- (S)-(+)-2-Methylpiperazine
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- $1.00 / 1kg
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2019-07-06
- CAS:74879-18-8
- Min. Order: 1kg
- Purity: As customer's need
- Supply Ability: CARA34
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| | (S)-(+)-2-Methylpiperazine Basic information |
| | (S)-(+)-2-Methylpiperazine Chemical Properties |
| Melting point | 91-93 °C(lit.) | | alpha | 13.5 º (c=1, toluene) | | Boiling point | 155-156 °C | | density | 0.9305 (estimate) | | refractive index | 1.4378 (estimate) | | Fp | 149 °F | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | pka | 9.31±0.40(Predicted) | | form | Crystalline Powder, Crystals and/or Chunks | | color | White to yellow | | Optical Rotation | [α]20/D +6.8°, c = 1 in ethanol | | Water Solubility | soluble | | Sensitive | Air Sensitive & Hygroscopic | | BRN | 3647995 | | InChI | 1S/C5H12N2/c1-5-4-6-2-3-7-5/h5-7H,2-4H2,1H3/t5-/m0/s1 | | InChIKey | JOMNTHCQHJPVAZ-YFKPBYRVSA-N | | SMILES | C[C@H]1CNCCN1 | | CAS DataBase Reference | 74879-18-8(CAS DataBase Reference) |
| Hazard Codes | F,Xi,C | | Risk Statements | 11-36/37/38-34 | | Safety Statements | 16-26-36/37/39-45-36 | | RIDADR | UN 1325 4.1/PG 2 | | WGK Germany | 3 | | RTECS | TM1225020 | | HazardClass | 4.1 | | PackingGroup | III | | HS Code | 29335990 | | Storage Class | 4.1B - Flammable solid hazardous materials | | Hazard Classifications | Eye Irrit. 2
Flam. Sol. 1
Skin Irrit. 2
STOT SE 3 |
| | (S)-(+)-2-Methylpiperazine Usage And Synthesis |
| Chemical Properties | white to yellow crystalline powder or chunks | | Uses | Valuable synthon for quinoline antibacterials. | | Synthesis | General procedure for the synthesis of (R)-(-)-2-methylpiperazine and (S)-2-methylpiperazine from 2-methylpiperazine:
1. In a 2L four-necked flask equipped with a thermometer, a vacuum stirrer and a cooling tube, 270 g (1.8 mol) of L-tartaric acid, 108 g (1.8 mol) of acetic acid and 270 g of water were added and stirred until completely dissolved.
2. add (±)-2-methylpiperazine 300 g (3.0 mol) and water 300 g. Heat to 85 °C or higher until completely dissolved.
3. cool to 68-74°C, add diastereomerically precipitated crystals of (R)-2-methylpiperazine and L-tartaric acid and age for 1 hour.
4. cooled to 12-18 °C over 5 h and filtered to obtain 440 g of wet biomass (diastereomeric salt) with a liquid content of 22.7 wt% and an optical purity of 92.3% ee.
5. 644 g of water and 440 g of the resulting crystals ((R)-2-methylpiperazine pure content = 132 g) were added to a 2L four-neck flask, followed by 162 g (2.2 mol) of calcium hydroxide, heated to 80 °C, and aged for 5 hours.
6. Cooled to 25 °C and filtered to give 586 g of crystals (mainly calcium L-tartrate) and 660 g of filtrate (containing 130 g of (R)-2-methylpiperazine).
7. The filtrate was concentrated under reduced pressure to a (R)-2-methylpiperazine concentration of 30%, 356 g of toluene was added, and the water was removed by azeotropic boiling by heating to 84-87 °C.
8. 212 g of toluene was distilled under reduced pressure, cooled to 47 °C, 0.01 g of (R)-2-methylpiperazine crystal seed was added and aged for 1 hour.
9. cooled to 5 °C, aged for 2 h, filtered and dried under vacuum to give 45 g of (R)-2-methylpiperazine crystals (chemical purity 100%, optical purity 99.5% ee).
10. For the synthesis of (S)-2-methylpiperazine, a similar procedure was used but with (S)-2-methylpiperazine as starting material, resulting in 66.8 g of (S)-2-methylpiperazine crystals (chemical purity 99.9%, optical purity 80.0%ee). | | References | [1] Patent: JP2016/37495, 2016, A. Location in patent: Paragraph 0046-0052 |
| | (S)-(+)-2-Methylpiperazine Preparation Products And Raw materials |
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