4-Methyl-5-thiazoleethanol

Base Information

• Chemical Name: 4-Methyl-5-thiazoleethanol
• CAS No.: 137-00-8
• Deprecated CAS: 8042-97-5
• Molecular Formula: C6H9NOS
• Molecular Weight: 143.21
• Hs Code.: 29341000
• European Community (EC) Number: 205-272-6
• NSC Number: 41831,23262
• UNII: 3XYV4I47I8
• DSSTox Substance ID: DTXSID3044382
• Nikkaji Number: J5.626J
• Wikidata: Q27093940
• Metabolomics Workbench ID: 45833
• ChEMBL ID: CHEMBL1236482
• Mol file: 137-00-8.mol

Synonyms:2-(4-methyl-1,3-thiazol-5-yl)ethanol;4-methyl-5-hydroxyethylthiazole;4-methyl-5-thiazoleethanol;5-(2-hydroxyethyl)-4-methylthiazole;thiamine thiazole hydrochloride;thiamine thiazole phosphate

Chemical Property of 4-Methyl-5-thiazoleethanol

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.00297mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: n20/D 1.550(lit.)
• Boiling Point: 272.4 °C at 760 mmHg
• PKA: 14.58±0.10(Predicted)
• Flash Point: 109.7 °C
• PSA: 61.36000
• Density: 1.206 g/cm³
• LogP: 0.98630
• Storage Temp.: Store below +30°C.
• Sensitive.: Stench
• Solubility.: alcohol: soluble(lit.)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 143.04048508
• Heavy Atom Count: 9
• Complexity: 89.1

Purity/Quality:

99% ^*data from raw suppliers

4-Methyl-5-thiazoleethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC=N1)CCO
• Description: 4-Methy 1-5-thiazoleethanol has the characteristic disagreeable odor of thiazole compounds. It is somewhat pleasant and nut-like on extreme dilution. It may be prepared by reduction of ethyl- 4-methylthiazole-5-acetate using LiAlH4; by condensation of thioformamide with bromoacetopropanol or with y,y-dichloro-y,ydiacetodipropyl ether.
• Uses: 4-Methyl-5-thiazoleethanol has been used in the synthesis of novel thiazolium halogenide ionic liquids.

Technology Process of 4-Methyl-5-thiazoleethanol

There total 79 articles about 4-Methyl-5-thiazoleethanol 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%

acetic acid 2-(4-methyl-thiazol-5-yl)-ethyl ester (656-53-1) → 5-hydroxyethyl-4-methylthiazole (137-00-8,8042-97-5)

Guidance literature:

With water; sodium hydroxide; In toluene; Industrial scale;

Reference yield: 94.0%

1-methyl-1H-imidazole (616-47-7) + 1'-methylthiaminium diperchlorate (73333-47-8) → 5-hydroxyethyl-4-methylthiazole (137-00-8,8042-97-5) + C11H17N5(2+)*2ClO4(1-)

Guidance literature:

In methanol; for 3.5h; Heating;

DOI:10.1055/s-1980-28971

Reference yield: 94.0%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1'-methylthiaminium diperchlorate (73333-47-8) → 5-hydroxyethyl-4-methylthiazole (137-00-8,8042-97-5) + C12H19N5(2+)*2ClO4(1-)

Guidance literature:

In methanol; for 3.5h; Heating;

DOI:10.1055/s-1980-28971

upstream raw materials:

2,3-dichloro-2-methyl-tetrahydro-furan

thiocarboxamide

2-ethoxy-3-chloro-2-methyl-tetrahydro-furan

2-(4-methyl-2,5-dihydro-thiazol-5-yl)-ethanol

Downstream raw materials:

3-benzyl-5-(3-hydroxyethyl)-4-methylthiazol-3-ium bromide

4-Methyl-5-[2-(4-nitro-phenoxy)-ethyl]-thiazole

2-(4-methylthiazol-5-yl)ethyl 4-methylbenzenesulfonate

4-methyl-1,3-thiazole-5-carbaldehyde

Refernces

• 1、 Wu, Min,Papish, Elizabeth T.,Begley, Tadhg P.. "Mechanistic studies on thiaminase I: Identification of the product of thiamin degradation in the absence of the nucleophilic cosubstrate". . p. 45 - 48. Retrieved 2000.
• 2、 Stoll et al.. "-". . p. 2065. Retrieved 1967.
• 3、 Verrett,Cerecedo. "-". . p. 1695. Retrieved 1957.
• 4、 Williams et al.. "". . p. 229,536, 1093. Retrieved 1935.
• 5、 Zoltewicz, John A.. "Facile Nucleophilic Substitution Reactions of 1'-Methylthiaminium Salts". . p. 218 - 219. Retrieved 1980.
• 6、 Williams,Ronzio. "-". . p. 2409. Retrieved 1952.
• 7、 Linnett,Walker. "Biosynthesis of thiamine. II. Origin of the carbon atom in the 2-position of the thiazole component.". . p. 796 - 799. Retrieved 1967.
• 8、 Hetrick, Kenton J.,Raines, Ronald T.. "Assessing and utilizing esterase specificity in antimicrobial prodrug development". . . Retrieved 2021/12/30.
• 9、 Lakshman, Mahesh K.,Tine, Fatou A.,Khandaker, Tashrique A.,Basava, Vikram,Agyemang, Nana B.,Benavidez, Michael S.A.,Ga?i, Marikone,Guerrera, Lisa,Zajc, Barbara. "KHF2: A mild and selective desilylating agent for phenol tert-butyldimethylsilyl (TBDMS) ethers". supporting information. p. 381 - 385. Retrieved 2017/02/10.