CAS 120-46-7 Dibenzoylmethane (HCID 8433)

Names & identifiers

Preferred name: Dibenzoylmethane
IUPAC: 1,3-diphenylpropane-1,3-dione
English name: Dibenzoylmethane
Molecular formula: C15H12O2
Molecular weight: 224.25

Names & synonyms

Dibenzoylmethane120-46-71,3-Diphenylpropane-1,3-dione1,3-DIPHENYL-1,3-PROPANEDIONE1,3-Propanedione, 1,3-diphenyl-2-BenzoylacetophenonePhenyl phenacyl ketoneomega-BenzoylacetophenoneRhodiastab 83Karenzu DK2DTXSID3041247ANS7ME8OKC

Show more names

DBM1,3-Diphenylpropanedione1,3-diphenyl-3-propanedionekarenzudk2phenylphenacylketoneDBM83

NSC-6266DTXCID1021247CHEBI:75417204-398-9RefChem:132859GAMMA-HYDROXYCHALKONE1,3-Diphenyl-propane-1,3-dioneDibenzoyl-methane

Database identifiers

CAS: 120-46-7
PubChem CID: 8433
DTXSID: DTXSID3041247
ChEMBL: CHEMBL371523
ChEBI: CHEBI:75417
UNII: ANS7ME8OKC
EC Number: 204-398-9
Nikkaji: J10.072B

Properties

Computed structural properties

XLogP: 3.1
Topological polar surface area: 34.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 4
Heavy atoms: 17
Formal charge: 0
Complexity: 243

Experimental & physicochemical properties

Physical Description · 2 items

Large Crystals; Dry Powder

Solid; [Merck Index] Light yellow crystalline powder; [Alfa Aesar MSDS]

Collision Cross Section165.9 Å² [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3041247]；154.4 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3041247]

Physicochemical properties

Melting point: 77 · 77-79 °C(lit.)
Boiling point: 219 · 219-221 °C18 mm Hg(lit.)
Density: 0.8 g/cm3 · 0.800 g/cm3
vapor pressure: 0.01 Pa · 0.01Pa at 20℃
refractive index: 1.66 · 1.6600 (estimate)
Flash point: 219 · 219-221°C/18mm
storage temp.: 30 °C · Store below +30°C.
solubility: Chloroform (Slightly), Methanol (Slightly, Sonicated)
pka: 8.95 · 8.95±0.10(Predicted)
form: Crystals
color: Light yellow to yellow
Water Solubility: It is Soluble in ether, chloroform, and aqueous sodium hydroxide. Insoluble in water.
Merck: 14 · 14,3009
BRN: 514910 · 514910
Henry's Law Constant: 7.5 · 7.5×103 mol/(m3Pa) at 25℃, Zhang et al. (2010)
Stability: Stable. Incompatible with strong oxidizing agents.
InChI: 1S/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2
InChIKey: NZZIMKJIVMHWJC-UHFFFAOYSA-N
SMILES: O=C(CC(=O)c1ccccc1)c2ccccc2
LogP: 4.59 at · 4.59 at 25℃
CAS DataBase Reference: 120 · 120-46-7(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 7 ME8OKC · ANS7ME8OKC
NIST Chemistry Reference: 1 · 1,3-Propanedione, 1,3-diphenyl-(120-46-7)
EPA Substance Registry System: 1 · 1,3-Propanedione, 1,3-diphenyl- (120-46-7)
UNSPSC Code: 12352115 · 12352115
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P271-P280
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
RTECS: 1930000 · TZ1930000
Hazard Note: Irritant
TSCA: TSCA listed
HS Code: 29143900 · 29143900
Storage Class: 11 · 11 - Combustible Solids
Toxicity: 500 mg/kg · rat,LD,oral,> 500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 28, 1953.
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 32.7% (84 of 257) of reports.

