piperazine
2-bromoethanol
A
1-(2-hydroxyethyl)piperazine
B
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water for 2.5h; pH=8.5; pH-value; Reagent/catalyst; Inert atmosphere; | A 86.2% B n/a |
Conditions | Yield |
---|---|
With hydrogen at 180 - 200℃; under 60006 Torr; for 10h; Product distribution / selectivity; Autoclave; Inert atmosphere; | 79% |
With water at 150℃; under 26478.3 Torr; Anfangsdruck, unter CO2; | |
With phosphoric acid at 250℃; unter CO2; |
1-(2-hydroxyethyl)piperazine
2-bromoethanol
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In acetonitrile for 18h; Reflux; Inert atmosphere; | 45% |
ethanolamine
A
1-(2-hydroxyethyl)piperazine
B
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In water at 140℃; for 96h; Inert atmosphere; Heating; | A 30% B 27% |
oxirane
piperazine
A
1-(2-hydroxyethyl)piperazine
B
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With methanol | |
With methanol |
Conditions | Yield |
---|---|
With methanol | |
Yield given; |
Conditions | Yield |
---|---|
at 105℃; | |
With ethanol |
phenylacetonitrile
2,2'-iminobis[ethanol]
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
auf Siedetemperatur; |
Conditions | Yield |
---|---|
With sodium carbonate; ethylene dibromide |
Conditions | Yield |
---|---|
With water |
2-Spirocyclohexyl-3-(β-hydroxyethyl)oxazolidine
A
1,4-bis(2-hydroxyethyl)piperazine
B
cyclohexanone
Conditions | Yield |
---|---|
With PPA at 200℃; for 10h; Product distribution; |
Conditions | Yield |
---|---|
at 250 - 275℃; unter Druck; |
benzonitrile
2,2'-iminobis[ethanol]
A
1,4-bis(2-hydroxyethyl)piperazine
B
ammonia
C
benzoic acid
Conditions | Yield |
---|---|
die Umsetzung mit Benzylcyanid verlaeuft analog; |
Conditions | Yield |
---|---|
In acetone |
Conditions | Yield |
---|---|
In acetone |
Conditions | Yield |
---|---|
With disodium hydrogenphosphate In water at 120℃; Large scale; |
Conditions | Yield |
---|---|
With ytterbium(III) triflate at 180℃; for 25h; Reagent/catalyst; |
carbon dioxide
2,2'-iminobis[ethanol]
A
1,4-bis(2-hydroxyethyl)piperazine
B
N-(2'-hydroxyethyl)-2-oxazolidone
Conditions | Yield |
---|---|
With alumina In ethanol at 250℃; under 112511 Torr; Catalytic behavior; Concentration; Temperature; Pressure; High pressure; Flow reactor; Supercritical conditions; |
Conditions | Yield |
---|---|
With alumina at 250℃; under 75007.5 Torr; High pressure; Flow reactor; Supercritical conditions; |
1,4-bis(2-hydroxyethyl)piperazine
2-Thiophenecarbonyl chloride
C18H22N2O4S2
Conditions | Yield |
---|---|
In benzene for 1h; Heating; | 91% |
1,4-bis(2-hydroxyethyl)piperazine
1,4-bis(2-chloroethyl)piperazine dihydrochloride
Conditions | Yield |
---|---|
With thionyl chloride In chloroform; N,N-dimethyl-formamide for 6.5h; Heating; | 88% |
Conditions | Yield |
---|---|
In benzene for 1h; Heating; | 87% |
Conditions | Yield |
---|---|
Stage #1: butyric acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.283333h; Stage #2: 1,4-bis(2-hydroxyethyl)piperazine In dichloromethane at 20℃; | 87% |
Conditions | Yield |
---|---|
In water; isopropyl alcohol Na salt added to a soln. of AgNO3 in H2O and isopropanol, an aq. soln. of HOC2H4N(C2H4)2NC2H4OH added dropwise; crystd. for 4 d in the dark at room temp.; elem. anal.; | 86% |
1,4-bis(2-hydroxyethyl)piperazine
acetic anhydride
1,4-bis-(2-acetoxy-ethyl)-piperazine
Conditions | Yield |
---|---|
With sulfuric acid Cooling with ice; | 85% |
1,4-bis(2-hydroxyethyl)piperazine
N,N'-bis(2-bromoethyl)piperazine dihydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide for 24h; Reflux; Inert atmosphere; | 84% |
With water; hydrogen bromide |
1,4-bis(2-hydroxyethyl)piperazine
diphenylborinic acid
(N->B),(N->B)'-bisdiphenyl-[2,2'-(1,4-piperazinediethoxy)]bisborane
Conditions | Yield |
---|---|
In methanol addn. of 2 equiv. of B-compd. to piperazine derivative soln. at -78°C (pptn.); filtration (under N2), washing (hexane), drying; | 78% |
1,4-bis(2-hydroxyethyl)piperazine
2-(2,4,5-trichlorophenoxy)acetyl chloride
1,4-bis<2-(2,4,5-trichlorophenoxyacetoxy)ethyl>piperazine dihydrochloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide 1.) 60 deg C, 2.) 100 deg C, 5 h.; | 71% |
1,4-bis(2-hydroxyethyl)piperazine
benzene-1,3,5-tricarboxylic acid
N,N-dimethyl-formamide
zinc(II) chloride
Conditions | Yield |
---|---|
at 100℃; for 24h; | 65% |
1,4-bis(2-hydroxyethyl)piperazine
2-mercapto-3H-quinazolin-4-one
Conditions | Yield |
---|---|
Stage #1: 1,4-bis(2-hydroxyethyl)piperazine; 2-mercapto-3H-quinazolin-4-one In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Mitsunobu Displacement; Microwave irradiation; Inert atmosphere; Stage #2: With di-isopropyl azodicarboxylate; trimethylphosphane In N,N-dimethyl-formamide; toluene at 0 - 40℃; for 0.5h; Mitsunobu Displacement; Microwave irradiation; Inert atmosphere; | 63% |
