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298174

Sigma-Aldrich

Sodium tetrachloroaurate(III) dihydrate

99%

Synonym(s):

Sodium gold chloride

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About This Item

Linear Formula:
NaAuCl4 · 2H2O
CAS Number:
13874-02-7
Molecular Weight:
397.80
EC Number:
239-241-3
MDL number:
MFCD00149162
UNSPSC Code:
12352302
PubChem Substance ID:
24857964
NACRES:
NA.23

Quality Level

100

assay

99%

form

solid

reaction suitability

reagent type: catalyst
core: gold

SMILES string

O.O.[Na+].Cl[Au-](Cl)(Cl)Cl

InChI

1S/Au.4ClH.Na.2H2O/h;4*1H;;2*1H2/q+3;;;;;+1;;/p-4

InChI key

OEERDTKOVZFOHF-UHFFFAOYSA-J

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General description

Sodium tetrachloroaurate(III) dihydrate (NaAuCl4·2H2O) is the least expensive gold catalyst that is widely used in many organic transformations such as nucleophilic addition to multiple bonds, nonsymmetrical etherization, and nucleophilic substitution of propargylic alcohols.

Application

Sodium tetrachloroaurate(III) dihydrate can be used as a catalyst:
  • To synthesize 1,5-benzodiazepine and quinoxaline derivatives, which are important heterocycles in pharmaceuticals.
  • For efficient deprotection of tert-butyl(dimethyl)silyl (TBS) protecting groups by a simple and mild method.
It can also be used as a precursor in the synthesis of gold nanoparticles.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ6893
MKCN9867
MKCN3868
MKCM0485
MKCK4883

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Shenting Zhu et al.
International journal of nanomedicine, 14, 5017-5032 (2019-08-03)
Background: Epigallocatechin gallate (EGCG), the major anti-inflammatory compound in green tea, has been shown to suppress osteoclast (OC) differentiation. However, the low aqueous solubility of EGCG always leads to poor bioavailability, adverse effects, and several drawbacks for clinical applications. Purpose:
Yumeki Tani et al.
Royal Society open science, 6(5), 190293-190293 (2019-06-21)
Here we found that gold nanoparticles (AuNPs) enhance the optical force acting on vesicles prepared from phospholipids via hydrophobic and electrostatic interactions. A laser beam was introduced into a cuvette filled with a suspension of vesicles and it accelerated them
Douglas E. Berning et al.
Inorganic chemistry, 36(13), 2765-2769 (1997-06-18)
The reactions of water-soluble bisphosphines (HOH(2)C)(2)PC(6)H(4)P(CH(2)OH)(2) (1) and (HOH(2)C)(2)PCH(2)CH(2)P(CH(2)OH)(2) (2) with NaAuCl(4), in aqueous media, or AuClPPh(3), in biphasic media (aqueous/organic), produced the water/alcoholic-soluble Au(I) complexes [Au{(HOH(2)C)(2)PC(6)H(4)P(CH(2)OH)(2)}(2)]Cl (3), [Au{(HOH(2)C)(2)PCH(2)CH(2)P(CH(2)OH)(2)}(2)]Cl (4), and [Au(2){(HOH(2)C)(2)PCH(2)CH(2)P(CH(2)OH)(2)}(2)]Cl(2) (5) in near quantitative yields. Stability and cysteine-challenge
Hsien-Ting Chiu et al.
Theranostics, 7(12), 3034-3052 (2017-08-26)
Recently, living cells with tumor-homing properties have provided an exciting opportunity to achieve optimal delivery of nanotherapeutic agents. However, premature payload leakage may impair the host cells, often leading to inadequate
Xianqing Tian et al.
Talanta, 93, 79-85 (2012-04-10)
Graphene decorated with gold nanoparticles (AuNPs-β-CD-Gra) has been synthesized by in situ thermal reduction of graphene oxide and HAuCl(4) with β-cyclodextrin (β-CD) under alkaline condition. The AuNPs-β-CD-Gra product was well characterized by infrared spectroscopy, X-ray powder diffraction, scanning electron microscopy
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