| Identification | More | [Name]
Benzophenone | [CAS]
119-61-9 | [Synonyms]
AKOS BBS-00004333
ALPHA-OXODIPHENYLMETHANE
ALPHA-OXODITANE
BENZOPHENONE
BENZOYLBENZENE
BPN
DIPHENYL KETONE
DIPHENYLMETHANONE
FEMA 2134
Adjutan 6016
ADK STAB 1413
a-Oxodiphenylmethane
a-Oxoditane
Benzene, benzoyl-
benzoyl-benzen
diphenylketone(benzophenone)
Diphenyl-methanon
Kayacure bp
Ketone, diphenyl
ketone,diphenyl | [EINECS(EC#)]
204-337-6 | [Molecular Formula]
C13H10O | [MDL Number]
MFCD00003076 | [Molecular Weight]
182.22 | [MOL File]
119-61-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Benzophenone is a combustible, white, crystalline
solid with a rose-like odor | [Melting point ]
47-51 °C(lit.)
| [Boiling point ]
305 °C(lit.)
| [density ]
1.11 | [vapor density ]
4.21 (vs air)
| [vapor pressure ]
1 mm Hg ( 108 °C)
| [FEMA ]
2134 | [refractive index ]
1.5893 | [Fp ]
>230 °F
| [storage temp. ]
Refrigerator | [solubility ]
ethanol: soluble100mg/mL, clear, colorless (80% ethanol) | [form ]
Crystalline Powder or Flakes | [color ]
White to off-white | [Odor]
Characteristic. | [Stability:]
Stable. Incompatible with strong oxidizing agents, strong reducing agents. Combustible. | [Odor Type]
balsamic | [Water Solubility ]
insoluble (<0.1 g/100 mL at 25 ºC) | [Usage]
Reported to bind monsaccharides in the presence of polysaccharides | [Detection Methods]
GC,NMR | [JECFA Number]
831 | [Merck ]
14,1098 | [BRN ]
1238185 | [Dielectric constant]
13.0（20℃） | [Contact allergens]
Unsubstituted benzophenone is largely used in chemical
applications. It acts as a marker for photoallergy to
ketoprofen. | [InChIKey]
RWCCWEUUXYIKHB-UHFFFAOYSA-N | [LogP]
3.18 at 25℃ | [CAS DataBase Reference]
119-61-9(CAS DataBase Reference) | [IARC]
2B (Vol. 101) 2013 | [NIST Chemistry Reference]
Benzophenone(119-61-9) | [EPA Substance Registry System]
119-61-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,N,Xn,F | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R62:Possible risk of impaired fertility.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation .
R11:Highly Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S37/39:Wear suitable gloves and eye/face protection .
S29:Do not empty into drains .
S60:This material and/or its container must be disposed of as hazardous waste .
S36:Wear suitable protective clothing .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S36/37:Wear suitable protective clothing and gloves .
S33:Take precautionary measures against static discharges .
S16:Keep away from sources of ignition-No smoking .
S9:Keep container in a well-ventilated place . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
2
| [RTECS ]
DI9950000
| [F ]
10 | [TSCA ]
Yes | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29143900 | [Hazardous Substances Data]
119-61-9(Hazardous Substances Data) |
| Hazard Information | Back Directory | [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
. | [Synthesis Reference(s)]
Tetrahedron Letters, 36, p. 2285, 1995 DOI: 10.1016/0040-4039(95)00191-E
Chemical and Pharmaceutical Bulletin, 34, p. 3595, 1986 DOI: 10.1248/cpb.34.3595 | [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. | [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). | [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.] |
| Questions And Answer | Back Directory | [description]
Diphenyl ketone [119-61-9], benzophenone, C6H5COC6H5, C13H10O, Mr 182.22. The stable form of diphenyl ketone consists of colorless rhombic prismatic crystals. Several unstable forms with lower melting points also exist. Diphenyl ketone is insoluble in water and readily soluble in organic solvents. Diphenyl ketone and substituted diphenyl ketones in particular are used mainly as photoinitiators for UV-curable printing inks and coatings. Diphenyl ketone is also used as an intermediate for pharmaceuticals and agricultural chemicals. It is employed in the perfume industry as a fixative and as a fragrance with a flowery note. | [Chemical Properties]
Shiny white prismatic crystals with a sweet taste, smell like a rose, melting point is 47-49 ℃, boiling point is 306 ℃, insoluble in water, soluble in alcohol, ether and chloroform.
