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302309

Sigma-Aldrich

2-Cyanoethyl N,N-diisopropylchlorophosphoramidite

2-Cyanoethyl N,N-diisopropylchlorophosphoramidite

Cl 13.5-15.5 %

Synonym(s):

Chloro(diisopropylamino)-β-cyanoethoxyphosphine

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$40.30
1 G
$93.90
5 G
$317.00

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250 MG
$40.30
1 G
$93.90
5 G
$317.00

About This Item

Linear Formula:
[(CH3)2CH]2NP(Cl)OCH2CH2CN
CAS Number:
89992-70-1
Molecular Weight:
236.68
Beilstein/REAXYS Number:
3588525
MDL number:
MFCD00011544
UNSPSC Code:
12352100
PubChem Substance ID:
24858245
NACRES:
NA.22

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form

liquid

Quality Level

200

composition

Cl, 13.5-15.5%

density

1.061 g/mL at 25 °C (lit.)

functional group

amine
nitrile

storage temp.

−20°C

SMILES string

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

InChI key

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]

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Description
Pricing

pictograms

FlameCorrosion
GHS02,GHS05

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Danger

hcodes

H250,H314

Hazard Classifications

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

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3934
MKCV4856
MKCS1998
STBK9602
STBK9600

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Organic Process Research & Development, 10, 1238-1238 (2006)
Tetrahedron Letters, 34, 6189-6189 (1993)
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, 45, 509-509 (2004)
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
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