110-21-4

Basic information

• Product Name: BIUREA
• Synonyms: N,N'-DICARBAMOYLHYDRAZINE;N,N'-DICARBAMYLHYDRAZINE;1,1’-hydrazobis(formamide);1,1’-hydrazobis-formamid;1,1-hydrazoformamide;1,2-bis(aminocarbonyl)-hydrazin;1,2-hydrazinedicarboxamide;1,2-Hydrazinedicarboxamine
• CAS NO: 110-21-4
• Molecular Formula: C₂H₆N₄O₂
• Molecular Weight: 118.09
• EINECS: 203-747-2
• Product Categories: Pharmaceutical Intermediates;Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 110-21-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 247-250 °C
• Boiling Point: 220.6°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.6040
• Vapor Pressure: 0.000165mmHg at 25°C
• Refractive Index: 1.4462 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Sulfuric Acid (Sparingly, Heated)
• PKA: 10.06±0.43(Predicted)
• CAS DataBase Reference: BIUREA(CAS DataBase Reference)
• NIST Chemistry Reference: BIUREA(110-21-4)
• EPA Substance Registry System: BIUREA(110-21-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 110-21-4(Hazardous Substances Data)

Usage

Chemical Properties

WHITE POWDER

Uses

Hydrazine-1,2-dicarboxamide is a useful compound in the process of producing protected anode active material particles for rechargeable lithium batteries.

General Description

White powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

BIUREA is chemically classified as an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Fire Hazard

The flash point of BIUREA is not available, however BIUREA is probably non-flammable.

Purification Methods

Crystallise the diamide from water, wash the crystals with EtOH then Et2O and dry in vacuum over P2O5. It does not decompose on drying at 110o /48hours. Its solubility in H2O is 1% at 0o. [Andrieth & Mohr Inorg Synth IV 26 1953, Beilstein 3 H 116, 3 I 56, 3 III 229.]

InChI:InChI=1/C2H6N4O2/c3-1(7)6(5)2(4)8/h5H2,(H2,3,7)(H2,4,8)

Synthetic route

Azodicarboxamid (123-77-3) → hydrazodicarboxamide (110-21-4)

Conditions	Yield
With hydrazine hydrate In acetonitrile at 20℃; for 1.5h;	98%
With hydrogen sulfide; water beim Kochen;
With hydrogenchloride beim Kochen;
With water; sodium carbonate beim Kochen;

sodium chlorobiuret salt → hydrazodicarboxamide (110-21-4)

Conditions	Yield
With ammonia; aluminum (III) chloride; zinc(II) chloride In water at 10 - 60℃; for 1h;	97%
With ammonia; aluminum (III) chloride; zinc(II) chloride In water at 10 - 60℃; for 1h;	96%
With ammonia; cadmium(II) chloride; zinc(II) chloride In water at 10 - 60℃; for 1h;	96%

BIURET (108-19-0) → hydrazodicarboxamide (110-21-4)

Conditions	Yield
Stage #1: BIURET With sodium hypochlorite In water at 5 - 10℃; Stage #2: With ammonia; zinc(II) chloride In water at 100℃; for 0.5h; Product distribution / selectivity;	96%
Stage #1: BIURET With sodium hypochlorite In water at 5 - 10℃; Stage #2: With ammonia In water at 100℃; for 0.5h; Product distribution / selectivity;	95%
Stage #1: BIURET With sodium hypochlorite In ethanol; water at 5 - 10℃; Stage #2: With ammonia In ethanol; water at 100℃; for 0.5h; Product distribution / selectivity;	85%

chlorobiuret sodium salt → hydrazodicarboxamide (110-21-4)

Conditions	Yield
With ammonia; zinc(II) chloride In water at 10 - 100℃; for 0.5h; Product distribution / selectivity;	93%
With ammonia; hydrogenchloride In water at 10 - 100℃; for 0.5h; Product distribution / selectivity;	92%
With ammonia; nickel diacetate In water at 10 - 100℃; for 0.5h; Product distribution / selectivity;	92%
With ammonia In water at 10 - 100℃; for 0.5h; Product distribution / selectivity;	87%

(E)-2-(3,4,5-trimethoxybenzylidene)hydrazine carboxamide (81824-93-3) → hydrazodicarboxamide (110-21-4) + (1E, 2E)-1,2-bis(3,4,5-trimethoxybenzylidene)hydrazine (7251-01-6)