| [application]
Sunscreen cosmetics is the hot new products of cosmetics, almost all sunscreens contain benzophenone compound on the current market. Benzophenone compounds that protect the skin from harm, often is used to produce high product. In recent years, the cosmetics consumption of benzophenone grows continuesly. Recent studies suggest that fluorescence is also a harmful ultraviolet light source, so benzophenone expands the range of applications in the field of cosmetics, it has been extended to hair conditioners, lotions and lipsticks. In addition, the perfume fixative agent also can give spice sweet flavor, is used in many perfumes and soap flavor.
Banana Boat company has developed a UVA ultraviolet-absorbing technology called AvoTriplex, which is benzophenone-based, adding a stabilizer to prevent the benzophenone from breaking down in the sun. Enhancer is also added into the formula, and stabilizer may act synergistically, to optimize benzophenone sunscreen capacity.
| [Uses]
- Benzophenone Mainly used for the preparation of vanilla, butter and other flavor，It can be used as a fixative agent. Its weak sweet bay leaves fragrant , can be widely used in low-grade flavors, such as roses, bay leaves, sweet curd, shy flower, lily of the valley, sunflower, orchid, hawthorn flowers, incense and Wei Oriental flavor and other flavors. It is also used as an antioxidant in soaps, and occasionally used for almonds, berries, fruit, butter, nuts, peaches, vanilla beans and other food flavors in trace amount.
- Uses for photosensitive resins, coatings and adhesives.
- Benzophenone is an intermediate of UV absorbers, organic pigments, pharmaceuticals, perfume, insecticide . It is used for the production of bicyclic Piperidine Benztropine hydrobromide, diphenhydramine hydrochloride in the pharmaceutical industry . The product itself is a styrene polymerization inhibitor and a perfume fixative. Giving sweet taste to flavors, it is used in many perfumes and soap flavors.
- It is commonly used in soap flavor, used in ultraviolet absorbers, pigments, pharmaceuticals and reagents production, and also is low temperature fast curing agent for fluorine rubber. It serves to manufacturers to package the product in clear glass or plastic.
- Benzophenone is widely employed as a photo initiator in UV-curing applications such as inks, imaging and clear coatings in the printing industry. It acts as a UV blocker to prevent photo-degradation of the packaging polymers or its contents.
- It is light initiator for UV products, pharmaceutical intermediates, fragrances, light stabilizers etc.
- It is light pigment, medicine, perfume, pesticides intermediates, it can also be used for UV-curable resins, inks and coatings initiator.
| [indicator]
Benzophenone is widely used in the synthesis experiment as an indicator, it can be used as a indicator while handling toluene, benzene, THF, acetonitrile ect.; if there is a beautiful blue after added, it can be distillated and used, it is the best to kept in sodium, but the reason of generating blue is still a puzzle.
Here is the reason from a foreign book about reactions mechanism : a radical anion generated by the one called carbonyl radical, benzophenone acts as the indicator is that benzophenone oxygen atoms in sodium capture electrons to generate dark blue carbonyl radical; the radicals perspective on the electrical aspect is stable, mainly used to indicate 'anaerobic conditions',Widely used.
After the addition of benzophenone, more blue of the solution, indicating less oxygen in the solution, indirectly instructing the little water. However, whether the solution turns blue, is related to the added amount of benzophenone and processing solvent, THF (300ml) contains lots of water, and needs more than about 6 hours to reflux, and of course, it is related to the amount of processing solvent, the more the longer, toluene , benzene and other samples containing less aqueous need less reflux time, it is best to add the common desiccants to pretreat, such as: potassium carbonate, sodium sulfate, sodium hydroxide, etc., so that the processing time will be shortened. | [Toxicity]
GRAS(FEMA)。
LD502897mg/kg(Mice, orally)。
| [Production method]
There are different methods for synthesizing benzophenone. One method involves condensing benzyl chloride and benzene, followed by oxidation with nitric acid. Another method involves condensing benzene and carbon tetrachloride, followed by hydrolysis. In laboratory production, benzophenone is typically synthesized using aluminum chloride as a catalyst, with benzene reacting with benzoyl chloride. The final method involves condensing benzene and benzoyl chloride in the presence of aluminum chloride, followed by crystallization from ethanol. |
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