Chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I) - ≥99.95% metals basis , CAS No.852445-83-1

CAS: 852445-83-1 Cat. No.: C284031 Molecular Weight: 621.01 EC Number: 635-902-9

GRADE & PURITY ≥99.95% metals basis

Synonyms

852445-83-1|(1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)(chloro)gold|Chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I)|[1,3-bis[2,6-di(propan-2-yl)phenyl]imidazol-2-ylidene]-chlorogold|1,3-Bis(2,6-di-isopropylphenyl)imi

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Product class

M-C, Homogeneous Catalysts, N-Heterocyclic Carbene Ligands

Reaction type

CH-Activation, Carboxylation, Cyclization, Cyclopropanation, Hydration, Hydroamination, Isomerization

Chemical properties

Chemical formula

C27H36N2ClAu

Empirical formula

[(IPr)AuCl]

Molecular weight

621.01

Metal

Au

Theoretical metal content

32

Physical state

powder

Color

white

Metal purity

99.95

Applications & references

Rearrangement of allylic acetates.

Reference: Org. Lett. 2007, 9, 2653 (DOI: 10.1021/ol070843w); Organomet. 2011, 30, 5463 (DOI: 10.1021/om200705y)

Olefin cyclopropanation.

Reference: Tetrah. 2009, 65, 1790 (DOI: 10.1016/j.tet.2008.10.114)

Alkane C-H-bond functionalization.

Reference: Organomet. 2006, 25, 2237 (DOI: 10.1021/om0507474)

Carboxylation of C-H bonds.

Reference: J. Am. Chem. Soc. 2010, 132, 8858 (DOI: 10.1021/ja103429q)

Hydration of alkynes.

Reference: J. Am. Chem. Soc. 2009, 131, 448 (DOI: 10.1021/ja809403e)

Hydroarylation-aromatization of arenes-diynes.

Reference: Organomet. 2012, 31, 644 (DOI: 10.1021/om200946m)

Cyclization of aryl-substituted propargylamides.

Reference: Eur. J. Org. Chem. 2011, 4595 (DOI: 10.1002/ejoc.201100342)

Cycloisomerization of enyl etsters and allenyl esters.

Reference: Chem. Eur. J. 2009, 15, 3243 (DOI: 10.1002/chem.200801387)

Tandem hydroamination-hydroarylation reaction.

Reference: Org. Lett. 2007, 9, 2645 (DOI: 10.1021/ol070814l)

Tandem 1,2-indole migration and aura-Nazarov cyclization reaction of 3-propargylindoles.

Reference: Beilstein J. Org. Chem. 2011, 7, 786 (DOI:10.3762/bjoc.7.89)

Cascade insertion and cyclization of water with substituted phenyldiazoacetates.

Reference: Beilstein J. Org. Chem. 2011, 7, 631 (DOI:10.3762/bjoc.7.74)

Specifications

Synonyms

852445-83-1 | (1, 3-Bis(2, 6-diisopropylphenyl)-1, 3-dihydro-2H-imidazol-2-ylidene)(chloro)gold | Chloro[1, 3-bis(2, 6-diisopropylphenyl)imidazol-2-ylidene]gold(I) | [1, 3-bis[2, 6-di(propan-2-yl)phenyl]imidazol-2-ylidene]-chlorogold | 1, 3-Bis(2, 6-di-isopropylphenyl)imi

Specifications & Purity

≥99.95% metals basis

Legal Information

Product of Umicore

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99.95% metals basis

Names and Identifiers

• Canonical Smiles: CC(C)C1=C(C(=CC=C1)C(C)C)N2C=CN(C2=[Au]Cl)C3=C(C=CC=C3C(C)C)C(C)C
• IUPAC Name: [1,3-bis[2,6-di(propan-2-yl)phenyl]imidazol-2-ylidene]-chlorogold
• InChIKey: CNJQLSINQGKZAW-UHFFFAOYSA-M
• INCHI: 1S/C27H36N2.Au.ClH/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;;/h9-16,18-21H,1-8H3;;1H/q;+1;/p-1
• Isomeric SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N2C=CN(C2=[Au]Cl)C3=C(C=CC=C3C(C)C)C(C)C
• WGK Germany: 3
• Molecular Weight: 621.01
• Reaxy-Rn: 17875276
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=17875276&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Cumenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Cumenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Cumenes
• Alternative Parents: Phenylpropanes Aniline and substituted anilines Imidazolines Organic transition metal salts Enamines Azacyclic compounds Hydrocarbon derivatives Carbenes
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenylpropane - Cumene - Aniline or substituted anilines - 4-imidazoline - Azacycle - Organic metal salt - Organic transition metal salt - Organoheterocyclic compound - Enamine - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Carbene - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 621.000 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 620.223 Da
• Monoisotopic Mass: 620.223 Da
• Topological Polar Surface Area: 6.500 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 559.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

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