PRODUCTS

CARBAMOYLIMINOUREA

Carbamoyliminourea is a nitrogen-rich compound combining urea and imino functionalities.
Carbamoyliminourea is mainly used as an intermediate in chemical synthesis and polymer-related applications.
Carbamoyliminourea's high polarity and reactivity make it suitable for systems requiring strong intermolecular interactions.

CAS Number: 123-77-3
EC Number: 204-650-8
Chemical Formula: C2H4N4O2
Molecular Mass: 116.080 g·mol−1

Synonyms: carbamoyliminourea, Diazene-1,2-dicarboxamide, azodicarbonamid, NSC674447, AZDA, (E)-azodicarbonamide, AzodicarbonamideTechnical, SCHEMBL26646, SCHEMBL36851, SCHEMBL9921280, CHEMBL3183489, AKOS028108416, DB-041742, NS00008341, Q415646, Q56607609, 380228-24-0, (E)-(carbamoylimino)urea, (E)-1,2-Diazendicarboxamid, (E)-1,2-Diazenedicarboxamide, (E)-1,2-Diazènedicarboxamide, (E)-Azodicarbonamide, (E)-Diazene-1,2-dicarboxamide, 1,2-Diazenedicarboxamide, (E)-, 123-77-3, 56Z28B9C8O, ADA, azodicarbonamida, Azodicarbonamide, Azodicarboxamide, C,C′-azodi(formamide), (1E)-1-aminocarbonyliminourea, (CARBAMOYLIMINO)UREA, (E)-aminocarbonyliminourea, (E)-carbamoyliminourea, (Z)-carbamoyliminourea, 1,1′-Azobis(formamide), 1,1′-Azobis[formamide], 1,1′-Azobiscarbamide, 1,1′-Azobisformamide, 1,1′-Azodiformamide, 380228-24-0, 97%, ABFA, aminocarbonyliminourea, AZDA, AZM 2S, Azobis CA 110B, Azobis CA 51C, Azobiscarbonamide, Azobiscarboxamide, Azobisformamide, Azocel, AZODICARBAMIDE, Azodicarboamide, Azodicarbonamide, 1,1-Azobisformamide, Dicarbamoyldiimide, Azodicarboxylic acid diamide, AZODIFORMAMIDE, Azodiformamide;1,1′-Azobisformamide, Azoform A, Azoformamide, Azoplastone, carbamoyliminourea, Celogen AZ, Celogen AZ 130, Celogen AZ 199, Celosen AZ, ChKhz 21R, Diazene-1,2-dicarboxamide, Diazenedicarboxamide, E927A, EINECS 204-650-8, Evipor, Ficel EP-A, Formamide, 1,1′-azobis-, Genitron AC, Genitron AC 2, Genitron AC 4, Genitron EPC, Kempore, Kempore 60/40, Kempore R 125, LN: ZVNUNVZY, Lucel ADA, Nitropore, Paramid K1, Pinhole ACR 3, Pinhole AK 2, Poramid K 1, Porofor adc/R, Porofor Chkhz 21, Porofor Chkhz 21R, Porofor DhKhZ 21, Porofor-lk 1074 (bayer), Unifoam AZ, Unifoam AZH 25, Uniform AZ, Vinyfor, Yunihomu AZ, δ(1,1′)-Biurea, δ1,1′-Biurea

Carbamoyliminourea is a chemical compound with the molecular formula C2H4O2N4.
Carbamoyliminourea is a yellow to orange-red, odorless, crystalline powder.

Carbamoyliminourea is sometimes called "the yoga mat chemical" because of widespread use in foamed plastics.
Carbamoyliminourea was first described by John Bryden in 1959.

Carbamoyliminourea is a nitrogen-rich organic compound characterized by the presence of urea and imino functional groups within the same molecular structure. Carbamoyliminourea exhibits high polarity and strong hydrogen-bonding capability due to multiple amide (–CONH–) and imino (–C=NH) functionalities.
Carbamoyliminourea is typically used as an intermediate in chemical synthesis and in specialized formulations where reactivity, nitrogen content, and compatibility with aqueous or polar systems are important.

