119-61-9

Basic information

• Product Name: Benzophenone
• Synonyms: a-Oxoditane;Benzene, benzoyl-;benzoyl-benzen;diphenylketone(benzophenone);Diphenyl-methanon;Kayacure bp;Ketone, diphenyl;ketone,diphenyl
• CAS NO: 119-61-9
• Molecular Formula: C13H10O
• Molecular Weight: 182.22
• EINECS: 204-337-6
• Product Categories: Pharmaceutical Intermediates;Additives for Plastic;Organics;Fluorescent Labels and Indicators;Analytical Chemistry;Environmental Endocrine Disruptors;Estradiol, etc. (Environmental Endocrine Disruptors);Functional Materials;Photopolymerization Initiators;Fluorescent Labels & Indicators;Aromatics;Intermediates;organic chemical;Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;B;Bioactive Small Molecules;Cell Biology;Essential Chemicals;Inorganic Salts;Reagent Plus;Research Essentials;Solutions and Reagents;Flavor & Fragrance Intermediates
• Mol File: 119-61-9.mol
• Article Data: 3229

Chemical Properties

• Melting Point: 47-51 °C(lit.)
• Boiling Point: 305 °C(lit.)
• Flash Point: >230 °F
• Appearance: White to off-white/Crystalline Powder or Flakes
• Density: 1.11
• Vapor Density: 4.21 (vs air)
• Vapor Pressure: 1 mm Hg ( 108 °C)
• Refractive Index: 1.5893
• Storage Temp.: Refrigerator
• Solubility: ethanol: soluble100mg/mL, clear, colorless (80% ethanol)
• Water Solubility: insoluble (
• Stability: Stable. Incompatible with strong oxidizing agents, strong reducing agents. Combustible.
• Merck: 14,1098
• BRN: 1238185
• CAS DataBase Reference: Benzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: Benzophenone(119-61-9)
• EPA Substance Registry System: Benzophenone(119-61-9)

Safety Data

• Hazard Codes: Xi,N,Xn,F
• Statements: 36/37/38-52/53-50/53-67-65-62-51/53-48/20-11-40
• Safety Statements: 26-61-37/39-29-60-36-62-36/37-33-16-9
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: DI9950000
• F: 10
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 119-61-9(Hazardous Substances Data)

Usage

description

Benzophenone appears as colorless prismatic crystals, with sweetness and aroma of roses, melting point is 47-49 ℃, the relative density is 1.1146, refractive index is 1.6077. It is soluble in alcohol, ether, chloroform and other organic solvents and monomers, insoluble in water. It is a free radical photoinitiator, are mainly used in free radical UV curing systems , such as coatings, inks, adhesives and so on, and also used as the intermediates of organic pigments, pharmaceuticals, perfume, and insecticide . In the pharmaceutical industry, it is mainly used for the production of bicyclic Piperidine Benztropine hydrobromide, diphenhydramine hydrochloride. This product is styrene polymerization inhibitor and perfume fixative agent, to impart a sweet flavor with spices, widely used in the perfume and soap flavor. Attentions should be paid to the products to prevent moisture, sun , heat in the storage and transportation process, the temperature should not exceed 45 ℃. benzophenone structure

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. 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.

Chemical Properties

Benzophenone is a combustible, white, crystalline solid with a rose-like odor. soluble in ethanol, ether, chloroform and other organic solvents and monomers, insoluble in water. It is a free radical photoinitiator, mainly used in free radical UV curing systems, such as coatings, inks, adhesives, etc. It can be prepared in several ways, for example, by Friedel–Crafts reaction of benzene and benzoyl chloride with aluminum chloride, or of benzene and carbon tetrachloride, and oxidation of diphenylmethane.

Occurrence

Reported found in Vitis vinifera L., black tea, cherimoya (Annona cherimola), mountain papaya (Carica pubescens) and soursop (Annona muricata L.)

Uses

Benzophenone is used as a synthetic intermediate for manufacture of pharmaceuticals and agricultural chemicals. It is also used as a photoinitiator in UV-curable printing inks, as a fragrance in perfumes, as a flavor enhancer in foods. Benzophenone can be added as a UV-absorbing agent to plastics, lacquers, and coatings at concentrations of 2–8%.

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.

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

General Description

Benzophenone appears as white solid with a flowery odor. May float or sink in water.

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.