Warning

H317 (66.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 257 reports by companies from 6 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 84 of 257 reports by companies.；There are 5 notifications provided by 173 of 257 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 4 items

Chemical: 1,3-Propanedione, 1,3-diphenyl-

1,3-Propanedione, 1,3-diphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanedione, 1,3-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: 13-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11371

1,3-Propanedione, 1,3-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses changes in liver and uterine weights in 2-week constant oral studies of mice; [RTECS] May cause irritation; [Alfa Aesar MSDS]

Hazard Classes and CategoriesSkin Sens. 1 (66.1%)

Regulatory information

Regulatory Information · 4 items

Chemical: 1,3-Propanedione, 1,3-diphenyl-

1,3-Propanedione, 1,3-diphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanedione, 1,3-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: 13-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11371

1,3-Propanedione, 1,3-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
tsca: TSCA listed
rtecs: TZ1930000
hs_code: 29143900
Toxicity: rat,LD,oral,> 500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 28, 1953.
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 22-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
REACH Registrations: Active
Precautionary statements: P261-P271-P280

Chemistry & industry

Uses & manufacturing

UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA]

U.S. Production2023: 700,000 - <850,000 lb；2022: 850,000 - <1,000,000 lb；2021: 550,000 - <700,000 lb；2020: 700,000 - <850,000 lb

Consumer UsesHeat stabilizer；Other

Industry UsesProcessing aids not otherwise specified；Heat stabilizer；Other

Use Classification · 2 items

Plastics -> Other stabilisers

Plastics -> Polymer Type -> PVC (soft); PVC (rigid); PET

General Manufacturing Information · 2 items

Plastics Material and Resin Manufacturing；All Other Chemical Product and Preparation Manufacturing；Plastics Product Manufacturing

1,3-Propanedione, 1,3-diphenyl-: ACTIVE

Applications · 3 items

OccurrenceDibenzoylmethane(DBM) is a 1,3-diketone derivative of acetylacetone that has both methyl groups replaced with phenyl groups.Although smaller in size and lacking hydroxyl and methoxy groups，DBM resembles the turmeric spice curcumin (CUR),a diferuloylmethane. Both molecules are metal-chelating agents，contain a B-diketone flanked by two aryl groups,and exhibit anti-proliferative and anticarcinogenic activity. In addition to sharing structural similarity with DBM,CUR,which is also a naturally occurring compound is found in the plant Curcuma longa and has numerous medicinal uses.DBM and its many naturally occurring derivatives are minor constituentsof licorice. DBM has been isolated from licorice root extracts and otherspecies of Glycyrrhiza.

UsesDibenzoylmethane is a new kind of PVC heat stabilizer, it has better transparency, nontoxic and odorless. In case of combined use with Calcium/Zinc, Barium/Zin and other heat stabilizer, it can greatly improve the initial color, transparency, long term stability of PVC, and also can improve the precipitation and “zinc burning” problem during the process. It has very good synergy with zinc soaps, and can protect the PVC color. This material can absorb UV at 290nm, which has the effect as light stabilizer and act as long term stabilizer for PVC products.

UsesDibenzoylmethane is a compound known to inhibit tumorigenesis in mice.

Preparation methods

Preparationdibenzoylmethane is prepared by condensation of ethyl benzoate with acetophenone.

Upstream & downstream products

Downstream products

3,5-Diphenylpyrazole 1,2,4,5-tetraphenylbenzene 1,2-Bis(p-tolylsulfonyl)hydrazine, N,Nμ-Ditosylhydrazine, 4-Methylbenzenesulfonic acid 2-[(4-methylphenyl)sulfonyl]hydrazide 3-Benzoyl-2-phenylnaphtho[2,3-b]furan-4,9-dione 1-Butanone, 4-(4-nitrophenyl)-1-phenyl-

Suppliers100 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]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

INTATRADE GmbH+49 3493/605464 · [email protected]

韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Dibenzoylmethane is a beta-diketone that is acetylacetone (acac) in which both methyl groups have been replaced by phenyl groups. It is a minor constituent of the root extract of licorice (Glycyrrhiza glabra) and exhibits antimutagenic and anticancer effects. It has a role as an antineoplastic agent, a metabolite and an antimutagen. It is a beta-diketone and an aromatic ketone.