5-Methylfuran-2-carbonyl chloride

Base Information

• Chemical Name: 5-Methylfuran-2-carbonyl chloride
• CAS No.: 14003-11-3
• Molecular Formula: C6H5ClO2
• Molecular Weight: 144.558
• Hs Code.: 2932190090
• European Community (EC) Number: 625-189-2
• DSSTox Substance ID: DTXSID30374943
• Wikidata: Q82163508
• Mol file: 14003-11-3.mol

Synonyms:5-Methylfuran-2-carbonyl chloride;14003-11-3;5-Methyl-furan-2-carbonyl chloride;5-Methyl-2-furoyl chloride;2-Furancarbonyl chloride, 5-methyl-;MFCD03421416;5-Methylfuran-2-carbonylchloride;5-Methylfuran-2-carbonyl chloride, 97%;SCHEMBL353183;DTXSID30374943;ZURUVZFDEVKNCE-UHFFFAOYSA-N;2-Furancarbonylchloride,5-methyl-;GEO-01822;AKOS000302233;AS-62445;5-methyl-furan-2-carboxylic acid chloride;BB 0261501;FT-0620651;EN300-383286;J-007345

Chemical Property of 5-Methylfuran-2-carbonyl chloride

Chemical Property:

• Vapor Pressure: 0.306mmHg at 25°C
• Melting Point: 27-30 °C
• Refractive Index: 1.496
• Boiling Point: 201.6 °C at 760 mmHg
• Flash Point: 75.7 °C
• PSA: 30.21000
• Density: 1.258 g/cm³
• LogP: 1.96700
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 143.9978071
• Heavy Atom Count: 9
• Complexity: 124

Purity/Quality:

98%min ^*data from raw suppliers

5-Methylfuran-2-carbonyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 34-36
• Safety Statements: 26-36/37/39-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(O1)C(=O)Cl

Technology Process of 5-Methylfuran-2-carbonyl chloride

There total 7 articles about 5-Methylfuran-2-carbonyl chloride 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: 98.0%

5-methylfuran-2-carboxylic acid (1917-15-3) → 5-methylfuran-2-carbonyl chloride (14003-11-3)

Guidance literature:

With thionyl chloride;

Reference yield: 67.0%

4-methoxy-7-phenyl-benzothiazol-2-ylamine (383864-83-3) → 5-methylfuran-2-carbonyl chloride (14003-11-3) + 5-methyl-furan-2-carboxylic acid (4-methoxy-7-phenyl-benzothiazol-2-yl)-amide

Guidance literature:

Reference yield:

5-Methylfurfural (620-02-0) → 5-methylfuran-2-carbonyl chloride (14003-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium permanganate / water; acetone / 25 °C

2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 25 °C / Inert atmosphere

With potassium permanganate; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; water; acetone;

DOI:10.1021/acs.orglett.9b00216

upstream raw materials:

5-methylfuran-2-carboxylic acid

methyl 5-methyl-2-furancarboxylate

methyl 5-(chloromethyl)-2-furoate

4-methoxy-7-phenyl-benzothiazol-2-ylamine

Downstream raw materials:

N-(5-methyl-furan-2-carbonyl)-anthranilic acid

amide of 5-methylfuran-2-carboxylic acid

2-phenyl-1-(5-methyl-2-furyl)-1-ethanone

N-(5-methyl-2-furoyl)-3-aminobenzoic acid

Refernces

• 1、 Singh,Arthur. "-". . p. 73,80. Retrieved 1970.
• 2、 Miao, Haoqian,Shevchenko, Nikolay,Otsuki, Andrew L.,Mascal, Mark. "Diversification of the Renewable Furanic Platform via 5-(Chloromethyl)furfural-Based Carbon Nucleophiles". . p. 303 - 305. Retrieved 2020/10/12.
• 3、 Chen, Gong,Huang, Jie,Li, Qiong,Wang, Shui-Bo. "Copper-catalyzed: Ortho -C(sp2)-H amination of benzamides and picolinamides with alkylamines using oxygen as a green oxidant". . p. 4802 - 4814. Retrieved 2020/07/13.