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ChemicalBook >> CAS DataBase List >>Homopiperazine

Homopiperazine

CAS No.
505-66-8
Chemical Name:
Homopiperazine
Synonyms
1,4-DIAZEPANE;HPRZ;Gao Paiqin;HOMOPIPERAZINE;hoMopiperazate;High-piperazine;Homo-Piperazines;AKOS BBS-00004278;1,4-Diazepane 97%;Homopiperazine>
CBNumber:
CB7138982
Molecular Formula:
C5H12N2
Molecular Weight:
100.16
MDL Number:
MFCD00006933
MOL File:
505-66-8.mol
MSDS File:
SDS
Last updated:2024-08-21 22:41:43

Homopiperazine Properties

Melting point 38-40 °C (lit.)
Boiling point 169 °C (lit.)
Density 0.95
refractive index 1.4378 (estimate)
Flash point 148 °F
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
form Crystalline Mass
pka 11.02±0.20(Predicted)
color White to light yellow
Water Solubility Soluble in water.
Sensitive Air Sensitive & Hygroscopic
BRN 102711
CAS DataBase Reference 505-66-8(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 95CL167W8T
NIST Chemistry Reference Homopiperazine(505-66-8)
EPA Substance Registry System 1H-1,4-Diazepine, hexahydro- (505-66-8)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS06
Signal word  Danger
Hazard statements  H311-H314
Precautionary statements  P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P361+P364
Hazard Codes  C,Xi
Risk Statements  21-34
Safety Statements  26-36/37/39-45-27
RIDADR  UN 3259 8/PG 2
WGK Germany  1
RTECS  HM3850000
F  3-10-23
Hazard Note  Irritant/Corrosive
TSCA  Yes
HazardClass  8
PackingGroup  III
HS Code  29339900
NFPA 704
1
3 1

Homopiperazine price More Price(26)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich H16604 Homopiperazine 98% 505-66-8 25g $104 2024-03-01 Buy
TCI Chemical H0572 Homopiperazine >98.0%(GC)(T) 505-66-8 25g $135 2024-03-01 Buy
Alfa Aesar A15751 Homopiperazine, 98% 505-66-8 25g $119 2024-03-01 Buy
Alfa Aesar A15751 Homopiperazine, 98% 505-66-8 100g $330 2024-03-01 Buy
Alfa Aesar A15751 Homopiperazine, 98% 505-66-8 500g $682.5 2023-01-06 Buy
Product number Packaging Price Buy
H16604 25g $104 Buy
H0572 25g $135 Buy
A15751 25g $119 Buy
A15751 100g $330 Buy
A15751 500g $682.5 Buy

Homopiperazine Chemical Properties,Uses,Production

Important pharmaceutical intermediates

Homopiperazine is a nitrogen-containing seven-membered ring hetero-atomic compound and is an important pharmaceutical intermediate. The majority of its derivatives has strong biological activity and medicinal value and can be used for synthesizing homopiperazine hydrochloride, cyclizine, carbamazepine, chlorcyclizine and other drugs. Western medicine often takes homopiperazine as raw material for the modified quinoline and isoquinoline derivatives, quinolone derivative, thiazolidine carboxylic acid amide derivatives and other drugs, and for the synthesis of pyridazine, nitroxyl-containing benzylamine derivatives, water-soluble azole and other drugs which has good efficacy for the treatment of cardiovascular disease, interstitial plasma cell pneumonia especially for AIDS patients with Pneumocystis pneumonia, asthma, central nervous system disorders including depression and anxiety disorders. For example, 1-(5-isoquinoline-sulfonyl) homopiperazine hydrochloride is effective in the treatment of symptoms such as chronic angina disease, vitiligo, depression, anxiety, cerebral vasospasm and cerebral vasospasm caused cerebral ischemia and other symptoms.
Homopiperazine and its high-piperazine derivatives have become important pharmaceutical intermediates and have exhibited great potential of being sedative, anti-psychotic, anti-inflammatory and anti-neurotic and is an important product of a connecting link between the proceeding and the following in the chemical industry and pharmaceutical industry and have been widely applied to the pharmaceuticals, pesticides, surfactants, energetic materials and other fields.
Currently the domestic heterocyclic compounds are mainly used for producing the quinolone antibacterial drugs. This drug, through inhibiting the bacterial DNA gyrase, blocks the DNA replication and produces the antimicrobial effects. According to the report of ARMIGER H et al, after using homopiperazine as substitute of piperazine for the synthesis of drugs like cyclizine, homo-chlorcyclizine and other drugs, animal experiments had demonstrated that the activity of antihistamine drugs had been significantly enhanced. Its main products include quinoline and isoquinoline derivatives, quinolone derivative, thiazolidine carboxylic acid amide derivatives and other drugs, as well as the synthesis of disubstituted pyridazine, the nitroxyl-containing benzyl amine derivatives and water-soluble azole drug.
The derivative of homopiperazine molecule with the hydrogen atom in the amino group being substituted by long-chain alkyl or alkoxy can be used as wetting agents, emulsifying agents, detergents, coloring agents; homopiperazine and its derivatives, because of containing staining keratin filament, can be used as oxidation coloring agents and have vibrant colors and high solidness properties. It plays an important role in the dyeing, especially in the dyeing of human hair.
Polymers containing homopiperazine monomer have many unique properties such as being able to improve the melting point and improve their solubility. Resin and synthetic fiber containing such a polymer have been applied to a variety of special fields.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Preparation

