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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
Beilstein:
5279621
MDL number:
MFCD00145204
UNSPSC Code:
12352005
PubChem Substance ID:
24863894
NACRES:
NA.22

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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

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.

Disclaimer

May darken in storage.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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