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685089

Sigma-Aldrich

(R,R,S)-DiazaPhos-PPE

Synonym(s):

2,2′-[(1R,3R)-2,3,5,10-Tetrahydro-5,10-dioxo-2-phenyl-1H-[1,2,4]diazaphospholo[1,2-b]phthalazine-1,3-diyl]bis[N-[(1S)-1-phenylethyl]benzamide]

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About This Item

Empirical Formula (Hill Notation):
C46H39N4O4P
CAS Number:
615257-74-4
Molecular Weight:
742.80
MDL number:
MFCD10566993
UNSPSC Code:
12352005
PubChem Substance ID:
329760941
NACRES:
NA.22

form

solid

optical activity

[α]20/D +105°, c = 1 in THF

mp

258-262 °C

SMILES string

C[C@H](NC(=O)c1ccccc1[C@@H]2N3N([C@H](P2c4ccccc4)c5ccccc5C(=O)N[C@@H](C)c6ccccc6)C(=O)c7ccccc7C3=O)c8ccccc8

InChI

1S/C46H39N4O4P/c1-30(32-18-6-3-7-19-32)47-41(51)35-24-12-16-28-39(35)45-49-43(53)37-26-14-15-27-38(37)44(54)50(49)46(55(45)34-22-10-5-11-23-34)40-29-17-13-25-36(40)42(52)48-31(2)33-20-8-4-9-21-33/h3-31,45-46H,1-2H3,(H,47,51)(H,48,52)/t30-,31-,45+,46+/m0/s1

InChI key

XLHCPIVFAWUOET-JBVOVCRZSA-N

Application

Diazaphospholane Ligands for Catalytic Asymmetric Transformations
Diazaphospholane ligands display excellent levels of conversion and selectivity in Rh-catalyzed asymmetric hydroformylation reactions.

Legal Information

Product is sold for R&D purpose only and use by end user in the manfacture of products of commerce is not permitted. Product is sold in association with DowpharmaSM a business unit of The Dow Chemical Company. U.S. Pat. 7,071,357B.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
12127JH

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Thomas P Clark et al.
Journal of the American Chemical Society, 127(14), 5040-5042 (2005-04-07)
Azines made by the reaction of hydrazine with ortho-formylbenzoic acid react with 1,2-diphosphinobenzene and either succinyl chloride or phthaloyl chloride in ca. 30% yield to give rac-bis-3,4-diazaphospholanes bearing benzoic acid groups in the 2 and 5 positions. Condensation of the
Highly regio- and enantioselective asymmetric hydroformylation of olefins mediated by 2,5-disubstituted phospholane ligands.
Alex T Axtell et al.
Angewandte Chemie (International ed. in English), 44(36), 5834-5838 (2005-08-13)

Articles

Diazaphospholane Ligands for Catalytic Asymmetric Transformations

Diazaphospholane Ligands for Catalytic Asymmetric Transformations: Professor Landis and co-workers developed a series of new ligands based on chiral 3,4-diazaphospholane structures.

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