Skip to Content
MilliporeSigma
All Photos(3)

Key Documents

305995

Sigma-Aldrich

2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite

97%

Synonym(s):

Bis(diisopropylamino)(2-cyanoethoxy)phosphine

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
{[(CH3)2CH]2N}2POCH2CH2CN
CAS Number:
Molecular Weight:
301.41
Beilstein/REAXYS Number:
3590103
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

liquid

refractive index

n20/D 1.470 (lit.)

bp

100 °C/0.5 mmHg (lit.)

density

0.949 g/mL at 25 °C (lit.)

functional group

amine

storage temp.

−20°C

SMILES string

CC(C)N(C(C)C)P(OCCC#N)N(C(C)C)C(C)C

InChI

1S/C15H32N3OP/c1-12(2)17(13(3)4)20(19-11-9-10-16)18(14(5)6)15(7)8/h12-15H,9,11H2,1-8H3

InChI key

RKVHNYJPIXOHRW-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite was used:
  • in preparation of prosphoramidite reagent, required for synthesis of 12-mer oligodeoxynucleotide
  • as phosphorylating agent in synthesis of 1,2-diacyl-sn-glycerophosphatidylserine
  • in situ preparation of deoxyribonucleoside phosphoramidites
  • in 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)-thymine
  • as reagent for synthesizing phosphitylated nucleotides

Related product

Product No.
Description
Pricing

pictograms

FlameExclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

119.3 °F - closed cup

flash_point_c

48.5 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Vyacheslav V Filichev et al.
Bioorganic & medicinal chemistry, 12(11), 2843-2851 (2004-05-15)
Hexofuranosyl nucleosides are considered as conformationally restricted acyclic nucleosides using a furanose ring to link the diol backbone to the nucleobase. The phosphoramidite of 1-(2,3-dideoxy-beta-D-erythro-hexofuranosyl)thymine was synthesized from thymidine with formation of a new stereocentre at C-5' and the nucleoside
Lubomir V Nechev et al.
Chemical research in toxicology, 15(5), 607-613 (2002-05-23)
3-(2-Deoxy-beta-D-erythro-pentofuranosyl)-6-hydroxy-5,6,7,8-tetrahydropyrimido[1,2-a]purin-10(3H)-one is formed in low yield by the reaction of acrolein with 2'-deoxyguanosine. The nucleoside and an oligodeoxynucleotide containing it have been synthesized. For preparation of the nucleoside 2'-deoxyguanosine was alkylated at the N1 position using 1-bromo-3-butene to give 1-(3-butenyl)-2'-deoxyguanosine.
Arvind Misra et al.
Bioconjugate chemistry, 15(3), 638-646 (2004-05-20)
Synthesis of modified oligonucleotides in which the specific cytidine nucleoside analogues linked at 2'-OH position via a carbamate bond with an amino ethyl derivative of dansyl fluorophore is reported. For the multiple labeling of oligonucleotides, a strategy involving prelabeling at
Improved synthesis of (Pri2 N)2POCH2CH2CN.
J Nielsen et al.
Nucleic acids research, 15(8), 3626-3626 (1987-04-24)
Jonathan K Watts et al.
Nucleic acids research, 35(5), 1441-1451 (2007-02-08)
The synthesis of oligonucleotides containing 2'-deoxy-2'-fluoro-4'-thioarabinonucleotides is described. 2'-Deoxy-2'-fluoro-5-methyl-4'-thioarabinouridine (4'S-FMAU) was incorporated into 18-mer antisense oligonucleotides (AONs). 4'S-FMAU adopts a predominantly northern sugar conformation. Oligonucleotides containing 4'S-FMAU, unlike those containing FMAU, were unable to elicit E. coli or human RNase

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service