InChI:InChI=1/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

Synthetic route

1,1-Diphenylethylene (530-48-3) → benzophenone (119-61-9)

Conditions	Yield
Stage #1: 1,1-Diphenylethylene for 0.05h; Inert atmosphere; Stage #2: With tert.-butylhydroperoxide at 102℃; for 24h; Inert atmosphere;	100%
With oxygen at 110℃; for 8h; Temperature; Schlenk technique;	99%
With oxygen at 110℃; for 8h; Temperature; Sealed tube;	99%

1,1-Diphenylmethanol (91-01-0) → benzophenone (119-61-9)

Conditions	Yield
With acetone; zirconic acid In benzene at 80℃; for 8h;	100%
With bis(2,2'-bipyridyl) copper(II) permanganate In dichloromethane for 0.5h; Ambient temperature;	100%
With tert.-butylhydroperoxide; polystyrene-bound phenylselenic acid In tetrachloromethane for 24h; Heating;	100%

Diphenylmethane (101-81-5) → benzophenone (119-61-9)

Conditions	Yield
With potassium permanganate; iron(III) chloride In acetone at -78 - 20℃; for 16h;	100%
With chromyl chloride In dichloromethane at 22℃; for 0.5h; ultrasound sonication;	99%
With tert.-butylhydroperoxide; C45H52CuN4O3 In decane; acetonitrile at 70℃; for 18h;	99%

Benzilic acid (76-93-7) → benzophenone (119-61-9)

Conditions	Yield
With pyridine chromium peroxide In dichloromethane for 0.3h; Product distribution; Ambient temperature; effect of various chromium(VI) based oxidants;	100%
In acetic acid for 0.25h; Heating;	100%
With sodium hydroxide; copper(III) periodate for 0.05h; Heating; oxidative decarboxylation of α-hydroxy acids; var. α-hydroxy acids, also Cu(III) tellurate as oxidant;	95%

methanol (67-56-1) + 2,2-Dimethyl-4,4-diphenyl-3,3-bis(trimethylsilyl)-1-oxa-2-silacyclobutan (80431-43-2) → benzophenone (119-61-9) + 1-(Dimethylmethoxysilyl)-1,1-bis(trimethylsilyl)ethan (68260-20-8)

Conditions	Yield
In benzene at 110℃; for 40h; Rate constant; half live time;	A n/a B 100%

Benzophenone imine (1013-88-3) → benzophenone (119-61-9)

Conditions	Yield
Stage #1: Benzophenone imine With chloro-trimethyl-silane; sodium iodide In acetonitrile at 20℃; Stage #2: With water In acetonitrile for 0.0833333h;	100%
With hydrogenchloride; water at 40℃;	86%
With water at 25℃; Rate constant; effect of pH on the rate constants;

2,2-diphenyl-1,3-benzodithiole (61666-80-6) → benzophenone (119-61-9)

Conditions	Yield
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran for 0.166667h; Ambient temperature;	100%

2,2-diphenyl-1,3-oxathiolane (33735-40-9) → benzophenone (119-61-9)

Conditions	Yield
With 2,2,2-trifluoroethanol; oxygen; vanadium(V) oxychloride for 5h; deprotection; Heating;	100%
Stage #1: 2,2-diphenyl-1,3-oxathiolane In ethanol at 20℃; Stage #2: With water In ethanol at 20℃;	98%
With silver(I) nitrite; iodine In tetrahydrofuran for 0.5h; Mechanism; Ambient temperature; other mono- and dithioacetals;	96%

2,2-diphenyl-1,3-dithiolane (6317-10-8) → benzophenone (119-61-9)

Conditions	Yield
With K-10 clay supported iron(III) nitrate nonahydrate In dichloromethane for 3h; Ambient temperature; with K-10 clay-supported copper(II) nitrate trihydrate;	100%
With trichloroisocyanuric acid; silver nitrate In water; acetonitrile Ambient temperature;	100%
With hydrogenchloride; sodium nitrate In tetrachloromethane; water for 1h; Ambient temperature; other reagent;	100%

diphenylmethyl trimethylsilyl ether (14629-59-5) → benzophenone (119-61-9)

Conditions	Yield
With 2,6-dicarboxypyridinium fluorochromate In acetonitrile at 20℃; for 0.0833333h; Reflux;	100%
With nitrogen dioxide at 20℃; for 0.5h;	100%
With chromium(VI) oxide; tert.-butylhydroperoxide; triphenylhydroxysilane In dichloromethane for 24h; Ambient temperature;	99%

2,2-diphenyl-1,3-dithiane (10359-08-7) → benzophenone (119-61-9)

