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Piperazine

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Name

Piperazine

EINECS 203-808-3
CAS No. 110-85-0 Density 0.874 g/cm3
PSA 24.06000 LogP -0.16320
Solubility Soluble in water, ethanol. Insoluble in diethyl ether Melting Point 109-112 °C(lit.)
Formula C4H10N2 Boiling Point 149.324 °C at 760 mmHg
Molecular Weight 86.1368 Flash Point 49.726 °C
Transport Information UN 2579 8/PG 3 Appearance needle-like white or colorless crystals
Safety 22-26-36/37/39-45-61 Risk Codes 34-42/43-52/53
Molecular Structure Molecular Structure of 110-85-0 (1,4-Diazacyclohexane) Hazard Symbols CorrosiveC
Synonyms

1,4-Diazacyclohexane;1,4-Piperazine;Antiren;Diethylenediamine;Dispermine;Eraverm;Hexahydropyrazine;Lumbrical;Pipersol;Pyrazinehexahydride;Uvilon;Vermex;Wurmirazin;Piperazine anhydrous;

Article Data 308

Piperazine Synthetic route

111-41-1

2-(2-Aminoethylamino)ethanol

110-85-0

piperazine

Conditions
ConditionsYield
With hydrogen; sodium sulfate In 1,4-dioxane at 180℃; under 66756.7 Torr; for 6h; Reagent/catalyst; Autoclave;80.7%
With aluminum oxide; nitrogen at 400 - 450℃;
With 1,4-dioxane; nickel at 200℃;
628-87-5

iminodiacetonitrile

A

110-85-0

piperazine

B

111-40-0

1,5-diamino-3-azapentane

Conditions
ConditionsYield
With ammonia; hydrogen; potassium hydroxide In ethanol at 80℃; under 90009 Torr; Pressure; Reagent/catalyst; Solvent; Temperature; Time;A 1.03%
B 97.53%
107-21-1

ethylene glycol

A

110-85-0

piperazine

B

141-43-5

ethanolamine

Conditions
ConditionsYield
With ammonia; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 155℃; under 42754.3 Torr; for 12h; Autoclave;
With ammonia; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 180℃; under 27002.7 Torr; for 12h; Autoclave;
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 155℃; for 12h; Temperature; Inert atmosphere; Autoclave;
107-15-3

ethylenediamine

111-40-0

1,5-diamino-3-azapentane

A

110-85-0

piperazine

B

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
With ZSM-5 type zeolite In water at 370℃; pH=10; Temperature; pH-value;A 63%
B 17%
With ZSM-5 type zeolite In water at 330℃; pH=10; Temperature; pH-value;A 44%
B 56%
With ZSM-5 type zeolite with Na exchange rate of 62percent In water at 290℃; Reagent/catalyst; Temperature;
With Na-ion exchanged ZSM-5 type zeolite In water at 290 - 600℃; Gas phase;
With β-type iron silicate at 320℃; Reagent/catalyst;
107-21-1

ethylene glycol

107-15-3

ethylenediamine

110-85-0

piperazine

Conditions
ConditionsYield
With hydrogen; sodium sulfate at 210℃; under 88508.9 Torr; for 6h; Reagent/catalyst; Autoclave;70%
With 1,4-dioxane; hydrogen; nickel at 200℃; under 28 Torr;
With palladium on magnesium oxide In acetonitrile at 160℃; for 6.5h; Autoclave; Inert atmosphere;80 %Chromat.
140-31-8

aminoethylpiperazine

A

110-85-0

piperazine

B

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
With ZSM-5 type zeolite In water at 350℃;A 26%
B 53%
With water; Na-type ZSM-5(2) at 350 - 370℃;A 20.2%
B 47.7%
Na-type ZSM-5(6) at 355 - 380℃;A 18.9%
B 39.9%
4461-39-6

2-[(3-aminopropyl)amino]ethanol

110-85-0

piperazine

Conditions
ConditionsYield
With phosphorus pentachloride In tetrachloromethane at 30 - 60℃; for 20h; Inert atmosphere;90%
107-15-3

ethylenediamine

110-85-0

piperazine

Conditions
ConditionsYield
With tetralin; nickel at 150℃;
With tetralin; hydrogen; nickel at 170℃;
With monoaluminum phosphate at 400 - 430℃;
106-57-0

