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305995

Sigma-Aldrich

2-氰乙基 N,N,N′,N′-四异丙基亚磷酰二胺

97%

别名:

双(二异丙基氨基)(2-氰乙氧基)膦

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1 G
$138.00
5 G
$289.00

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1 G
$138.00
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About This Item

线性分子式:
{[(CH3)2CH]2N}2POCH2CH2CN
CAS号:
102691-36-1
分子量:
301.41
Beilstein:
3590103
MDL编号:
MFCD00012213
UNSPSC代码:
12352100
PubChem化学物质编号:
24858468
NACRES:
NA.22

$138.00

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质量水平

200

方案

97%

表单

liquid

折射率

n20/D 1.470 (lit.)

沸点

100 °C/0.5 mmHg (lit.)

密度

0.949 g/mL at 25 °C (lit.)

官能团

amine
nitrile

储存温度

−20°C

SMILES字符串

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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应用

2-氰基乙基N,N,N′,N′-四异丙基亚磷酰二胺被用于：
  • 制备合成12-聚体寡脱氧核苷酸所需的亚磷酰胺试剂[1]
  • 作为合成1,2-二酰基-sn-甘油磷脂酰丝氨酸的磷酸化试剂[2]
  • 脱氧核糖核苷亚磷酰胺的原位 制备[3]
  • 制备2′-脱氧-2′-氟-3′-O-(β-氰基乙基-N,N-二异丙基磷酰基)-5′-O-(4-甲氧基三苯甲基)-4′-硫代-β-D-阿拉伯尿苷和1-(3-O-(β-氰基乙基-N,N-二异丙基磷酰基)-2-脱氧-2-氟-5-O-(4,4′-二甲氧基三苯甲基)-4-硫代-β-D-阿拉伯糖)-胸腺嘧啶[4]
  • 作为亚磷酸化核苷酸的合成试剂[5]

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价格

象形图

FlameExclamation mark
GHS02,GHS07

警示用语：

Warning

危险分类

Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1B

储存分类代码

3 - Flammable liquids

WGK

WGK 2

闪点(°F)

119.3 °F - closed cup

闪点(°C)

48.5 °C - closed cup

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

历史批次信息供参考:

分析证书(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
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
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.
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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  1. How can I determine the shelf life / expiration / retest date of this product?

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    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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  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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