(S)-(+)-2-Methylpiperazine Chemical Properties

Melting point:

91-93 °C(lit.)

Boiling point:

155-156 °C

alpha 

13.5 º (c=1, toluene)

Density 

0.9305 (estimate)

refractive index 

1.4378 (estimate)

Flash point:

149 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Crystalline Powder, Crystals and/or Chunks

pka

9.31±0.40(Predicted)

color 

White to yellow

optical activity

[α]20/D +6.8°, c = 1 in ethanol

Water Solubility 

soluble

Sensitive 

Air Sensitive & Hygroscopic

BRN 

3647995

InChIKey

JOMNTHCQHJPVAZ-YFKPBYRVSA-N

CAS DataBase Reference

74879-18-8(CAS DataBase Reference)

Safety Information

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

MSDS

• Language:English Provider:(S)-(+)-2-Methylpiperazine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(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

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