370-81-0

Basic information

• Product Name: Bis(cyclohexanone)oxaldihydrazone
• Synonyms: DICYCLOHEXANONE OXALYLDIHYDRAZONE;CUPFERAZONE;CUPRIZON;CUPRIZON 1;CUPRIZONE;CUPRIZONE I;CUPRIZON I;biscyclohexanone
• CAS NO: 370-81-0
• Molecular Formula: C₁₄H₂₂N₄O₂
• Molecular Weight: 278.35
• EINECS: 206-729-2
• Mol File: 370-81-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 210-214 °C(lit.)
• Boiling Point: 421.17°C (rough estimate)
• Appearance: White/Powder
• Density: 1.0823 (rough estimate)
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: 2-8°C
• PKA: 10.78±0.20(Predicted)
• Water Solubility: Soluble in alcohol. Insoluble in water.
• BRN: 2388004
• CAS DataBase Reference: Bis(cyclohexanone)oxaldihydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(cyclohexanone)oxaldihydrazone(370-81-0)
• EPA Substance Registry System: Bis(cyclohexanone)oxaldihydrazone(370-81-0)

Safety Data

• Hazard Codes: Xn
• Statements: 21/22
• Safety Statements: 24/25-2
• WGK Germany: 3
• RTECS: RO2520000
• TSCA: Yes
• Hazardous Substances Data: 370-81-0(Hazardous Substances Data)

Usage

Description

Bis(cyclohexanone)oxaldihydrazone is a white powder chemical compound known for its various applications in different fields, particularly in the study of mitochondrial metabolism, human demyelinating diseases, and as a ligand in Ullmann-type C-N bond forming reactions.

Uses

Used in Analytical Chemistry:
Bis(cyclohexanone)oxaldihydrazone is used as a reagent for the quantitative spectroscopic determination of copper, which is essential for various analytical processes.
Used in Medical Research:
In the field of medical research, Bis(cyclohexanone)oxaldihydrazone is utilized in the study of human demyelinating diseases such as multiple sclerosis. It also plays a role in understanding components of neuroinflammation, contributing to the advancement of treatments for these conditions.
Used in Experimental Studies:
Bis(cyclohexanone)oxaldihydrazone is essential for experimental studies of mitochondrial metabolism, which is crucial for understanding cellular energy production and its implications in various diseases.
Used in Organic Chemistry:
Bis(cyclohexanone)oxaldihydrazone acts as a ligand and catalyzes Ullmann-type C-N bond forming reactions in the presence of copper salt, which is significant in the synthesis of various organic compounds and materials.

Safety Profile

Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also OXALATES.

InChI:InChI=1/C14H22N4O2/c19-13(17-15-11-7-3-1-4-8-11)14(20)18-16-12-9-5-2-6-10-12/h1-10H2,(H,17,19)(H,18,20)

Synthetic route

oxalic acid hydrazide (996-98-5) + cyclohexanone (108-94-1) → cuprizone (370-81-0)

Conditions	Yield
With hydrogenchloride; ethanol; water

cuprizone (370-81-0) + phosphonic acid diethyl ester (762-04-9) → tetraethyl [(1,2-dioxoethane-1,2-diyl)bis(hydrazine-2,1-diyl-cyclohexane-1,1-diyl)]bisphosphonate (1415724-74-1)

Conditions	Yield
With tetra[tert-butylphthalocyanine]aluminum chloride at 80℃; for 5h; Inert atmosphere;	90%

cuprizone (370-81-0) → N2,N2-dicyclohexyloxalohydrazide (1222194-69-5)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1.5h; Inert atmosphere;	80%

di(tetra-n-butylammonium) dimolybdate + cuprizone (370-81-0) → 3{(C4H9)4N}(1+)*{Mo4O15(OH)(C14H22N4)}(3-)={Mo4O15(OH)(C14H22N4)}{(C4H9)4N}3 + {Mo3O8(OCH3)(MoO4)2}(3-)*3{(C4H9)4N}(1+)*0.5CH2Cl2={Mo3O8(OCH3)(MoO4)2}{(C4H9)4N}3*0.5CH2Cl2 (120904-99-6)

Conditions	Yield
In dichloromethane addn. of hydrazide deriv. in CH2Cl2 to Mo-complex in CH2Cl2; stirring overnight at room temp.; addn. of diethyl ether; recrystn. (CH2Cl2/MeOH/ether 3:2:1); elem. anal.; after 3 days at room temp.: carbonyl insertion product;	A n/a B 30%

cuprizone (370-81-0) + copper(II) sulfate (7758-99-8) + sodium hydroxide (1310-73-2) → Na(1+)*Cu(C6H10N2COCONNH2)2(1-)=NaCu(C6H10N2COCONNH2)2

Conditions	Yield
In water ligand added to aq. soln. of CuSO4 with stirring, pH adjusted to 8 by NaOH; EtOH added; elem. anal.;

Cu[1,4,7-triazacyclononane] (64560-64-1) + cuprizone (370-81-0) → 3C6H15CuN3(2+)*C14H22N4O2

Conditions	Yield
In acetonitrile for 1h;

Cu[1,4,7-triazacyclononane] (64560-64-1) + cuprizone (370-81-0) → C6H15CuN3(2+)*C14H22N4O2

Conditions	Yield
In acetonitrile for 1h;

Cu[1,4,7-triazacyclononane] (64560-64-1) + cuprizone (370-81-0) → C6H15CuN3(2+)*3C14H22N4O2

Conditions	Yield
In acetonitrile for 1h;

Upstream product

• 996-98-5 oxalic acid hydrazide 
• 108-94-1 cyclohexanone 

Downstream Products

• 1222194-69-5 N₂,N₂-dicyclohexyloxalohydrazide 
• 1415724-74-1 tetraethyl [(1,2-dioxoethane-1,2-diyl)bis(hydrazine-2,1-diyl-cyclohexane-1,1-diyl)]bisphosphonate