Conditions	Yield
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran Ambient temperature;	100%
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 0.333333h; Micellar solution;	100%
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide In water; acetonitrile at 20℃; for 0.75h;	100%

dimethoxydiphenylmethane (2235-01-0) → benzophenone (119-61-9)

Conditions	Yield
With water; Nafion-H In acetone for 0.5h;	100%
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 1h; Ambient temperature;	100%
sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In water at 30℃; for 0.5h;	99%

tetraphenylethane-1,2-diol (464-72-2) → benzophenone (119-61-9)

Conditions	Yield
With N-Bromosuccinimide; triphenylbismuthane; potassium carbonate In water; acetonitrile for 2h; Ambient temperature;	100%
With naphthalene-1,4-dicarbonitrile; oxygen for 90h; Irradiation;	100%
With dinitrogen tetraoxide; ferric nitrate In ethyl acetate Heating; further oxidizing agent;	100%

benzophenone-dibenzyldithioacetal (29055-89-8) → dibenzyl disulphide (150-60-7) + benzophenone (119-61-9)

Conditions	Yield
With hydrogenchloride; sodium nitrate In tetrachloromethane; water for 1h; Ambient temperature; other reagent;	A n/a B 100%

2-diphenylmethyliumyl-3,5-dioxo-4-phenyl-1,2,4-triazolidin-1-ide (2693-32-5) → benzophenone (119-61-9) + 4-Phenylurazole (15988-11-1)

Conditions	Yield
With water for 1080h;	A 100% B 100%
With atmospheric moisture storage conditions;

(1R,5S)-4-Methyl-1,3,5,7,7-pentaphenyl-6-oxa-2,4-diaza-bicyclo[3.2.0]hept-2-ene (108099-97-4) → benzophenone (119-61-9) + 1-methyl-2,4,5-triphenyl-1H-imidazole (22397-44-0)

Conditions	Yield
In various solvent(s) at 120℃; for 2.5h; Thermodynamic data; cycloreversion of further oxetane derivatives;	A 100% B 100%

benzoyl chloride (98-88-4) + C6H5Cu*ILi → benzophenone (119-61-9)

Conditions	Yield
In various solvent(s) -78 deg C, 0.5 h, 0 deg C, 0.5 h;	100%

acetic acid (64-19-7) + 4,4a-dihydro-3,3-dimethyl-1-phenyl-4,4-bis(trimethylsilyl)-3H-2-oxa-3-silanaphthaline (80431-42-1) → benzophenone (119-61-9) + Acetyldimethylsilyl-bis(trimethylsilyl)methan

Conditions	Yield
In benzene at 90℃; for 3h; Rate constant; half live time;	A n/a B 100%

2-diphenylmethylene-1,3-benzodithiole 1,1,3,3-tetraoxide (112520-04-4) → benzophenone (119-61-9) + 2H-benzo[d][1,3]dithiole 1,1,3,3-tetraoxide (112520-09-9)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane for 0.5h; Product distribution; Heating; further educt: 2-diphenylmethylene-1,3-benzodithiole 1,1-dioxide;	A 100% B 88%
With potassium hydroxide In 1,4-dioxane for 0.5h; Heating; Yields of byproduct given;	A n/a B 88%

4,4a-dihydro-3,3-dimethyl-1-phenyl-4,4-bis(trimethylsilyl)-3H-2-oxa-3-silanaphthaline (80431-42-1) + tert-butyl alcohol (75-65-0) → benzophenone (119-61-9) + tert-Butoxydimethylsilyl-bis(trimethylsilyl)methan (87161-31-7)

Conditions	Yield
In benzene at 90℃; for 1.5h; Rate constant; half live time;	A n/a B 100%

benzoyl chloride (98-88-4) + phenylmagnesium bromide (100-58-3) → benzophenone (119-61-9)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 0℃;	100%
Stage #1: benzoyl chloride With 1-methyl-pyrrolidin-2-one In toluene at 0℃; for 0.5h; Stage #2: phenylmagnesium bromide In tetrahydrofuran; toluene at -10 - 0℃; for 4.25h; chemoselective reaction;	89%
In 2-methyltetrahydrofuran at 25℃; for 1h; Solvent; Concentration; Flow reactor; Green chemistry;	85%

benzophenone azine (983-79-9) → benzophenone (119-61-9)

