119-61-9 Usage
Chemical Description
Benzophenone is a ketone compound, sodium borohydride is a reducing agent, trifluoroacetic acid is a strong acid, methanol is a solvent, Ag2O is a silver oxide used as an activator, NaH is a strong base, per-0-acetylglycopyranose is a glycoside, and SnC4 is a Lewis acid used as an activator.
Chemical Description
Benzophenone is an organic compound containing two benzene rings and a ketone group.
Chemical Description
Benzophenone is a white crystalline solid used as a photoinitiator in polymer chemistry.
Chemical Description
Benzophenone is a ketone with the chemical formula C13H10O.
Uses
Used in Flavor and Fragrance Industry:
Benzophenone is used as a fixative agent in perfumes and soaps, imparting a sweet, floral scent. Its weak sweet bay leaves fragrance allows it to 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.
Used in Food Industry:
Benzophenone is used as a flavor enhancer in trace amounts for almonds, berries, fruit, butter, nuts, peaches, and vanilla beans.
Used in Soap Industry:
Benzophenone is commonly used in soap flavor and serves as an antioxidant in soaps.
Used in UV Absorbers, Pigments, and Pharmaceuticals:
Benzophenone is used in the production of ultraviolet absorbers, pigments, pharmaceuticals, and reagents. It is also used as a low-temperature fast curing agent for fluorine rubber.
Used in Printing Industry:
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.
Used in Cosmetics Industry:
Benzophenone compounds are used in sunscreen cosmetics to protect the skin from harmful ultraviolet light. The use of benzophenone in cosmetics has been expanding to hair conditioners, lotions, and lipsticks.
Used in Pharmaceutical Industry:
Benzophenone is an intermediate for the production of bicyclic Piperidine Benztropine hydrobromide and diphenhydramine hydrochloride.
Used in Agriculture:
Benzophenone is used as a synthetic intermediate for the manufacture of pharmaceuticals and agricultural chemicals.
Used in UV-Curable Resins, Inks, and Coatings:
Benzophenone is used as a photoinitiator in UV-curable resins, inks, and coatings.
Used in Research:
Benzophenone has been reported to be found in various plants, such as Vitis vinifera L., black tea, cherimoya, mountain papaya, and soursop, and is used in research for its potential applications and properties.
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. 1. Condensation of benzyl chloride and benzene , and then by nitric acid oxidation. 2. The condensation of benzene and carbon tetrachloride, and then by hydrolysis. In the laboratory, the production is based on aluminum chloride as a catalyst, prepared by reacting benzene with benzoyl chloride.3.Condensation of benzene and benzoyl chloride in the presence of aluminum chloride, and then crystallized from ethanol.
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-EChemical and Pharmaceutical Bulletin, 34, p. 3595, 1986 DOI: 10.1248/cpb.34.3595
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Ketones, such as Benzophenone, 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. Benzophenone can react with oxidizing materials.
Health Hazard
Ingestion causes gastrointestinal disturbances. Contact causes eye irritation and, if prolonged, irritation of skin.
Fire Hazard
Flash point data for Benzophenone are not available, but Benzophenone is probably combustible.
Contact allergens
Unsubstituted benzophenone is largely used in chemical
applications. It acts as a marker for photoallergy to
ketoprofen.
Safety Profile
Moderately toxic by ingestion andintraperitoneal routes. Combustible when heated.Incompatible with oxidizers. When heated todecomposition it emits acrid and irritating fumes.
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.
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).
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.
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.]
Incompatibilities
Oxidizing materials, such as dichromates
and permanganates.
Check Digit Verification of cas no
The CAS Registry Mumber 119-61-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 9 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 119-61:
(5*1)+(4*1)+(3*9)+(2*6)+(1*1)=49
49 % 10 = 9
So 119-61-9 is a valid CAS Registry Number.
