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392723 Sigma-Aldrich

(DHQ)2PHAL

≥95%

Synonym: Hydroquinine 1,4-phthalazinediyl diether

  • CAS Number 140924-50-1

  • Empirical Formula (Hill Notation) C48H54N6O4

  • Molecular Weight 778.98

  •  Beilstein/REAXYS Number 5475677

  •  MDL number MFCD00191975

  •  PubChem Substance ID 24864480

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Cinchona Alkaloids, Dihydroxylation,
Quality Level   200
assay   ≥95%
optical activity   [α]22/D +336°, c = 1.2 in methanol
mp   178 °C (dec.) (lit.)
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-/m1/s1
InChI key   YUCBLVFHJWOYDN-PPIALRKJSA-N

Description

General description

DHQ)2PHAL is a modified cinchona alkaloid.

Application

(DHQ)2PHAL may be used in the following processes:
• As a catalyst Asymmetric and chemoselective N-allylic alkylation of indoles with Morita-Baylis-Hillman carbonates to form pyrrolo[1,2-a]indole and pyrrolo[3,2,1-ij]quinoline derivatives.
• As a ligand for the osmium catalyzed-Sharpless asymmetric dihydroxylation step of (S)-a-benzoyloxy carboxylic acids multistep synthesis.
• As a ligand for the carbamate based asymmetric aminohydroxylation of styrene derivatives to form N-carbamate protected R-arylglycinols.

Ligand for Sharpless Asymmetric Dihydroxylation employed in an enantioselective preparation of syn-3,5-hydroxycarboxylates from (E,E)- or (E,Z)-1,3-dienoates.

Packaging

500 mg in glass bottle

Physical form

Asymmetric dihydroxylation of unsaturated esters with trisubstituted C=C bonds.

Legal Information

Sold under license from Sterling Pharma Solutions Limited.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
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

Cinchona Alkaloids

Asymmetric phase-transfer catalysis (PTC) has been recognized as a “green” alternative to many homogeneous synthetic organic transformations, and has found widespread application. Synthetically modif...
Aldrich ChemFiles 2007, 7.9, 16.
Keywords: Addition reactions, Alkylations, Aminations, Asymmetric synthesis, Catalysis, Methods

Peer-Reviewed Papers
15

References

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