Methyl 2-(chloromethyl)oxazole-4-carboxylate

Base Information

• Chemical Name: Methyl 2-(chloromethyl)oxazole-4-carboxylate
• CAS No.: 208465-72-9
• Molecular Formula: C6H6ClNO3
• Molecular Weight: 175.572
• Hs Code.: 2934999090
• European Community (EC) Number: 695-764-0
• DSSTox Substance ID: DTXSID30376806
• Nikkaji Number: J1.332.302J
• Wikidata: Q72489318
• Mol file: 208465-72-9.mol

Synonyms:208465-72-9;methyl 2-(chloromethyl)oxazole-4-carboxylate;methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate;Methyl (2-Chloromethyl)oxazole-4-carboxylate;4-Oxazolecarboxylic acid, 2-(chloromethyl)-, methyl ester;Methyl(2-chloromethyl)oxazole-4-carboxylate;Methyl 2-chloromethyl-4-oxazolecarboxylate;SCHEMBL393999;DTXSID30376806;CMUKPCIZFMTLKD-UHFFFAOYSA-N;MFCD06660133;AKOS005255693;DS-10527;methyl2-(chloromethyl)oxazole-4-carboxylate;A4533;AM20080901;FT-0647001;2-(chloromethyl)-5-methyloxazole-4-carboxylate;EN300-245236;methyl 2-(chloro-methyl)-1,3-oxazole-4-carboxylate;W-206566;2-chloromethyl-oxazole-4-carboxylic acid methyl ester;2-(Chloromethyl)oxazole-4-carboxylic acid methyl ester

Chemical Property of Methyl 2-(chloromethyl)oxazole-4-carboxylate

Chemical Property:

• Vapor Pressure: 0.0686mmHg at 25°C
• Melting Point: 74 °C
• Refractive Index: 1.494
• Boiling Point: 229.697 °C at 760 mmHg
• PKA: -2.41±0.10(Predicted)
• Flash Point: 92.718 °C
• PSA: 52.33000
• Density: 1.34 g/cm³
• LogP: 1.20000
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 175.0036207
• Heavy Atom Count: 11
• Complexity: 153

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl2-(Chloromethyl)oxazole-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=COC(=N1)CCl

Technology Process of Methyl 2-(chloromethyl)oxazole-4-carboxylate

There total 6 articles about Methyl 2-(chloromethyl)oxazole-4-carboxylate 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%

dichloroacetonitrile (3018-12-0) + methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) → methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate (208465-72-9)

Guidance literature:

dichloroacetonitrile; With sodium methylate; In methanol; dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride; In methanol; dichloromethane; at 25 ℃; for 12h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 - 50 ℃; for 17h; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.01.051

Reference yield: 98.0%

methyl 2-(bromomethyl)oxazole-4-carboxylate (175551-77-6) → methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate (208465-72-9)

Guidance literature:

With lithium chloride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(98)00499-7

Reference yield: 96.0%

2-dichloromethyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester (289030-37-1) → methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate (208465-72-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 0.0166667h;

DOI:10.1021/ol051345v

upstream raw materials:

methyl 2-(bromomethyl)oxazole-4-carboxylate

2-dichloromethyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

methyl 2-(dichloromethyl)-1,3-oxazole-4-carboxylate

sodium methylate

Downstream raw materials:

(R)-methyl 2-((2-chloro-5-(((1-(3-chlorophenyl)ethyl)amino)-methyl)phenoxy)methyl)oxazole-4-carboxylate

C₂₅H₂₅ClFN₃O₄

C₂₅H₂₅ClFN₃O₄

C₂₅H₂₆BrN₃O₄

Refernces

• 1、 Cardwell, Kevin S.,Hermitage, Stephen A.,Sjolin, Asa. "A new method for the formation of 2,4-disubstituted oxazoles: Internal transfer of oxidation state through a molecular framework". . p. 4239 - 4242. Retrieved 2000.
• 2、 -. "MACROCYCLIC FUSED PYRRAZOLES AS MCL-1 INHIBITORS". Paragraph 0956. . Retrieved 2020/08/13.
• 3、 -. "N-[2-(3-AMINO-2,5-DIMETHYL-1,1-DIOXIDO-5,6-DIHYDRO-2H-1,2,4-THIADIAZIN-5-YL)-1,3-THIAZOL-4-YL] AMIDES USEFUL AS BACE INHIBITORS". Page/Page column 62; 63. . Retrieved 2017/04/11.