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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

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

671274-BULK:
671274-1G:
671274-VAR:

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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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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