Important pharmaceutical intermediates Preparation Uses
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Homopiperazine

Important pharmaceutical intermediates Preparation Uses
Product Name
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
Formula Weight
100.16
MOL File
505-66-8.mol
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Homopiperazine Property

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)
pka
11.02±0.20(Predicted)
form 
Crystalline Mass
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)
NIST Chemistry Reference
Homopiperazine(505-66-8)
EPA Substance Registry System
1H-1,4-Diazepine, hexahydro- (505-66-8)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H311Toxic in contact with skin

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H16604
Product name
Homopiperazine
Purity
98%
Packaging
25g
Price
$104
Updated
2024/03/01
TCI Chemical
Product number
H0572
Product name
Homopiperazine
Purity
>98.0%(GC)(T)
Packaging
25g
Price
$135
Updated
2024/03/01
Alfa Aesar
Product number
A15751
Product name
Homopiperazine, 98%
Packaging
25g
Price
$119
Updated
2024/03/01
Alfa Aesar
Product number
A15751
Product name
Homopiperazine, 98%
Packaging
100g
Price
$330
Updated
2024/03/01
Alfa Aesar
Product number
A15751
Product name
Homopiperazine, 98%
Packaging
500g
Price
$682.5
Updated
2023/01/06
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Homopiperazine Chemical Properties,Usage,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.

Homopiperazine Preparation Products And Raw materials

Raw materials

Sodium hydride Ammonium hydroxide Ethylenediamine Oxamide tert-Butyl methyl ether N,N-Dimethylformamide Potassium hydroxide Acetone Sodium sulfate Toluene Benzyltriethylammonium bromide Phenol Potassium carbonate Nickel Sodium Sodium borohydride Triethylamine 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE Chloroform N,N'-Bis(ethylene)-p-Toluenesulfonamide Sulfurous Acid 1,3-Dibromopropane Tosyl chloride Malonaldehyde bis(diethyl acetal) Hydrogen bromide Tetrahydrofuran Diethyl ether Ethyl acetate Hydrochloric acid Sodium bicarbonate Hydrogen Dichloromethane 1,3-Diaminopropane Acetic acid Methanol Phosphorus tribromide 1-Butanol Tetraoctylammonium bromide Sulfuric acid Ammonia

Preparation Products

1-BENZYL-1,4-DIAZEPANE 1-(4-FLUOROBENZYL)-1,4-DIAZEPANE N-ACETYLHOMOPIPERAZINE ethyl 1,4-diazepane-1-carboxylate 1-Formylhomopiperazine 1-(2-PHENYLETHYL)HOMOPIPERAZINE 1-Boc-hexahydro-1,4-diazepine Benzyl 1-homopiperazine carboxylate
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Homopiperazine Suppliers

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Pure Chemistry Scientific Inc.
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View Lastest Price from Homopiperazine manufacturers

Hebei Dangtong Import and export Co LTD
Product
Homopiperazine 505-66-8
Price
US $100.00-60.00/Grams
Min. Order
100Grams
Purity
99.99%
Supply Ability
100Tons
Release date
2023-03-06
Hebei Chuanghai Biotechnology Co,.LTD
Product
Homopiperazine 505-66-8
Price
US $5.00-2.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-21
Hebei Ganmiao New material Technology Co., LTD
Product
Homopiperazine 505-66-8
Price
US $10.00-7.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
20ton
Release date
2024-06-06

505-66-8, HomopiperazineRelated Search:

N-(3-HYDROXYPROPYL)ETHYLENEDIAMINE Isoquinoline 1-(p-Toluenesulfonyl)hoMopiperazine, 95% 1,4-ditosyl-1,4-diazepane Fasudil diMer Fasudil Impurity 17 H-9 2HCL N,N'-Bis(ethylene)-p-Toluenesulfonamide Fasudil IMpurity 1 Fasudil Impurity 1 HCl 2 QUINOLINE-8-SULFONIC ACID Fasudil Impurity 18 5-Isoquinolinesulfonic acid Fasudil IMpurity 2 (Isoquinoline-8-sulfonic acid) Fasudil Impurity 19 Fasudil Impurity 21 Fasudil Impurity 24 Fasudil Impurity 10

  • 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
  • Homopiperazine, 99%, extra pure
  • Homopiperazine in stock Factory
  • 1,4-DIAZACYCLOHEPTANE
  • 1,4-DIAZEPANE
  • 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&gt
  • Homopiperazine ISO 9001：2015 REACH
  • 505-66-8
  • 55-66-8
  • Building Blocks
  • Heterocyclic Building Blocks
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