Carbanilide

HCID 7595CAS 102-07-8

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

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、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

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Urea Compounds

Industrial compound

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesBoiling point
LogP · 2 items

3.00

3.0

Density · 2 items

1.239 (NTP, 1992) - Denser than water; will sink

1.239

Color/Form · 3 items

RHOMBIC BIPYRAMIDAL PRISMS FROM ALCOHOL

ORTHORHOMBIC PRISMS FROM ALCOHOL

COLORLESS PRISMS

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 3 items

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

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 item

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

Fire FightingFires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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 · 1 item

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) · 1 item

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

Non-Human Toxicity ExcerptsINCR IN FREQUENCY OF REVERSION FROM STREPTOMYCIN DEPENDENCE TO INDEPENDENCE IN STRAIN SD-4-73 OF ESCHERICHIA COLI WAS UTILIZED TO MEASURE MUTAGENICITY OF CHEMICALS. CARBANILIDE WAS NONMUTAGENIC.

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,

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

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 · 2 items

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 · 5 items

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 · 3 items

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

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
淄博泰立泽化工有限公司0533-5200592 13173271895 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
Additional notes · 1 item

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

36 records

Linked notes

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