All Photos(1)

Documents

382426

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine

Name: (<I>R</I>)-(+)-1,1′-Binaphthyl-2,2′-diamine
Brand: ALDRICH

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

Sign Into View Organizational & Contract Pricing

All Photos(1)

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

Quality Level

200

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

Chiral Catalysts & Ligands

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

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Chem. Abstr., 123, 101213k-101213k (1995)

Yamamoto, Y. et al.

The Journal of Organic Chemistry, 56, 1112-1112 (1991)

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)

Chen, G.-M. et al.

Gaodeng Xuexiao Huaxue Xuebao, 16, 216-216 (1995)