Glycine anhydride

110-85-0

piperazine

Conditions
ConditionsYield
With methanesulfonic acid; ruthenium(1,1,1-tris(di(3,5-dimethylphenyl)phosphinomethyl)ethane)(η4-trimethylenemethane); hydrogen In tetrahydrofuran at 180℃; under 75007.5 Torr; for 16h; Autoclave; Schlenk technique;84%
With i-Amyl alcohol; sodium
With sulfuric acid
With hydrogenchloride at 20℃;
107-21-1

ethylene glycol

A

110-85-0

piperazine

B

141-43-5

ethanolamine

C

107-15-3

ethylenediamine

Conditions
ConditionsYield
With ammonia; C28H44BNOP2Ru In toluene at 180℃; under 21002.1 Torr; for 24h; Product distribution / selectivity; Autoclave; Inert atmosphere;
With ammonia; hydrogen; chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II) In toluene at 180℃; under 49580 Torr; for 12h; Product distribution / selectivity; Autoclave; Inert atmosphere;
With ammonia; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 155℃; under 31503.2 Torr; for 12h; Autoclave;

Piperazine Consensus Reports

Reported in EPA TSCA Inventory.

Piperazine Standards and Recommendations

DOT Classification:  8; Label: Corrosive

Piperazine Specification

The Piperazine, with the CAS registry number 110-85-0, is also known as 1,4-Diazacyclohexane. It belongs to the product categories of Blocks; BuildingBlocks; Organics; Heterocycles; Isotope Labelled Compounds. Its EINECS number is 203-808-3. This chemical's molecular formula is C4H10N2 and molecular weight is 86.13. What's more, its systematic name is Piperazine. Its classification codes are: (1) Agricultural Chemical; (2)Anthelmintic; (3)Anthelmintics; (4)Anti-Infective Agents; (5)Antinematodal agents; (6)Antiparasitic Agents; (7)Drug / Therapeutic Agent; (8)Human Data; (9)Skin / Eye Irritant; (10)Unspecified / Unclassified pesticide. This chemical should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides, heat and fire. This chemical is commonly used as a pharmaceutical intermediate. It is also used in the manufacture of plastics, resins, pesticides, brake fluid and other industrial materials.

Physical properties of Piperazine are: (1)ACD/LogP: -1.171; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.41; (4)ACD/LogD (pH 7.4): -3.28; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 24.06 Å2; (13)Index of Refraction: 1.424; (14)Molar Refractivity: 25.143 cm3; (15)Molar Volume: 98.521 cm3; (16)Polarizability: 9.968×10-24cm3; (17)Surface Tension: 27.6 dyne/cm; (18)Density: 0.874 g/cm3; (19)Flash Point: 49.726 °C; (20)Enthalpy of Vaporization: 38.624 kJ/mol; (21)Boiling Point: 149.324 °C at 760 mmHg; (22)Vapour Pressure: 4.0 mmHg at 25°C.

Uses of Piperazine: it can be used to produce 1-(3-methyl-butyl)-piperazine by heating. It will need reagent triethylamine and solvent ethanol with the reaction time of 17 hours. The yield is about 62%.

Piperazine can be used to produce 1-(3-methyl-butyl)-piperazine by heating

When you are using this chemical, please be cautious about it as the following:
This chemical can cause burns. It may cause sensitisation by inhalation and skin contact. This substance is harmful to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should not breathe dust. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible). You should avoid releasing it to the environment, and you need refer to special instructions/safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: C1CNCCN1
(2)Std. InChI: InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
(3)Std. InChIKey: GLUUGHFHXGJENI-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 75mg/kg (75mg/kg) BEHAVIORAL: SLEEP

GASTROINTESTINAL: NAUSEA OR VOMITING
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 478, 1969.
mouse LC50 inhalation 5400mg/m3/2H (5400mg/m3) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: EXCITEMENT
Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 15, Pg. 116, 1979.
mouse LD50 intraperitoneal 1900mg/kg (1900mg/kg)   Progress in Biochemical Pharmacology. Vol. 1, Pg. 542, 1965.
mouse LD50 intravenous 1180mg/kg (1180mg/kg)   Drugs in Japan Vol. 6, Pg. 635, 1982.
mouse LD50 oral 600mg/kg (600mg/kg)   Bollettino Chimico Farmaceutico. Vol. 103, Pg. 414, 1964.
rabbit LD50 skin 4mL/kg (4mL/kg)   Union Carbide Data Sheet. Vol. 7/16/1965,
rat LD50 intramuscular > 2500mg/kg (2500mg/kg)   Drugs in Japan Vol. 6, Pg. 635, 1982.
rat LD50 intravenous 1340mg/kg (1340mg/kg)   Drugs in Japan Vol. 6, Pg. 635, 1982.
rat LD50 oral 1900mg/kg (1900mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: EXCITEMENT
Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 15, Pg. 116, 1979.
rat LD50 subcutaneous 3700mg/kg (3700mg/kg)   Drugs in Japan Vol. 6, Pg. 635, 1982.

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