Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

682985

Sigma-Aldrich

(11bS, 11′bS)-4,4′-(Oxydi-2,1-phenylene)bis-dinaphtho[2,1-d: 1′, 2′-f][1,3,2]dioxaphosphepin

Synonym(s):

S, S-Reetz D-Diphosphonite

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

About This Item

Empirical Formula (Hill Notation):
C52H32O5P
CAS Number:
898830-89-2
Molecular Weight:
767.78
MDL number:
MFCD09842741
UNSPSC Code:
12352005
PubChem Substance ID:
329760785
NACRES:
NA.22

form

solid

optical activity

[α]22/D -85.0°, c = 1 in chloroform

mp

174-186 °C

SMILES string

O1P(Oc2ccc3ccccc3c2-c4c1ccc5ccccc45)c6ccccc6Oc7ccccc7P8Oc9ccc%10ccccc%10c9-c%11c(O8)ccc%12ccccc%11%12

InChI

1S/C52H32O5P2/c1-5-17-37-33(13-1)25-29-43-49(37)50-38-18-6-2-14-34(38)26-30-44(50)55-58(54-43)47-23-11-9-21-41(47)53-42-22-10-12-24-48(42)59-56-45-31-27-35-15-3-7-19-39(35)51(45)52-40-20-8-4-16-36(40)28-32-46(52)57-59/h1-32H

InChI key

UYGCVTAJLJBNHG-UHFFFAOYSA-N

Application

This diphosphonite ligand has been successfully employed in asymmetric Rh-catalyzed conjugate addition reactions of arylboronic acids to enones, as well as in asymmetric hydrogenation reactions of β-keto esters.

Signal Word

Danger

Hazard Statements

H228,H315,H336,H361,H373

Hazard Classifications

Flam. Sol. 1 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 Inhalation - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

682985-VAR:
682985-BULK:
682985-100MG:4548173286471
682985-500MG:4548173286488

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
04515PH
03212HH

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

Reetz, M. T.; Li, X.
Advanced Synthesis & Catalysis, 348, 1157-1157 (2006)
M T Reetz et al.
Organic letters, 3(25), 4083-4085 (2001-12-12)
[reaction: see text] BINOL-based diphosphonites having achiral backbones are useful ligands in the Rh-catalyzed conjugate addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds. The nature of the achiral backbone determines the direction and degree of enantioselectivity, with er values of

Protocols

Testing Food for Fipronil Contamination

Test your food for fipronil contamination using our analytical standards, certified reference materials, solvents, and columns for analysis.

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