746118

Sigma-Aldrich

Sodium difluoroheptylazidosulfinate

95%

Synonym(s):
Sodium 7-azido-1,1-difluoroheptanesulfinate, Baran DAAS-Na Reagent, Sodium 1,1-difluoro-7-azido-heptylsulfinate
Empirical Formula (Hill Notation):
C7H12F2N3NaO2S
CAS Number:
Molecular Weight:
263.24
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

assay

95%

reaction suitability

reagent type: catalyst
reaction type: C-H Activation

reagent type: linker

storage temp.

2-8°C

SMILES string

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

Application

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.

Packaging

100 mg in glass insert

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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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