2-Chloro-1-(2,4,6-trihydroxyphenyl)ethanone

Base Information

• Chemical Name: 2-Chloro-1-(2,4,6-trihydroxyphenyl)ethanone
• CAS No.: 110865-03-7
• Molecular Formula: C8H7 Cl O4
• Molecular Weight: 202.594
• NSC Number: 118825
• DSSTox Substance ID: DTXSID50297882
• Nikkaji Number: J1.540.763H
• Wikidata: Q82039375
• Mol file: 110865-03-7.mol

Synonyms:2-chloro-1-(2,4,6-trihydroxyphenyl)ethanone;110865-03-7;2-CHLORO-1-(2,4,6-TRIHYDROXYPHENYL)-ETHANONE;2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one;Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)- (9CI);NSC118825;SCHEMBL5707803;DTXSID50297882;NSC-118825;5127-60-6;FT-0710834;F70504;2-chloro-1-(2,4,6-trihydroxy-phenyl)-ethanone;EN300-1966496

Chemical Property of 2-Chloro-1-(2,4,6-trihydroxyphenyl)ethanone

Chemical Property:

• PSA: 77.76000
• LogP: 1.22490
• Solubility.: Dichloromethane (Partially); Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 202.0032864
• Heavy Atom Count: 13
• Complexity: 185

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-1-(2,4,6-trihydroxyphenyl)ethanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1O)C(=O)CCl)O)O
• Uses: 2-Chloro-1-(2,4,6-trihydroxyphenyl)ethanone is an intermediate in synthesizing Diosmetin 3’,7-Diglucuronide-d3 (D485042), a labelled Diosmetin 3’,7-Diglucuronide (D485040), which is a metabolite of Diosmetin (D485000) which is a flavonoid often administered in the treatment of chronic venous insufficiency, hemorrhoids, and related affections.

Technology Process of 2-Chloro-1-(2,4,6-trihydroxyphenyl)ethanone

There total 6 articles about 2-Chloro-1-(2,4,6-trihydroxyphenyl)ethanone 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: 87.0%

3,5-dihydroxyphenol (108-73-6) + chloroacetonitrile (107-14-2) → 2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one (110865-03-7)

Guidance literature:

3,5-dihydroxyphenol; chloroacetonitrile; With hydrogenchloride; zinc(II) chloride; In diethyl ether; at 0 ℃; for 0.25h;

With hydrogenchloride; at 100 ℃; for 1h;

DOI:10.3987/com-01-9182

Reference yield: 65.0%

3,5-dihydroxyphenol (108-73-6) + chloroacetyl chloride (79-04-9) → 2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one (110865-03-7)

Guidance literature:

3,5-dihydroxyphenol; With aluminum (III) chloride; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

chloroacetyl chloride; In 1,2-dichloro-ethane; at 20 - 80 ℃; for 6h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c00735

Reference yield: 25.0%

2-(2-chloro-1-iminoethyl)-1,3,5-benzenetriol hydrochloride → 2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one (110865-03-7)

Guidance literature:

With hydrogenchloride; In water; for 1h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2018.05.003

upstream raw materials:

3,5-dihydroxyphenol

chloroacetonitrile

chloroacetyl chloride

Downstream raw materials:

5,7-diisopropoxy-2-(4-isopropoxyphenyl)-4H-benzopyran-4-one

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

1-(2,4,6-Trihydroxy-phenyl)-2-(triphenyl-λ⁵-phosphanylidene)-ethanone

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Refernces

• 1、 Li, Yan,Qiang, Xiaoming,Luo, Li,Li, Yuxing,Xiao, Ganyuan,Tan, Zhenghuai,Deng, Yong. "Synthesis and evaluation of 4-hydroxyl aurone derivatives as multifunctional agents for the treatment of Alzheimer's disease". . p. 2342 - 2351. Retrieved 2016.
• 2、 Pan, Guojun,Ma, Yantao,Yang, Ke,Zhao, Xia,Yang, Hui,Yao, Qingwei,Lu, Kui,Zhu, Tao,Yu, Peng. "Total synthesis of (±)-Anastatins A and B". . p. 4472 - 4475. Retrieved 2015.
• 3、 -. "COMPOUNDS HAVING HEPATIAL DISEASE EFFECTIVE". Paragraph 0167-0169. . Retrieved 2021/01/29.
• 4、 Sum, Tze Jing,Sum, Tze Han,Galloway, Warren R.J.D.,Twigg, David G.,Ciardiello, Joe J.,Spring, David R.. "Synthesis of structurally diverse biflavonoids". . p. 5089 - 5101. Retrieved 2018/05/23.