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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3590103
Assay:
97%
Form:
liquid
Quality Level
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
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
Disclaimer
Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.
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Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1B
Storage Class
3 - Flammable liquids
wgk
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
Regulatory Information
危险化学品
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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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 305995-1G | 04061837656460 |
| 305995-5G | 04061826668597 |