information; experimental part. p. 2698 - 2700. Retrieved 2012/05/20.