InChI:InChI=1/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
119-61-9Relevant articles and documents
Substituent and Solvent Effects in the Reactions of Diaryldiazomethanes with 2,3-Dichloro-5,6-dicyanobenzoquinone
Oshima, Takumi,Nagai, Toshikazu
, p. 2039 - 2044 (1981)
Kinetic studies have been made of the reactions of fifteen meta- and para-substituted diphenyldiazomethanes(DDMs) with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in benzene.The second order rate constants, k, increased with the electron-donability of the substituents, and the value could be correlated with the Yukawa-Tsuno equation: log k/k0 = -2.33(?0 + 0.47Δ+) + 0.017, (r = 0.996, 30 deg C).The ρ value, -2.33, indicates the development of a positive charge at the diazo carbon in the transition state, while the R value, 0.47, confirms the moderate stabilization of the positive charge by the ?-electronic contribution of the para substituents.The rate constants have also been determined for the reaction of diphenyldiazomethane(DDM) with DDQ in 28 aprotic solvents.The effects of solvents can be interpreted in terms of the basicity and the steric nature of the solvents.The products of these reactions were poly(2,3-dichloro-5,6-dicyanohydroquinone benzhydryl ether)s, which were easily convertible into benzophenones and α,α-dimethoxydiphenylmethane, together with 2,3-dichloro,5,6-dicyanohydroquinone, under the influence of water and methanol.These solvolysis products were also obtained in excellent yields in the initial presence of these additives.
COMPARISON OF PHOTOINDUCED ELECTRON TRANSFER REACTIONS OF AROMATIC CARBONYL VS. CYANO COMPOUNDS WITH ELECTRON DONORS IN CONDENSED PHASE: THE IMPORTANCE OF THE SPIN STATE OF THE GEMINATE ION PAIR FOR OBTAINING HIGH ION YIELDS.
Haselbach, Edwin,Vauthey, Eric,Suppan, Paul
, p. 7335 - 7344 (1988)
Photoinduced electron transfer reactions in acetonitrile with benzophenone, anthraquinone, 9-cyanoanthracene and 9,10-dicyanoanthracene as electron acceptors, and with 1,4-diazabicyclooctane and N,N-dimethylaniline as electron donors have been studied with ns-laser flash photolysis and fluorescence quenching measurements.For these systems the resulting free ion yield depends on the spin state of the geminate ion pair: its separation is very efficient if formed in a triplet state (carbonyl compounds/donors), while it is very inefficient if formed in a singlet state (cyanoantracenes/donors).In the triplet systems, geminate back electron transfer is limited by the rate of spin flip.
Oxovanadium(v)-catalyzed deoxygenative homocoupling reaction of alcohols
Sakuramoto, Takashi,Donaka, Yosuke,Tobisu, Mamoru,Moriuchi, Toshiyuki
, p. 17571 - 17576 (2019)
Oxovanadium(v)-catalyzed transformation of alcohols in the presence of hydrazine derivatives was demonstrated. The direct hydrazination reaction of 1,3-diphenylprop-2-en-1-ol with 1,1-diphenylhydrazine in the presence of VO(OSiPh3)3 as a catalyst and MS3A as a dehydrating reagent proceeded to afford the corresponding hydrazination product. On the contrary, the utilization of 1,1-dimethylhydrazine instead of 1,1-diphenylhydrazine was found to induce the deoxygenative homocoupling reaction of the allyl alcohol to give the corresponding 1,5-diene as a major product. In addition to the deoxygenative homocoupling product, the allyl amine into which aniline was introduced was also obtained by using 1,2-diphenylhydrazine in the reaction of 1,3-diphenyl-2-methylprop-2-en-1-ol. Oxovanadium(v)-catalyzed deoxygenative homocoupling reaction of benzyl alcohols could also be performed in the presence of 1,1-dimethylhydrazine.
Ligand-free palladium-catalyzed aerobic oxidative coupling of carboxylic anhydrides with arylboronic acids
Yin, Weiyan,He, Haifeng,Zhang, Yani,Long, Tong
, p. 2402 - 2406 (2014)
We report a new, effective and environmentally friendly protocol for selective aerobic oxidative coupling of arylboronic acids with carboxylic anhydrides in the presence of ligand-free palladium catalyst. The aryl benzoates are obtained in good to excellent yields.
