4-Hydroxybenzophenone

Base Information

• Chemical Name: 4-Hydroxybenzophenone
• CAS No.: 1137-42-4
• Molecular Formula: C13H10O2
• Molecular Weight: 198.221
• Hs Code.: 29145000
• European Community (EC) Number: 214-507-1
• NSC Number: 1887
• UNII: 04R2LWS0MS
• DSSTox Substance ID: DTXSID5036684
• Nikkaji Number: J94.835G
• Wikidata: Q27116055
• Metabolomics Workbench ID: 67637
• ChEMBL ID: CHEMBL194487
• Mol file: 1137-42-4.mol

Synonyms:4-hydroxybenzophenone;4-hydroxybenzophenone, ion(1-);para-hydroxybenzophenone

Chemical Property of 4-Hydroxybenzophenone

Chemical Property:

• Appearance/Colour: white to gray to brown powder.
• Vapor Pressure: 6.5E-06mmHg at 25°C
• Melting Point: 132-135 °C(lit.)
• Refractive Index: 1.615
• Boiling Point: 367.3 °C at 760 mmHg
• PKA: 8.14±0.13(Predicted)
• Flash Point: 156.7 °C
• PSA: 37.30000
• Density: 1.194 g/cm³
• LogP: 2.62320
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 198.068079557
• Heavy Atom Count: 15
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxybenzophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)O
• Uses: Metabolite of benzophenone. 4-Hydroxybenzophenone is used in the field of organic synthesis. It is used as pharmaceutical intermediate of clomifene citrate.

Technology Process of 4-Hydroxybenzophenone

There total 127 articles about 4-Hydroxybenzophenone 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: 99.0%

4-cyanophenol (767-00-0) + phenylboronic acid (98-80-6) → 4-Hydroxybenzophenone (1137-42-4)

Guidance literature:

With ammonium chloride; bipyridine-cyclopalladated ferrocenylimine complex; In water; at 100 ℃; for 24h;

DOI:10.1055/s-2007-992359

Reference yield: 99.0%

(4-benzoylphenyl)boronic acid → 4-Hydroxybenzophenone (1137-42-4)

Guidance literature:

With [Rh2(bpy)2(μ-OAc)2(OAc)2]; oxygen; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 18h; under 760.051 Torr; Irradiation;

DOI:10.1021/acs.joc.9b02777

Reference yield: 98.0%

(p-hydroxyphenyl)boronic acid (71597-85-8) + tert-butyl benzoyl(tert-butoxycarbonyl)carbamate (135364-97-5) → 4-Hydroxybenzophenone (1137-42-4)

Guidance literature:

With [(η³-1-^tBu-indenyl)Pd(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)(Cl)]; potassium carbonate; In tetrahydrofuran; water; at 23 ℃; for 15h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.7b03191

upstream raw materials:

4-Methoxybenzophenone

benzophenone

benzoic acid phenyl ester

sodium phenoxide

Downstream raw materials:

(4-Hydroxy-phenyl)-phenyl-[2]pyridyl-methanol

4-acetoxybenzophenone

4-salicyloyloxy-benzophenone

<4-(Benzoyloxy)phenyl>phenylketon

Refernces

• 1、 Lee, Byoung Se,Mahajan, Suresh,Clapham, Bruce,Janda, Kim D.. "Suspension Ring-Opening Metathesis Polymerization: The Preparation of Norbornene-Based Resins for Application in Organic Synthesis". . p. 3319 - 3329. Retrieved 2004.
• 2、 Singh, Fateh V.,Milagre, Humberto M.S.,Eberlin, Marcos N.,Stefani, Helio A.. "Synthesis of benzophenones from geminal biaryl ethenes using m-chloroperbenzoic acid". . p. 2312 - 2316. Retrieved 2009.
• 3、 Rebeiro, Geeta L.,Khadilkar, Bhushan M.. "Benzoylation in room temperature ionic liquids". . p. 1605 - 1608. Retrieved 2000.
• 4、 He, Xing,Cao, Yu,Lang, Xian-Dong,Wang, Ning,He, Liang-Nian. "Integrative Photoreduction of CO2 with Subsequent Carbonylation: Photocatalysis for Reductive Functionalization of CO2". . p. 3382 - 3387. Retrieved 2018.
• 5、 Chenevert,Voyer. "Photochemical rearrangement of phenyl benzoate in the presence of cyclodextrins and amylose". . p. 5007 - 5008. Retrieved 1984.
• 6、 Olah, George A.,Arvanaghi, Massoud,Krishnamurthy, V. V.. "Heterogeneous Catalysis by Solid Superacids. 17. Polymeric Perfluorinated Resin Sulfonic Acid (Nafion-H) Catalyzed Fries Rearrangement of Aryl Esters". . p. 3359 - 3360. Retrieved 1983.
• 7、 Siano, Gastón,Crespi, Stefano,Bonesi, Sergio M.. "Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment?". . p. 1298 - 1309. Retrieved 2021/05/07.
• 8、 Shi, Yaocheng,Wang, Feng,Yang, Chenggen,Yu, Lei. "PhSe(O)OH/NHPI-catalyzed oxidative deoximation reaction using air as oxidant". . . Retrieved 2021/09/06.