Homopiperazine can be synthesized using amino compounds such as N-(2-cyanoethyl)-ethylenediamine, N-(β-hydroxy)-1,3-propanediamine, ethylenediamine as raw material so that homopiperazine has various kinds of synthetic routes according to different raw materials.
With the development of China's petrochemical industry, for the synthesis of the starting raw material of homopiperazine, alcohols and ethylene diamine, it not only has low price but also can get high-quality product as well as extremely abundant source. Currently, though there are homopiperazine domestic manufacturers, but the technology is lagged behind, the quality is not high and the production output is limited, all the above points are in urgent need for being transformed and improved. From this perspective, it is imperative for accelerating the process of development of fine chemical products of homopiperazine with a wide range of application. Therefore, the market prospect of the homopiperazine is very broad.
Using ethylenediamine as the raw material: the method uses the easily available ethylenediamine as the initial raw material, further goes through sulfonylation, cyclization, de-sulfonylation, 3-step reaction for synthesizing homopiperazine with the total yield being 78%. Within this synthetic method, during the first step of ethylenediamine sulfonylation, the addition of a phase transfer catalyst can significantly improve the product yield with the yield being 86%. During the second step of cyclization reaction, selection of NaH/ DMF reaction system can enable the completion of the cyclization reaction under milder reaction conditions. Finally, under HBr/HAc/PhOH reaction conditions, remove the sulfonyl group with a yield being 91% to give the final product homopiperazine. The results indicate that it is an excellent homopiperazine synthesis route of various kinds of advantages including easily available raw materials, simple operation and high yield with certain prospects for industrial application.

Uses

It can be used as organic and pharmaceutical synthesis intermediates, for example, being applied to the synthesis of fasudil hydrochloride.
Homopiperazine acts as a corrosion inhibitor for iron. It has also been used in the preparation of potent H3 receptor antagonists for use as treatments for neurodegenerative conditions such as Alzheimer disease.

Chemical Properties

white to light yellow crystalline mass

Uses

pharmaceutical intermediate

Uses

Homopiperazine is used to prepare 1,4-bis-(2-thiazolyl)-1,4-diazacycloheptane by reacting with 2-bromo-thiazole. It acts as an intermediate for repaglinide and fasudil hydrochloride. It is also used in the preparation of potent H3 receptor antagonists, which is used for the treatment of neurodegenerative conditions. Further, it is used in vesicant, cosmetic, emulsifier and energetic material. It acts as a corrosion inhibitor for iron. In pharmaceuticals, it is employed as antipyretic and reducing blood sugar, adiposity, calm, antipsychotic and anti-nervous.

structure and hydrogen bonding

The conformation of Homopiperazine is shown below, and the N–C–C–N torsion angle of 58.2(4)° confirms that the left-hand end of the molecule has an almost ideal chair-type conformation, which is only slightly distorted by the insertion of the extra atom at the right-hand end. The two nitrogen lone pairs are aligned in opposite directions, which facilitates the formation of a hydrogen-bonded network due to interaction with the NH of adjacent molecules.    Crystal data for C5H12N2, M = 100.16 g mol-1, colorless prism, crystal dimensions 0.10 × 0.10 × 0.10 mm3, tetragonal, space group I–42d (No. 122), a = b = 7.208(2), c = 23.094(7) Å, α = β = γ = 90.00°, V = 1199.9(6) Å3, Z = 8, Dcalc = 1.109 g cm-3, T = 93 K, R1 = 0.0637, Rw2 = 0.1633 for 536 reflections with I > 2σ(I), and 37 variables, Rint 0.0374, goodness of fit on F2 1.137. Data have been deposited at the Cambridge Crystallographic Data Centre as CCDC 2049324[1].