Co(ii)-cluster-based metal-organic frameworks as efficient heterogeneous catalysts for selective oxidation of arylalkanes
Fan, Yanru,Li, Xiao,Gao, Kuan,Liu, Yu,Meng, Xiangru,Wu, Jie,Hou, Hongwei
, p. 1666 - 1673 (2019)
To explore metal-organic frameworks (MOFs) based on Co-clusters as heterogeneous catalysts to selectively catalyze the reaction of C-H bond oxidation of aromatic alkanes to their corresponding ketones, three MOFs {[Co5(pmbcd)2(μ3-OH)2(H2O)4(DMF)2]·4DMF}n (MOF 1), {[Co2(pmbcd)(bpea)2]·2H2O·2DMF}n (MOF 2), and {[Co2(pmbcd)(dpp)2]·3H2O·2DMF}n (MOF 3) (H4pmbcd = 9,9′-(1,4-phenylenebis(methylene))bis(9H-carbazole-3,6-dicarboxylic acid), bpea = 1,2-bis(4-pyridyl)ethane, dpp = 1,3-di(4-pyridyl)propane) were successfully synthesized and structurally characterized. MOF 1 was constructed from a pentanuclear Co(ii) cluster and exhibited a porous framework with channels of 8 × 10 ?2 along the b axis. MOF 2 was constructed from [Co2(CO2)4] units and presented a porous three-dimensional (3D) framework with channels of 11 × 13 ?2 along the b axis and of 10 × 12 ?2 along the c axis. MOF 3 was a flat two-dimensional (2D) layer based on binuclear Co(ii) units when dpp as an auxiliary ligand was introduced. The Co5-cluster-based MOF 1 exhibited excellent catalytic activity for the direct C-H bond activation of arylalkanes to ketones in H2O under room temperature because of its high density of Lewis acidic sites within the frameworks and suitable channel size to access the catalytic sites. It also presented the spatial confinement effect and catalyzed the reaction with high regioselectivity, forming mono-ketones as the sole products. Easy product separation, simple reaction procedures, and recyclability of these catalysts make the catalytic system attractive. Our work highlights the superiority of the MOF-based materials as heterogeneous catalysts.
Oxidation of phenylhydrazones of α-keto esters with hypervalent organoiodine reagents
Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Shinada, Tetsuro
, p. 7191 - 7194 (1993)
α-Ketoacids and ketones can easily be regenerated in high yield from their phenylhydrazones via hydroxy azo compounds upon oxidation with hupervalent iodine reagents.
Ionic liquid [bmim]Br assisted chemoselective benzylic [Formula presented] oxidations using tert-butyl hydroperoxide
Naidu, Shivaji,Reddy, Sabbasani Rajasekhara
, p. 441 - 445 (2016)
A mild and efficient, ionic-liquid-assisted green protocol for the chemoselective oxygenation of benzylic C-H bonds to corresponding ketones using ionic liquid [bmim]Br with tert-butyl hydroperoxide has been developed. The method reported in this paper has the advantages of [bmim]Br acting as recyclable solvent and reagent. The usage of additives such as acids or bases and metal salts is not required. The developed strategy is further extended to oxidation of secondary alcohols to respective ketones under similar optimized reaction conditions.
Mechanism of thermal decomposition of diphenyldiazomethane in the presence of oxygen
Komissarov,Nazarov,Yamilova
, p. 261 - 264 (1997)
The kinetics, products, and mechanism of thermal decomposition of diphenyldiazomethane (RN2, R = Ph2C) in the presence of oxygen were studied. Thermolysis is accompanied by chemiluminescence. An-emitter of chemiluminescence (3RO) forms in the reaction of benzophenone 0-oxide ROO with RN2.
Thiol ester-boronic acid cross-coupling. Catalysis using alkylative activation of the palladium thiolate intermediate
Savarin, Cecile,Srogl, Jiri,Liebeskind, Lanny S.
, p. 3229 - 3231 (2000)
(matrix presented) Thiol esters and boronic acids do not participate in cross-coupling in the presence of palladium catalysts. However, efficient palladium-catalyzed thiol ester-boronic acid cross-coupling is observed when simple alkylating agents are present. Alkylative conversion of the very stable palladium-thiolate bond to a labile palladium-thioether bond is presumed to be crucial to the catalysis. Of the systems studied, 4-halo-n-butyl thiol esters were most effective in this cross-coupling.
Kinetics, products, and mechanism of the reaction of diphenylcarbonyl oxide with sulfoxides
Nazarov,Chainikova,Krupin,Khursan,Kalinichenko,Komissarov
, p. 1496 - 1500 (2000)
The kinetics of the reactions of diphenylcarbonyl oxide with dimethyl, di-n-hexyl, diphenyl, dibenzyl, and n-hexylbenzyl sulfoxides in acetonitrile was studied by flash photolysis at 295 K. The oxidation of sulfoxide affords the corresponding sulfone as t
