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713694

Sigma-Aldrich

(S)-(−)-2′-Amino-1,1′-binaphthalen-2-ol

97%

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Synonym(s):
(S)-(−)-2-Amino-2′-hydroxy-1,1′-binaphthalene, (S)-NOBIN
Empirical Formula (Hill Notation):
C20H15NO
CAS Number:
137848-29-4
Molecular Weight:
285.34
MDL number:
MFCD01882346
UNSPSC Code:
12352005
PubChem Substance ID:
329763211
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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Application

(S)-(-)-2′-Amino-1,1′-binaphthalen-2-ol or (S)-NOBIN, is a non-symmetrically substituted 1,1′-binaphthalene ligand. It can be used as a catalyst in the asymmetric synthesis of unnatural α-alkyl amino acids by phase-transfer catalysis (PTC). (S)-NOBIN can also be employed as starting material to prepare N-monoalkyl and N,N-dialkyl (S)-NOBIN analogs by reacting with aldehydes via reductive amination reaction. N-monoaryl derivatives are obtained from NOBIN via Hartwig−Buchwald arylation reaction.

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)

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2?-Amino-[1, 1?-binaphthalen]-2-ol
Kocovsky P
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)

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