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392731 Sigma-Aldrich

(DHQD)2PHAL

Green Alternative

≥95%

Synonym: Hydroquinidine 1,4-phthalazinediyl diether

  • CAS Number 140853-10-7

  • Empirical Formula (Hill Notation) C48H54N6O4

  • Molecular Weight 778.98

  •  Beilstein/REAXYS Number 5475678

  •  MDL number MFCD00198107

  •  PubChem Substance ID 24864481

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Cinchona Alkaloids, Dihydroxylation,
assay   ≥95%
optical activity   [α]22/D −262°, c = 1.2 in methanol
greener alternative product score   old score: 13
new score: 3
Find out more about DOZN™ Scoring.
greener alternative product characteristics   Waste Prevention
Less Hazardous Chemical Syntheses
Safer Solvents and Auxiliaries
Learn more about the Principles of Green Chemistry.
mp   160 °C (dec.) (lit.)
greener alternative category   Re-engineered
SMILES string   CC[C@H]1CN2CCC1CC2[C@@H](Oc3nnc(O[C@H](C4CC5CCN4C[C@@H]5CC)c6ccnc7ccc(OC)cc67)c8ccccc38)c9ccnc%10ccc(OC)cc9%10
InChI   1S/C48H54N6O4/c1-5-29-27-53-21-17-31(29)23-43(53)45(35-15-19-49-41-13-11-33(55-3)25-39(35)41)57-47-37-9-7-8-10-38(37)48(52-51-47)58-46(44-24-32-18-22-54(44)28-30(32)6-2)36-16-20-50-42-14-12-34(56-4)26-40(36)42/h7-16,19-20,25-26,29-32,43-46H,5-6,17-18,21-24,27-28H2,1-4H3/t29-,30-,31-,32-,43+,44+,45-,46-/m0/s1
InChI key   YUCBLVFHJWOYDN-HVLQGHBFSA-N

Description

General description

(DHQD)2PHAL is a modified cinchona alkaloid derivative mainly used as a ligand for enantioselective catalysis.

Application

(DHQD)2PHAL may be used as ligand for:
• Osmium trioxide catalyzed asymmetric dihydroxylation of olefins.
• Palladium catalyzed Suzuki-Miyaura coupling of aryl/heteroaryl halides with aryl boronic acids in aqueous medium and in the absence of phosphine/organic solvent.
• Copper(I)-catalyzed azide-alkyne cycloaddition reaction to synthesize 1,2,3-triazoles in water.

Hydroquinidine 1,4-phthalazinediyl diether [(DHQD)2PHAL] can be used:
• As a ligand for Sharpless asymmetric dihydroxylation.
• For enantioselective α-fluorination of carbonyl compounds.

Packaging

1 g in glass bottle

Legal Information

Sold under license from Rhodia Pharma Solutions.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Barry Sharpless Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Barry Sharpless Group – Professor Product Portal
Keywords: Asymmetric synthesis, Building blocks, Chemical reactions, Click chemistry, Oxidations, Solvents, transformation

Cinchona Alkaloids - Aldrich ChemFiles 2008, 8.2, 74.

Cinchona alkaloids and their derivatives have proven to catalyze an astonishing array of enantioselective transformations, providing access to chiral products of high enantiopurity.1 The presence of ...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 74.
Keywords: Addition reactions, Aminations, Antimicrobials, Asymmetric synthesis, Catalysis, Desymmetrizations, Dihydroxylations, Ligands, Reductive aminations

Peer-Reviewed Papers
15

References

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