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670650

Sigma-Aldrich

(1R,2R)-trans-N-Boc-1,2-cyclohexanediamine

97%

Synonym(s):

(1R)-trans-N-Boc-1,2-diaminocyclohexane

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About This Item

Empirical Formula (Hill Notation):
C11H22N2O2
CAS Number:
146504-07-6
Molecular Weight:
214.30
Beilstein:
7023564
MDL number:
MFCD08726023
UNSPSC Code:
12352108
PubChem Substance ID:
329760379
NACRES:
NA.22

Assay

≥96.5%
97%

form

solid

optical activity

[α]/D -26±2°, c = 1 in chloroform

optical purity

ee: ≥99.0%

SMILES string

CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1N

InChI

1S/C11H22N2O2/c1-11(2,3)15-10(14)13-9-7-5-4-6-8(9)12/h8-9H,4-7,12H2,1-3H3,(H,13,14)/t8-,9-/m1/s1

InChI key

AKVIZYGPJIWKOS-RKDXNWHRSA-N

Application

(1R,2R)-trans-N-Boc-1,2-cyclohexanediamine can be used as:
  • An organocatalyst in the intramolecular desymmetrization of cyclohexanones to yield 2-azabicyclo[3.3.1]nonane.
  • A starting material in the synthesis of a chiral nickel catalyst applicable for the Michael addition reaction of 1,3-dicarbonyl compounds to yield nitroalkenes.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

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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Enantioselective Desymmetrization of Prochiral Cyclohexanones by Organocatalytic Intramolecular Michael Additions to α,β-Unsaturated Esters
Gammack Y, et al.
Angewandte Chemie (International Edition in English), 54(16), 4899-4903 (2015)
Robust and Recyclable Self-Supported Chiral Nickel Catalyst for the Enantioselective Michael Addition
Bissessar D, et al.
advanced synthesis and catalysis, 358(12), 1982-1988 (2016)
Robust and Recyclable Self-Supported Chiral Nickel Catalyst for the Enantioselective Michael Addition
Bissessar D, et al.
Advanced Synthesis & Catalysis, 358(12), 1982-1988 (2016)

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