Applications of Carbamoyliminourea:
Carbamoyliminourea is primarily used as a chemical intermediate in the synthesis of resins, additives, and specialty chemicals.
Carbamoyliminourea can be applied in formulations requiring high nitrogen functionality, such as curing agents, modifiers, or reactive components in polymer systems.
Additionally, Carbamoyliminourea may be used in laboratory-scale synthesis and research applications involving urea-based compounds and nitrogen-containing structures.

Blowing agent:
The principal use of Carbamoyliminourea is in the production of foamed plastics as a blowing agent.
The thermal decomposition of Carbamoyliminourea produces nitrogen, carbon monoxide, carbon dioxide, and ammonia gases, which are trapped in the polymer as bubbles to form a foamed article.

Carbamoyliminourea is used in plastics, synthetic leather, and other industries and can be pure or modified.
Modification affects the reaction temperatures.

Pure Carbamoyliminourea generally reacts around 200 °C.
In the plastic, leather, and other industries, modified Carbamoyliminourea (average decomposition temperature 170 °C) contains additives that accelerate the reaction or react at lower temperatures.

An example of the use of Carbamoyliminourea as a blowing agent is found in the manufacture of vinyl (PVC) and EVA-PE foams, where it forms bubbles upon breaking down into gas at high temperature.
Vinyl foam is springy and does not slip on smooth surfaces.

Carbamoyliminourea is useful for carpet underlay and floor mats.
Commercial yoga mats made of vinyl foam have been available since the 1980s; the first mats were cut from carpet underlay.

Food additive:
As a food additive, Carbamoyliminourea is used as a flour bleaching agent and a dough conditioner in some countries such as the US and Canada (up to 45 ppm), but not in the European Union.
Carbamoyliminourea reacts with moist flour as an oxidizing agent.

The main reaction product is biurea, which is stable during baking.
Secondary reaction products include semicarbazide (aminourea) and ethyl carbamate (urethane).

Carbamoyliminourea is known by the E number E927.
Many restaurants in the US fast food industry removed E927 from foodstuffs in response to negative publicity.

Synthesis of Carbamoyliminourea:

Carbamoyliminourea is prepared in two steps via treatment of urea with hydrazine to form biurea, as described in this idealized equation:
2 O=C(NH2)2 + H2N−NH2 → H2N−C(=O)−NH−NH−C(=O)−NH2 + 2 NH3

Oxidation of biurea with gaseous chlorine yields Carbamoyliminourea:
H2N−C(=O)−NH−NH−C(=O)−NH2 + Cl2 → H2N−C(=O)−N=N−C(=O)−NH2 + 2 HCl

Production of Carbamoyliminourea:
Carbamoyliminourea is typically produced through controlled reactions involving urea derivatives and nitrogen-containing intermediates under mild to moderate conditions.
A common route involves the condensation of urea with cyanamide or related imino compounds, where the carbamoyl (–CONH–) and imino (–C=NH) functionalities are formed simultaneously.

The reaction is generally carried out in aqueous or polar solvent systems to ensure proper dissolution and interaction of reactants, often under controlled temperature to prevent side reactions or decomposition.
During synthesis, pH and temperature are carefully regulated to favor the formation of the desired carbamoyliminourea structure and to avoid excessive polymerization or by-product formation.

After completion, the product is typically isolated by crystallization or precipitation, followed by filtration, washing, and drying to obtain a purified solid form.
The resulting compound may undergo additional purification steps depending on the required application and purity level.

Stability and Reactivity of Carbamoyliminourea:

Chemical stability:
Stable under normal conditions.

Reactivity:
Reactive due to amide and imino groups.
May participate in condensation.
Hydrogen-bonding interactions.

Conditions to avoid:
Excessive heat.
Moisture.
Strong oxidizing conditions.

