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Sigma-Aldrich

(DHQD)2PHAL

greener alternative

≥95%

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Synonym(s):
Hydroquinidine 1,4-phthalazinediyl diether
Empirical Formula (Hill Notation):
C48H54N6O4
CAS Number:
140853-10-7
Molecular Weight:
778.98
Beilstein:
5475678
MDL number:
MFCD00198107
UNSPSC Code:
12352005
PubChem Substance ID:
24864481
NACRES:
NA.22

Assay

≥95%

form

powder

optical activity

[α]22/D −262°, c = 1.2 in methanol

greener alternative product score

old score: 5
new score: 3
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greener alternative product characteristics

Waste Prevention
Less Hazardous Chemical Syntheses
Safer Solvents and Auxiliaries
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

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

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General description

(DHQD)2PHAL is a dimer that can be used as a chiral amine catalyst for asymmetric halogenations.

(DHQD)2PHAL is a modified cinchona alkaloid derivative mainly used as a ligand for enantioselective catalysis.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Less Hazardous Chemical Syntheses”, "Safer Solvents and Auxiliaries" and “Inherently Safer Chemistry for Accident Prevention”. Click here to view its DOZN scorecard.

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.

Legal Information

Sold under license from Rhodia Pharma Solutions.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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(DHQD) 2 PHAL ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition reactions in water at room temperature.
Ali AA, et al.
Royal Society of Chemistry Advances, 4(110), 64388-64392 (2014)
Chemical Fixation of Carbon Dioxide Co-Catalyzed by a Combination of Schiff Bases or Phenols and Organic Bases.
Shen YM, et al.
European Journal of Organic Chemistry, 2004(14), 3080-3089 (2004)
Tetrahedron Asymmetry, 16, 3913-3913 (2005)
Syntheses and crystal structures of the cinchona alkaloid derivatives used as ligands in the osmium-catalyzed asymmetric dihydroxylation of olefins.
Amberg W, et al.
The Journal of Organic Chemistry, 58(4), 844-849 (1993)
Pd (OAc) 2 and (DHQD) 2 PHAL as a simple, efficient and recyclable/reusable catalyst system for Suzuki-Miyaura cross-coupling reactions in H 2 O at room temperature.
Saikia B, et al.
New. J. Chem., 39(4), 2440-2443 (2015)
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