4-[4-(4-Aminophenyl)-1-piperazinyl]phenol
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![4-[4-(4-Aminophenyl)-1-piperazinyl]phenol structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220811/8c254dcce8564867ba26dbe4a6f842bf.png "4-[4-(4-Aminophenyl)-1-piperazinyl]phenol")
4-[4-(4-Aminophenyl)-1-piperazinyl]phenol
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CAS No:
74853-08-0
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Formula:
C16H19N3O
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Chemical Name:
4-[4-(4-Aminophenyl)-1-piperazinyl]phenol
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Synonyms:
Phenol,4-[4-(4-aminophenyl)-1-piperazinyl]-;4-[4-(4-Aminophenyl)-1-piperazinyl]phenol;1-(4-Aminophenyl)-4-(4-hydroxyphenyl)piperazine
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CAS No:
4-[4-(4-Aminophenyl)-1-piperazinyl]phenol Basic Attributes
269.34
269.34
1308068-626-2
DTXSID00436961
2933599090
Safety Information
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-[4-(4-Aminophenyl)-1-piperazinyl]phenol Use and Manufacturing
Under nitrogen, 430 g (1.34 mol) N-(4-Hydroxyphenyl)-N'-(4'-nitrophenyl)-piperazine are suspended in 2.8 liters methoxyethanol at 20° - 25° C. After the addition of 52 g palladium ((5percent on charcoal, 50percent water wet) (Degussa Typ E1049)) the suspension is degassed (3 times) and heated to 70° - 75° C. A solution of 497 g sodium hypophosphite monohydrate in 1.12 liters water is slowly added over 2 -2.5 hours at 70° - 75° C. (After addition of about 10 ml the evolution of hydrogenation starts and the temperature has to be kept at 75° - 80° C; towards the end of the addition external heating is needed). After complete addition, the reaction mixture is stirred at 70° - 75° C and the reaction is followed by TLC (silicagel, n-hexane/ethylacetate 1/2). After complete conversion (30 - 45 minutes, color turns from brown-yellow to grey) the suspension is cooled to 25° - 30° C and diluted with 2.4 liters water. The pH is adjusted to <=2 by the addition of about 400 ml concentrated HCl (about 10 minutes) at 25° to 30° C and stirred at this temperature for about 15 minutes. The catalyst is filtered off and washed with 600 ml water. The combined filtrates are warmed to 35° to 40° C and the pH is adjusted to 7.1 +/- 1 at 35° to 40° C by the addition of about 760 ml concentrated sodium hydroxide (slightly exothermic). The resulting suspension is cooled to 20° - 25° C and stirred at that temperature for 30 minutes. The product is filtered off under nitrogen (about 40 minutes) and washed twice with 1.6 liters water, followed by 400 ml water/methanol (1:1) and 800 ml methanol. The product is dried under vacuum at 50° C (slight stream of nitrogen) to constant weight. [] Yield317 g (88percent)Assay (HPLC)99.7percent pure by area
Computed Properties
Molecular Weight:269.34
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:269.152812238
Monoisotopic Mass:269.152812238
Topological Polar Surface Area:52.7
Heavy Atom Count:20
Complexity:288
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-[4-(4-Aminophenyl)-1-piperazinyl]phenol
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