Key Documents

531979

(S,S)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminoaluminum chloride

Name: (S,S)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminoaluminum chloride
Brand: ALDRICH

Synonym(s):

(S,S)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminoaluminum(III) chloride

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About This Item

Empirical Formula (Hill Notation):

C₃₆H₅₂AlClN₂O₂

CAS Number:

307926-51-8

Molecular Weight:

607.24

NACRES:

NA.22

PubChem Substance ID:

24877851

UNSPSC Code:

12352101

MDL number:

MFCD02684548

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Properties

mp

>350 °C (lit.)

Quality Level

100

SMILES string

CC(C)(C)c1cc2\C=N\[C@H]3CCCC[C@@H]3\N=C\c4cc(cc(c4O[Al](Cl)Oc2c(c1)C(C)(C)C)C(C)(C)C)C(C)(C)C

InChI

1S/C36H54N2O2.Al.ClH/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;;1H/q;+3;/p-3/b37-21+,38-22+;;/t29-,30-;;/m0../s1

InChI key

KGVBCKDZFMLRMA-RUIQGICGSA-K

Description

Application

(S,S)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminoaluminum chloride can be used as a chiral catalyst:

In the preparation of substituted hydroxyalkyl aminooxazole derivatives by reacting isocyanides with aldehydes.
In the cyanation of α,β-unsaturated imides to yield saturated imides.

Legal Information

Sold under license from Sterling Pharma Solutions Limited.

pictograms

GHS07

signalword

Warning

hcodes

H302 + H312 + H332

pcodes

P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

04718JI

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Articles

Salen Ligands

The first reports of salen used as ligands with manganese for asymmetric epoxidation reactions.

Salen配体

Salen配体：Jacobsen和Katsuki在1990年分别发表了第一篇关于salen作为锰的配体用于不对称环氧化反应的报道。

Cooperative dual catalysis: application to the highly enantioselective conjugate cyanation of unsaturated imides.

Glenn M Sammis et al.

Journal of the American Chemical Society, 126(32), 9928-9929 (2004-08-12)

Cooperative heterobimetallic catalysis was used as a design principle to achieve a highly reactive system for the enantioselective conjugate addition of cyanide to alpha,beta-unsaturated imides. A dual-catalyst pathway involving chiral (salen)Al complex 1b and chiral (pybox)Er complex 4b provides measurable

Highly enantioselective, catalytic conjugate addition of cyanide to alpha, beta-unsaturated imides

Sammis GM and Jacobsen EN

Journal of the American Chemical Society, 125(15), 4442-4443 (2003)

Chiral salen-aluminum complex as a catalyst for enantioselective alpha-addition of isocyanides to aldehydes: asymmetric synthesis of 2-(1-hydroxyalkyl)-5-aminooxazoles.

Shi-Xin Wang et al.

Organic letters, 9(18), 3615-3618 (2007-08-10)

In the presence of a catalytic amount of (salen)Al(III)Cl complex (4e), reaction between alpha-isocyanoacetamides (1) and aldehydes (2) afforded the corresponding 5-aminooxazoles (3) in good yields and enantioselectivity.

Global Trade Item Number

SKU	GTIN
531979-1G	04061826083925