2-Cyanoethyl N,N-diisopropylchlorophosphoramidite Chemical Properties

Boiling point:

103-105°C 0,08mm

Density 

1.061 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.479

Flash point:

>230 °F

storage temp. 

−20°C

solubility 

Miscible with chloroform and dichloromethane.

form 

Crystalline Powder

pka

0.83±0.70(Predicted)

color 

clear to very slightly hazy colorless

Sensitive 

Moisture Sensitive

BRN 

3588525

Stability:

Hygroscopic, Moisture Sensitive

InChI

InChI=1S/C9H18ClN2OP/c1-8(2)12(9(3)4)14(10)13-7-5-6-11/h8-9H,5,7H2,1-4H3

InChIKey

QWTBDIBOOIAZEF-UHFFFAOYSA-N

SMILES

P(N(C(C)C)C(C)C)(Cl)OCCC#N

CAS DataBase Reference

89992-70-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,T

Risk 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

HS Code 

29299090

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

Hazard Classifications

Eye Dam. 1
Pyr. Liq. 1
Skin Corr. 1B

MSDS

• Language:English Provider:2-Cyanoethyl N,N-diisopropylchlorophosphoramidite
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Cyanoethyl N,N-diisopropylchlorophosphoramidite Usage And Synthesis

Chemical Properties

Slightly Hazy Yellow Liquid

Uses

A protecting reagent in DNA synthesis. Also a phosphorylating agent

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.

Synthesis

Under argon protection, N,N-diisopropylethylamine ( 1eq ) was added to a stirred solution of dry 1 -butyl-3 -methylimidazolium bis[ (trifluoromethyl)sulfonylimide] in ionic liquid ( 1 eq ) and PCl3 ( 1 eq ), and then the above mixture was stirred vigorously for 5 min, followed by the addition of 3 -hydroxypropionitrile ( 1 eq ). The reaction mixture was stirred for 30 min, then diisopropylamine ( 2 eq ) was added to the above mixture, and the reaction was continued for 40 min with stirring before the reaction mixture was extracted with dry ether, the ether layer was separated, and the corresponding product was stabilized by the addition of 1-ethyl-3-methylimidazolium tris (pentafluoroethyl) trifluorophosphate ( [ C2mim ] [ FAP ] ) into the organic layer, and the product was concentrated under vacuum to remove the organic solvent. The target product molecule 2-cyanoethyl N,N-diisopropylchlorophosphoramidite was obtained by concentrating under vacuum to remove the organic solvent.

2-Cyanoethyl N,N-diisopropylchlorophosphoramidite(89992-70-1)Related Product Information

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• Epichlorohydrin
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• (+)-Diisopinocampheyl chloroborane
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• Difluorochloromethane
• ISOPROPYLAMINE HYDROCHLORIDE
• Chloroacetic acid
• Diisopropylamine hydrochloride
• 3-Hydroxypropionitrile
• CHLORO(DIISOPROPYLAMINO)METHOXYPHOSPHINE
• 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite
• 2-Cyanoethylphosphine
• CHLORO(DIMETHYLAMINO)METHOXY-PHOSPHINE