Conditions	Yield
With 2-phenyl-1,2-benzoisoselenazol-3(2H)-one; dihydrogen peroxide In methanol; water at 65℃; for 72h;	100%
With ammonium cerium(IV) nitrate In water; acetonitrile at 50℃; for 16h; Oxidation;	90%
With potassium permanganate; montmorillonite K-10 for 0.5h;	90%
With 3-carboxypyridinium chlorochromate In acetonitrile for 3h; Heating;	87%

diazodiphenylmethane (908093-98-1) → benzophenone (119-61-9) + N2, N2O

Conditions	Yield
With oxygen; methylene blue In benzene at 20℃; for 0.5h; Mechanism; Irradiation; N2/N2O ratio; var. solvent; other diazomethanes;	A 100% B n/a

benzylic acid → benzophenone (119-61-9)

Conditions	Yield
With tris paraperiodate In benzene for 1h; Heating;	100%

2-Fluorobenzoyl chloride (393-52-2) + 1,4-dimethoxybezene (150-78-7) → benzophenone (119-61-9) + 2-methoxy-9H-xanthen-9-one (1214-20-6)

Conditions	Yield
With hydrogenchloride In AlCl3; 1,2-dichloro-ethane	A n/a B 100%

N-cinnamyl-α,α-diphenyl-L-prolinol → benzophenone (119-61-9) + C13H15NO

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate In tetrahydrofuran; water; tert-butyl alcohol diastereoselective reaction;	A 100% B 35%

[(hydrotris(3-phenyl-5-methylpyrazol-1-yl)borate)FeII(benzilate)] → benzophenone (119-61-9)

Conditions	Yield
With oxygen In benzene for 0.75h;	100%

1,1-Diphenylmethanol (91-01-0) + diisopropyl-carbodiimide (693-13-0) → benzophenone (119-61-9) + N1,N2-Diisopropylformamidine (44843-38-1, 57585-44-1)

Conditions	Yield
With ruthenium complex In toluene at 120℃; for 24h; Inert atmosphere; Sealed tube;	A 100% B 74 %Spectr.

bis(ethylthio)diphenylmethane (7282-09-9) → benzophenone (119-61-9)

Conditions	Yield
With K-10 clay supported copper(II) nitrate trihydrate In dichloromethane for 4h; Ambient temperature; with K-10 clay-supported iron(III) nitrate nonahydrate;	99.5%
With K-10 clay supported copper(II) nitrate trihydrate In dichloromethane for 4h; Ambient temperature; K-10 clay supported iron(III) nitrate nonahydrate;	99.5%
With dihydrogen peroxide; vanadia; ammonium bromide In dichloromethane; water at 0 - 5℃; for 2h;	95%

Diphenylacetonitrile (86-29-3) → benzophenone (119-61-9)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene for 3h;	99%
With tetrabutylammomium bromide; oxygen In N,N-dimethyl-formamide Hg cathode, Pt anode, -1.0 V vs SCE;	95%
With oxygen; potassium carbonate In water; dimethyl sulfoxide Ambient temperature;	95%

ethyl 2-bromoisobutyrate (600-00-0) + benzophenone (119-61-9) → Ethyl 3-hydroxy-2,2-dimethyl-3,3-diphenylpropanoate (59697-75-5)

Conditions	Yield
With iodine; zinc In 1,4-dioxane for 0.166667h; Reformatsky reaction; ultrasound irradiation;	100%
With magnesium; benzene
With zinc; benzene
With zinc

benzophenone (119-61-9) + phenylsilane (694-53-1) → bis-benzhydryloxy-phenyl-silane (18834-17-8)

Conditions	Yield
With Et2OFe(catecholate-porous organic polymer) In benzene-d6 at 23℃; for 0.0833333h;	100%

benzophenone (119-61-9) → 1,1-Diphenylmethanol (91-01-0)

Conditions	Yield
With zinc(II) tetrahydroborate In acetonitrile for 16h; Mechanism; Ambient temperature;	100%
With zinc(II) tetrahydroborate In acetonitrile for 16h; Ambient temperature;	100%
With samarium; 1,2-Diiodoethane In 1,2-dimethoxyethane for 24h; Ambient temperature;	100%

benzophenone (119-61-9) → benzoic acid phenyl ester (93-99-2)