References

[1] R. Aitken, A. Slawin, Dheirya K. Sonecha. “Homopiperazine (Hexahydro-1,4-diazepine).” Molbank 2021 1 (2021): M1200.

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View Lastest Price from Homopiperazine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Homopiperazine pictures 2024-10-24 Homopiperazine
505-66-8
 US $100.00-60.00 / Grams 100Grams 99.99% 100Tons Hebei Dangtong Import and export Co LTD
Homopiperazine pictures 2024-10-11 Homopiperazine
505-66-8
 US $5.00-2.00 / KG 1KG 99% 10000kg Hebei Chuanghai Biotechnology Co,.LTD
Homopiperazine pictures 2024-08-20 Homopiperazine
505-66-8
 US $10.00-7.00 / kg 1kg 98% 20ton Hebei Ganmiao New material Technology Co., LTD
  • Homopiperazine pictures
  • Homopiperazine
    505-66-8
  • US $100.00-60.00 / Grams
  • 99.99%
  • Hebei Dangtong Import and export Co LTD
  • Homopiperazine pictures
  • Homopiperazine
    505-66-8
  • US $5.00-2.00 / KG
  • 99%
  • Hebei Chuanghai Biotechnology Co,.LTD
  • Homopiperazine pictures
  • Homopiperazine
    505-66-8
  • US $10.00-7.00 / kg
  • 98%
  • Hebei Ganmiao New material Technology Co., LTD
1H-1,4-Diazepine, hexahydro- hexahydro-1h-4-diazepine Trimethyleneethylenediamine HEXAHYDRO-1,4-DIAZEPINE HEXAHYDRO-1H-1,4-DIAZEPINE HOMOPIPERAZINE HPRZ AKOS BBS-00004278 2,3,4,5,6,7-HEXAHYDRO-1H-1,4-DIAZEPINE 1,4-PERHYDRODIAZEPINE Gao Paiqin 1,4-DIAZACYCLOHEPTANE PERHYDRO-1,4-DIAZEPINE TIMTEC-BB SBB004367 HOJNEYSUCKLEEXTRACT 1,4-Diazacycloheptane, 2,3,4,5,6,7-Hexahydro-1H-1,4-diazepine 1,4-Diazacycloheptane~Hexahydro-1,4-diazepine Homopiperazine,98% [1H]-1,4-Azepine, hexahydro Homopiperazine 97% HOMOPIPERAZINE / 1,4-DIAZACYCLOHEPTANE HEXAHYDRO-1H-4-DIAZEPINE/HOMOPIPERAZINE 3,7-Diazacycloheptane Homopiperazine ,99% Homopiperazine,1,4-Diazacycloheptane, 2,3,4,5,6,7-Hexahydro-1H-1,4-diazepine Homopiperazine 1g [505-66-8] Homo-Piperazines High-piperazine HoMopiperazine, 98% 100GR hoMopiperazate 1,4-Diazepane 97% 1,4-DIAZACYCLOHEPTANE 1,4-DIAZEPANE 1,4-PERHYDRODIAZEPINE 2,3,4,5,6,7-HEXAHYDRO-1H-1,4-DIAZEPINE AKOS BBS-00004278 HEXAHYDRO-1,4-DIAZEPINE HEXAHYDRO-1H-1,4-DIAZEPINE HOMOPIPERAZINE HPRZ PERHYDRO-1,4-DIAZEPINE TIMTEC-BB SBB004367 HoMopiperazine, extra pure Homopiperazine, 99%, extra pure Homopiperazine in stock Factory Homopiperazine> Homopiperazine ISO 9001：2015 REACH 1,4-DIAZEPANE 505-66-8 55-66-8 Building Blocks Heterocyclic Building Blocks Piperazines Building Blocks C4 to C8 Chemical Synthesis Heterocyclic Building Blocks Piperazines chemical additive Piperaizine Pharmaceutical intermediate