H-D-PROLINOL
D-(-)Prolinol
CAS: 68832-13-3
Molecular Formula: C5H11NO
H-D-PROLINOL - Names and Identifiers
| Name | D-(-)Prolinol |
| Synonyms | H-D-PRO-OL D-PROLINOL D-prolinol D(-)PROLINOL H-D-PROLINOL D(-)Prolinol D-Pro-ol(oil) D-(-)Prolinol (+)-D-PROLINOL (R)-(-)-2-Hydroxymethylpyrrolidine (2R)-2-(hydroxymethyl)pyrrolidinium (R)-(-)-PyrrolidinemethanolD-Prolinol (R)-(-)-2-(Hydroxymethyl)pyrrolidine (R)-(-)-2-Pyrrolidinemethanol (R)-(-)-2-(Hydroxymethyl)pyrrolidine (R)-(-)-2-Pyrrolidinemethanol |
| CAS | 68832-13-3 |
| EINECS | 629-147-4 |
| InChI | InChI=1/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/p+1/t5-/m1/s1 |
| InChIKey | HVVNJUAVDAZWCB-RXMQYKEDSA-N |
H-D-PROLINOL - Physico-chemical Properties
| Molecular Formula | C5H11NO |
| Molar Mass | 101.15 |
| Density | 1.036g/mLat 20°C(lit.) |
| Melting Point | 75℃ |
| Boling Point | 74-76°C2mm Hg(lit.) |
| Specific Rotation(α) | -31 º (c=1, toluene) |
| Flash Point | 187°F |
| Solubility | Chloroform (Slightly), Methanol (Slightly), Toluene (Slightly) |
| Vapor Presure | 0.0423mmHg at 25°C |
| Appearance | Transparent liquid |
| Specific Gravity | 1.025 |
| Color | Clear to slightly hazy colorless to amber |
| BRN | 1523669 |
| pKa | 14.77±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,2-8°C |
| Sensitive | Air Sensitive |
| Refractive Index | n20/D 1.485 |
| MDL | MFCD00064321 |
H-D-PROLINOL - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| 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. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. S26/36 - |
| UN IDs | NA 1993 / PGIII |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 3-10-23 |
| HS Code | 29339900 |
| Hazard Note | Irritant/Air Sensitive |
| Hazard Class | IRRITANT |
H-D-PROLINOL - Reference Information
| Use | D-prolinol is a chiral amino alcohol used as a chiral resolving agent in organic synthesis. In recent years, with the rapid development of asymmetric catalytic technology, D-prolinol has become an excellent ligand for metal coordination catalysis, which is widely used in asymmetric metal alkylation reaction, Michael addition reaction, phase transfer catalysis and other important organic synthesis. |
| synthesis method | There are two main methods for the synthesis of D-prolinol:(1) indirect reduction method: D-proline was esterified, neutralized and then reduced with NaBH4. (2) Direct reduction method: D-proline was directly reduced with allih4. The former process is cumbersome, low yield (42. 6%); The latter is harsh operation, low temperature ice bath dropping, high cost, dark color. The author uses NaBH4 to add auxiliary I 2 reduction system to directly reduce D-proline to D-prolinol (see figure below), with low cost, good quality and stable process, easy to operate, easy to industrialization. |
Last Update：2024-04-09 15:16:52
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