Conditions	Yield
With trifluorormethanesulfonic acid; 3-chloro-benzenecarboperoxoic acid In dichloromethane for 6h; Ambient temperature;	100%
With hydrogenchloride In chloroform at 20℃; for 8h; Baeyer-Villiger oxidation;	100%
With dihydrogen peroxide; iodine; acetic acid at 20℃; for 0.166667h; Baeyer-Villiger oxidation;	93%

benzophenone (119-61-9) → Benzophenone oxime (574-66-3)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol Heating;	100%
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux;	100%
With hydroxylamine hydrochloride In ethanol at 50 - 60℃; for 1.5h;	100%

benzophenone (119-61-9) → Diphenylmethane (101-81-5)

Conditions	Yield
With hydrogen; aluminum oxide; K5PV2Mo10O40 at 300℃; under 17480 Torr; for 3.33333h; Catalytic hydrogenation;	100%
With iodine; hypophosphorous acid In acetic acid for 24h; Reduction; Heating;	100%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 10h; chemoselective reaction;	100%

benzophenone (119-61-9) → benzophenone hydrazone (5350-57-2)

Conditions	Yield
With hydrazine hydrate In ethanol for 12h; Heating;	100%
With hydrazine hydrate; acetic acid In ethanol at 100℃; for 21h; Inert atmosphere;	100%
With hydrazine hydrate In ethanol for 4h; Reflux;	100%

benzophenone (119-61-9) → 1,1,2,2-tetraphenylethylene (632-51-9)

Conditions	Yield
With woollins’ reagent In toluene for 20h; Heating;	100%
With titanium tetrachloride; zinc In tetrahydrofuran at 0 - 70℃; for 12h; Inert atmosphere;	98%
With pyridine; titanium tetrachloride; zinc In 1,4-dioxane for 0.0833333h; microwave irradiation;	97%

benzophenone (119-61-9) → tetraphenylethane-1,2-diol (464-72-2)

Conditions	Yield
With hydrogen sulfide; phosphorous acid trimethyl ester In diethylene glycol dimethyl ether for 2.75h; Product distribution; Irradiation; variation of solvents, reagents and conditions;	100%
With hydrogen sulfide; phosphorous acid trimethyl ester In diethylene glycol dimethyl ether for 2.75h; Irradiation;	100%
With iodine; magnesium In diethyl ether; benzene for 0.5h; pinacol coupling; sonication;	99%

benzophenone (119-61-9) + ethane-1,2-dithiol (540-63-6) → 2,2-diphenyl-1,3-dithiolane (6317-10-8)

Conditions	Yield
Nafion-H In benzene Heating;	100%
With cobalt(II) bromide In dichloromethane for 4h; Ambient temperature;	99%
With amberlyst-15 In acetonitrile for 1h;	99.91%

benzophenone (119-61-9) + allyl bromide (106-95-6) → 1,1-diphenyl-3-buten-1-ol (4165-79-1)

Conditions	Yield
With ammonium acetate; zinc In tetrahydrofuran at 0℃; for 0.0166667h; Barbier reaction;	100%
With manganese; chloro-trimethyl-silane; indium In tetrahydrofuran at 20℃; for 4h; Alkylation;	98%
With manganese; chloro-trimethyl-silane; indium In tetrahydrofuran at 20℃; for 4h; Barbier allylation;	98%

benzophenone (119-61-9) + propargyl bromide (106-96-7) → 1,1-diphenyl-but-3-yn-1-ol (29430-66-8)

Conditions	Yield
With zinc In tetrahydrofuran for 0.5h;	100%
Stage #1: propargyl bromide With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at -78℃; for 0.333333h; Stage #2: benzophenone In diethyl ether at -78 - 20℃; for 2h; Stage #3: With hydrogen cation In diethyl ether	96%
Stage #1: benzophenone; propargyl bromide With dysprosium; sodium iodide; mercury dichloride In tetrahydrofuran at -14 - 20℃; Propargylation; Stage #2: With hydrogenchloride In water Hydrolysis;	92%

1,3-Benzothiazole (95-16-9) + benzophenone (119-61-9) → α,α-diphenyl-2-benzothiazolyl-methanol (120821-94-5)

Conditions	Yield
With t-Bu-P4 base In toluene at -78℃; for 1h;	100%
Stage #1: 1,3-Benzothiazole; benzophenone With tetrakis{[tris(dimethylamino)phosphoranyliden]amino}phosphonium fluoride; tris(trimethylsilyl)amine In toluene at 25℃; for 24h; Inert atmosphere; Stage #2: In tetrahydrofuran Reagent/catalyst;	94%
With n-butyllithium In tetrahydrofuran; hexane -78 deg C, 1 h; 10 min;	88%

benzophenone (119-61-9) + 3-methoxyphenyl bromide (2398-37-0) → (3-methoxyphenyl)(diphenyl)methanol (78238-98-9)

