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254037

Sigma-Aldrich

Chloro(triphenylphosphine)gold(I)

≥99.9% trace metals basis

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Synonym(s):
(Ph3P)AuCl, Triphenylphosphinegold(I) chloride
Linear Formula:
[(C6H5)3P]AuCl
CAS Number:
14243-64-2
Molecular Weight:
494.71
EC Number:
238-117-6
MDL number:
MFCD00009588
UNSPSC Code:
12352300
PubChem Substance ID:
24855348
NACRES:
NA.22

Quality Level

100

Assay

≥99.9% trace metals basis

form

solid

reaction suitability

core: gold
reagent type: catalyst

SMILES string

Cl[Au].c1ccc(cc1)P(c2ccccc2)c3ccccc3

InChI

1S/C18H15P.Au.ClH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;/h1-15H;;1H/q;+1;/p-1

InChI key

IFPWCRBNZXUWGC-UHFFFAOYSA-M

Related Categories

Application

Gold Catalysts — 21st Century ′Gold Rush′
Catalyst employed in the cyclization of O-propargyl carbamates to alkylideneoxazolidinones via a 5-exo-digonal pathway at room temperature. Also catalyzes the cycloisomerization of enynes containing a cyclic olefin into highly-fused, polycyclic dienes at room temperature.
Reagent is used with cocatalytic halide abstraction agent to activate π-systems toward addition by heteroatom and carbon nucleophiles.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Leseurre, L. et al.
Organic Letters, 9 (2007)
Sang Ick Lee et al.
The Journal of organic chemistry, 71(25), 9366-9372 (2006-12-02)
Gold(I)-catalyzed cyclization of enynes containing an olefinic cycle has been studied. The introduction of an olefinic ring instead of a terminal alkene in enynes dramatically increased the yield of the reaction. Enynes having an olefinic cycle were prepared by a
Elena Barreiro et al.
Journal of inorganic biochemistry, 102(2), 184-192 (2007-09-18)
The reaction of triphenylphosphinegold(I) chloride in ethanol in a 1:1 molar ratio with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x: p=3-phenyl-, Clp=3-(2-chlorophenyl)-, -o-mp=3-(2-methoxyphenyl)-, -p-mp=3-(4-methoxyphenyl)-, -o-hp=3-(2-hydroxyphenyl)-, -p-hp=3-(4-hydroxyphenyl)-, diBr-o-hp=3-(3,5-dibromo-2-hydroxyphenyl)-, f=3-(2-furyl)-, t=3-(2-thienyl)-, -o-py=3-(2-pyridyl)-; spa=2-sulfanylpropenoato] gave compounds of the type [Au(PPh(3))(Hxspa)], which were isolated and characterized
Ming Zhang et al.
Molecules (Basel, Switzerland), 17(3), 2812-2822 (2012-03-08)
An efficient method for the synthesis of β-enaminones and β-enaminoesters using a combination of [(PPh(3))AuCl]/AgOTf as catalyst has been developed. The reaction between 1,3-dicarbonyl compounds and primary amines was carried out under solvent-free conditions with low catalyst loading in good
Synlett, 3309-3309 (2006)
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