1,1-HYDRAZOFORMAMIDE

1,1-Hydrazoformamide has also been described in connection with blowing-agent systems and blowing aids.
1,1-Hydrazoformamide is used in the preparation of protected anode active-material particles for rechargeable lithium batteries.
1,1-Hydrazoformamide is also important analytically because it can occur as a decomposition or transformation product of azodicarbonamide.

CAS Number: 110-21-4
EC Number / EINECS: 203-747-2
Molecular formula: C₂H₆N₄O₂
Molecular weight: 118.09 g/mol

SYNONYMS:
Biurea, Diurea, Hydrazodicarbonamide, Hydrazodicarboxamide, Hydrazodiformamide, Hydradicarbonamide, Hydrazocarbonamide, N,N'-Dicarbamoylhydrazine, N,N'-Dicarbamylhydrazine, N,N'-Biscarbamoylhydrazine, Dicarbamoylhydrazine, 1,1-Hydrazoformamide, 1,1-Hydrazobis(formamide), 1,1'-Hydrazobis-formamide, 1,2-Hydrazinedicarboxamide, 1,2-Hydrazinedicarboxamine, 1,2-Bis(aminocarbonyl)hydrazine, Hydrazine, 1,2-bis(aminocarbonyl)-, Hydrazine, 1,2-dicarbamoyl-, Bicarbamamide, Bicarbamimidic acid, Formamide, 1,1'-hydrazobis-, Formimidic acid, 1-semicarbazido-, Hydrazinecarboximidic acid, 2-(aminocarbonyl)-, Hydrazinedicarboxylic acid diamide, Urea, ureido-, Ureidourea, Pseudourea, 3-ureido-, Semicarbazide, 1-carbamoyl-, Semicarbazide, 1-(1-hydroxyformimidoyl)-, (Carbamoylamino)urea, Hydrazine-N,N'-bis(carboxamide), NSC 1897, CCRIS 5976, HSDB 5014, Biurea, Hydrazodicarbonamide, Hydrazodiformamide, N,N'-Dicarbamoylhydrazine, Bicarbamamide, Bicarbamimidic acid, Formamide, 1,1'-hydrazobis-, Formimidic acid, 1-semicarbazido-, Hydrazine, 1,2-bis(aminocarbonyl)-, Hydrazine, 1,2-dicarbamoyl-, Hydrazinecarboximidic acid, 2-(aminocarbonyl)-, Hydrazocarbonamide, Hydrazodicarboxamide, Pseudourea, 3-ureido-, Semicarbazide, 1-(1-hydroxyformimidoyl)-, Semicarbazide, 1-carbamoyl-, Urea, ureido-, Ureidourea, Hydradicarbonamide, Hydrazinedicarboxylic acid diamide, N,N'-Biscarbamoylhydrazine, NSC 1897, 1,1-hydrazoformamide, Hydrazodicarbonamide, 1,2-hydrazinedicarboxamide, DIUREA, BIUREA, p-urazine, Ureidourea, Biurea,99%, dicarbamide, Bicarbamamide, Urea, ureido-, Biurea, Bicarbamamide, Ureidourea, Hydrazocarbonamide, Urea, ureido-, Bicarbamimidic acid, Hydrazodicarbonamide, Hydrazodicarboxamide, Hydradicarbonamide, Ureidoureacarboxamide, Pseudourea, 3-ureido-, 1,1-Hydrazoformamide, 1,2-HYDRAZINEDICARBOXAMIDE, Semicarbazide, 1-carbamoyl-, N,N-Biscarbamoylhydrazine, Bicarbamimidic acid (VAN), Hydrazine, 1,2-dicarbamoyl-, Formamide, 1,1-hydrazobis-, 1,1-Hydrazobis(formamide), 1,1-Hydrazinebisformamide, Biurea, 110-21-4, 1,2-HYDRAZINEDICARBOXAMIDE, Ureidourea, Bicarbamamide, Bicarbamimidic acid, Hydrazodicarbonamide, Hydrazodicarboxamide, Hydradicarbonamide, Hydrazocarbonamide, Urea, ureido-, Pseudourea, 3-ureido-, Semicarbazide, 1-carbamoyl-, Ureidoureacarboxamide, N,N'-Biscarbamoylhydrazine, 1,1-Hydrazoformamide, Hydrazinedicarboxylic acid diamide, Formimidic acid, 1-semicarbazido-, 1,1'-Hydrazobis(formamide), Hydrazine, 