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Merck
CN

382434

(S)-(−)-1,1′-Binaphthyl-2,2′-diamine

99%

Synonym(s):

(S)-(−)-1,1′-Bi(2-naphthylamine), (S)-(−)-1,1′-Binaphthalene-2,2′-diamine, (S)-(−)-2,2′-Diamino-1,1′-binaphthalene, (S)-(−)-DABN

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About This Item

Linear Formula:
H2NC10H6C10H6NH2
CAS Number:
18531-95-8
Molecular Weight:
284.35
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24863896
MDL number:
MFCD00145204
Beilstein/REAXYS Number:
2419071

Key Documents

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Product Name

(S)-(−)-1,1′-Binaphthyl-2,2′-diamine, 99%

InChI

1S/C20H16N2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12H,21-22H2

SMILES string

Nc1ccc2ccccc2c1-c3c(N)ccc4ccccc34

InChI key

DDAPSNKEOHDLKB-UHFFFAOYSA-N

assay

99%

optical activity

[α]20/D −157°, c = 1 in pyridine

optical purity

ee: 99% (HPLC)

mp

242-244 °C (lit.)

Quality Level

200

Related Categories

Application

(S)-(-)-1,1′-Binaphthyl-2,2′-diamine may be used in the synthesis of (S)-(+)-N,N′-dimethyl-N,N′-bis{3-[bis-(1-methyl-2-benzimidazolyl methyl)]-amino]-propyl}-1,1′-binaphthyl-2,2′-diamine, an octadentate ligand that can form dinuclear and trinuclear copper(II) complexes. It may also be used in the synthesis of (Sa)-N-[2´-amino-(1,1´-binaphthyl)-2-yl]-4-methylbenzenesulfonamide.
Used in the synthesis of chiral lactones.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBB0982
BCBB0982V
02907CH
010467/1
10827CE

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Models for biological trinuclear copper clusters. Characterization and enantioselective catalytic oxidation of catechols by the copper (II) complexes of a chiral ligand derived from (S)-(-)-1, 1'-binaphthyl-2, 2'-diamine.
Mimmi MC, et al.
Dalton Transactions, 14, 2192-2201 (2004)
(Sa, S)-N-[2'-(4-Methylphenylsulfonamido)-1, 1'-Binaphthyl-2-Yl] Pyrrolidine-2-Carboxamide: An Organocatalyst for the Direct Aldol Reaction.
Vizoquez SF, et al.
Organic Syntheses, 317-329 (2012)
The Journal of Organic Chemistry, 56, 1112-1112 (1991)

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