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	100%
With magnesium 1.) ether, 2.) a) RT, 6 h, b) reflux, 1 h; Yield given. Multistep reaction;
With n-butyllithium

benzophenone (119-61-9) + (Z)-ethyl cinnamate (4610-69-9) → (Z)-4-Hydroxy-3,4,4-triphenyl-but-2-enoic acid ethyl ester (78522-57-3)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine In tetrahydrofuran at -100℃; for 1.25h; Product distribution; other solvents, amount of reagents and different reaction times;	100%
With 2,2,6,6-tetramethyl-piperidine In tetrahydrofuran at -100℃; for 1.25h;	100%

benzophenone (119-61-9) + trimethyl(2-methylenebut-3-enyl)silane (70901-64-3) → 3-methylene-5,5-diphenyl-5-(trimethylsiloxy)pentene (86361-23-1)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 2.5h;	100%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 2.5h;	100%

benzophenone (119-61-9) + Methyltriphenylphosphonium bromide (1779-49-3) → 1,1-Diphenylethylene (530-48-3)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran Stage #2: benzophenone In tetrahydrofuran at 20℃; for 6h; Wittig reaction;	100%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran at 20℃; Inert atmosphere;	94%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 0.25h; Inert atmosphere; Stage #2: benzophenone In diethyl ether at 0℃; for 15h; Inert atmosphere;	87%

benzophenone (119-61-9) + (dichloroalumino)(trichlorotitanio)methane (111317-20-5) → 1,1-Diphenylethylene (530-48-3)

Conditions	Yield
In toluene for 0.5h; Heating;	100%

Upstream product

• 56-23-5 Carbon tetrachloride 
• 75-44-5 PHOSGENE 
• 7446-70-0 Aluminium chloride 
• 98-88-4 Benzoyl chloride 

Downstream Products

• 304-88-1 N-Phenylbenzohydroxamic acid 
• 14470-28-1 4-Methoxytriphenylchloromethane 
• 13669-70-0 3-Methyl-7-phenyl-6-oxa-3-azabicyclo[6.4.0]dodeca-8,10,12-triene 
• 6665-86-7 7-HYDROXYFLAVONE 
• 83166-17-0 TAMPRAMINE 
• 22101-87-7 alpha-[1-(aminomethyl)propyl]benzhydryl alcohol 
• 464-72-2 Benzopinacole 
• 1622-61-3 Clonazepam 
• 54533-85-6 Nizofenone 
• 22101-20-8 2-(alpha-hydroxybenzhydryl)butyronitrile 
• 21222-05-9 3,3'-DINITROBENZOPHENONE 
• 36476-78-5 3-Azetidinecarboxylic acid 
• 1775-95-7 2-Amino-5-nitrobenzophenone 
• 89778-26-7 Toremifene 
• 91-01-0 Benzhydrol 
• 31251-03-3 Fluotrimazol 
• 2185-86-6 Basic Blue 11 
• 1088-11-5 Nordazepam 
• 1013-88-3 Benzophenone imine 
• 141699-55-0 1-N-Boc-3-hydroxyazetidine 
• 1016-77-9 3-Bromobenzophenone 
• 4547-02-8 BENZP-DINITRIDE-THIO-KETONE 
• 5350-57-2 Benzophenone hydrazone 
• 4834-61-1 4-Benzoyl Acetanilide 
• 3254-89-5 Difenidol hydrochloride 

Recommend Products

• 101-81-5  Diphenylmethane 
• 109-99-9  tetrahydrofuran 
• 64-17-5  ethanol 
• 981-24-8  1,1,2,2-tetraphenyl-ethanol 
• 141-52-6  sodium ethanolate 
• 19490-90-5  diphenyl(2-pyridyl)methanol 
• 110-86-1  pyridine 
• 3197-49-7  1,1-diphenyl-2-pyridin-4-yl-ethanol 
• 108-89-4  picoline 
• 30836-60-3  4-methyl-2-(diphenylhydroxymethyl)pyridine 
• 1620-30-0  diphenyl(pyridin-4-yl)methanol 
• 54750-97-9  4-lithiopyridine 
• 6705-32-4  1,1-diphenyl-2-pyrazin-2-yl-ethanol 
• 109-08-0  2-Methylpyrazine 

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