1,2-dicarbamoyl-, Semicarbazide, 1-(1-hydroxyformimidoyl)-, Formamide, 1,1'-hydrazobis-, Hydrazine, 1,2-bis(aminocarbonyl)-, Bicarbamimidic acid (VAN), NSC 1897, CCRIS 5976, DTXSID6024628, Hydrazinecarboximidic acid, 2-(aminocarbonyl)-, HSDB 5014, POJ4UOY01H, EINECS 203-747-2, AI3-28537, NSC-1897, DTXCID404628, HYDRAZINE-N,N'-BIS(CARBOXAMIDE), 1,2-HYDRAZINEDICARBOXAMIDE [HSDB], Urea, ureido, 1,1Hydrazoformamide, Pseudourea, 3ureido, HYDRAZODICARBAMIDE, N,N'Biscarbamoylhydrazine, RefChem:412078, Semicarbazide, 1carbamoyl, DICARBAMOYLHYDRAZINE, Hydrazine, 1,2dicarbamoyl, 1,1'Hydrazobis(formamide), Formamide, 1,1'hydrazobis, 1,1-HYDRAZOFORM AMIDE, Formimidic acid, 1semicarbazido, Hydrazine, 1,2bis(aminocarbonyl), Semicarbazide, 1(1hydroxyformimidoyl), Hydrazinecarboximidic acid, 2(aminocarbonyl), hydrazine-1,2-dicarboxamide, (carbamoylamino)urea, N,N'-Dicarbamoylhydrazine, MFCD00025398, Hydrazodiformamide, UNII-POJ4UOY01H, Diharnstoff, Hydrazine,2-dicarbamoyl-, Formamide,1'-hydrazobis-, 1,1'-Hydrazinebisformamide, N,N'-Dicarbamoylhydrazine, SCHEMBL21785, SCHEMBL588495, CHEMBL3188383, Hydrazine,2-bis(aminocarbonyl)-, NSC1897, ALBB-013477, Tox21_300989, AKOS005174048, SB86000, 1,2-Hydrazinedicarboxamide 13C2,15N2, NCGC00248246-01, NCGC00254891-01, AS-59029, CAS-110-21-4, DB-040907, B0512, CS-0149929, NS00021512, D81814, EN300-7413859, F369662, Q4919204, 77107-48-3, Biurea, Hydrazodicarbonamide, Hydrazodiformamide, N,N'-Dicarbamoylhydrazine, Bicarbamamide, Bicarbamimidic acid, Formamide, 1,1'-hydrazobis-, Formimidic acid, 1-semicarbazido-, Hydrazine, 1,2-bis(aminocarbonyl)-, Hydrazine, 1,2-dicarbamoyl-, Hydrazinecarboximidic acid, 2-(aminocarbonyl)-, Hydrazocarbonamide, Hydrazodicarboxamide, Pseudourea, 3-ureido-, Semicarbazide, 1-(1-hydroxyformimidoyl)-, Semicarbazide, 1-carbamoyl-, Urea, ureido-, Ureidourea, Hydradicarbonamide, Hydrazinedicarboxylic acid diamide, N,N'-Biscarbamoylhydrazine, NSC 1897, 1,1-hydrazoformamide, 1,1'-Hydrazobis(formamide), AI3-28537, Bicarbamamide, Bicarbamimidic acid, Bicarbamimidic acid (VAN), Biurea, CCRIS 5976, EINECS 203-747-2, Formamide, 1,1'-hydrazobis-, Formimidic acid, 1-semicarbazido-, HDCA, HSDB 5014, Hydradicarbonamide, Hydrazine, 1,2-bis(aminocarbonyl)-, Hydrazine, 1,2-dicarbamoyl-, Hydrazinecarboximidic acid, 2-(aminocarbonyl)-, Hydrazinedicarboxylic acid diamide, Hydrazocarbonamide, Hydrazodicarbonamide, Hydrazodicarboxamide, N,N'-Biscarbamoylhydrazine, NSC 1897, Pseudourea, 3-ureido-, Semicarbazide, 1-(1-hydroxyformimidoyl)-, Semicarbazide, 1-carbamoyl-, UNII-POJ4UOY01H, Urea, ureido-, Ureidourea, Ureidoureacarboxamide, 1,1-Hydrazoformamide, 1,2-Hydrazinedicarboxamide, Biurea, Biurea, Bicarbamamide, Bicarbamimidic acid, N,N-Biscarbamoylhydrazine, Dicarbamoylhydrazine, Hydradicarbonamide, 1,2-Hydrazinedicarboxamide, Hydrazinedicarboxylic acid diamide, 1,1-Hydrazobis (formamide), Hydrazocarbonamide, Hydrazodicarbonamide Hydrazodicarboxamide, Ureidoureacarboxamide

