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Merck
CN

382426

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine

99%

Synonym(s):

(R)-(+)-1,1′-Bi(2-naphthylamine), (R)-(+)-1,1′-Binaphthalene-2,2′-diamine, (R)-(+)-2,2′-Diamino-1,1′-binaphthalene, (R)-(+)-DABN

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About This Item

Linear Formula:
H2NC10H6C10H6NH2
CAS Number:
18741-85-0
Molecular Weight:
284.35
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24863894
MDL number:
MFCD00145204
Beilstein/REAXYS Number:
5279621

Key Documents

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Product Name

(R)-(+)-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

Disclaimer

May darken in storage.

Application

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.
1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations, cyclopropanations, and formation of chiral lactones.

General description

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

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
BCBB0981
BCBB0981V
07307HH
049313/3
10404AH

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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)
Miyano, S.et al.
Bulletin of the Chemical Society of Japan, 57, 2171-2171 (1984)
Yamamoto, Y. et al.
The Journal of Organic Chemistry, 56, 1112-1112 (1991)
Chem. Abstr., 123, 101213k-101213k (1995)
Chen, G.-M. et al.
Gaodeng Xuexiao Huaxue Xuebao, 16, 216-216 (1995)
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