Methyl 5-(chloromethyl)-2-furoate

Base Information

• Chemical Name: Methyl 5-(chloromethyl)-2-furoate
• CAS No.: 2144-37-8
• Molecular Formula: C7H7ClO3
• Molecular Weight: 174.584
• Hs Code.: 29329900
• European Community (EC) Number: 218-405-8
• NSC Number: 117334
• DSSTox Substance ID: DTXSID40175706
• Nikkaji Number: J298.727I
• Wikidata: Q72489297
• Mol file: 2144-37-8.mol

Synonyms:Methyl 5-(chloromethyl)-2-furoate;2144-37-8;methyl 5-(chloromethyl)furan-2-carboxylate;Methyl 5-chloromethyl-2-furoate;2-Furancarboxylic acid, 5-(chloromethyl)-, methyl ester;5-chloromethyl-furan-2-carboxylic acid methyl ester;MFCD00020922;methyl 5-(chloromethyl)-2-furancarboxylate;5-chloromethylfuran-2-carboxylic acid methyl ester;NSC117334;Enamine_005466;methyl 5-chloromethylfuroate;SCHEMBL189224;methyl-5-chloromethyl-2-furate;methyl-5-chloromethyl-2-furoate;5-methoxycarbonylfurfuryl chloride;DTXSID40175706;methyl 5-chloromethyl-2-furanoate;HMS1409I10;EINECS 218-405-8;BBL007187;GEO-01797;STK251668;AKOS000267458;CS-W017480;NSC 117334;NSC-117334;SB60984;Methyl 5-(chloromethyl)-2-furoate,95%;methyl 5-chloromethylfuran-2-carboxylate;AS-38666;methyl5-(chloromethyl)furan-2-carboxylate;Methyl 5-(chloromethyl)-2-furoate, 97%;methyl-5-(chlormethyl)furan-2-carboxylate;BB 0220506;EU-0084081;FT-0628667;EN300-14727;5-chloromethylfuran-2-carboxylic acid methylester;A815381;5-(Chloromethyl)-2-furancarboxylic acid methyl ester;5-Chloromethyl-furan-2-carboxylic acid, methyl ester;Z56911965;5-(chloro-methyl)-furan-2-carboxylic acid methyl ester;F2135-0618

Chemical Property of Methyl 5-(chloromethyl)-2-furoate

Chemical Property:

• Appearance/Colour: white to yellowish low melting crystalline solid
• Vapor Pressure: 0.00781mmHg at 25°C
• Melting Point: 32-36 °C(lit.)
• Refractive Index: 1.493
• Boiling Point: 268.2 °C at 760 mmHg
• Flash Point: 116 °C
• PSA: 39.44000
• Density: 1.266 g/cm³
• LogP: 1.80500
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Chloroform, Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 174.0083718
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

99% ^*data from raw suppliers

Methyl 5-(chloromethyl)-2-furoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(O1)CCl
• Uses: Methyl 5-(Chloromethyl)-2-furoate can be used for inhibition of gram-negative bacterial for iron uptake. It can also be used to treat osteoporosis.

Technology Process of Methyl 5-(chloromethyl)-2-furoate

There total 20 articles about Methyl 5-(chloromethyl)-2-furoate 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: 95.0%

2-furoic acid methyl ester (611-13-2) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → methyl 5-(chloromethyl)-2-furoate (2144-37-8)

Guidance literature:

With hydrogenchloride; sulfuric acid; zinc(II) chloride; In dichloromethane; water; at 0 - 20 ℃;

Reference yield: 86.0%

Methyl ester of 5-hydroxymethylfuran 2-carboxylic acid (36802-01-4) → methyl 5-(chloromethyl)-2-furoate (2144-37-8)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/acs.jmedchem.0c02018

Reference yield: 70.0%

methanol (67-56-1) + 5-(chloromethyl)-2-furancarbonyl chloride (105850-77-9) → methyl 5-(chloromethyl)-2-furoate (2144-37-8)

Guidance literature:

With potassium carbonate; at 20 ℃; for 1h;

upstream raw materials:

2-furoic acid methyl ester

formaldehyd

Methyl ester of 5-hydroxymethylfuran 2-carboxylic acid

iron(III) chloride

Downstream raw materials:

5-benzoyloximethyl-furan-2-carboxylic acid methyl ester

methyl 5-(acetoxymethyl)furan-2-carboxylate

2-Carbonsaeuremethylester-5-cyanomethylfuran

methyl 5-diethylaminomethyl-2-furoate

Refernces

• 1、 Li, Zhongtang,Cai, Guanxing,Fang, Fan,Li, Wenchao,Fan, Minghua,Lian, Jingjing,Qiu, Yinli,Xu, Xiangqing,Lv, Xuehui,Li, Yiyan,Zheng, Ruqiu,Wang, Yuxi,Li, Zhongjun,Zhang, Guisen,Liu, Zhenming,Huang, Zhuo,Zhang, Liangren. "Discovery of Novel and Potent N-Methyl- d -aspartate Receptor Positive Allosteric Modulators with Antidepressant-like Activity in Rodent Models". . p. 5551 - 5576. Retrieved 2021/05/31.
• 2、 Sengupta, Prabal,Puri, Chetan S.,Chokshi, Hemant A.,Sheth, Chetana K.,Midha, Ajay S.,Chitturi, Trinadha Rao,Thennati, Rajamannar,Murumkar, Prashant R.,Yadav, Mange Ram. "Synthesis, preliminary biological evaluation and molecular modeling of some new heterocyclic inhibitors of TACE". experimental part. p. 5549 - 5555. Retrieved 2011/12/15.