2-Cyanoethyl N,N-diisopropylchlorophosphoramidite

Base Information

• Chemical Name: 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite
• CAS No.: 89992-70-1
• Molecular Formula: C₉H₁₈ClN₂OP
• Molecular Weight: 236.681
• Hs Code.: 29299090
• European Community (EC) Number: 628-591-6
• DSSTox Substance ID: DTXSID60370534
• Nikkaji Number: J382.966I
• Mol file: 89992-70-1.mol

Synonyms:89992-70-1;2-Cyanoethyl N,N-diisopropylchlorophosphoramidite;2-cyanoethyl-N,N-diisopropylchlorophosphoramidite;3-[chloro-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile;Phosphoramidochloridous acid, bis(1-methylethyl)-, 2-cyanoethyl ester;2-Cyanoethoxy(diisopropylamino)chlorophosphine;cyanoethyl n,n-diisopropyl phosphoamidochloridite;3-((chloro(diisopropylamino)phosphino)oxy)propanenitrile;MFCD00011544;C9H18ClN2OP;2-CyanoethylN,N-diisopropylchlorophosphoramidite;SCHEMBL285592;3-[chloro-(diisopropylamino)phosphanyl]oxypropanenitrile;DTXSID60370534;QWTBDIBOOIAZEF-UHFFFAOYSA-N;BCP04349;AKOS005063566;AC-1027;BP-22281;FT-0612112;2-cyanoethyl diisopropylchloro-phosphoramidite;2-cyanoethyl diisopropylphosphoramidochloridite;Chloro(diisopropylamino)(2-cyanoethoxy)phosphine;Cyanoethyl N,N'-diisopropyl Phosphoamidochlorite;Diisopropylaminochloro(beta-cyano)ethoxyphosphine;(chloro)(2-cyanoethoxy)(diisopropylamino)phosphine;2-cyanoethyl N,N-diisopropylchlorophosphoroamidite;2-cyanoethyl n,n-diisopropylphosphoramidochloridite;2-cyanoethyl-N, N-diisopropylchlorophosphoramidite;A843396;chloro-2-cyanoethoxy-N,N-diisopropylaminophosphine;2-CYANOETHYL DIISOPROPYLCHLOROPHOSPHORAMIDITE;J-700072;3-(chloro(diisopropylamino)phosphinooxy)propanenitrile;3'-[(2-Cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite;3-[chloro-[di(propan-2-yl)amino]phosphino]oxypropanenitrile;beta-cyanoethoxymonochloro(N,N-diisopropylamino) phosphine;3-[chloranyl-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile;2-Cyanoethyl N,N-diisopropylchlorophosphoramidite, Cl 13.5-15.5 %

Chemical Property of 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite

Chemical Property:

• Appearance/Colour: Slightly Hazy Yellow Liquid
• Refractive Index: n20/D 1.479
• Boiling Point: 343.8 ºC at 760 mmHg
• PKA: 0.83±0.70(Predicted)
• Flash Point: 110 ºC
• PSA: 49.85000
• Density: 1.061
• LogP: 3.50118
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with chloroform and dichloromethane.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 236.0845279
• Heavy Atom Count: 14
• Complexity: 194

Purity/Quality:

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

CyanoethylN,N-DiisopropylPhosphoamidochloridite ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C,T
• Statements: 5-34-29-20/21/22
• Safety Statements: 26-36/37/39-45-8

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCCC#N)Cl
• Uses: 2-Cyanoethyl diisopropylchlorophosphoramidite is a useful intermediate in organic synthesis. It acts as a protecting reagent in DNA synthesis. It is involved in the selective monophosphorylation of carbohydrates and nucleosides. It plays an essential role in the conversion of protected ribonucleosides to phosphoramidites. It is also utilized as phosphitylating reagent for 3'-hydroxyl groups in the synthesis of oligodeoxyribonucleotides.

Technology Process of 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite

There total 9 articles about 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite 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: 88.0%

2-cyanoethyl phosphorodichloridite (76101-30-9) + diisopropylamine (108-18-9) → 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1)

Guidance literature:

In diethyl ether; for 20h; -20 deg C to r.t;

DOI:10.1039/P19930000043

Reference yield:

diisopropylamine (108-18-9) + 3-Hydroxypropionitrile (109-78-4) → N,N-diisopropylphosphoramide dichloride (921-26-6) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + bis(2-cyanoethyl) diisopropylamidophosphite (102690-88-0)

Guidance literature:

3-Hydroxypropionitrile; With N-ethyl-N,N-diisopropylamine; 1-butyl-2,3-dimethylimidazolium bis-(trifluoromethanesulfonyl)amide; phosphorus trichloride;

diisopropylamine; for 0.666667h; chemoselective reaction;

DOI:10.1039/b905000k

Reference yield:

diisopropylamine (108-18-9) + 3-Hydroxypropionitrile (109-78-4) → 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + bis(2-cyanoethyl) diisopropylamidophosphite (102690-88-0)

Guidance literature:

3-Hydroxypropionitrile; With N-ethyl-N,N-diisopropylamine; 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide; phosphorus trichloride;

diisopropylamine; for 0.666667h; chemoselective reaction;

DOI:10.1039/b905000k

upstream raw materials:

2-cyanoethyl phosphorodichloridite

N,N-diisopropyl-1,1,1-trimethylsilylamine

diisopropylamine

N,N-diisopropylphosphoramide dichloride

Downstream raw materials:

Diisopropyl-phosphoramidous acid (2R,3R,5S)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(pyren-1-ylcarbamoyl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Refernces

• 1、 Ching, Shi Min,Tan, Wan Jun,Chua, Kim Lee,Lam, Yulin. "Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase". scheme or table. p. 6657 - 6665. Retrieved 2010/10/21.
• 2、 Amigues, Eric J.,Hardacre, Christopher,Keane, Gillian,Migaud, Marie E.,Norman, Sarah E.,Pitner, William R.. "Selective synthesis of chlorophosphoramidites using ionic liquids". experimental part. p. 1391 - 1396. Retrieved 2010/05/18.