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2,5-Piperazinedione

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Name

2,5-Piperazinedione

EINECS 203-411-5
CAS No. 106-57-0 Density 1.247 g/cm3
PSA 58.20000 LogP -1.11000
Solubility Soluble in water (142mg/L). Melting Point >300 °C(lit.)
Formula C4H6N2O2 Boiling Point 573.65 °C at 760 mmHg
Molecular Weight 114.104 Flash Point 301.886 °C
Transport Information N/A Appearance white to slightly yellow crystalline powder
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 106-57-0 (2,5-Piperazinedione) Hazard Symbols N/A
Synonyms

2,5-Diketopiperazine;2,5-Dioxopiperazine;Cyclo(glycylglycyl);Cyclodiglycine;Cycloglycylglycine;Diglycolyl diamide;Diketopiperazine;Glycine, N-glycyl-, cyclic peptide;Glycine, bimol. cyclic peptide;Glycylglycine lactam;NSC 26345;alpha,gamma-Diacipiperazine;

Article Data 121

2,5-Piperazinedione Synthetic route

556-50-3

glycylglycine

106-57-0

Glycine anhydride

Conditions
ConditionsYield
With 14C2H7N*14H(1+)*2H2O*2O(2-)*2Zr(4+)*O122P4W34(18-) In dimethyl sulfoxide at 70℃; for 24h; Solvent; Reagent/catalyst;100%
With silica gel In gas at 180 - 200℃; under 0.08 Torr;46%
With hydrogenchloride at 150 - 160℃; im Rohr;
56-40-6

glycine

106-57-0

Glycine anhydride

Conditions
ConditionsYield
In N,N-dimethyl-formamide under 12901.3 Torr; for 0.333333h; Microwave irradiation; Heating;95%
In ethylene glycol at 170 - 180℃; for 6h;62%
With Silochrom C-120 at 170 - 180℃; under 0.1 Torr;13%
5680-79-5

glycine ethyl ester hydrochloride

1122-91-4

4-bromo-benzaldehyde

A

106-57-0

Glycine anhydride

B

139575-14-7

methyl 2-[(E)-[(4-bromophenyl)methylidene]amino]acetate

Conditions
ConditionsYield
With magnesium sulfate; triethylamine In dichloromethane for 1h; Heating;A n/a
B 91%
100-52-7

benzaldehyde

762-04-9

phosphonic acid diethyl ester

459-73-4

GlyOEt*HCl

A

106-57-0

Glycine anhydride

B

ethyl N-[(diethoxyphosphoryl)(phenyl)methyl]glycinate

Conditions
ConditionsYield
With 4 A molecular sieve In dichloromethane for 24h; Kabachnik-Fields reaction;A n/a
B 85%
77930-07-5

C19H23N2O4PS

106-57-0

Glycine anhydride

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 70℃; for 336h;79%
37636-53-6

N,N'-dibromo-2,5-piperazinedione (NBP)

A

106-57-0

Glycine anhydride

B

1-(3,4-dihydro-2H-pyran-5-yl)-2,5-piperazinedione

trans-1-(3-bromo-2-tetrahydropyranyl)-2,5-piperazinedione

cis-1-(3-bromo-2-tetrahydropyranyl)-2,5-piperazinedione

Conditions
ConditionsYield
With ethyloxirane; 3,4-dihydro-2H-pyran In acetonitrile for 3h; Ambient temperature; Irradiation;A 75%
B 2%
C 5%
D 2%
77930-08-6

C19H21F2N2O5P

106-57-0

Glycine anhydride

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene for 504h;74%
113708-85-3

sodium butyl(nitrosulfo)acetate

A

106-57-0

Glycine anhydride

B

disodium butyl(aminodisulfo)acetate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol for 24h;A 40%
B 72%
5680-79-5

glycine ethyl ester hydrochloride

100-52-7

benzaldehyde

A

106-57-0

Glycine anhydride

B

66646-88-6, 120238-40-6, 138495-05-3

(E)-N-benzylideneglycine methyl ester

Conditions
ConditionsYield
With magnesium sulfate; triethylamine In dichloromethane for 1h; Heating;A n/a
B 65%
13437-63-3

methyl [({[(benzyloxy)carbonyl]amino}acetyl)amino]acetate

106-57-0

Glycine anhydride

Conditions
ConditionsYield
With hydrogen bromide; acetic acid In methanol for 12h; Ambient temperature;62%

2,5-Piperazinedione Specification

The 2,5-Piperazinedione, with the CAS registry number 106-57-0, is also known as Diglycolyl diamide. Its EINECS number is 203-411-5. This chemical's molecular formula is C4H6N2O2 and molecular weight is 114.1. What's more, its systematic name is piperazine-2,5-dione. Its classification code is Drug/Therapeutic Agent. It should be sealed and stored in a cool, ventilated and dry place. What's more, it should be protected from strong oxides, heat and fire. The workplace should be equipped with fire-fighting equipments. It is used as biochemical reagents. When using it, you should avoid contacting with skin and eyes.

Physical properties of 2,5-Piperazinedione are: (1)ACD/LogP: -2.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.56; (4)ACD/BCF (pH 5.5): 1; (5)ACD/KOC (pH 5.5): 1; (6)#H bond acceptors: 4; (7)#H bond donors: 2; (8)#Freely Rotating Bonds: 0; (9)Polar Surface Area: 40.62 Å2; (10)Index of Refraction: 1.467; (11)Molar Refractivity: 25.4 cm3; (12)Molar Volume: 91.5 cm3; (13)Surface Tension: 38.1 dyne/cm; (14)Density: 1.246 g/cm3; (15)Flash Point: 301.9 °C; (16)Enthalpy of Vaporization: 85.96 kJ/mol; (17)Boiling Point: 573.7 °C at 760 mmHg; (18)Vapour Pressure: 3.64E-13 mmHg at 25°C.

Preparation: this chemical can be prepared by glycine by heating. This reaction will need reagent SiO2 and solvent toluene with the reaction time of 20 hours. The yield is about 44.3%.

Uses of 2,5-Piperazinedione: it can be used to produce 1,4-diacetylpiperazine by heating. The reaction time is 6 hours. The yield is about 91%.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1C(=O)NCC(=O)N1
(2)InChI: InChI=1S/C4H6N2O2/c7-3-1-5-4(8)2-6-3/h1-2H2,(H,5,8)(H,6,7)
(3)InChIKey: BXRNXXXXHLBUKK-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intraperitoneal > 500mg/kg (500mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 227, 1954.

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