1,1-Hydrazoformamide is a useful compound in the process of producing protected anode active material particles for rechargeable lithium batteries.
1,1-Hydrazoformamide is a white powder.
1,1-Hydrazoformamide is insoluble in water.

1,1-Hydrazoformamide is a chemical compound more commonly known as biurea, hydrazodicarbonamide, or 1,2-hydrazinedicarboxamide.
1,1-Hydrazoformamide is an organic nitrogen-containing compound belonging to the hydrazine dicarboxamide/urea derivative family.

Its structure contains two carbamoyl groups connected through a hydrazine N–N bond, giving 1,1-Hydrazoformamide the structural formula NH₂–CO–NH–NH–CO–NH₂.
1,1-Hydrazoformamide is a relatively small, highly nitrogen-containing solid and is particularly important as a chemical intermediate for the manufacture of azodicarbonamide (ADC).

USES and APPLICATIONS of 1,1-HYDRAZOFORMAMIDE:
1,1-Hydrazoformamide uses and applications include: flame-proofing agent for plastics. 
Suggested storage of Biurea: Store refrigerated; keep tightly closed.
The principal industrial significance of 1,1-hydrazoformamide is its use as a chemical intermediate for the manufacture of azodicarbonamide.
Azodicarbonamide is widely used as a chemical blowing agent in polymer and rubber processing.

Therefore, 1,1-Hydrazoformamide is an important upstream intermediate in the production of materials used for foaming applications.
1,1-Hydrazoformamide is also relevant to polymer and rubber technology indirectly through azodicarbonamide production.
Azodicarbonamide decomposes upon heating and produces gaseous products that create cellular structures in polymers.

1,1-Hydrazoformamide itself is not simply interchangeable with azodicarbonamide; rather, it is primarily the precursor/intermediate from which the latter is produced.
1,1-Hydrazoformamide has also been described in connection with blowing-agent systems and blowing aids.
Patent literature reports the use of 1,1-Hydrazoformamide in modifying or assisting azodicarbonamide-based blowing systems, including adjustment of decomposition behavior.

1,1-Hydrazoformamide is used in the preparation of protected anode active-material particles for rechargeable lithium batteries.
This is a more specialized application compared with 1,1-Hydrazoformamide's major role as an azodicarbonamide intermediate.
1,1-Hydrazoformamide is also important analytically because it can occur as a decomposition or transformation product of azodicarbonamide.
Analytical methods have therefore been developed for determining 1,1-Hydrazoformamide in azodicarbonamide-containing materials.

-1,1-Hydrazoformamide is used in the battery industry:
1,1-Hydrazoformamide is used as a compound in the production of protected anode active material particles for rechargeable lithium batteries.
1,1-Hydrazoformamide plays a crucial role in enhancing the performance and efficiency of these batteries.

BENEFITS AND INDUSTRIAL IMPORTANCE of 1,1-HYDRAZOFORMAMIDE:
The main benefit of 1,1-hydrazoformamide from an industrial chemistry perspective is that it provides a practical chemical intermediate for producing azodicarbonamide.
1,1-Hydrazoformamide's relatively simple molecular structure and high nitrogen content make it suitable for this oxidation chemistry.
Its high melting point and crystalline nature also make 1,1-Hydrazoformamide substantially different from volatile hydrazine.

