382426

Sigma-Aldrich

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine

99%

Synonym(s):
(R)-(+)-2,2′-Diamino-1,1′-binaphthalene, (R)-(+)-1,1′-Binaphthalene-2,2′-diamine, (R)-(+)-1,1′-Bi(2-naphthylamine), (R)-(+)-DABN
Linear Formula:
H2NC10H6C10H6NH2
CAS Number:
Molecular Weight:
284.35
Beilstein/REAXYS Number:
5279621
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

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. 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.

Packaging

1 g in glass bottle

Caution

May darken in storage.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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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