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Sigma-Aldrich

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine

99%

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Synonym(s):
(R)-(+)-1,1′-Bi(2-naphthylamine), (R)-(+)-1,1′-Binaphthalene-2,2′-diamine, (R)-(+)-2,2′-Diamino-1,1′-binaphthalene, (R)-(+)-DABN
Linear Formula:
H2NC10H6C10H6NH2
CAS Number:
Molecular Weight:
284.35
Beilstein/REAXYS Number:
5279621
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

optical activity

[α]20/D +157°, c = 1 in pyridine

optical purity

ee: 99% (HPLC)

mp

242-244 °C (lit.)

SMILES string

Nc1ccc2ccccc2c1-c3c(N)ccc4ccccc34

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

InChI key

DDAPSNKEOHDLKB-UHFFFAOYSA-N

Related Categories

General description

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine is an axially dissymmetric binaphthyl ligand mainly used in enantioselective catalysis.

Application

1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations, cyclopropanations, and formation of chiral lactones.
1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations, cyclopropanations, and formation of chiral lactones. Its chiral sulphonamide, chiral diphenylphosphoramide and chiral diphenylthiophosphoramide derivatives are useful ligands for asymmetric addition reaction of diethylzinc to aldehydes in the presence of titanium(IV) alkoxide.

Caution

May darken in storage.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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Chem. Abstr., 123, 101213k-101213k (1995)
Trifluoromethanesulfonamide, diphenylphosphoramide and diphenylthiophosphoramide of (R)-(+)-1, 1'-binaphthyl-2, 2'-diamine as chiral catalyst ligands for the titanium (IV) alkoxide-promoted addition of diethylzinc to aldehydes.
Shi M and Sui WS.
Chirality, 12(7), 574-580 (2000)
Yamamoto, Y. et al.
The Journal of Organic Chemistry, 56, 1112-1112 (1991)
The Journal of Organic Chemistry, 56, 1112-1112 (1991)
Miyano, S.et al.
Bulletin of the Chemical Society of Japan, 57, 2171-2171 (1984)

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