MilliporeSigma
All Photos(1)

404438

Sigma-Aldrich

(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

98%

Sign Into View Organizational & Contract Pricing

Select a Size

Synonym(s):
(S,S)-Jacobsen’s ligand
Linear Formula:
[[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10
CAS Number:
Molecular Weight:
546.83
Beilstein:
5464823
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D +315 to 15°, c = 1 in methylene chloride

mp

203-206 °C (lit.)

SMILES string

CC(C)(C)c1cc(\C=N\[C@H]2CCCC[C@@H]2\N=C\c3cc(cc(c3O)C(C)(C)C)C(C)(C)C)c(O)c(c1)C(C)(C)C

InChI

1S/C36H54N2O2/c1-33(2,3)25-17-23(31(39)27(19-25)35(7,8)9)21-37-29-15-13-14-16-30(29)38-22-24-18-26(34(4,5)6)20-28(32(24)40)36(10,11)12/h17-22,29-30,39-40H,13-16H2,1-12H3/b37-21+,38-22+/t29-,30-/m0/s1

InChI key

FYNXDGNCEBQLGC-GTHUDTLPSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
668370474606301159
optical activity

[α]20/D +315 to 15°, c = 1 in methylene chloride

optical activity

[α]/D +50°, c = 1 in chloroform

optical activity

-

optical activity

[α]18/D +23°, c = 1 in acetic acid

mp

203-206 °C (lit.)

mp

93-102 °C

mp

>350 °C (lit.)

mp

127-130 °C (lit.)

Quality Level

100

Quality Level

400

Quality Level

200

Quality Level

200

Application

(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine is a chiral salen-type ligand used for preparing Jacobsen′s catalyst suitable for enantioselective epoxidation of olefins lacking functional groups.

Legal Information

Licensed through Research Corporation Technologies

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Chang, S. et al.
Journal of the American Chemical Society, 58, 6939-6939 (1993)
E.N. Jacobsen et al.
Journal of the American Chemical Society, 113, 7063-7063 (1991)
L. Deng et al.
The Journal of Organic Chemistry, 57, 4320-4320 (1992)

Articles

Salen Ligands

Salen Ligands: In 1990, Jacobsen and Katsuki independently published the first reports of salen used as ligands with manganese for asymmetric epoxidation reactions.

Chromatograms

application for HPLCapplication for HPLC

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