(R)-(+)-2,2-Diamino-1,1-binaphthalene
(R)-(+)-2,2'-Diamino-1,1'-binaphthyl
CAS: 18741-85-0
Molecular Formula: C20H16N2
(R)-(+)-2,2-Diamino-1,1-binaphthalene - Names and Identifiers
| Name | (R)-(+)-2,2'-Diamino-1,1'-binaphthyl |
| Synonyms | (R)-BINAM (R)-(+)-1,1-Bi(2-naphthylamine) (R)-(+)-1,1-Binaphthyl-2,2-diamine (R)-(+)-2,2'-Diamino-1,1'-binaphthyl (aR)-2,2'-Diamino-1,1'-binaphthalene (aR)-1,1'-Binaphthalene-2,2'-diamine (R)-(+)-2,2-Diamino-1,1-binaphthalene [aR,(+)]-1,1'-Binaphthalene-2,2'-diamine (R)-(+)-1,1''-BINAPHTHALENE-2,2''-DIAMINE (R-BINAM) ((R)-(+) -2,2''-DIAMINO-1''1-BINAPHTHYL) (R)-(+)-1,1μ-Binaphthalene-2,2μ-diamine, (R)-(+)-2,2μ-Diamino-1,1μ-binaphthalene, (R)-(+)-DABN (R)-(+)-1,1μ-Bi(2-naphthylamine), (R)-(+)-1,1μ-Binaphthalene-2,2μ-diamine, (R)-(+)-2,2μ-Diamino-1,1μ-binaphthalene, (R)-(+)-DABN |
| CAS | 18741-85-0 |
| EINECS | 628-471-3 |
(R)-(+)-2,2-Diamino-1,1-binaphthalene - Physico-chemical Properties
| Molecular Formula | C20H16N2 |
| Molar Mass | 284.35 |
| Density | 1.0447 (rough estimate) |
| Melting Point | 242-244°C(lit.) |
| Boling Point | 416.85°C (rough estimate) |
| Specific Rotation(α) | 156 º (c=1, pyridine) |
| Water Solubility | slightly soluble |
| Appearance | off-white to brown powder |
| Color | slightly beige |
| BRN | 5279621 |
| pKa | 3.79±0.10(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.6450 (estimate) |
| MDL | MFCD00145204 |
(R)-(+)-2,2-Diamino-1,1-binaphthalene - Risk and Safety
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | DU3090000 |
| FLUKA BRAND F CODES | 10 |
| HS Code | 29215900 |
(R)-(+)-2,2-Diamino-1,1-binaphthalene - Reference Information
| introduction | chiral aromatic amine compound (R)-( )-1,1 '-bi-2-naphthylamine is an important structural unit of some natural products, biologically active compounds, materials, chiral ligands and chiral catalysts. In the field of biological activity, natural product compounds such as (-)-streptonigrin contain phenol and arylamine fragments that are chirally connected to the axis, and are connected by a special chiral aromatic amine skeleton. This unique structure makes It becomes an antibiotic with significant biological activity, so this family of compounds has a wide range of biological activities such as anti-cancer, anti-bacteria, fungi, nematodes, viruses, etc. In the field of catalysis, chiral aromatic amines have been widely used as powerful chiral ligands or auxiliaries in asymmetric synthesis. |
| application | (R)-( )-1,1 '-bi-2-naphthylamine is an important structural unit of some natural products, biologically active compounds, materials, chiral ligands and chiral catalysts, mainly used in laboratory research and development. |
| preparation | (r)-( )-1,1 '-bi-2-naphthylamine is prepared as follows: in air environment, add 1a(5mmol),2b(15mmol), potassium carbonate (15mmol), potassium iodide (0.5mmol) and dimethyl sulfoxide (40ml) as reaction solvents in a 100ml round bottom flask, put it in an oil bath pan heated to 50 ℃ in advance and stir for 24 hours. Thin layer chromatography (TLC) point plate determines the end point of the reaction. When the TLC plate shows that the reaction raw material 1a completely disappears and is completely converted into double alkylation products, the reaction tube is lifted from the oil bath pan, potassium hydroxide (60mmol) is directly added into the round bottom flask, then put into the oil bath pan heated to 150 ℃ in advance and stirred for 4 hours. After the reaction is over, the round bottom flask is cooled to room temperature, and 40ml of water is added to quench the reaction, the target product (R)-( )-1,1 '-bi-2-naphthylamine was then extracted and dried by ethyl acetate and separated by column chromatography. |
| Uses | 1,1 '-binaphthal-2, 2'-diamine derivatives have been used in asymmetric hydrogenation reactions, cyclopropanation reactions and chiral lactones Formation. |
Last Update：2024-04-09 20:52:54
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