4-Chlorobenzhydrol

Base Information

• Chemical Name: 4-Chlorobenzhydrol
• CAS No.: 119-56-2
• Deprecated CAS: 118014-08-7
• Molecular Formula: C13H11ClO
• Molecular Weight: 218.683
• Hs Code.: 29062990
• European Community (EC) Number: 204-333-4
• NSC Number: 59990
• UNII: V5V8VYQ65X
• DSSTox Substance ID: DTXSID50870472
• Nikkaji Number: J23.092H
• Wikidata: Q27116410
• ChEMBL ID: CHEMBL2251568
• Mol file: 119-56-2.mol

Synonyms:4-Chlorobenzhydrol;119-56-2;(4-Chlorophenyl)(phenyl)methanol;P-CHLOROBENZHYDROL;Chlorobenzhydrol;Benzhydrol, 4-chloro-;4-Chlorodiphenylmethanol;(4-Chlorophenyl)phenylmethanol;(4-chlorophenyl)-phenylmethanol;Benzhydrol, p-chloro-;Benzenemethanol, 4-chloro-.alpha.-phenyl-;Chlorbenzhydrol;4-Chlorobenzhydryl alcohol;NSC 59990;UNII-V5V8VYQ65X;Benzenemethanol, 4-chloro-alpha-phenyl-;V5V8VYQ65X;CHEBI:35091;EINECS 204-333-4;NSC-59990;AI3-20881;4-Chloro Benzhydrol (Meclozine EP Impurity B);EC 204-333-4;(S)-4-chloro-diphenylmethanol;4-Chlorodiphenylcarbinol;4-Chlorobenzohydrol;4-Chloro benzhydrol;Meclozine impurity B;MFCD00004491;4-Chlorodiphenyl carbinol;4-Chlorobenzhydrol, 98%;4-CBH;CBHP [USP IMPURITY];SCHEMBL477379;CHEMBL2251568;AJYOOHCNOXWTKJ-UHFFFAOYSA-;DTXSID50870472;(4-Chloro-phenyl)-phenyl-methanol;(+/-)-4-CHLOROBENZHYDROL;NSC59990;STL450937;AKOS000121493;AKOS016844008;alpha-(4-chlorophenyl)-benzyl alcohol;AC-15870;AS-62173;C0989;CS-0186996;FT-0618180;4-CHLORO-.ALPHA.-PHENYLBENZENEMETHANOL;EN300-21103;.ALPHA.-(4-CHLOROPHENYL)BENZYL ALCOHOL;W-108506;Q27116410;Z104491516;MECLOZINE DIHYDROCHLORIDE IMPURITY B [EP IMPURITY];Meclozine impurity B, European Pharmacopoeia (EP) Reference Standard

Chemical Property of 4-Chlorobenzhydrol

Chemical Property:

• Appearance/Colour: White crystalline powder.
• Vapor Pressure: 1.45E-05mmHg at 25°C
• Melting Point: 58-60 °C(lit.)
• Refractive Index: 1.609
• Boiling Point: 352.2 °C at 760 mmHg
• PKA: 13.34±0.20(Predicted)
• Flash Point: 166.8 °C
• PSA: 20.23000
• Density: 1.221 g/cm³
• LogP: 3.42170
• Storage Temp.: Store below +30°C.
• Solubility.: insoluble
• Water Solubility.: insoluble
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 218.0498427
• Heavy Atom Count: 15
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

4-Chlorobenzhydrol ^*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

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=C(C=C2)Cl)O
• Uses: 4-Chlorobenzhydrol was used as internal standard to measure the N-demethyl antipyrine metabolite in urine by gas chromatography-mass spectrometry. It was also used in the identification of the antihistamine cetirizine as a relevant cross-reactant for the carbamazepine-specific enzyme-linked immunosorbent assay .

