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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.

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Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

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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Sigma-Aldrich

416932

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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

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

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