305995
2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite
97%
Synonym(s):
Bis(diisopropylamino)(2-cyanoethoxy)phosphine
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About This Item
Linear Formula:
{[(CH3)2CH]2N}2POCH2CH2CN
CAS Number:
Molecular Weight:
301.41
Beilstein:
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
nitrile
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
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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
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
Regulatory Information
危险化学品
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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
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
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
M Morillo et al.
Lipids, 31(5), 541-546 (1996-05-01)
A simple chemical method for the synthesis of 1,2-diacyl-sn-glycerophosphatidylserine (PS), with the same fatty acid composition in the sn-1 and sn-2 glycerol positions as egg phosphatidylcholine (PC), is described. PS synthesis was carried out by a phosphite-triester approach, using 2-cyanoethyl-N,N,N',N'-tetraisopropylphosphorodiamidite
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.
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