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Merck
CN

746118

Sigma-Aldrich

Sodium difluoroheptylazidosulfinate

95%

别名:

Baran DAAS-Na Reagent, Sodium 1,1-difluoro-7-azido-heptylsulfinate, Sodium 7-azido-1,1-difluoroheptanesulfinate

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About This Item

经验公式(希尔记法):
C7H12F2N3NaO2S
分子量:
263.24
UNSPSC代码:
12352125
PubChem化学物质编号:
NACRES:
NA.22

质量水平

检测方案

95%

形式

solid

反应适用性

reaction type: C-C Bond Formation
reagent type: catalyst
reaction type: C-H Activation

reagent type: linker

储存温度

2-8°C

SMILES字符串

[Na+].[O-]S(=O)C(F)(F)CCCCCCN=[N+]=[N-]

InChI

1S/C7H13F2N3O2S.Na/c8-7(9,15(13)14)5-3-1-2-4-6-11-12-10;/h1-6H2,(H,13,14);/q;+1/p-1

InChI key

FFNHIEJQAMGBCZ-UHFFFAOYSA-M

应用

Within heteroarene platforms, DAAS-Na allows for the direct introduction of a difluoroalkyl chain carrying an azide group, which is designed for the purpose of bioconjugation. Through a Huisgen cycloaddition (a "click" reaction), the azide moiety can then be reacted with a terminal alkyne that is bound to a functional molecule such as biomacromolecules. This effectively allows for a covalent linkage between a heteroarene and any target molecule, for example, between a heteroarene-containing drug and an antibody. This reagent was developed by the Baran Group and is one of several reagents for the direct alkylation of heterocycles.

Learn More at the Professor and Product Portal of Professor Phil S. Baran.

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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Qianghui Zhou et al.
Journal of the American Chemical Society, 135(35), 12994-12997 (2013-08-21)
A general C-H functionalization method for the tagging of natural products and pharmaceuticals is described. An azide-containing sulfinate reagent allows the appendage of azidoalkyl chains onto heteroaromatics, the product of which can then be attached to a monoclonal antibody by
Direct synthesis of fluorinated heteroarylether bioisosteres.
Qianghui Zhou et al.
Angewandte Chemie (International ed. in English), 52(14), 3949-3952 (2013-03-06)
Fionn O'Hara et al.
Journal of the American Chemical Society, 135(32), 12122-12134 (2013-07-19)
Radical addition processes can be ideally suited for the direct functionalization of heteroaromatic bases, yet these processes are only sparsely used due to the perception of poor or unreliable control of regiochemistry. A systematic investigation of factors affecting the regiochemistry

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