Name | (S)-2'-Amino-1,1'-binaphthalen-2-ol |
Synonyms | S-Nobin (S)-(-)-Nobin S-2'-Amino-1,1'-Binaphthalen-2-Ol (S)-2'-Amino-1,1'-binaphthalen-2-ol (S)-2-Amino-2'-Hydroxy-1,1'-Binaphthyl (S)-(-)-2-AMINO-2'-HYDROXY-1 1'-BINAPHT S)-(-)-2-Amino-2'-Hydroxy-1,1'-Binaphthol 1-(2-aMinonaphthalen-1-yl)naphthalen-2-ol (S)-2-Amino-2'-Hydroxy-1,1'-Dinaphthalene S-2'-Amino-1,1'-binaphthalen-2-ol, S-NOBIN (S)-(-)-2-Amino-2'-hydroxy-1,1'-binaphthalene (S)-(-)-1-(2-Amino-1-naphthyl)-2-naphthol(S)-(-)-NOBIN(S)-(-)-2'-Amino-1,1'-binaphthalen-2-ol |
CAS | 137848-29-4 |
Molecular Formula | C20H15NO |
Molar Mass | 285.34 |
Density | 1.275 |
Melting Point | 171.0 to 175.0 °C |
Boling Point | 471.5±30.0 °C(Predicted) |
Appearance | White to light red powder or crystal |
Color | White to Light red to Green |
pKa | 8.90±0.50(Predicted) |
Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
Sensitive | Argon filling operation and storage |
MDL | MFCD01882346 |
Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R41 - Risk of serious damage to eyes |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S60 - This material and its container must be disposed of as hazardous waste. S39 - Wear eye / face protection. |
UN IDs | UN 3077 9 / PGIII |
WGK Germany | 3 |
HS Code | 29222990 |
Application prospects | (S)-( )-2-amino -2 '-hydroxy -1,1'-binaphthalene is a common chiral synthesis reagent. NOBIN(2-amino -2 '-hydroxy -1,1'-binaphthalene) is an organic molecule used for asymmetric catalysis. NOBIN is associated with BINOL(1,1 ′-li-2, 2 ′-naphthol, abbreviated as 2-amino-2'-hydroxy -1,1 ′-binaphthalene) and other analogs, with both chiral axes and scaffolds for certain chemical reactions. NOBIN is an excellent catalyst for aldol reaction, which can produce reliable products, good yields and excellent diastereoselectivity. Although the rotation of the bond around the connecting ring is limited by the hydrogen atom, the enantiomeric pure NOBIN may be racemic when heated. Many chiral catalysts or metal catalyst ligands have been synthesized using 2-amino -2 '-hydroxy -1,1'-binaphthalene, and used for Diels-Alder reactions, Aldol condensation, alkylation of carbonyl compounds, reduction of latent chiral ketones, Michael addition and asymmetric epoxidation, showing good catalytic activity and enantioselectivity, showing broad application prospects. |
preparation | since the 70 s, more and more attention has been paid to the synthesis and resolution of racemic 2-amino -2 '-hydroxy -1,1'-binaphthalene and the asymmetric synthesis of 2-amino -2 '-hydroxy -1,1'-binaphthalene. The racemate 2-amino -2 '-hydroxy -1,1'-binaphthalene is basically obtained by the oxidative coupling of 2-naphthol and 2-naphthylamine, and the optically active body is often obtained by the resolution method. There are biological and chemical methods for the resolution of such compounds. The chemical resolution method uses the characteristics of the functional group of 2-amino -2 '-hydroxy -1,1'-binaphthalene to react with photoactive reagents to obtain diastereomers, and then use their properties to purify and decompose to obtain photoactive substances. In addition, enzyme and chromatographic methods are used for resolution. The resolution of 2-amino -2 '-hydroxy -1,1'-binaphthalene has been studied and reviewed. The synthesis of 2-amino -2 '-hydroxy -1,1'-binaphthalene is almost always obtained by oxidizing 2-naphthol and 2-naphthylamine with suitable oxidants. (S)-( )-2-amino -2 '-hydroxy -1,1'-binaphthalene synthesis reaction formula is as follows: fig. 1 (S)-( )-2-amino -2 '-hydroxy -1,1'-binaphthalene synthesis reaction formula |
Uses | Various chiral synthetic reagents. |