Conditions	Yield
In tetrahydrofuran at 120 - 150℃; Rearrangement; elimination;	A n/a B 87%

(E)-2-benzylidenehydrazine-1-carboxamide → hydrazodicarboxamide (110-21-4) + benzaldehyde benzylidenehydrazone (28867-76-7)

Conditions	Yield
In tetrahydrofuran at 120 - 150℃; Rearrangement; elimination;	A n/a B 85%

3,4-methylenedioxybenzaldehyde semicarbazone (16742-62-4) → hydrazodicarboxamide (110-21-4) + (2E,N'E)-3-(benzo[d][1,3]dioxol-5-yl)-N'-(benzo[d][1,3]dioxol-5-ylmethylene)-2-cyanoacrylohydrazide

Conditions	Yield
In tetrahydrofuran at 120 - 150℃; Rearrangement; elimination;	A n/a B 84%

(E)-2-(4-methoxybenzylidene)hydrazine carboxamide (120445-53-6) → hydrazodicarboxamide (110-21-4) + N,N'-Bis-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazine (41097-47-6)

Conditions	Yield
In tetrahydrofuran at 120 - 150℃; Rearrangement; elimination;	A n/a B 83%

2,4-dimethoxybenzaldehyde semicarbazone → hydrazodicarboxamide (110-21-4) + (1E,2E)-1,2-bis(3,4-dimethoxybenzylidene)hydrazine (134691-71-7)

Conditions	Yield
In tetrahydrofuran at 120 - 150℃; Rearrangement; elimination;	A n/a B 68%

N-acetoacetylphenylhydroxyloamine (27991-08-8) → hydrazodicarboxamide (110-21-4) + N-Phenylhydroxylamine (100-65-2) + 1-carbamido-3-methyl-2-pyrazolin-5-one (57303-41-0) + azoxybenzene (495-48-7)

Conditions	Yield
With semicarbazide hydrochloride; sodium carbonate In ethanol for 24h; Ambient temperature; Further byproducts given;	A 63% B 35% C 15.5% D 30%

triethyl 1,3,5-triazine-2,4,6-tricarboxylate (898-22-6) + hydrazine carboxamide (4426-72-6, 51433-48-8) → hydrazodicarboxamide (110-21-4) + Ethyloxamatcarbamylhydrazon (57041-78-8) + 3-oxo-5-imino-6-ethoxycarbonyl-2,3,4,5-tetrahydro-1,2,4-triazine (95234-60-9) + 3,5-diethoxycarbonyl-1,2,4-triazole (91173-78-3)

Conditions	Yield
In ethanol for 1h; Heating;	A 34% B 63% C 51% D 23%

triethyl 1,3,5-triazine-2,4,6-tricarboxylate (898-22-6) → hydrazodicarboxamide (110-21-4) + Ethyloxamatcarbamylhydrazon (57041-78-8) + 3-oxo-5-imino-6-ethoxycarbonyl-2,3,4,5-tetrahydro-1,2,4-triazine (95234-60-9) + 3,5-diethoxycarbonyl-1,2,4-triazole (91173-78-3)

Conditions	Yield
With hydrazine carboxamide In ethanol for 1h; Heating;	A 34% B 63% C 51% D 23%

trimethylsilyl isocyanate (1118-02-1) → hydrazodicarboxamide (110-21-4)

Conditions	Yield
With hydrazine In hexane at 60℃; for 6h;	62%

semicarbazide hydrochloride (563-41-7) + 4-chloro-3-(1-chlorovinyl)-6-methyl-2-pyrone (106089-51-4) → hydrazodicarboxamide (110-21-4) + 3,6-dimethylpyrano<4,3-c>pyrazol-4(1H)-one (106089-56-9)

Conditions	Yield
With sodium acetate In ethanol for 21h; Heating;	A n/a B 49%

semicarbazide hydrochloride (563-41-7) → hydrazodicarboxamide (110-21-4)

Conditions	Yield
With ethyl acetoacetate In water a) from 5 deg C to 10 deg C, 15 min, b) reflux, 3 h;	37%
With water; sodium carbonate
With selenium(IV) oxide; water at 60℃;

3,5-dimethylpyrazole-1-carboxamide (934-48-5) → hydrazodicarboxamide (110-21-4)

