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505-66-8

505-66-8 Structure

505-66-8 Structure
IdentificationMore
[Name]

HOMOPIPERAZINE
[CAS]

505-66-8
[Synonyms]

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
1H-1,4-Diazepine, hexahydro-
hexahydro-1h-4-diazepine
Trimethyleneethylenediamine
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
[EINECS(EC#)]

208-016-1
[Molecular Formula]

C5H12N2
[MDL Number]

MFCD00006933
[Molecular Weight]

100.16
[MOL File]

505-66-8.mol
Chemical PropertiesBack Directory
[Appearance]

white to light yellow crystalline mass
[mp ]

38-40 °C(lit.)
[bp ]

169 °C(lit.)
[Fp ]

148 °F
[Sensitive ]

Air Sensitive & Hygroscopic
[Detection Methods]

GC,NMR
[Detection Methods]

GC,NMR,MS
[BRN ]

102711
[CAS DataBase Reference]

505-66-8(CAS DataBase Reference)
[NIST Chemistry Reference]

Homopiperazine(505-66-8)
[Storage Precautions]

Air sensitive;Store under nitrogen
[Storage Precautions]

Moisture sensitive;Air sensitive
[EPA Substance Registry System]

505-66-8(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

C,Xi
[Risk Statements ]

R21:Harmful in contact with skin.
R34:Causes burns.
[Safety Statements ]

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) .
S27:Take off immediately all contaminated clothing .
[RIDADR ]

UN 3259 8/PG 2
[WGK Germany ]

1
[RTECS ]

HM3850000
[F ]

3-10-23
[Hazard Note ]

Irritant/Corrosive
[HazardClass ]

8
[PackingGroup ]

III
[HS Code ]

29339900
Raw materials And Preparation ProductsBack Directory
[Raw materials]

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

1-Boc-hexahydro-1,4-diazepine-->1-BENZYL-1,4-DIAZEPANE-->1-(4-FLUOROBENZYL)-1,4-DIAZEPANE-->BENZYL 1-HOMOPIPERAZINECARBOXYLATE-->N-ACETYLHOMOPIPERAZINE-->1-Formylhomopiperazine-->ethyl 1,4-diazepane-1-carboxylate-->1-(2-PHENYLETHYL)HOMOPIPERAZINE
Questions And AnswerBack Directory
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

HOMOPIPERAZINE(505-66-8)IR1
HOMOPIPERAZINE(505-66-8)IR2
HOMOPIPERAZINE(505-66-8)IR3
HOMOPIPERAZINE(505-66-8)13CNMR
HOMOPIPERAZINE(505-66-8)1HNMR
HOMOPIPERAZINE(505-66-8)MS
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Homopiperazine, 98%(505-66-8)
[Alfa Aesar]

Homopiperazine, 98%(505-66-8)
[Sigma Aldrich]

505-66-8(sigmaaldrich)
[TCI AMERICA]

Homopiperazine,>98.0%(GC)(505-66-8)
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Tags:505-66-8 Related Product Information
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