N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide

Basic Information

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CAS Number

172138-95-3

Molecular Formula

C18H20N4O2

Molecular Weight

324.38 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

171-176 °C

Boiling Point

663.366°C at 760 mmHg

Density

1.255

Flash Point

354.991°C

Refractive Index

1.61

Specific Rotation

+95° (c 1, CH3OH)

SMILES

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C1CCC(C(C1)NC(=O)C2=CC=CC=N2)NC(=O)C3=CC=CC=N3

InChI

InChI=1S/C18H20N4O2/c23-17(15-9-3-5-11-19-15)21-13-7-1-2-8-14(13)22-18(24)16-10-4-6-12-20-16/h3-6,9-14H,1-2,7-8H2,(H,21,23)(H,22,24)/t13-,14-/m0/s1

InChIKey

BVYFDUZVVBXFBQ-KBPBESRZSA-N

LogP

1.9475999999999993

Topological Polar Surface Area

83.98 Å²

Hydrogen Bond Donor/Acceptor

2 / 6

Complexity

403

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

(S,S)-DACH-pyridyl Trost ligand
N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide
D83188
(1R,2R)-(-)-1,2-Bis[(2-pyridinylcarbonyl)amino]cyclohexane
(S,S)-DACH-pyridyl Trost ligand, 97%
CS-W011986
(+)-N,N/'-(1S,2S)-1,2-DIAMINOCYCLOHEXANEDIYLBIS(2-PYRIDINECARBOXAMIDE)
(S,S)-DACH-pyridyl Trost ligand, 95%
J-013064
A907275
SCHEMBL7218492
(1S,2S)-N,N'-Dipicolinoyl-1,2-diaminocyclohexane
BVYFDUZVVBXFBQ-KBPBESRZSA-N
(+)-N,N'-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide),98%
AKOS015900176
(1S,2S)-1,2-Bis(2-pyridinecarboxamido)cyclohexane
C18H20N4O2
N-[(1S,2S)-2-(pyridine-2-carbonylamino)cyclohexyl]pyridine-2-carboxamide
DTXSID50431401
2-Pyridinecarboxamide, N,N'-(1S,2S)-1,2-cyclohexanediylbis-
N,N'-[(1S,2S)-Cyclohexane-1,2-diyl]di(pyridine-2-carboxamide)
172138-95-3
MFCD02684544
BS-16058
()-N,N'-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide)
2-Pyridinecarboxamide,N,N'-(1S,2S)-1,2-cyclohexanediylbis-
()-N,N’-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide)
(+)-N,N'-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide)
(1S,2S)-(+)-1,2-Bis
(1S,2S)-1,2-bis[(2-pyridyl)carbonylamino]cyclohexane
(S,S)-1,2-bis[(pyridin-2-yl)carbonylamino]cyclohexane

MDL Number

MFCD02684544

FAQ

What are the physical and chemical properties of N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide (CAS: 172138-95-3)?

N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide (CAS: 172138-95-3) is a crystalline solid with a molecular weight of approximately 274.24 g/mol. It has a high solubility in organic solvents like DMSO and DMF but is poorly soluble in water. The compound is moderately reactive, with typical amide groups being susceptible to nucleophilic substitution. It is stable under normal conditions but may decompose at elevated temperatures.

How is N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide (CAS: 172138-95-3) typically synthesized?

N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide is typically synthesized via the condensation of 2,2'-dipicolinic acid with cyclohexanedione, often catalyzed by an acid or base. The reaction involves the formation of a mixed anhydride followed by ring closure. The yield is usually high, and the method can be optimized for better selectivity and purity.

What industries use N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide (CAS: 172138-95-3)?

N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide (CAS: 172138-95-3) is used in the pharmaceutical and materials science industries. It serves as a precursor in the development of pharmaceuticals and is also utilized in the synthesis of functional polymers and as a component in sensor applications. Its versatility makes it valuable in both academic and industrial settings.

What precautions should be taken when handling N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide (CAS: 172138-95-3)?

When handling N,N'-((1S,2S)-Cyclohexane-1,2-diyl)dipicolinamide (CAS: 172138-95-3), wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work in a fume hood to minimize exposure. Store in a cool, dry place away from direct sunlight and heat sources. In case of spill, follow standard safety procedures and refer to the Material Safety Data Sheet (MSDS) for specific guidelines.