Conditions	Yield
In water for 0.75h; Heating;	26%

acetophenone semicarbazone (2492-30-0) → hydrazodicarboxamide (110-21-4)

Conditions	Yield
beim Erhitzen;

acetophenone semicarbazone (2492-30-0) → hydrazodicarboxamide (110-21-4) + acetophenonazine (729-43-1)

Conditions	Yield
at 240℃;
at 240℃;

bromocyane (506-68-3) → hydrazodicarboxamide (110-21-4)

Conditions	Yield
With water; hydrazinium sulfate

phorone (504-20-1) + semicarbazide hydrochloride (563-41-7) → hydrazodicarboxamide (110-21-4) + 2,6-dimethyl-6-semicarbazido-hept-2-en-4-one semicarbazone

Conditions	Yield
With ethanol; water; potassium acetate

carbamoyl azide (13125-56-9) → hydrazodicarboxamide (110-21-4)

Conditions	Yield
at 110 - 120℃; und Kochen der Reaktionsprodukte mit Wasser;
With benzene at 100 - 115℃; und Kochen der Reaktionsprodukte mit Wasser;

butan-2-one semicarbazone (624-46-4) → urazole (3232-84-6) + hydrazodicarboxamide (110-21-4) + butan-2-one azine (5921-54-0)

Conditions	Yield
beim Destillieren;

butan-2-one semicarbazone (624-46-4) → hydrazodicarboxamide (110-21-4)

Conditions	Yield
beim Erhitzen;

bromo-acetone semicarbazone + ethanol (64-17-5) → hydroxy-acetone semicarbazone (21178-87-0) + hydrazodicarboxamide (110-21-4)

4-semicarbazido-pentan-2-one semicarbazone + ethanol (64-17-5) → hydrazodicarboxamide (110-21-4)

ethanol (64-17-5) + 1-chloro-propan-2-one semicarbazone (53646-01-8) → hydroxy-acetone semicarbazone (21178-87-0) + hydrazodicarboxamide (110-21-4)

ethanol (64-17-5) + 6-methyl-4-semicarbazido-heptan-2-one semicarbazone → hydrazodicarboxamide (110-21-4)

ethanol (64-17-5) + 2-(1-semicarbazido-ethyl)-3-semicarbazono-butyric acid ethyl ester → hydrazodicarboxamide (110-21-4)

cyanic acid (420-05-3) → hydrazodicarboxamide (110-21-4)

hydrazodicarboxamide (110-21-4) → Azodicarboxamid (123-77-3)

Conditions	Yield
With acetic acid; copper(I) bromide at 20℃; under 760.051 Torr; for 12h; Reagent/catalyst; Temperature; Sealed tube;	99%
With tetra-N-butylammonium tribromide; sodium nitrite In 1,2-dimethoxyethane; water at 65℃; under 760.051 Torr; for 20h; Reagent/catalyst; Solvent; Pressure; Temperature; Sealed tube;	98%
With hydrogenchloride; iron(III) chloride; dihydrogen peroxide; ozone In water at 40℃; pH=2 - 5; Temperature;	97.4%

hydrazodicarboxamide (110-21-4) → 1,3,4-oxadiazole-2,5-diamine (2937-79-3)

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride In ethanol at 79 - 80℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	98%

stannous octoate + hydrazodicarboxamide (110-21-4) + 1-aminooctadecane (124-30-1) → 4-octadecyl-[1,2,4]triazolidine-3,5-dione (81329-56-8)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one	90%

2,3-diaminephenazine (655-86-7) + hydrazodicarboxamide (110-21-4) → phenazine benzimidazolone (106050-79-7)

Conditions	Yield
With hydrogenchloride; sodium chloride In water at 320℃; for 0.216667h;	89.9%

1-methyl-pyrrolidin-2-one (872-50-4) + hydrazodicarboxamide (110-21-4) → urazole (3232-84-6)

Conditions	Yield
In water; acetone	89%

hexan-1-amine (111-26-2) + hydrazodicarboxamide (110-21-4) → 4-hexyl-[1,2,4]triazolidine-3,5-dione (81329-55-7)

