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Dibenzoylmethane

Dibenzoylmethane structure

CAS No:
120-46-7
Formula:
C15H12O2
Chemical Name:
Dibenzoylmethane
Synonyms:
1,3-Propanedione,1,3-diphenyl-;1,3-Diphenyl-1,3-propanedione;ω-Benzoylacetophenone;Phenyl phenacyl ketone;Dibenzoylmethane;2-Benzoylacetophenone;Karenz DK 2;Rhodiastab 83;NSC 406806;NSC 52984;NSC 6266;DBM;AD 158;1,3-Diphenylpropan-1,3-dione;Rhodiastab 83P;DBM 83;PB 201;61346-73-4;2090414-61-0
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

yellowish-white powderChEBI: A beta-diketone that is acetylacetone (acac) in which both methyl groups have been replaced by phenyl groups.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 antica cer effects.

1,3-Diphenyl-1,3-propanedione (dibenzoylmethane, DBM) is an aromatic 1,3-diketone derivative of acetylacetone (acac), where both methyl groups in acac have been substituted by phenyl groups. It is a white solid melting at 77−78°C. Similar to acac, DBM exists in two tautomeric forms, with the keto-enol equilibrium of DBM shifting strongly towards the enol form, particularly in non-polar solvents such as benzene. This is the result of the stability of the intramolecular hydrogen bond in the cis-enol form which is further resonance-stabilized by conjugation with phenyl rings. Due to its high photostability, derivatives of DBM such as avobenzone, have found applications as sunscreen products.

DryPowder; DryPowder, PelletsLargeCrystals; OtherSolid

Dibenzoylmethane is a beta-diketone that is acetylacetone (acac) in which both methyl groups have been replaced by phenyl groups.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.

Dibenzoylmethane Basic Attributes

Molecular Weight：

224.25500

Exact Mass：

224.25

EC Number：

204-398-9

UNII：

ANS7ME8OKC

NSC Number：

6266

DSSTox ID：

DTXSID3041247

HScode：

2914399090

Characteristics

PSA：

34.14000

XLogP3：

3.1

Appearance：

DryPowder; DryPowder, PelletsLargeCrystals; OtherSolid

Density：

0.800 g/cm3

Melting Point：

70.5 °C

Boiling Point：

219-221 °C

Flash Point：

146.9ºC

Refractive Index：

1.623

Water Solubility：

It is soluble in ether, chloroform, and aqueous sodium hydroxide. Insoluble in water.

Storage Conditions：

Store at RT.

Vapor Pressure：

1.63E-06mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S24/25

RTECS Number：

TZ1930000

Marks：

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P261, P272, P280, P302+P352, P321, P333+P313, P363, P501

Hazard Statements：

H317

GHS Classification：

|Warning|H317 (93.94%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 150 companies from 7 notifications to the ECHA C&L Inventory.

Toxicity

Name	Type of Test	Exposure Route	Species Observed	Dose/Duration	Toxic Effects	Reference
ACUTE TOXICITY DATA	LD - Lethal dose	Oral	Rodent - rat	>500 mg/kg	Details of toxic effects not reported other than lethal dose value--	National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. (Washington, DC) Volume(issue)/page/year: 5,28,1953

Drug Information

MeSH Entry Terms：

dibenzoylmethane

Dibenzoylmethane Use and Manufacturing

Uses

1. Antineoplastic
2. Dibenzoylmethane as a new PVC heat stabilizer, high transmittance, non-toxic and tasteless; can greatly improve the early PVC coloring, transparency, long-term stability, and processing during precipitation and "zinc burn" and so on; widely used in medical, food packaging and other non-toxic transparent PVC products. Dibenzoylmethane above can absorb 290nm ultraviolet light, while light having a stabilizing effect on PVC products can provide long-term stable performance.

Additive used in heat stabilizers for PVC compounds

Agricultural products (non-pesticidal)

Production

1,000,000 - 10,000,000 lb

Manufacturing Info：

Agriculture, forestry, fishing and hunting|1,3-Propanedione, 1,3-diphenyl-: ACTIVE

Computed Properties

Molecular Weight:224.25
XLogP3:3.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:224.083729621
Monoisotopic Mass:224.083729621
Topological Polar Surface Area:34.1
Heavy Atom Count:17
Complexity:243
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Synthesis Route

7726-95-6

71418-92-3

Material

Benzaldehyde

Tetrahydrofuran

Hydrochloric acid

Ethyl benzoate

Benzoyl chloride

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