2-Hydroxy-2-phenylacetophenone

Base Information

• Chemical Name: 2-Hydroxy-2-phenylacetophenone
• CAS No.: 119-53-9
• Deprecated CAS: 579-44-2,9000-73-1,91845-21-5
• Molecular Formula: C14H12O2
• Molecular Weight: 212.248
• Hs Code.: 2914.49
• European Community (EC) Number: 204-331-3,209-441-5,232-556-7
• ICSC Number: 1214
• NSC Number: 8082
• UNII: L7J6A1NE81
• DSSTox Substance ID: DTXSID1020144
• Nikkaji Number: J52.646K,J20.621K
• Wikipedia: Benzoin_(organic_compound)
• Wikidata: Q426819
• NCI Thesaurus Code: C77026
• RXCUI: 1406
• Metabolomics Workbench ID: 125293
• ChEMBL ID: CHEMBL190677
• Mol file: 119-53-9.mol

Synonyms:(2R)-2-hydroxy-1,2-diphenyl-ethanone;Benzoylphenylcarbinol;Benzoin tincture;Bitter almond oil camphor;2-Hydroxy-1, 2-diphenylethanone;Acetophenone, 2-hydroxy-2-phenyl-;2-Hydroxy-2-phenylacetophenone;2-Hydroxy-1,2-diphenylethanone;Ethanone,2-hydroxy-1,2-diphenyl-;Phenyl-.alpha.-hydroxybenzyl ketone;(2S)-2-hydroxy-1,2-diphenyl-ethanone;Ketone, .alpha.-hydroxybenzyl phenyl;Anisoin;2-Hydroxy-1,2-diphenyl ethanone;

Chemical Property of 2-Hydroxy-2-phenylacetophenone

Chemical Property:

• Appearance/Colour: light yellow powder or crystals with a camphor-like odour
• Vapor Pressure: 2.78E-05mmHg at 25°C
• Melting Point: 134-138 °C(lit.)
• Refractive Index: 1.609
• Boiling Point: 342.999 °C at 760 mmHg
• PKA: 12.28±0.20(Predicted)
• Flash Point: 154.813 °C
• PSA: 37.30000
• Density: 1.18 g/cm³
• LogP: 2.60290
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: 0.3g/l
• Water Solubility.: Soluble in chlorine. Slightly soluble in water, ethanol and ether.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 212.083729621
• Heavy Atom Count: 16
• Complexity: 225

Purity/Quality:

99%, ^*data from raw suppliers

Benzoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)C2=CC=CC=C2)O
• Inhalation Risk: Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: May cause mechanical irritation.
• Uses: Benzoin is used as a flavor, antiseptic and photopolymerization catalyst. It is also used as a raw material in organic syntheses. It serves as a precursor to benzil, which is a photoinitiator. Further, it is used as degassing agent for powder coatings. In addition to this, it is used as an additive and in powder coating to remove the pinhole phenomenon. Degassing for powder coatings benzoin is a fragrant essential oil with bactericidal, anti-irritation, and anti-itching properties. It is considered a good ingredient for reducing skin redness and is a preservative of fats. Although its primary constituent is benzoic acid, it also contains canillin and an oily aromatic liquid. This balsamic resin is extracted by cutting deeply into the trunks of trees that grow primarily in Indonesia and Thailand.

Technology Process of 2-Hydroxy-2-phenylacetophenone

There total 495 articles about 2-Hydroxy-2-phenylacetophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

cis-stilben (645-49-8) → (1S,2R)-1,2-diphenylethane-1,2-diol (579-43-1) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzaldehyde (100-52-7)

Guidance literature:

With 4-methylmorpholine N-oxide; polyaniline-supported Os; In water; acetone; acetonitrile; at 20 ℃; for 3h;

DOI:10.1002/adsc.200606077

Reference yield: 75.0%

α-(2-cyanoethyl)benzoin (174869-02-4) → 4-oxo-4-phenylbutanenitrile (5343-98-6) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzaldehyde (100-52-7)

Guidance literature:

