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713708

Sigma-Aldrich

(R)-(+)-2′-Amino-1,1′-binaphthalen-2-ol

97%

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Synonym(s):
(R)-(+)-2-Amino-2′-hydroxy-1,1′-binaphthalene, (R)-NOBIN
Empirical Formula (Hill Notation):
C20H15NO
CAS Number:
137848-28-3
Molecular Weight:
285.34
MDL number:
MFCD01882346
UNSPSC Code:
12352005
PubChem Substance ID:
329763212
NACRES:
NA.22

Quality Level

100

Assay

≥96.5% (HPLC)
97%

form

crystals

optical purity

enantiomeric excess: ≥98.0%

InChI

1S/C20H15NO/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/h1-12,22H,21H2

InChI key

HIXQCPGXQVQHJP-UHFFFAOYSA-N

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General description

(R)-(+)-2′-Amino-1,1′-binaphthalen-2-ol is a non-symmetrically substituted 1,1′-binaphthalene ligand.

Application

(R)-(+)-2′-Amino-1,1′-binaphthalen-2-ol may be used as a catalyst in the asymmetric PTC (phase-transfer catalysis) synthesis of α-amino acids. (R)-NOBIN reacts with trans-azobenzene-4,4′-dicarbonyl chloride to form poly(ester-amide)s, which shows backbone light-regulated chiroptical response.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

CorrosionEnvironment
GHS05,GHS09

Signal Word

Danger

Hazard Statements

H318,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1

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’.

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Stimuli-responsive polymers. 10. Photo-regulation of optical rotations in azobenzene modified poly (ester-amide) s containing highly structured, atropisomeric backbone geometries.
Lynch JG and Jaycox GD.
Polymer, 55(16), 3564-3572 (2014)
Highly Efficient Catalytic Synthesis of a-Amino Acids under Phase-Transfer Conditions with a Novel Catalyst/Substrate Pair.
Belokon YN, et al.
Angewandte Chemie (International Edition in English), 40(10), 1948-1951 (2001)

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