(S)-N,N'-Dimethyl-1,1'-binaphthyldiamine

Basic Information

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CAS Number

93621-64-8

Molecular Formula

C22H20N2

Molecular Weight

312.42 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Hydrocarbons

Basic Physical Properties

SMILES

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CNC1=C(C2=CC=CC=C2C=C1)C3=C(C=CC4=CC=CC=C43)NC

InChI

InChI=1S/C22H20N2/c1-23-19-13-11-15-7-3-5-9-17(15)21(19)22-18-10-6-4-8-16(18)12-14-20(22)24-2/h3-14,23-24H,1-2H3

InChIKey

PXDKDUXMEHPNCO-UHFFFAOYSA-N

LogP

5.743400000000005

Topological Polar Surface Area

24.06 Å²

Hydrogen Bond Donor/Acceptor

2 / 2

Complexity

371

Synonyms & References

English

(+/-) -rac-N,N'-Dimethyl-1,1'-binaphthyldiamine
(S)-N,N-Dimethyl-1,1-binaphthyldiamine
SCHEMBL12787291
[1,1'-Binaphthalene]-2,2'-diamine, N,N'-dimethyl
D80895
(S)-N,N'-Dimethyl-1,1'-binaphthyldiamine, >=99.0%
MFCD10566977
(R)-N,N'-Dimethyl-1,1'-binaphthyldiamine, >=99.0%
CS-0103170
(R)-N2,N2'-dimethyl-[1,1'-binaphthalene]-2,2'-diamine
CS-0085817
(R)-N,N'-Dimethyl-1,1'-binaphthalene-2,2'-diamine
(R)-2,2'-Di(methylamino)-1,1'-binaphthalene
BS-18006
E74576
(R)-N,N'-Dimethyl-2,2'-diamino-1,1'-binaphthyl
(R)-N,N'-Dimethyl-1,1'-binaphthyldiamine
N2,N2'-DIMETHYL-[1,1'-BINAPHTHALENE]-2,2'-DIAMINE
(S)-N,N'-DIMETHYL-1,1'-BINAPHTHYLDIAMINE
N,N'-Dimethyl-1,1'-Binaphthyldiamine
SY037483
PXDKDUXMEHPNCO-UHFFFAOYSA-N
2,2 inverted exclamation mark -Di(methylamino)-1,1 inverted exclamation mark -binaphthalene
AKOS037649317
(S)-2,2 inverted exclamation mark -Di(methylamino)-1,1 inverted exclamation mark -binaphthalene
SY037481
N-methyl-1-[2-(methylamino)naphthalen-1-yl]naphthalen-2-amine
E77238
(S)-N,N'-Dimethyl-1,1'-binaphthalene-2,2'--diamine
93713-30-5
2-Naphthylamine, N-methyl-1-(2-dimethylamino-1-naphthyl)-

MDL Number

MFCD10566977

FAQ

What are the physical and chemical properties of (S)-N,N'-Dimethyl-1,1'-binaphthyldiamine (CAS: 93621-64-8)?

(S)-N,N'-Dimethyl-1,1'-binaphthyldiamine is a white crystalline solid with a molecular weight of approximately 404.4 g/mol. It has a high solubility in organic solvents such as dichloromethane and ethyl acetate, and is poorly soluble in water. This compound exhibits good stability under normal conditions but can react with strong acids and bases. It is commonly used in chiral catalysis and as a ligand in organometallic chemistry.

How is (S)-N,N'-Dimethyl-1,1'-binaphthyldiamine (CAS: 93621-64-8) typically synthesized?

(S)-N,N'-Dimethyl-1,1'-binaphthyldiamine is synthesized through a multistep process involving the coupling of 1,1'-binaphthyl with methanol in the presence of a suitable coupling reagent such as EDCI and DMAP. The reaction yields a mixture of diastereomers, which can be separated using column chromatography. Further derivatization can be achieved via alkylation or acylation reactions.

What industries use (S)-N,N'-Dimethyl-1,1'-binaphthyldiamine (CAS: 93621-64-8)?

(S)-N,N'-Dimethyl-1,1'-binaphthyldiamine is primarily used in pharmaceuticals, where it serves as a chiral ligand in asymmetric synthesis. It is also utilized in the synthesis of polymers and sensors, and as a ligand in organometallic chemistry, particularly in catalysis for the synthesis of chiral compounds.

What precautions should be taken when handling (S)-N,N'-Dimethyl-1,1'-binaphthyldiamine (CAS: 93621-64-8)?

When handling (S)-N,N'-Dimethyl-1,1'-binaphthyldiamine, it is essential to use personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work in a well-ventilated fume hood to avoid inhalation of fumes. Spills should be cleaned up using appropriate absorbent materials. Ensure proper storage in a cool, dry place away from heat and direct sunlight. Always consult the Safety Data Sheet (SDS) for detailed safety information.