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392731

Sigma-Aldrich

(DHQD)2PHAL

greener alternative

≥95%

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

assay

≥95%

form

powder

optical activity

[α]22/D −262°, c = 1.2 in methanol

greener alternative product score

old score: 13
new score: 3
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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

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 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.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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