1,1-Hydrazoformamide is therefore handled as a solid chemical intermediate rather than as a volatile hydrazine-type liquid.
Another important characteristic is1,1-Hydrazoformamide's position in the chemistry of chemical blowing agents.
Although 1,1-Hydrazoformamide itself is not the primary gas-generating blowing agent in the same way as azodicarbonamide, its conversion to azodicarbonamide connects 1,1-Hydrazoformamide directly to the manufacture of foamed plastics, rubber products and other cellular polymer materials

CHEMICAL RELATIONSHIP of 1,1-HYDRAZOFORMAMIDE WITH AZODICARBONAMIDE:
One of the most important characteristics of 1,1-hydrazoformamide is its role as the precursor to azodicarbonamide (ADA/ADCA).
1,1-Hydrazoformamide can be produced from urea and hydrazine, and it can subsequently be oxidized to azodicarbonamide.
In simplified form, the relationship is:

Urea + hydrazine → 1,1-Hydrazoformamide → oxidation → azodicarbonamide
The conversion of 1,1-Hydrazoformamide to azodicarbonamide involves oxidation of the N–N linkage.
1,1-Hydrazoformamide therefore occupies an important position in the industrial chemistry of azodicarbonamide.
Historical industrial literature specifically describes 1,1-Hydrazoformamide as an intermediate used for manufacturing azodicarbonamide.

REACTIVITY PROFILE of 1,1-HYDRAZOFORMAMIDE:
1,1-Hydrazoformamide is chemically classified as an amide.
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).

IMPORTANT DISTINCTION of 1,1-HYDRAZOFORMAMIDE:
1,1-Hydrazoformamide (biurea) is NOT azodicarbonamide.
1,1-Hydrazoformamide: C₂H₆N₄O₂, CAS 110-21-4
Azodicarbonamide: C₂H₄N₄O₂, CAS 123-77-3

The two substances are closely related chemically.
1,1-Hydrazoformamide is the reduced/hydrogenated precursor, while azodicarbonamide contains an N=N azo linkage and is the better-known chemical blowing agent.
1,1-Hydrazoformamide can be oxidized to azodicarbonamide.,

STRUCTURAL CHARACTERISTICS of 1,1-HYDRAZOFORMAMIDE:
1,1-Hydrazoformamide consists of two urea-like units connected through an N–N bond.
This can be represented as:
H₂N–C(=O)–NH–NH–C(=O)–NH₂

This structure explains several of 1,1-Hydrazoformamide's characteristics.
The two carbonyl groups provide strong hydrogen-bond acceptor sites, while the N–H groups provide hydrogen-bond donor sites.
The extensive intermolecular hydrogen bonding helps explain why 1,1-Hydrazoformamide is a crystalline, high-melting solid rather than a volatile liquid.

The molecule is also highly nitrogen-rich.
1,1-Hydrazoformamide's molecular formula contains four nitrogen atoms in a molecular weight of only about 118 g/mol.
This nitrogen-rich composition is particularly relevant to 1,1-Hydrazoformamide's industrial importance as a precursor to azodicarbonamide.

PHYSICAL and CHEMICAL PROPERTIES of 1,1-HYDRAZOFORMAMIDE:
Chemical name: 1,1-Hydrazoformamide
Preferred/common name: Biurea
IUPAC name: (Carbamoylamino)urea
CAS Number: 110-21-4
EC Number / EINECS: 203-747-2
PubChem CID: 8039
ChemSpider ID: 7748
Molecular formula: C₂H₆N₄O₂
Molecular weight: 118.09 g/mol

Exact mass: approximately 118.0491 Da
Monoisotopic mass: approximately 118.0491 Da
MDL number: MFCD00025398
UNII: POJ4UOY01H
InChIKey: ULUZGMIUTMRARO-UHFFFAOYSA-N
SMILES: NC(=O)NNC(N)=O
Structural formula: NH₂CONHN HCONH₂, conventionally written as NH₂–CO–NH–NH–CO–NH₂
Molecular formula: C₂H₆N₄O₂
Molecular weight: 118.09 g/mol

Exact mass: approximately 118.0491 Da
Molar mass: 118.09 g/mol
Physical state: Solid
Appearance: White powder / white to off-white crystalline solid
Melting point: approximately 247–250 °C
Boiling point: approximately 220.6 °C 
Density: approximately 1.6040 g/cm³
Refractive index: approximately 1.4462, listed as an estimate.
Water solubility: Poor/low; ChemicalBook describes it as insoluble in water, while older chemical literature cited there reports approximately 1% solubility in water at 0 °C. The apparent difference reflects the fact that solubility depends strongly on temperature and experimental conditions.

