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671274

Sigma-Aldrich

(R,R)-(−)-N,N′-Dimethyl-1,2-cyclohexanediamine

≥97.0% (GC)

Synonym(s):

(R,R)-(−)-N,N′-Dimethyl-1,2-diaminocyclohexane, trans-1,2-Bis(methylamino)cyclohexane

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About This Item

Empirical Formula (Hill Notation):
C8H18N2
CAS Number:
68737-65-5
Molecular Weight:
142.24
MDL number:
MFCD00671527
UNSPSC Code:
12352116
PubChem Substance ID:
24885095
NACRES:
NA.22

Assay

≥97.0% (GC)

optical activity

[α]/D -145±5°, c = 4.47 in chloroform

mp

39-44 °C

storage temp.

2-8°C

SMILES string

CN[C@@H]1CCCC[C@H]1NC

InChI

1S/C8H18N2/c1-9-7-5-3-4-6-8(7)10-2/h7-10H,3-6H2,1-2H3/t7-,8-/m1/s1

InChI key

JRHPOFJADXHYBR-HTQZYQBOSA-N

General description

(R,R)-(-)-N,N′-Dimethyl-1,2-cyclohexanediamine is a N,N′-dimethylated derivative of enantiopure 1,2-diaminocyclohexane. It can be formed during the hydrolysis of (R3a,R7a)-1,3-(dimethyl)-2-phenyl-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3,2-benzodiazaphosphole 2-oxide using HCl-methanol.

Application

(R,R)-(−)-N,N′-Dimethyl-1,2-cyclohexanediamine can be used:
  • As a ligand in the preparation of 4H-benzo[f]imidazo[1,4]diazepin-6-one through multi-component Ullmann coupling reaction.
  • In one of the key synthetic steps for the preparation of tricyclic γ-secretase modulators.
  • To prepare chiral fluorous diamino-diol proligand, which is used in the synthesis of zirconium metal complexes applicable as catalysts in 1-hexene polymerization.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

165.2 °F - closed cup

Flash Point(C)

74 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC5147V
BGBC2601V
BGBC1786V
BGBC0277V
1402754V

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Microwave-assisted synthesis of 4H-benzo [f] imidazo [1, 4] diazepin-6-ones via a post-Ugi copper-catalyzed intramolecular Ullmann coupling
Li Z, et al.
Tetrahedron Letters, 55(13), 2070-2074 (2014)
An efficient method for the synthesis of N,N'-dimethyl-1, 2-diamines.
Tye H, et al.
Tetrahedron Letters, 43(1), 155-158 (2002)
Design and optimization of tricyclic gamma-secretase modulators
Shi J, et al.
Bioorganic & Medicinal Chemistry Letters, 26(5), 1498-1502 (2016)
Chiral Fluorous Dialkoxy-Diamino Zirconium Complexes: Synthesis and Use imn Stereospecific Polymerization of 1-Hexene
Kirillov E, et al.
Chemistry?A European Journal , 13(3), 923-935 (2007)

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