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Sigma-Aldrich

2-Cyanoethyl N,N-diisopropylchlorophosphoramidite

2-Cyanoethyl N,N-diisopropylchlorophosphoramidite

Cl 13.5-15.5 %

Synonyme(s) :

Chloro(diisopropylamino)-β-cyanoethoxyphosphine

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250 MG
55,90 $
1 G
149,00 $
5 G
524,00 $

About This Item

Formule linéaire :
[(CH3)2CH]2NP(Cl)OCH2CH2CN
Numéro CAS:
Poids moléculaire :
236.68
Beilstein:
3588525
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22

55,90 $


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Forme

liquid

Composition

Cl, 13.5-15.5%

Indice de réfraction

n/D 1.476-1.480

pb

103 -105 °C/0.1 hPa

Densité

1.061 g/mL at 25 °C (lit.)

Groupe fonctionnel

amine
nitrile

Température de stockage

−20°C

Chaîne SMILES 

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

InChI

1S/C9H18ClN2OP/c1-8(2)12(9(3)4)14(10)13-7-5-6-11/h8-9H,5,7H2,1-4H3

Clé InChI

QWTBDIBOOIAZEF-UHFFFAOYSA-N

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Application

2-Cyanoethyl N,N-diisopropylchlorophosphoramidite was employed:
  • for selective monophosphorylation of carbohydrates and nucleosides[1]
  • for conversion of protected ribonucleosides to phosphoramidites[2]
  • as phosphitylating reagent for 3′-hydroxyl groups in the synthesis of oligodeoxyribonucleotides[3][4][5][6]
  • in a scalable, solution-phase oligonucleotide synthesis employing phosphoramidite chemistry and DMT-, iBu- and Bz-protected monomers. Intermediates were isolated by extraction without further purification[7]

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

FlameCorrosion

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1B

Code de la classe de stockage

4.2 - Pyrophoric and self-heating hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

230.0 °F - closed cup

Point d'éclair (°C)

110 °C - closed cup

Équipement de protection individuelle

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Certificats d'analyse (COA)

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Yousef Ahmadibeni et al.
The Journal of organic chemistry, 70(3), 1100-1103 (2005-01-29)
Two classes of aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite to produce the corresponding polymer-bound phosphitylating reagents. These were reacted with a number of unprotected nucleosides and carbohydrates in the presence of 1H-tetrazole.
Tetrahedron Letters, 34, 6189-6189 (1993)
A Ono et al.
Bioconjugate chemistry, 4(6), 499-508 (1993-11-01)
Novel 2'-deoxyuridine analogues carrying aminoalkyl linkers at the 1'-position of the sugar residues were synthesized and incorporated into oligonucleotides, then intercalating groups such as an anthraquinone derivative and a pyrene derivative were attached to the amino groups. Duplexes consisting of
Organic Process Research & Development, 10, 1238-1238 (2006)
Tetrahedron Letters, 35, 5221-5221 (1994)

Questions

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  1. 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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  2. 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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