With tetra-n-butylammonium cyanide; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1248/cpb.46.6

Reference yield: 60.0%

benzyl alcohol (100-51-6,185532-71-2) → 1,2-diphenyl-1,2-ethanediol (492-70-6,655-48-1,2325-10-2,38270-73-4,52340-78-0,579-43-1) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzaldehyde (100-52-7) + benzil (134-81-6)

Guidance literature:

With air; 2,2'-thiobis(2,4-di-tert-butylphenol); triethylamine; copper(l) chloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/(SICI)1521-3773(19980904)37:16<2217::AID-ANIE2217>3.0.CO;2-D

upstream raw materials:

benzaldehyde

acetaldehyde

acrylonitrile

ortho-tolylmagnesium bromide

Downstream raw materials:

(1RS,2RS)-1,2-diphenyl-1-o-tolyl-ethane-1,2-diol

7-bromo-1,2-diphenyl-naphtho[2,1-b]furan

α-benzoylbenzyldiphenylacetate

(Z)-N’-(2-hydroxy-1,2-diphenylethylidene)isonicotinohydrazide

Refernces

• 1、 McEwen et al.. "-". . p. 4587. Retrieved 1956.
• 2、 Krawczyk, Ewa,Koprowski, Marek,Skowronska, Aleksandra,Luczak, Jerzy. "α-Hydroxy ketones in high enantiomeric purity from asymmetric oxidation of enol phosphates with (salen) manganese(III) complex". . p. 2599 - 2602. Retrieved 2004.
• 3、 Langer, Robert,Iron, Mark A.,Konstantinovski, Leonid,Diskin-Posner, Yael,Leitus, Gregory,Ben-David, Yehoshoa,Milstein, David. "Iron borohydride pincer complexes for the efficient hydrogenation of ketones under mild, base-free conditions: Synthesis and mechanistic insight". . p. 7196 - 7209. Retrieved 2012.
• 4、 Pletcher, Derek,Slevin, Louise. "Influence of magnesium(II) ions on cathodic reactions in aprotic solvents: the reduction of benzoate esters". . p. 2005 - 2012. Retrieved 1995.
• 5、 Miyashita, Akira,Suzuki, Yumiko,Kobayashi, Motoi,Kuriyama, Naomi,Higashino, Takeo. "Azolium salts as effective catalysts for benzoin condensation and related reactions". . p. 509 - 512. Retrieved 1996.
• 6、 Berreau, Lisa M.,Borowski, Tomasz,Grubel, Katarzyna,Allpress, Caleb J.,Wikstrom, Jeffrey P.,Germain, Meaghan E.,Rybak-Akimova, Elena V.,Tierney, David L.. "Mechanistic studies of the O2-dependent aliphatic carbon-carbon bond cleavage reaction of a nickel enolate complex". . p. 1047 - 1057. Retrieved 2011.
• 7、 Konno, Akinori,Fukui, Kouta,Fuchigami, Toshio,Nonaka, Tsutomu. "ANODIC GENERATION OF POLYBROMOCHLORIDE IONS AND THEIR UTILIZATION AS PRECISELY-CONTROLLED OXIDIZING REAGENTS FOR EX-CELL INDIRECT ELECTROOXIDATION OF ALCOHOLS". . p. 887 - 894. Retrieved 1991.
• 8、 William, Julius M.,Kuriyama, Masami,Onomura, Osamu. "Boronic acid-catalyzed selective oxidation of 1,2-diols to α-hydroxy ketones in water". . p. 934 - 940. Retrieved 2014.
• 9、 Mohanazadeh, Farajollah,Aghvami, Majid. "Thiazolium salt immobilized on ionic liquid: An efficient catalyst and solvent for preparation of α-hydroxyketones". . p. 2467 - 2475. Retrieved 2007.
• 10、 Orsini, Monica,Chiarotto, Isabella,Sotgiu, Giovanni,Inesi, Achille. "Polarity reversal induced by electrochemically generated thiazol-2-ylidenes: The Stetter reaction". . p. 3511 - 3517. Retrieved 2010.