Skip to Content
Merck
All Photos(3)

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
All Photos(3)

About This Item

Linear Formula:
{[(CH3)2CH]2N}2POCH2CH2CN
CAS Number:
102691-36-1
Molecular Weight:
301.41
Beilstein:
3590103
MDL number:
MFCD00012213
UNSPSC Code:
12352100
PubChem Substance ID:
24858468
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.)

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

Related Categories

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
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302,H317,H412

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

119.3 °F - closed cup

Flash Point(C)

48.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

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
Christoph Rosenbohm et al.
Bioorganic & medicinal chemistry, 12(9), 2385-2396 (2004-04-15)
LNA guanine and 2,6-diaminopurine (D) phosphoramidites have been synthesized as building blocks for antisense oligonucleotides (ON). The effects of incorporating LNA D into ON were investigated. As expected, LNA D containing ON showed increased affinity towards complementary DNA (Delta Tm
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
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.
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
View All Related Papers

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