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392731

Sigma-Aldrich

(DHQD)2PHAL

greener alternative

≥95%

Sinônimo(s):

Hydroquinidine 1,4-phthalazinediyl diether

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About This Item

Fórmula empírica (Notação de Hill):
C48H54N6O4
Número CAS:
Peso molecular:
778.98
Beilstein:
5475678
Número MDL:
Código UNSPSC:
12352005
ID de substância PubChem:
NACRES:
NA.22

Ensaio

≥95%

Formulário

powder

atividade óptica

[α]22/D −262°, c = 1.2 in methanol

pontuação do produto alternativo mais ecológico

old score: 5
new score: 3
Find out more about DOZN™ Scoring

características do produto alternativo mais ecológico

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

pf

160 °C (dec.) (lit.)

categoria alternativa mais ecológica

cadeia de caracteres SMILES

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

chave InChI

YUCBLVFHJWOYDN-HVLQGHBFSA-N

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Descrição geral

(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.

Aplicação

(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.

Informações legais

Sold under license from Rhodia Pharma Solutions.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


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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.
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Syntheses and crystal structures of the cinchona alkaloid derivatives used as ligands in the osmium-catalyzed asymmetric dihydroxylation of olefins.
Amberg W, et al.
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Enantioselective fluorination mediated by cinchona alkaloid derivatives/selectfluor combinations: Reaction scope and structural information for N-fluorocinchona alkaloids.
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