Incompatible materials:
Strong oxidizers.
Strong acids.
Bases.

Hazardous decomposition:
Carbon oxides (CO.
CO₂).
Nitrogen-containing gases upon thermal decomposition.

Handling and Storage of Carbamoyliminourea:

Handling:
Avoid inhalation.
Ingestion.
Contact with skin or eyes.
Use appropriate PPE.

Storage:
Store in a cool, dry, well-ventilated area in tightly closed containers.

Conditions:
Protect from moisture.
Contamination.

First Aid Measures of Carbamoyliminourea:

Inhalation:
Move to fresh air.
Seek medical attention if symptoms occur.

Skin contact:
Wash with soap and water.
Remove contaminated clothing.

Eye contact:
Rinse with water for several minutes.

Ingestion:
Rinse mouth.
Do not induce vomiting.
Seek medical advice.

Firefighting Measures of Carbamoyliminourea:

Extinguishing media:
Water spray.
Foam.
Dry chemical.
CO₂.

Hazards:
May release toxic nitrogen oxides during combustion.

Protection:
Use self-contained breathing apparatus (SCBA).

Accidental Release Measures of Carbamoyliminourea:

Precautions:
Use PPE.
Avoid dust formation.

Cleanup:
Collect material mechanically.
Place in suitable containers.

Environment:
Prevent release into water systems.

Exposure Controls/Personal Protective of Carbamoyliminourea:

Controls:
Ensure adequate ventilation.

Respiratory:
Use dust mask if necessary.

Hands:
Wear protective gloves.

Eyes:
Safety goggles recommended.

Skin:
Protective clothing.

Identifiers of Carbamoyliminourea:
CAS: 123-77-3
Molecular Weight (g/mol): 116.08
MDL Number: MFCD00007958
InChI Key: XOZUGNYVDXMRKW-AATRIKPKSA-N
PubChem CID: 5462814
IUPAC Name: (E)-carbamoyliminourea
SMILES: C(=O)(N)N=NC(=O)N

CAS Number: 123-77-3
ChEMBL: ChEMBL28517
ChemSpider: 4575589
ECHA InfoCard: 100.004.229
EC Number: 204-650-8
E number: E927a (glazing agents, ...)
PubChem CID: 31269
UNII: 56Z28B9C8O
CompTox Dashboard (EPA): DTXSID0024553
InChI: InChI=1S/C2H4N4O2/c3-1(7)5-6-2(4)8/h(H2,3,7)(H2,4,8)/b6-5+
Key: XOZUGNYVDXMRKW-AATRIKPKSA-N
InChI=1/C2H4N4O2/c3-1(7)5-6-2(4)8/h(H2,3,7)(H2,4,8)/b6-5+
Key: XOZUGNYVDXMRKW-AATRIKPKBW
SMILES: O=C(/N=N/C(=O)N)N

Properties of Carbamoyliminourea:
Chemical formula: C2H4N4O2
Molar mass: 116.080 g·mol−1
Appearance: Yellow to orange/red crystalline powder
Melting point: 225 °C (437 °F; 498 K) (decomposes)

Molecular Weight: 116.08 g/mol
XLogP3-AA: -1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 116.03342538 Da
Monoisotopic Mass: 116.03342538 Da
Topological Polar Surface Area: 111 Å²
Heavy Atom Count: 8
Complexity: 123
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 1
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Carbamoyliminourea:
Melting Point: 195.0°C to 202.0°C
Assay Percent Range: 97%
Packaging: Plastic bottle
Molecular Formula: C2H4N4O2
Linear Formula: H2NCON=NCONH2
Quantity: 500 g
Beilstein: 03,IV,246
Merck Index: 15,912
Formula Weight: 116.08
Percent Purity: 97%

Names of Carbamoyliminourea:

IUPAC name:
Carbamoyliminourea

Other names:
Azodicarboxamide
Azobisformamide
C,C'-Azodi(formamide)
Diazenedicarboxamide
Ayngaroxamide