General Description
White solid with a flowery odor. May float or sink in water.
Reactivity Profile
Ketones, such as BENZOPHENONE(119-61-9), are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. This compound can react with oxidizing materials.
Air & Water Reactions
Insoluble in water.
Health Hazard
Ingestion causes gastrointestinal disturbances. Contact causes eye irritation and, if prolonged, irritation of skin.
Potential Exposure
Benzophenone is used in UV curing
of inks and coatings; as an intermediate; as an odor fixative
in fragrances, flavoring, soaps; in the manufacture of pharmaceuticals
and insecticides; in organic syntheses.
Fire Hazard
Flash point data for this chemical are not available, but BENZOPHENONE is probably combustible.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, rinse
mouth and get medical attention.
Shipping
UN1224 Ketones, liquid, n.o.s., Hazard Class: 3;
Labels: 3—Flammable liquid, Technical Name Required.
UN3077 Environmentally hazardous substances, solid, n.o.s.,
Hazard class: 9; Labels: 9—Miscellaneous hazardous material,
Technical Name Required.
Incompatibilities
Oxidizing materials, such as dichromates
and permanganates.
Occurrence
Reported found in Vitis vinifera L., black tea, cherimoya (Annona cherimola), mountain papaya (Carica pubescens)
and soursop (Annona muricata L.)
Definition
ChEBI: Benzophenone is the simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups. It has a role as a photosensitizing agent and a plant metabolite.
Preparation
By Friedel–Craft condensation of benzene with benzoyl chloride in the presence of aluminum chloride.
Production Methods
Benzophenone is commercially synthesized by the atmospheric
oxidation of diphenylmethane using a catalyst of
copper naphthenate. Alternatively, it can be produced by a
Friedel–Crafts acylation of benzene using either benzoyl
chloride or phosgene in the presence of aluminum chloride
.
reaction suitability
reagent type: reductant
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: Will attack some plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Materials Uses
Among the diverse electroactive components employed in the molecular design of OLED materials, the benzophenone core has attracted much attention as a fragment for the synthesis of organic semiconductors. On the other hand, benzophenone also functions as a classical phosphor with high intersystem crossing efficiency. This characteristic makes it a compelling candidate for effective reverse intersystem crossing, with potential in leading to the development of thermally activated delayed fluorescent (TADF) emitters[1].
Safety Profile
Moderately toxic by ingestion andintraperitoneal routes. Combustible when heated.Incompatible with oxidizers. When heated todecomposition it emits acrid and irritating fumes.
Carcinogenicity
Lifetime dermal carcinogenicity
studies in mice and rabbits did not show any tumor excess
in the treated animals. Female Swiss mice and
New Zealand White rabbits of both sexes were treated dermally
with 0, 5, 25, or 50% of benzophenone (0.02 mL) twice
a week for 120 or 180 weeks. Weekly examination of the
rabbits did not reveal any reduction in survival or appearance
of tumors. Mice treated with benzophenone did not show any
excess in the number of tumor-bearing animals or in total
number of tumors compared to untreated control animals.
Although three skin tumors were observed in the benzophenone-
treated mice (one case of squamous cell carcinoma and
two cases of squamous cell papilloma), there were also three
tumors (one carcinoma and toe papillomas) observed in the
control animals.
Metabolism
Benzophenone's main metabolic pathway in the rabbit is by reduction to benzhydrol, which is excreted conjugated with glucuronic acid(Williams, 1959).
Solubility in organics
Insoluble in water and glycerin, slightly soluble in Propylene glycol, 6% soluble in alcohol, soluble inmost perfume oils.
storage
Color Code—Green: General storage may be used.Store in a cool, well-ventilated area away from sources ofignition and incompatible materials.
Purification Methods
Crystallise it from MeOH, EtOH, cyclohexane, *benzene or pet ether, then dry in a current of warm air and store it over BaO or P2O5. It is also purified by zone melting and by sublimation [Itoh J Phys Chem 89 3949 1985, Naguib et al. J Am Chem Soc 108 128 1986, Gorman & Rodgers J Am Chem Soc 108 5074 1986, Ohamoto & Teranishi J Am Chem Soc 108 6378 1986, Naguib et al. J Phys Chem 91 3033 1987]. [Beilstein 7 III 2048, 7 IV 1357.]
Toxics Screening Level
The initial threshold screening level (ITSL) for benzophenone is 100 μg/m3 with an annual
averaging time.
References
[1] Blazevicius, D., Grigalevicius, S. (2024). A Review of Benzophenone-Based Derivatives for Organic Light-Emitting Diodes. Nanomaterials, 43 4.
https://doi.org/10.3390/nano14040356