Solubility in sulfuric acid: Sparingly soluble when heated.
pKa: approximately 10.06 ± 0.43, but this is a predicted value, not a directly established experimental constant.
Color: White to off-white.
Odor: No significant characteristic odor is generally reported.
Flash point: Not available.
Flammability: ChemicalBook indicates that the substance is probably non-flammable; however, this should not be interpreted as meaning that the material is completely free of fire-related hazards under all conditions.
Storage: Store sealed in a dry environment at room temperature and protect the material from unnecessary exposure to incompatible chemicals.
Water behavior: It has low water solubility.
Chemical class: Organic amide/hydrazine derivative; specifically a hydrazine dicarboxamide/biurea compound.

Functional groups: Two carbamoyl/urea-type carbonyl groups and a hydrazine N–N linkage.
Hydrogen-bonding ability: The molecule contains multiple N–H groups capable of hydrogen bonding and carbonyl oxygen atoms capable of accepting hydrogen bonds.
Polarity: Relatively polar compared with small hydrocarbons because of its four nitrogen atoms, two carbonyl groups and multiple N–H groups.
Thermal behavior: It is thermally stable enough to exist as a high-melting crystalline solid, but high-temperature processing can result in decomposition rather than simple volatilization.
Chemical reactivity: As an amide-containing compound, it is generally much less basic than hydrazine itself. ChemicalBook describes amides as weak bases and notes that reactions with strong dehydrating or reducing agents can produce hazardous products. Combustion of nitrogen-containing organic material can generate nitrogen oxides
Chemical name: 1,1-Hydrazoformamide
Common name: Biurea
IUPAC name: (Carbamoylamino)urea

CAS No.: 110-21-4
EC No.: 203-747-2
PubChem CID: 8039
ChemSpider ID: 7748
Molecular formula: C₂H₆N₄O₂
Molecular weight: 118.09 g/mol
Exact mass: ~118.0491 Da
Appearance: White to off-white crystalline solid/powder
Melting point: 247–250 °C
Density: ~1.604 g/cm³

Water solubility: Low/poor
pKa: ~10.06 ± 0.43 predicted
Chemical class: Hydrazine dicarboxamide / urea derivative
Main industrial role: Intermediate for azodicarbonamide production
Other application: Specialized chemical intermediate, including reported use in rechargeable lithium-battery anode-material processing
Main safety concern: Irritation of eyes, skin and respiratory system; avoid dust inhalation and direct contact
Storage: Sealed, dry, room-temperature storage under appropriate chemical-storage conditions
Flammability: No conventional flash point reported; generally described as probably non-flammable, but hazardous decomposition/combustion products remain possible.
CBNumber:CB4365907
Molecular Formula:C2H6N4O2

Molecular Weight:118.09
MDL Number:MFCD00025398
MOL File:110-21-4.mol
Melting Point: 247-250 °C
Boiling Point: 220.6°C (rough estimate)
Density: 1.6040
Refractive Index: 1.4462 (estimate)
Storage Temperature: Sealed in dry, Room Temperature
Solubility: Sulfuric Acid (Sparingly, Heated)
pKa: 10.06±0.43 (Predicted)

Form: Solid
Color: White to Off-White
CAS Database Reference: 110-21-4 (CAS Database Reference)
EWG's Food Scores: 1
FDA UNII: POJ4UOY01H
EPA Substance Registry System: Biurea (110-21-4)
IUPAC Name: (carbamoylamino)urea
Canonical SMILES: C(=O)(N)NNC(=O)N
InChI Key: ULUZGMIUTMRARO-UHFFFAOYSA-N
Boiling Point: 330.5ºC at 760 mmHg
Melting Point: 247-250ºC

Flash Point: 153.7ºC
Density: 1.594g/cm³
Appearance: WHITE POWDER
EC Number: 203-747-2
Exact Mass: 118.04900
H-Bond Acceptor: 2
H-Bond Donor: 4
Molecular Weight: 118.10 g/mol
XLogP3-AA: -2.1
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 118.04907545 Da
Monoisotopic Mass: 118.04907545 Da

Topological Polar Surface Area: 110 Ų
Heavy Atom Count: 8
Formal Charge: 0
Complexity: 96.6
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

FIRST AID MEASURES of 1,1-HYDRAZOFORMAMIDE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of 1,1-HYDRAZOFORMAMIDE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of 1,1-HYDRAZOFORMAMIDE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of 1,1-HYDRAZOFORMAMIDE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of 1,1-HYDRAZOFORMAMIDE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of 1,1-HYDRAZOFORMAMIDE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available

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