Benzophenone
Names | |
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Preferred IUPAC name
Diphenylmethanone[1] | |
Other names | |
Identifiers | |
3D model (
JSmol ) |
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1238185 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.003.943 |
EC Number |
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4256 | |
KEGG | |
PubChem CID
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RTECS number
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UNII | |
UN number | 1224 |
CompTox Dashboard (EPA)
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Properties | |
C13H10O | |
Molar mass | 182.222 g·mol−1 |
Appearance | White solid |
Odor | Geranium-like[2] |
Density | 1.11 g/cm3[2] |
Melting point | 48.5 °C (119.3 °F; 321.6 K)[2] |
Boiling point | 305.4 °C (581.7 °F; 578.5 K)[2] |
Insoluble[2] | |
organic solvents
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1 g/7.5 mL in tetrachloromethane: better with increasing tetrachloromethane content[3]
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-109.6·10−6 cm3/mol | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Harmful (XN) |
GHS labelling: | |
Warning | |
H373, H411 | |
P260, P273, P314, P391, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 110 °C (230 °F; 383 K) |
Safety data sheet (SDS) | External MSDS by JT Baker |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzophenone is the
Uses
Benzophenone can be used as a photo initiator in ultraviolet (UV)-curing applications[4] such as inks, imaging, and clear coatings in the printing industry. Benzophenone prevents UV light from damaging scents and colors in products such as perfumes and soaps.
Benzophenone can also be added to plastic packaging as a UV blocker to prevent photo-degradation of the packaging polymers or its contents. Its use allows manufacturers to package the product in clear glass or plastic (such as a
In biological applications, benzophenones have been used extensively as photophysical probes to identify and map peptide–protein interactions.[6]
Benzophenone is used as an additive in flavorings or perfumes for "sweet-woody-geranium-like notes."[7]
Synthesis
Benzophenone is produced by the copper-catalyzed oxidation of diphenylmethane with air.[8]
A laboratory route involves the reaction of benzene with
Another route of synthesis is through a palladium(II)/oxometalate catalyst. This converts an alcohol to a ketone with two groups on each side.[11]
Another, less well-known reaction to produce benzophenone is the pyrolysis of anhydrous calcium benzoate.[12]
Organic chemistry
Benzophenone is a common
.Benzophenone radical anion
Alkali metals reduce benzophenone to the deeply blue colored
- M + Ph2CO → M+Ph2CO•−
Generally sodium is used as the alkali metal. Sodium-benzophenone ketyl is used in the purification of organic solvents, particularly ethers, because it reacts with water and oxygen to give non-volatile products.
- M + M+Ph2CO•− → (M+)2(Ph2CO)2−
Commercially significant derivatives and analogues
There are over 300 natural benzophenones, with great structural diversity and biological activities. They are being investigated as potential sources of new drugs.
2-Amino-5-chlorobenzophenone is used in the synthesis of benzodiazepines.[19]
Safety
It is considered "essentially nontoxic."[8] Benzophenone is however banned as a food additive by the US Food and Drug Administration, despite the FDA's continuing stance that this chemical does not pose a risk to public health under the conditions of its intended use.[20][21] Benzophenone derivatives are known to be pharmacologically active. From a molecular chemistry point of view interaction of benzophenone with B-DNA has been demonstrated experimentally.[22] The interaction with DNA and the successive photo-induced energy transfer is at the base of the benzophenone activity as a DNA photosensitizer and may explain part of its therapeutic potentialities.
In 2014, benzophenones were named Contact Allergen of the Year by the American Contact Dermatitis Society.[23]
Benzophenone is an endocrine disruptor capable of binding to the pregnane X receptor.[24]
References
- ^ ISBN 978-0-85404-182-4.
- ^ a b c d e f g Merck Index (11th ed.). p. 1108.
- .
- PMID 20728089.
- ^ Dornath, Paul John (2010). "Analysis of Chemical Leaching from Common Consumer Plastic Bottles Under High Stress Conditions" (PDF). p. 32. Archived from the original (PDF) on 26 February 2015. Retrieved 26 February 2015.
- PMID 8180191.
- ^ Arctander, Steffen. Perfume And Flavor Chemicals: (Aroma Chemicals).
- ^ ISBN 978-3527306732.
- ^ Marvel, C. S.; Sperry, W. M. (1941). "Benzophenone". Organic Syntheses; Collected Volumes, vol. 1, p. 95.
- .
- .
- .
- ^ PMID 11848774.
- ISBN 978-0-7506-7571-0.
- ISBN 978-0-632-04819-9.
- S2CID 17801540.
- ISSN 0100-4042.
- PMID 24972079.
- ISSN 1554-8120.
- ^ "FDA Bans Use of 7 Synthetic Food Additives After Environmental Groups Sue". NPR.org. Retrieved 2018-10-09.
- ^ 83 FR 50490
- PMID 22698517.
- ^ Doug Brunk (2014-03-14). "Benzophenones named 2014 Contact Allergen of the Year : Dermatology News". Skinandallergynews.com. Archived from the original on 2016-03-22. Retrieved 2016-06-16.
- PMID 14613717.