Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

692794

Sigma-Aldrich

(S,S)-DACH-phenyl Trost ligand

95%

Synonym(s):

(1S,2S)-(–)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphinobenzoyl)

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

About This Item

Empirical Formula (Hill Notation):
C44H40N2O2P2
CAS Number:
169689-05-8
Molecular Weight:
690.75
MDL number:
MFCD01631274
UNSPSC Code:
12352002
PubChem Substance ID:
329761528
NACRES:
NA.06

Quality Level

100

Assay

95%

form

solid

optical activity

[α]20/D -134°, c = 1 in methanol

mp

136-142 °C

functional group

amide
phosphine

SMILES string

O=C(N[C@H]1CCCC[C@@H]1NC(=O)c2ccccc2P(c3ccccc3)c4ccccc4)c5ccccc5P(c6ccccc6)c7ccccc7

InChI

1S/C44H40N2O2P2/c47-43(37-27-13-17-31-41(37)49(33-19-5-1-6-20-33)34-21-7-2-8-22-34)45-39-29-15-16-30-40(39)46-44(48)38-28-14-18-32-42(38)50(35-23-9-3-10-24-35)36-25-11-4-12-26-36/h1-14,17-28,31-32,39-40H,15-16,29-30H2,(H,45,47)(H,46,48)/t39-,40-/m0/s1

InChI key

AXMSEDAJMGFTLR-ZAQUEYBZSA-N

Related Categories

Application

Trost Ligands for Asymmetric Allylic Alkylation
Asymmetric allylic alkylation ligand.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Legal Information

Sold in collaboration with Dr. Reddy′s Laboratories for research purposes only.

Storage Class Code

11 - Combustible Solids

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.

JAN Code

692794-250MG:
692794-BULK:
692794-VAR:
692794-1G:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCG6754
BCCC6898
BCBW0835
BCBT0134
BCBQ1549V

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

Aldrichimica Acta, 40, 59-59 (2007)
Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.
Barry M Trost et al.
Chemical reviews, 103(8), 2921-2944 (2003-08-14)
Trost, B.M. et al.
Aldrichimica Acta, 40, 59-59 (2007)
Asymmetric Transition Metal-Catalyzed Allylic Alkylations.
Barry M. Trost et al.
Chemical reviews, 96(1), 395-422 (1996-02-01)
Trost, B.M. et al.
Journal of the American Chemical Society, 124, 11616-11616 (2004)

Articles

Trost Ligands

The Trost group at Stanford University has pioneered the use of C-2 symmetric diaminocyclohexyl (DACH) ligands in AAA, allowing for the rapid synthesis of a diverse range of chiral products with a limited number of chemical transformations.

Asymmetric Allylic Alkylation

Palladium-catalyzed asymmetric allylic alkylation (AAA) has proven to be an exceptionally powerful method for the efficient construction of stereogenic centers.

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