Technology Process of 4-Chlorobenzhydrol

There total 76 articles about 4-Chlorobenzhydrol 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: 100.0%

4-chlorobenzophenone (134-85-0) → (4-chlorophenyl)phenylmethanol (119-56-2)

Guidance literature:

With N-methylpyrrolidine zinc borohydride; In tetrahydrofuran; for 0.666667h; Heating;

DOI:10.1081/SCC-120015705

Reference yield: 97.0%

4-chlorobenzaldehyde (104-88-1) + phenylboronic acid (98-80-6) → (4-chlorophenyl)phenylmethanol (119-56-2)

Guidance literature:

With [(quinone)Rh(COD)]^-*K⁺; water; at 75 ℃; for 3h;

DOI:10.1021/ja0537981

Reference yield: 94.0%

triphenylboroxine (3262-89-3) + 4-chlorobenzaldehyde (104-88-1) → (4-chlorophenyl)phenylmethanol (119-56-2)

Guidance literature:

triphenylboroxine; With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; potassium phosphate; 4-chlorobenzophenone; In tetrahydrofuran; at 20 ℃;

4-chlorobenzaldehyde; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2009.12.033

upstream raw materials:

4-chlorobenzaldehyde

benzaldehyde

4-chlorophenylmagnesium iodide

sodium isopropylate

Downstream raw materials:

(+/-)-[2-(4-chloro-benzhydryloxy)-ethyl]-dimethyl-amine

(4-Chloro-phenyl)-phenyl-methanol

1-chloro-4-(methoxy(phenyl)methyl)benzene

1-chloro-4-(chloro(phenyl)methyl)benzene

Refernces

• 1、 Lee, Jun-Sik,Velarde-Ortiz, Raffet,Guijarro, Albert,Wurst, Joshua R.,Rieke, Reuben D.. "Low-Temperature Formation of Functionalized Grignard Reagents from Direct Oxidative Addition of Active Magnesium to Aryl Bromides". . p. 5428 - 5430. Retrieved 2000.
• 2、 Venkat Narsaiah,Narsimha. "Efficient synthesis of antihistamines clocinizine and chlorcyclizine". . p. 538 - 541. Retrieved 2012.
• 3、 Oezdemir, Ismail,Yigit, Murat,Cetinkaya, Engin,Cetinkaya, Bekir. "Novel azolinium/rhodium system catalyzed addition of arylboronic acids to aldehydes". . p. 1371 - 1379. Retrieved 2006.
• 4、 Komeyama, Kimihiro,Sakiyama, Shunsuke,Iwashita, Kento,Osaka, Itaru,Takaki, Ken. "Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst". . p. 1413 - 1420. Retrieved 2018.
• 5、 Mati, Mirela,Denegri, Bernard,Kronja, Olga. "Nucleofugality of aliphatic carboxylates in mixtures of aprotic solvents and water". . p. 375 - 384. Retrieved 2014.
• 6、 Yamataka, Hiroshi,Miyano, Nobutaka,Hanafusa, Terukiyo. "Comparative Mechanistic Study of the Reaction of Benzophenone with n-BuMgBr and n-BuLi". . p. 2573 - 2575. Retrieved 1991.
• 7、 Ogata,Nagura. "". . p. 3680,3682,3683. Retrieved 1974.
• 8、 Son, Seung Uk,Kim, Sang Bok,Reingold, Jeffrey A.,Carpenter, Gene B.,Sweigart, Dwight A.. "An anionic rhodium η4-quinonoid complex as a multifunctional catalyst for the arylation of aldehydes with arylboronic acids". . p. 12238 - 12239. Retrieved 2005.
• 9、 Arao, Takafumi,Kondo, Kazuhiro,Aoyama, Toyohiko. "Nickel-catalyzed 1,2-addition of arylboroxines to aromatic aldehydes". . p. 4115 - 4117. Retrieved 2007.
• 10、 Gibson,Foster,Eastham,Tooze,Cole-Hamilton. "Highly efficient C-C coupling reactions using metallated benzylphosphine complexes of palladium". . p. 779 - 780. Retrieved 2001.