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305995

Sigma-Aldrich

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:
102691-36-1
Molecular Weight:
301.41
Beilstein:
3590103
MDL number:
MFCD00012213
UNSPSC Code:
12352100
PubChem Substance ID:
24858468
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

200

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[1]
  • as phosphorylating agent in synthesis of 1,2-diacyl-sn-glycerophosphatidylserine[2]
  • in situ preparation of deoxyribonucleoside phosphoramidites[3]
  • 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[4]
  • as reagent for synthesizing phosphitylated nucleotides[5]

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Description
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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV3858
MKCS7193
MKCR6334
MKCJ8691
MKCB0853V

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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
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
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
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. In 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite reagent is there any stabilizer is added! what is the stabilizer added for the storage of the above reagent.

    1 answer

    1. There is no stabilizer added, but the product is handled and stored under nitrogen due to its moisture sensitivity.

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