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531979

Sigma-Aldrich

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

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
MDL number:
MFCD02684548
UNSPSC Code:
12352101
PubChem Substance ID:
24877851
NACRES:
NA.22

mp

>350 °C (lit.)

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

Related Categories

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

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

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

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’.

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Sigma-Aldrich

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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)
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
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.

Articles

Salen Ligands

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

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