Carbanilide
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Basic information
- CAS
102-07-8- Standard SMILES
O=C(Nc1ccccc1)Nc1ccccc1- InChIKey
GWEHVDNNLFDJLR-UHFFFAOYSA-N- Molecular formula
- C13H12N2O
- Average molar mass
- 212.25 g/mol
- Monoisotopic mass
- 212.09496301
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
1,3-Diphenylurea102-07-8N,N'-DiphenylureaCARBANILIDEDiphenylureaUrea, N,N'-diphenyl-Diphenylcarbamides-Diphenylureasym-DiphenylureaAcardite IAcarditeN-Phenyl-N'-phenylurea
Show more names
N,N-DIPHENYLUREACentralitePROXIMPHAMZeonet Uacarditei
1,3-DiphenylcarbamideKarbanilidUSAF EK-534N,N'-DifenylmocovinaUrea, 1,3-diphenyl-Karbanilid [Czech]NSC 2274011,3-diphenyl-urea
Database identifiers
- CAS
102-07-8- PubChem CID
- 7595
- DTXSID
DTXSID2025183- ChEMBL
CHEMBL354676- ChEBI
CHEBI:41320- UNII
- 94YD8RMX5B
- EC Number
- 203-003-7
- Nikkaji
- J5.003B
Properties
Computed structural propertiesFilling in
- 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
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesBoiling point
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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
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)
REACH registered substance: 1,3-diphenylurea (EC: 203-003-7)
Urea, N,N'-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsFlash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)
Hazards SummaryNo evidence of mutagenicity; [HSDB] May cause irritation; [Alfa Aesar MSDS]
Reactive GroupAmides and Imides
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).
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.
Cellular LocationsMembrane
Uses & manufacturing
Uses
Used in organic synthesis; [HSDB]
IN ORG SYNTHESIS
U.S. Production2023: 22,370 lb
Industry UsesIntermediate
Methods of ManufacturingOBTAINED DURING PREPARATION OF PHENYLUREA FROM ANILINE HYDROCHLORIDE & UREA: DAVIS, BLANCHARD, ORG SYN 3, 95 (1923).
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.
Related reactions
36 records
Compound notes
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