2-Chloro-1,3,5-trimethoxybenzene

Base Information

• Chemical Name: 2-Chloro-1,3,5-trimethoxybenzene
• CAS No.: 67827-56-9
• Molecular Formula: C9H11ClO3
• Molecular Weight: 202.638
• European Community (EC) Number: 684-755-7
• NSC Number: 151978
• DSSTox Substance ID: DTXSID6070645
• Nikkaji Number: J429.640K
• Wikidata: Q81998022
• Mol file: 67827-56-9.mol

Synonyms:2-Chloro-1,3,5-trimethoxybenzene;67827-56-9;Chlorophloroglucinol trimethyl ether;Benzene, 2-chloro-1,3,5-trimethoxy-;NSC151978;2,4,6-trimethoxychlorobenzene;O(C)c1cc(OC)cc(OC)c1Cl;DTXSID6070645;SCHEMBL15883267;1,3,5-Trimethoxy-2-chlorobenzene;AKOS017547723;NSC 151978;NSC-151978

Chemical Property of 2-Chloro-1,3,5-trimethoxybenzene

Chemical Property:

• Vapor Pressure: 0.00416mmHg at 25°C
• Boiling Point: 288°Cat760mmHg
• Flash Point: 112.8°C
• PSA: 27.69000
• Density: 1.168g/cm³
• LogP: 2.36580
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 202.0396719
• Heavy Atom Count: 13
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=C(C(=C1)OC)Cl)OC
• Uses: 2-Chloro-1,3,5-trimethoxybenzene is a building block. It was used as a reactant in the Pd-catalyzed borylation of sterically demanding aryl halides by bis(pinacolato)diboron to produce arylboronates.

Technology Process of 2-Chloro-1,3,5-trimethoxybenzene

There total 9 articles about 2-Chloro-1,3,5-trimethoxybenzene 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: 96.0%

1,2,3-trimethoxybenzene (621-23-8) → 2,4,6-trimethoxychlorobenzene (67827-56-9)

Guidance literature:

With N-chloro-succinimide; at 20 ℃; for 2h; regioselective reaction;

DOI:10.1021/acs.joc.7b02920

Reference yield: 88.0%

1,2,3-trimethoxybenzene (621-23-8) → 2,4,6-trimethoxychlorobenzene (67827-56-9) + dichloro-2,4 trimethoxy-1,3,5 benzene (77440-84-7)

Guidance literature:

With dihydrogen peroxide; acetic acid; lithium chloride; In water; 1,2-dichloro-ethane; at 60 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c0cc04889e

Reference yield: 82.0%

1,2,3-trimethoxybenzene (621-23-8) + N-chlorophthalimide (3481-09-2) → 2,4,6-trimethoxychlorobenzene (67827-56-9)

Guidance literature:

With tris[2-(4,6-difluorophenyl)pyridinato-C₂,N]iridium(III); potassium carbonate; acetic acid; In acetonitrile; at 25 ℃; for 24h; Irradiation;

DOI:10.1039/c4cc03905j

upstream raw materials:

1,2,3-trimethoxybenzene

3-chloro-2,4,6-trimethoxy-benzoic acid

1-lithium-2,4,6-trimethoxybenzene

2,4,6-trimethoxybenzoic acid

Downstream raw materials:

3-chloro-2,4,6-trimethoxybenzaldehyde

2-Chloro-1,3,5-trimethoxy-4-phenylsulfanyl-benzene

(N-2,4,6-trimethoxyphenyl)-2,6-dimethyl-aniline

4,4,5,5-tetramethyl-2-(2,4,6-trimethoxyphenyl)-1,3,2-dioxaborolane

Refernces

• 1、 Ji, Yuan-Zhao,Li, Hui-Jing,Wang, Yi-Ruo,Wu, Yan-Chao,Zhang, Zheng-Yan. "Sulfoxide-Promoted Chlorination of Indoles and Electron-Rich Arenes with Chlorine as Nucleophile". supporting information. . Retrieved 2020/02/05.
• 2、 Granados, Albert,Jia, Zhiyu,del Olmo, Marc,Vallribera, Adelina. "In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes". . p. 2812 - 2818. Retrieved 2019/04/08.