N,N'-DIACETYLGLYCINE ANHYDRIDE Chemical Properties

Melting point:

99-100°C

Boiling point:

424.4±38.0 °C(Predicted)

Density 

1.375±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

-1.74±0.20(Predicted)

color 

White to Light yellow to Light orange

BRN 

188115

InChI

InChI=1S/C8H10N2O4/c1-5(11)9-3-8(14)10(6(2)12)4-7(9)13/h3-4H2,1-2H3

InChIKey

CBBKKVPJPRZOCM-UHFFFAOYSA-N

SMILES

N1(C(C)=O)CC(=O)N(C(C)=O)CC1=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-43-36/38-22

Safety Statements 

26-36/37/39-36/37

WGK Germany 

3

HS Code 

2933.59.9500

HazardClass 

IRRITANT

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1

N,N'-DIACETYLGLYCINE ANHYDRIDE Usage And Synthesis

Description

N,N'-diacetylglycine anhydride, also known as diacetylated glycylglycine, can be obtained by acylation of glycylglycine with acetic anhydride. N,N'-diacetylglycine anhydride can be used to prepare DL-neopentylglycine derivatives.

Application

N,N'-diacetylglycine anhydride can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical and pharmaceutical synthesis process.

Preparation

After the mixed reaction of glycylglycine and acetic anhydride, ethyl acetate and petroleum ether are added in sequence to obtain the intermediate N,N'-diacetylglycine anhydride.

Synthesis

GENERAL METHOD: 2,5-Piperazinedione (500 mg, 2.5 mmol) was mixed with ethanoic anhydride (20 mL) and reacted at 150°C overnight. Upon completion of the reaction, the excess acetic anhydride was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to afford 1,4-diacetylpiperazine-2,5-dione.

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2554 - 2561
[2] Synthesis (Germany), 2014, vol. 46, # 5, p. 621 - 628
[3] European Journal of Medicinal Chemistry, 2014, vol. 83, p. 236 - 244
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 11, p. 1217 - 1224
[5] Tetrahedron, 2012, vol. 68, # 36, p. 7374 - 7379

N,N'-DIACETYLGLYCINE ANHYDRIDE(3027-05-2)Related Product Information

• 1-Acetylpiperazine
• 3,6-Pyridazinedione, 1,2-diacetyltetrahydro-
• 1,4-DIFORMYLPIPERAZINE
• GLYCINE ANHYDRIDE
• 1,4-DIACETYL-3,6-DIBENZYLTETRAHYDRO-2,5-PYRAZINEDIONE
• 1-ACETYL-4-METHYLPIPERAZINE HYDROCHLORIDE
• 1-Piperazinecarbaldehyde
• Piperazine, 1,4-diacetyl- (6CI,8CI,9CI)
• 1-ETHYLPIPERAZIN-2-ONE
• N,N'-DIACETYLGLYCINE ANHYDRIDE
• SARCOSINE ANHYDRIDE
• 1-Methylpiperazin-2-one
• 2-Piperazinone
• N,N'-DIACETYLETHYLENEDIAMINE
• 1-FORMYL-4-METHYLPIPERAZINE