| Identification | More | [Name]
(S)-(+)-2-Methylpiperazine | [CAS]
74879-18-8 | [Synonyms]
PIPERAZINE, 2-METHYL-, (2S)-
(S)-(+)-2-METHYLPIPERAZINE
(S)-2-METHYLPIPERAZINE
S-MP
L-(+)-2-Methylpiperazine S-(+)-2-Methylpiperazine
(S)-(+)-2-Methylpiperazine,98+%
(S)-(+)-2-Methylpiperazine,99+%,ee99+%
L-(+)-2-Methylpiperazine
(S)-(+)-2-METHYLPIPERAZINE , EE 99%
(S)-(+)-2-METHYLPIPERZINE
2-(S)-METHYLPIPERAZINE
(S)-(+)-2-Mmethylpiperazine, 98% | [Molecular Formula]
C5H12N2 | [MDL Number]
MFCD00171452 | [Molecular Weight]
100.16 | [MOL File]
74879-18-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to yellow crystalline powder or chunks | [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. ]
Flammables area | [form ]
Crystalline Powder, Crystals and/or Chunks | [pka]
9.31±0.40(Predicted) | [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) | [Storage Precautions]
Heat sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
F,Xi,C | [Risk Statements ]
R11:Highly Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
R34:Causes burns. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
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 .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing . | [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 |
| Hazard Information | Back Directory | [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 |
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