89992-70-1

Basic information

• Product Name: 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite
• Synonyms: 2-CYANOETHYL N,N-DIISOPROPYLCHLOROPHOSPHORAMIDITE;2-CYANOETHYL DIISDPROPYLCHLOROPHOSPHORAMIDITE;2-CYANOETHYL DIISOPROPYLCHLOROPHOSPHORAMIDITE;CHLORO(DIISOPROPYLAMINO)-BETA-CYANOETHOXYPHOSPHINE;CYANOETHYL N,N-DIISOPROPYL PHOSPHOAMIDOCHLORIDITE;2-CYANOETHYL DIISOPROPYLCHLOROPHOSPHORAMIDITE, 14.0%-15.7% CL;2-Cyanoethoxy-N,N'-Diisopropyl Chlorophosphoramidate;Phosphoramidochloridous acid, bis(1-methylethyl)-, 2-cyanoethyl ester
• CAS NO: 89992-70-1
• Molecular Formula: C9H18ClN2OP
• Molecular Weight: 236.68
• EINECS: 1592732-453-0
• Product Categories: Phospholipids - 13C & 2H;Phosphorylating and Phosphitylating Agents
• Mol File: 89992-70-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 103-105°C 0,08mm
• Flash Point: >230 °F
• Appearance: clear to very slightly hazy colorless/Crystalline Powder
• Density: 1.061 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.479
• Storage Temp.: −20°C
• Solubility: Miscible with chloroform and dichloromethane.
• PKA: 0.83±0.70(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 3588525
• CAS DataBase Reference: 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite(89992-70-1)
• EPA Substance Registry System: 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite(89992-70-1)

Safety Data

• Hazard Codes: C,T
• Statements: 5-34-29-20/21/22
• Safety Statements: 26-36/37/39-45-8
• RIDADR: UN 2845 4.2/PG 1
• WGK Germany: 3
• F: 10
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 89992-70-1(Hazardous Substances Data)

Usage

Description

2-Cyanoethyl N,N-diisopropylchlorophosphoramidite is a slightly hazy yellow liquid that serves as a versatile intermediate in organic synthesis. It is characterized by its unique chemical properties, which make it a valuable component in various chemical reactions and processes.

Uses

Used in Organic Synthesis:
2-Cyanoethyl N,N-diisopropylchlorophosphoramidite is used as a protecting reagent in DNA synthesis, playing a crucial role in the selective monophosphorylation of carbohydrates and nucleosides. This selective reactivity allows for the precise manipulation of complex organic molecules, making it an indispensable tool in the field of organic chemistry.
Used in Nucleic Acid Chemistry:
In the realm of nucleic acid chemistry, 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite is used as a phosphitylating reagent for 3'-hydroxyl groups. This application is particularly important in the synthesis of oligodeoxyribonucleotides, where it aids in the formation of stable phosphite triesters, facilitating the construction of DNA strands.
Used in the Conversion of Protected Ribonucleosides:
2-Cyanoethyl N,N-diisopropylchlorophosphoramidite plays an essential role in the conversion of protected ribonucleosides to phosphoramidites. This conversion is a critical step in the synthesis of modified oligonucleotides, which are used in various applications, including the development of new drugs and the study of genetic information.
Overall, 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite is a multifaceted chemical intermediate with a wide range of applications in organic synthesis, nucleic acid chemistry, and the development of modified oligonucleotides. Its unique properties and reactivity make it a valuable asset in the field of chemistry and related industries.

Upstream product

• 76101-30-9 2-cyanoethyl phosphorodichloridite 
• 17425-88-6 N,N-diisopropyl-1,1,1-trimethylsilylamine 
• 108-18-9 diisopropylamine 
• 109-78-4 3-Hydroxypropionitrile 
• 921-26-6 N,N-diisopropylphosphoramide dichloride 

Downstream Products

• 226882-18-4 2'-O-methyl-5'-O-(monomethoxytrityl)-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanosine 3'-(2-cyanoethyl diisopropylphosphoramidite) 
• 1426239-87-3 (2R,3S,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-oxo-1-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)-1H-purin-9(6H)-yl)tetrahydrofuran-3-yl 2-cyanoethyldiisopropyl phosphoramidite 

Relevant articles and documents

Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry

Ionic liquids have been used in combination with ball milling on a range of chlorophosphoramidite reagents to phosphitylate nucleosides and 2-deoxynucleosides. The enhanced stability offered by the ionic liquid mediated processes combined with efficient mass transfer induced by ball milling has enabled excellent yields to be obtained even when using small dialkyl amino groups as well as the more commonly used diisopropylamino protection.

Selective synthesis of chlorophosphoramidites using ionic liquids

A range of chlorophosphoramidites have been prepared in ionic liquids and compared with material synthesised in molecular solvents. Through the use of ionic liquids as reaction media the moisture sensitivity and impurity issues hampering existing traditio

Solid-phase synthesis of symmetrical 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters

(Chemical Equation Presented) Four classes of phosphitylating reagents were subjected to reactions with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound mono-, di-, tri-, and tetraphosphitylating reagents. The solid-phase reagents were reacted with unprotected nucleosides (e.g., thymidine, adenosine, 3′-azido-3′- deoxythymidine, cytidine, or inosine) in the presence of 5-(ethylthio)-1H- tetrazole. Polymer-bound nucleosides underwent oxidation with fert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters in 59-78% yield.