Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

682977

Sigma-Aldrich

(11bR,11′bR)-4,4′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis-dinaphtho[2,1-d:1′, 2′-f][1,3,2]dioxaphosphepin

Synonym(s):

R, R-Reetz X-Diphosphonite

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C55H36O5P2
CAS Number:
349114-63-2
Molecular Weight:
838.82
MDL number:
MFCD09842740
UNSPSC Code:
12352005
PubChem Substance ID:
329760784
NACRES:
NA.22
Pricing and availability is not currently available.

form

solid

Quality Level

100

optical activity

[α]22/D +270°, c = 1 in chloroform

mp

198-217 °C

SMILES string

CC1(C)c2cccc(P3Oc4ccc5ccccc5c4-c6c(O3)ccc7ccccc67)c2Oc8c(cccc18)P9Oc%10ccc%11ccccc%11c%10-c%12c(O9)ccc%13ccccc%12%13

InChI

1S/C55H36O5P2/c1-55(2)41-21-11-23-47(61-57-43-29-25-33-13-3-7-17-37(33)49(43)50-38-18-8-4-14-34(38)26-30-44(50)58-61)53(41)56-54-42(55)22-12-24-48(54)62-59-45-31-27-35-15-5-9-19-39(35)51(45)52-40-20-10-6-16-36(40)28-32-46(52)60-62/h3-32H,1-2H3

InChI key

DXZANFKSPAISOB-UHFFFAOYSA-N

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
700665676004675806
(11bR,11′bR)-4,4′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis-dinaphtho[2,1-d:1′, 2′-f][1,3,2]dioxaphosphepin

682977

(11bR,11′bR)-4,4′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis-dinaphtho[2,1-d:1′, 2′-f][1,3,2]dioxaphosphepin

(11bR)-2,6-Di-9-phenanthrenyl-4-hydroxy-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide

700665

(11bR)-2,6-Di-9-phenanthrenyl-4-hydroxy-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide

(R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(di(3,5-xylyl)phosphino)-3,3′-bipyridine 97%

676004

(R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(di(3,5-xylyl)phosphino)-3,3′-bipyridine

(R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine 97%

675806

(R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

optical activity

[α]22/D +270°, c = 1 in chloroform

optical activity

[α]22/D −44.0°, c = 1 in DMSO

optical activity

[α]20/D +125°, c = 1 in chloroform

optical activity

[α]20/D +98°, c = 1 in chloroform

mp

198-217 °C

mp

390-400 °C

mp

190-194 °C

mp

261-265 °C

Application

This diphosphonite ligand has been successfully employed in Noyori-type asymmetric transfer hydrogenation of prochiral ketones.[1]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
09719LH
03012HH

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Manfred T Reetz et al.
Journal of the American Chemical Society, 128(4), 1044-1045 (2006-01-26)
A BINOL-derived diphosphonite having a xanthene backbone is an excellent bidentate ligand in Ru-catalyzed 2-propanol-based transfer hydrogenation of aryl/alkyl and alkyl/alkyl ketones (ee = 76-99%). Even notoriously difficult ketones such as isopropyl methyl ketone are reduced with extraordinarily high enantioselectivity

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service