Phenylurea
1-Phenylurea · VH · N-PHENYLUREA · Urea, N-phenyl- · phenyl-ure · PHENYLUREA · stabilizervh · Urea,phenyl-
Identifiers & Physical Properties
| CAS No. | 64-10-8 |
|---|---|
| Molecular formula | C7H8N2O |
| Average molar mass | 136.15 g/mol |
| Monoisotopic mass | 136.06366288 g/mol |
| SMILES | NC(=O)Nc1ccccc1 |
| InChIKey | LUBJCRLGQSPQNN-UHFFFAOYSA-N |
| PubChem CID | 6145 |
| ChEMBL | CHEMBL168445 |
| ChEBI | CHEBI:180992 |
| EC No. | 200-576-5 |
| DTXSID | DTXSID8042507 |
Chemical & Physical Properties
| XLogP | 0.8 |
|---|---|
| Topological polar surface area | 55.1 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 1 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 119 |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| Physical Description | Phenyl urea pesticide, liquid, poisonous appears as a liquid dissolved or suspended in a liquid carrier. Contains any of several related compounds (Diuron, Fenuron, Linuron, Neburon, Siduron, Monuron) formally derived from urea. Carrier is water emulsifiable. Toxic by inhalation, skin absorption, or ingestion. Obtain the technical name of the specific pesticide and carrier from the shipping papers and contact CHEMTREC, 800-424-9300 for response information. |
| Melting point | 145-147 °C(lit.) |
| Boiling point | 238 °C |
| Density | 1,302 g/cm3 |
| Vapor density | >1 (vs air) |
| Refractive index | 1.5769 (estimate) |
| Flash point | 238°C |
| Storage conditions | Keep in dark place,Sealed in dry,Room Temperature |
| Solubility | H2O: 10 mg/mL, clearSoluble in water. |
| pKa (acidity coefficient) | 13.37±0.50(Predicted) |
| Physical state | Powder, Crystals and/or Chunks |
| Color | White to light yellow |
| Merck | 14,7319 |
| BRN | 1934615 |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| InChI | 1S/C7H8N2O/c8-7(10)9-6-4-2-1-3-5-6/h1-5H,(H3,8,9,10) |
| InChIKey | LUBJCRLGQSPQNN-UHFFFAOYSA-N |
| SMILES | NC(=O)Nc1ccccc1 |
| CAS DataBase Reference | 64-10-8(CAS DataBase Reference) |
| FDA UNII | 862I85399W |
| EPA Substance Registry System | Urea, phenyl- (64-10-8) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H319 |
| GHS precautionary statements | P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501-P301+P312a-P330-P501a |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn |
| Risk statements (R) | 22 |
| Safety statements (S) | 22-36/37-24/25 |
| Water hazard class (WGK) | 3 |
| RTECS number | YU0650000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29242100 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Acute Tox. 4 Oral |
| Toxicity | LD50 oral in rat: 2gm/kg |
Safety & Regulations
| GHS classification | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 47 reports by companies from 3 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatory information | Chemical: Urea, N-phenyl-Phenylurea: Does not have an individual approval but may be used under an appropriate group standard |
| DOT label | Poison |
| Fire hazards | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Health hazards | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Reactive group | Amides and Imides |
| Reactivity Profile | Organic 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). Contains any of several related compounds (Diuron, Fenuron, Linuron, Neburon, Siduron, Monuron) formally derived from urea. |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Fire fighting | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| First aid | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Nonfire spill response | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Isolation and Evacuation | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | YU0650000 |
| Customs code | 29242100 |
| Toxicity | LD50 oral in rat: 2gm/kg |
| Risk statements (R) | 22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 22-36/37-24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302-H315-H319 |
| Hazard class | Acute Tox. 4 Oral |
| GHS precautionary statements | P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501-P301+P312a-P330-P501a |
Applications & Uses
Uses
Phenylureas are commonly used soil-applied herbicides for control of grass and small-seeded broadleaf weeds.
Uses
Phenyl urea is used in organic synthesis. It acts as an efficient ligand for palladium-catalyzed Heck and Suzuki reactions of aryl bromides and iodides.
General Description
Phenylurea is the core structural unit of phenylurea herbicides (PUHs), such as diuron, fenuron, linuron, monuron, isoproturon, monolinuron and chlortoluron. As photosynthesis inhibitors, phenylurea herbicides are widely used in various crops for the pre-emergence and post-emergence control of broadleaf and annual weeds. These herbicides are used on major food crops, including maize (Zea mays) and tomato (Solanum lycopersicum), to control weeds such as lamb’s quarters (Chenopodium album), amaranth (Amaranthus spp.) and barnyard grass (Echinochloa crus-galli)[1].
Preparation & Synthesis
Preparation
Phenylurea is synthesized by the reaction of aniline and urea. Put urea, hydrochloric acid and aniline into the reaction pot, heat and stir, reflux at 100-104°C for 1 hour, add water and stir, cool, filter, wash the filter cake with water, and dry to obtain the finished product of phenylurea.