1,4-bis(2-hydroxyethyl)piperazine
chlorure de dimethyl-5,8 dioxa-2,11 aza-5 azonia-8 phospha-1 bicyclo 6.3.0 undecane
Conditions | Yield |
---|---|
With triethylamine In chloroform for 2h; Ambient temperature; | 62% |
1,4-bis(2-hydroxyethyl)piperazine
naproxen
Conditions | Yield |
---|---|
With pyridine; dicyclohexyl-carbodiimide In tetrahydrofuran -20 deg C, 10 min; 0 deg C, 24 h; RT, 24 h; | 49% |
1,4-bis(2-hydroxyethyl)piperazine
sodium tungstate (VI) dihydrate
phosphoric acid
Conditions | Yield |
---|---|
With HNO3; NaCl In water Na2WO4*2H2O dissolving in 1 M NaCl, addn. of 4 M HNO3 to pH 3.5, addn. of HOCH2CH2N(CH2CH2)2NCH2CH2OH and 85% H3PO4, addn. of 4 M HNO3 to pH 6.3, addn. of Ni(NO3)2*6H2O, heating to 50°C for 15 min; centrifugation, crystn. by slow evapn. at pH 6.1, isolation of crystals over the course of a week, elem. anal.; | 46.89% |
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 50℃; Inert atmosphere; | 46% |
Conditions | Yield |
---|---|
Stage #1: butyric acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.283333h; Stage #2: 1,4-bis(2-hydroxyethyl)piperazine In dichloromethane at 20℃; | 45% |
1,4-bis(2-hydroxyethyl)piperazine
2,4,6-trimethylphenoxyacetyl chloride
(2,4,6-Trimethyl-phenoxy)-acetic acid 2-(4-{2-[2-(2,4,6-trimethyl-phenoxy)-acetoxy]-ethyl}-piperazin-1-yl)-ethyl ester; hydrochloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide 1.) 60 deg C, 2.) 100 deg C, 5 h.; | 43% |
1,4-bis(2-hydroxyethyl)piperazine
maleic acid monomethyl ester
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 23℃; for 14h; | 42% |
1,4-bis(2-hydroxyethyl)piperazine
maleic acid monomethyl ester
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 23℃; for 14h; | 42% |
1,4-bis(2-hydroxyethyl)piperazine
sodium tungstate (VI) dihydrate
phosphoric acid
sodium chloride
Conditions | Yield |
---|---|
With NaOH; nitric acid In water W compd. dissolved in aq. NaCl, acidified to pH 7.5 (nitric acid), amineadded, phosphoric acid added, pH adjusted to 6.8 (NaOH), aq. Mn compd. added; ppt. centrifuged, soln. heated to 60°C for 15 min, crysts. filtered; elem. anal.; | 39% |
1,4-bis(2-hydroxyethyl)piperazine
4,4'-dimethoxytrityl chloride
Conditions | Yield |
---|---|
With dmap; triethylamine In pyridine Ambient temperature; | 37% |
1,4-bis(2-hydroxyethyl)piperazine
sodium tungstate (VI) dihydrate
phosphoric acid
sodium chloride
Conditions | Yield |
---|---|
With NaOH; nitric acid In water W compd. dissolved in aq. NaCl, acidified to pH 3.5 (nitric acid), amineadded, phosphoric acid added, pH adjusted to 6.05 (NaOH), aq. Mn compd. added; ppt. centrifuged, soln. stored for 3 wk., crysts. filtered; elem. anal.,TGA; | 25% |
Conditions | Yield |
---|---|
With sulfuric acid Cooling with ice; | 23% |
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With dmap; triethylamine In pyridine at 20℃; | 13% |
Reported in EPA TSCA Inventory.
The CAS registry number of 1,4-Piperazinediethanol is 122-96-3. The IUPAC name is with the molecular formula C8H18N2O2. In addition, it is a white crystalline powder which can be used as chemical reagents and organic intermediates. What's more, it should be stored in a cool and dry place.
Physical properties about this chemical are: (1)ACD/LogP: -1.14; (2)ACD/LogD (pH 5.5): -2.28; (3)ACD/LogD (pH 7.4): -1.21; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 4.91; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 24.94 Å2; (12)Index of Refraction: 1.507; (13)Molar Refractivity: 47.3 cm3; (14)Molar Volume: 158.7 cm3; (15)Polarizability: 18.75 ×10-24cm3; (16)Surface Tension: 43.4 dyne/cm; (17)Density: 1.097 g/cm3; (18)Flash Point: 166.2 °C; (19)Enthalpy of Vaporization: 63.34 kJ/mol; (20)Boiling Point: 305.7 °C at 760 mmHg; (21)Vapour Pressure: 7.58E-05 mmHg at 25°C.
Uses of 1,4-Piperazinediethanol: it can be used to get 1,4-bis-(2-chloro-ethyl)-piperazine; dihydrochloride. This reaction will need reagent SOCl2 and solvents dimethylformamide and CHCl3. The reaction time is 6.5 hours by heating. The yield is about 88%.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and gloves. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: OCCN1CCN(CC1)CCO
(2)Std. InChI: InChI=1S/C8H18N2O2/c11-7-5-9-1-2-10(4-3-9)6-8-12/h11-12H,1-8H2
(3)Std. InChIKey: VARKIGWTYBUWNT-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | > 10mL/kg (10mL/kg) | American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962. | |
rat | LD50 | oral | 3730uL/kg (3.73mL/kg) | American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962. |
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