2-(Chloromethyl)-5-hydroxy-4H-pyran-4-one

Base Information

• Chemical Name: 2-(Chloromethyl)-5-hydroxy-4H-pyran-4-one
• CAS No.: 7559-81-1
• Deprecated CAS: 54839-86-0
• Molecular Formula: C6H5ClO3
• Molecular Weight: 160.557
• Hs Code.: 2932990090
• European Community (EC) Number: 815-637-7
• NSC Number: 298537,10216
• UNII: UB7QQW2D47
• DSSTox Substance ID: DTXSID6064741
• Nikkaji Number: J113.018H
• Wikidata: Q27290995
• ChEMBL ID: CHEMBL506570
• Mol file: 7559-81-1.mol

Synonyms:2-chloromethyl-5-hydroxy-4-pyranone;2-chloromethyl-5-hydroxy-4H-pyran-4-one;2-ClMe-5-HOP;chlorokojic acid

Chemical Property of 2-(Chloromethyl)-5-hydroxy-4H-pyran-4-one

Chemical Property:

• Vapor Pressure: 2.3E-05mmHg at 25°C
• Melting Point: 164-165oC
• Boiling Point: 321.9°Cat760mmHg
• PKA: 7.80±0.10(Predicted)
• Flash Point: 148.5°C
• PSA: 50.44000
• Density: 1.514g/cm³
• LogP: 1.08420
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 159.9927217
• Heavy Atom Count: 10
• Complexity: 217

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-?(Chloromethyl)?-?5-?hydroxy-4H-?pyran-?4-?one ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(OC=C(C1=O)O)CCl
• Uses: 2-?(Chloromethyl)?-?5-?hydroxy-4H-?pyran-?4-?one is an intermediate in synthesizing Allo Maltol (A546700), the esters of 5-hydroxy-2-methyl-4H-pyran-4-one are used as novel tyrosinase inhibitors for skin-lightening cosmetic compositions.

Technology Process of 2-(Chloromethyl)-5-hydroxy-4H-pyran-4-one

There total 3 articles about 2-(Chloromethyl)-5-hydroxy-4H-pyran-4-one 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%

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7) → chlorokojic acid (7559-81-1,54839-86-0)

Guidance literature:

With thionyl chloride; at 20 ℃; for 0.166667h;

Reference yield: 70.0%

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7) + thionyl chloride (7719-09-7) → chlorokojic acid (7559-81-1,54839-86-0)

Guidance literature:

In DMF (N,N-dimethyl-formamide); at 10 - 20 ℃; for 2.5h;

Reference yield:

→ chlorokojic acid (7559-81-1,54839-86-0)

Guidance literature:

upstream raw materials:

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

thionyl chloride

Downstream raw materials:

5-hydroxy-2-phenothiazin-10-ylmethyl-pyran-4-one

2-(ethylcarbamimidoylmercapto-methyl)-5-hydroxy-pyran-4-one; hydrochloride

2-chloromethyl-5-hydroxy-3-(α-hydroxy-benzyl)-pyran-4-one

5-benzoyloxy-2-chloromethyl-pyran-4-one

Refernces

• 1、 -. "ALA hybrid 3-hydroxypyridone derivative as well as preparation method and application thereof". Paragraph 0112; 0114; 0160-0161. . Retrieved 2021/07/17.
• 2、 Azuma, Hideki,Morishima, Yasuhito,Nakaguro, Keijin,Kato, Reiko,Nagasaki, Takeshi. "A new “Mitsunobu homocoupling” reaction using aldol adducts of kojic acid". . . Retrieved 2021/07/20.