Conditions	Yield
With sodium hydroxide In N-methy pyrrolidone	81%
In 1-methyl-pyrrolidin-2-one	81%

hydrazodicarboxamide (110-21-4) + 4,4'-diaminodicyclohexylmethane (1761-71-3) → 4,4'-bis-(1,2,4-triazolidine-3,5-dion-4-yl)-dicyclohexylmethane (81529-52-4)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one; water	75%

hydrazodicarboxamide (110-21-4) → 2,3-dihydro-[1,3,4]-oxadiazole-2,5-diamine

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 140℃; for 5h; Inert atmosphere;	75%

hydrazodicarboxamide (110-21-4) + benzylamine (100-46-9) → 4-benzyl-1,2,4-triazolidine-3,5-dione (16312-86-0)

Conditions	Yield
With sodium hydroxide In 1-methyl-pyrrolidin-2-one	70%
In 1-methyl-pyrrolidin-2-one	70%

hydrazodicarboxamide (110-21-4) → sodium hypochlorite (7681-52-9) + sodium azide + hydrogen azide (916329-38-9)

Conditions	Yield
With sodium hydroxide; sulfuric acid In water ice cooling; distn. with H2SO4;	A n/a B n/a C 9%
With NaOH; H2SO4 In water ice cooling; distn. with H2SO4;	A n/a B n/a C 9%

Upstream product

• 64-17-5 ethanol 
• 625-77-4 N-acetylacetamide 
• 563-41-7 semicarbazide hydrochloride 
• 506-78-5 cyanogen iodide 
• 4426-72-6 hydrazine carboxamide 
• 624-74-8 diiodoacetylene 
• 4494-12-6 N-butyrylbutyramide 
• 614-28-8 N-benzoylbenzamide 
• 141-52-6 sodium ethanolate 
• 105-53-3 diethyl malonate 
• 56-23-5 tetrachloromethane 
• 1574-10-3 benzaldehyde semicarbazone 
• 100-63-0 phenylhydrazine 
• 108-88-3 toluene 

Downstream Products

• 79491-05-7 4-(4-methylphenyl)-1,2,4-triazolidine-3,5-dione 
• 120208-94-8 4-o-tolyl-[1,2,4]triazolidine-3,5-dione 
• 16312-79-1 4-methylurazole 
• 16050-65-0 4-ethyl-[1,2,4]triazolidine-3,5-dione 
• 15988-11-1 4-Phenylurazole 
• 603-54-3 N,N-diphenylurea 
• 109500-44-9 4-(4-hexyl-phenyl)-[1,2,4]triazolidine-3,5-dione 
• 3232-84-6 urazole 
• 123-77-3 Azodicarboxamid 
• 3148-73-0 Diacetylhydrazin 
• 102-07-8 bis(diphenyl)urea 
• 7681-52-9 sodium hypochlorite 
• 916329-38-9 hydrogen azide 
• 81529-52-4 4,4'-bis-(1,2,4-triazolidine-3,5-dion-4-yl)-dicyclohexylmethane 

Related news

Comparative studies by IR, Raman, and surface-enhanced Raman spectroscopy of azodicarbonamide, BIUREA (cas 110-21-4) and semicarbazide hydrochloride08/22/2019

Azodicarbonamide is widely applied in the food industry as a new flour gluten fortifier in China, Canada, the United States, and some other countries, whose metabolites of biurea and semicarbazide hydrochloride are reaction products during baking. In this study, IR, Raman and surface-enhanced Ra...detailed

A DFT approach for simple and solvent assisted-proton movement: BIUREA (cas 110-21-4) as a case of study08/21/2019

306 conformers of Biurea as a biologically important molecule were optimized and frequency calculation was performed for each conformer. Then, these conformers were classified in seven tautomeric categories. Five most stable tautomers were selected and their stabilities were investigated careful...detailed

Relevant articles and documents

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Method and apparatus for preparing hydrazo-dicarbonamide using urea as starting material

The present invention relates to a method and apparatus for preparing hydrazodicarbonamide using urea as starting material economically and environmentally desirably. The apparatus includes a pyrolysis furnace to obtain biuret and ammonia by pyrolyzing urea; a recrystallization reactor to purify the biuret obtained from the pyrolysis furnace; a first reactor to obtain an metal monohalobiuret salt by reacting the biuret with metal hypohalogen compound or with halogen and base; a second reactor to synthesize the hydrazodicarbonamide by reacting the monohalobiuret metal salt with ammonia; and an ammonia evaporator to separate the excess ammonia from hydrazodicarbonamide and to supply the separated ammonia to an ammonia concentrator.