Basic information
- Standard SMILES
O=C(Nc1ccccc1)Nc1ccccc1- InChIKey
GWEHVDNNLFDJLR-UHFFFAOYSA-N- Molecular formula
- C13H12N2O
- Average molar mass
- 212.25 g/mol
- Monoisotopic mass
- 212.094963
Overview
1,3-diphenylurea is an off-white powder. (NTP, 1992)
Names & identifiers
- Preferred name
- Carbanilide
- IUPAC
- 1,3-diphenylurea
- English name
- 1,3-Diphenylurea
- Molecular formula
- C13H12N2O
- Molecular weight
- 212.25
Names & synonyms
Show more names
Database identifiers
- CAS
102-07-8、26763-63-3- PubChem CID
- 7595
- DTXSID
DTXSID2025183- ChEMBL
CHEMBL354676- ChEBI
CHEBI:41320- UNII
- 94YD8RMX5B
- EC Number
- 203-003-7
- Nikkaji
- J5.003B
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 41.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 196
Experimental & physicochemical properties
Chemical Classes
Nitrogen Compounds -> Urea Compounds
Industrial compound
LogP
3.00
3.0
Density
1.239 (NTP, 1992) - Denser than water; will sink
1.239
Color/Form
RHOMBIC BIPYRAMIDAL PRISMS FROM ALCOHOL
ORTHORHOMBIC PRISMS FROM ALCOHOL
COLORLESS PRISMS
Solubility
less than 0.1 mg/mL at 64 °F (NTP, 1992)
SPARINGLY SOL IN WATER (0.15 G/L); SAPRINGLY SOL IN ALCOHOL, ACETONE, CHLOROFORM ; MODERATELY SOL IN PYRIDINE (69.0 G/L).
SOL IN ACETIC ACID, ETHER; INSOL IN BENZENE
0.15 mg/mL
Boiling Point
504 °F at 760 mmHg (Decomposes) (NTP, 1992)
260 °C (DECOMPOSE)
Melting Point
460 °F (NTP, 1992)
238 °C
239 - 240 °C
Physical Description
1,3-diphenylurea is an off-white powder. (NTP, 1992)
Large Crystals
Colorless solid; [HSDB] Off-white powder; [Alfa Aesar MSDS]
Solid
Other Experimental Properties
SUBLIMES IN CURRENT OF HYDROGEN AT 220 °C
UV: 5-361 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /Urea, 1,1-diphenyl/
Physicochemical properties
- Melting point
- 239 · 239-241 °C(lit.)
- Boiling point
- 262 °C · 262 °C(lit.)
- Density
- 1 · 1,239 g/cm3
- vapor pressure
- 0 · 0-0Pa at 20-25℃
- refractive index
- 1.692 · 1.6920 (estimate)
- Flash point
- 260 °C · 260°C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 50 mg/mL, · pyridine: soluble50mg/mL, clear to very slightly hazy, colorless to faintly yellow
- form
- Crystalline Powder
- pka
- 14.15 · 14.15±0.70(Predicted)
- color
- White
- Water Solubility
- 150.3 mg/L · 150.3mg/L(temperature not stated)
- Merck
- 14 · 14,1785
- BRN
- 782650 · 782650
- Stability
- Stable. Incompatible with strong oxidizing agents.
- InChI
- 1S/C13H12N2O/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15,16)
- InChIKey
- GWEHVDNNLFDJLR-UHFFFAOYSA-N
- SMILES
- O=C(Nc1ccccc1)Nc2ccccc2
- LogP
- 2.97 · 2.97
- CAS DataBase Reference
- 102 · 102-07-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 94 YD8RMX5B · 94YD8RMX5B
- NIST Chemistry Reference
- Urea, N,N'-diphenyl-(102-07-8)
- EPA Substance Registry System
- Carbanilide (102-07-8)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- RTECS
- 9800000 · FD9800000
- TSCA
- TSCA listed
- HS Code
- 29242100 · 29242100
- Storage Class
- 11 · 11 - Combustible Solids
- Hazardous Substances Data
- 102 · 102-07-8(Hazardous Substances Data)
- Toxicity
- 50 · mouse,LD50,intraperitoneal,200mg/kg (200mg/kg),National Technical Information Service. Vol. AD277-689,
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 20% (1 of 5) of reports.
Warning
H302 (80%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Urea, N,N'-diphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Urea, N,N'-diphenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 26-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20899
Urea, N,N'-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard
Reactivity Profile
1,3-DIPHENYLUREA is 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).
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- FD9800000
- hs_code
- 29242100
- Toxicity
- mouse,LD50,intraperitoneal,200mg/kg (200mg/kg),National Technical Information Service. Vol. AD277-689,
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- REACH Registrations
- Active
- Precautionary statements
- P264-P270-P301+P312-P330-P501
- Hazardous Substances Data
- 102-07-8(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
TOBACCO CALLUS PROPAGATED ON MINERAL MEDIUM CONTAINING N,N'-DIPHENYLUREA LABELED IN UREYLENE CARBON, AS SOURCE OF CYTOKININ. METABOLITE IDENTIFIED AS O-BETA-D-GLUCOSIDE IS APPROX 125 TIMES LESS ACTIVE THAN PARENT COMPD IN PROMOTING TOBACCO CELL DIVISION.
TISSUE CULTURE STUDIES WITH N,N'-DIPHENYLUREA INDICATED CONVERSION INTO AN ACTIVE FORM.
Uses & manufacturing
Uses
Used in organic synthesis; [HSDB]
IN ORG SYNTHESIS
General Manufacturing Information
Transportation Equipment Manufacturing
Urea, N,N'-diphenyl-: ACTIVE
N,N'-DIPHENYLUREA USED AS THE SOURCE OF CYTOKININ FOR CYTOKININ-DEPENDENT TOBACCO CALLUS WAS FOUND TO CONTAIN 3 CYTOKININ-ACTIVE RIBONUCLEOSIDES. HOWEVER, NO EVIDENCE WAS FOUND TO ASSOCIATE THE MODE OF ACTION OF THE NON-PURINE CYTOKININ, N,N'-DIPHENYLUREA WITH TRNA.
IT PROMOTED CALLUS GROWTH AT HIGH CONCN, ALTHOUGH GROWTH OF MOST OF CALLUS TISSUES WAS IRREGULAR.
MIXT OF N,N'-DIPHENYLUREA (PDU), GIBBERELLIC & 2-NAPHTHOXYACETIC ACIDS TESTED. MIXT OF LATTER 2 INCR SET & FINAL YIELD & ADDN OF DPU DID NOT IMPROVE THE RESULT.
Applications
Description1,3-Diphenylurea is a cytokinin.1,2 It increases fresh weight of tobacco plant tissue when used at concentrations ranging from 1 to 16 mg/L in growth media.1 1,3-Diphenylurea (32 and 100 µM) increases the growth of cultured P. lunatus callus tissue.2 Exogenous 1,3-diphenylurea (32 and 100 µM) added during first-passage culture induces second-passage cytokinin autonomy in cultured P. lunatus tissue.WARNING This product is not for human or veterinary use.
Uses1,3-Diphenylurea is mainly used as an intermediate for the drug sulfanilamide, and its chlorosulfonated product can be used as the main raw material for sulfamethoxazole.
General Description1,3-Diphenylurea is a cytokinin compound present in fruit and vegetables.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: 1,3-diphenylurea is a member of the class of phenylureas that is urea in which one of the hydrogens of each amino group is replaced by a phenyl group. It is present in coconut milk (Cocos nucifera). It has a role as a plant metabolite and a cytokinin.
Related reactions
Linked notes
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