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Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Product Name
Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
CAS No.
161798-01-2
Chemical Name
Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
Synonyms
ETHYL 2-(3-FORMYL-4-HYDROXYPHENYL)-4-METHYL-1,3-THIAZOLE-5-CARBOXYLATE;Febuxostat-23;Febuxostat PI-2;-4-hydroxyphenyL;Febuxostat Impurity 1;Febuxostat Impurities1;Febuxostat Impurity Z17;Febuxostat intermediate3;Ethyl 2-(3-formyl-4-hydroxyphenyl);Febuxostat Inter. (avoid the patent)
CBNumber
CB12128604
Molecular Formula
C14H13NO4S
Formula Weight
291.32
MOL File
161798-01-2.mol
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Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate Property

Melting point:
116 °C
Boiling point:
446.7±55.0 °C(Predicted)
Density 
1.335
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
6.81±0.20(Predicted)
color 
Pale Yellow to Yellow
InChI
InChI=1S/C14H13NO4S/c1-3-19-14(18)12-8(2)15-13(20-12)9-4-5-11(17)10(6-9)7-16/h4-7,17H,3H2,1-2H3
InChIKey
NJRGQNNSIAFIJC-UHFFFAOYSA-N
SMILES
S1C(C(OCC)=O)=C(C)N=C1C1=CC=C(O)C(C=O)=C1
CAS DataBase Reference
161798-01-2(CAS DataBase Reference)
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Safety

HS Code 
2934100090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

TCI Chemical
Product number
E1394
Product name
Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
Packaging
5G
Price
$58
Updated
2025/07/31
TCI Chemical
Product number
E1394
Product name
Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
Packaging
25G
Price
$173
Updated
2025/07/31
TRC
Product number
E918105
Product name
Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
Packaging
250mg
Price
$105
Updated
2021/12/16
TRC
Product number
E918105
Product name
Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
Packaging
500mg
Price
$185
Updated
2021/12/16
Ark Pharm
Product number
P000219190
Product name
Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
Purity
98%
Packaging
250mg
Price
$6
Updated
2021/12/16
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Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate Chemical Properties,Usage,Production

Description

Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate is a pharmaceutical intermediate used in the preparation of the xanthine oxidase inhibitor febuxostat, which is used in the treatment of hyperuricaemia and gout. It is also used in the synthesis of novel thiazolyl α-aminophosphonates.

Chemical Properties

Yellow or yellow powder

Uses

Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate is a product prepared via reaction 4-Hydroxybenzene-1-benzothiomide with ethyl-2-chloro acetoacetate. An antibacterial agent and antifungal activity against C.albicans.

Synthesis

161797-99-5

100-97-0

161798-01-2

The general procedure for the synthesis of ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate from ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate and urotropine was as follows: 120 kg of polyphosphoric acid was added to a clean and dry 200 L reactor, stirred and heated to 40-50°C. After stirring, 20 kg ( 76.0 mol) ethyl 2-(4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylate and 11 kg (76.3 mol) hexamethylenetetramine (HMTA) were added sequentially. After the addition was completed, the reaction mixture was heated to 93°C for 3 hours. After completion of the reaction, the reaction solution was slowly poured into dilute aqueous glacial acetic acid solution for hydrolysis for 20 min. The reaction mixture was extracted with 300 L of ethyl acetate in three portions and the organic phases were combined. To the organic phase, 10 kg of anhydrous sodium sulfate was added for drying, and after filtration, the filtrate was concentrated under reduced pressure to obtain 210 mg of ethyl acetate solvent. To the concentrate, 100 kg of water was added and stirred to induce crystallization, followed by centrifugal separation and drying, resulting in 18.0 kg of light yellow intermediate product in 81.3% yield. The intermediate 2-(3-formyl-4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylic acid ethyl ester was tested to be 99.4%, and the dicarboxylic acid impurity content was 0.008%.

References

[1] Patent: CN106366048, 2017, A. Location in patent: Paragraph 0007; 0008; 0009; 0010; 0011; 0012
[2] Patent: WO2012/14117, 2012, A1. Location in patent: Page/Page column 12
[3] Patent: WO2012/131590, 2012, A1. Location in patent: Page/Page column 15; 21-23
[4] Patent: WO2012/168948, 2012, A2. Location in patent: Page/Page column 10-11
[5] Letters in Organic Chemistry, 2015, vol. 12, # 3, p. 217 - 221

Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate Preparation Products And Raw materials

Raw materials

Preparation Products

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Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate Suppliers

Americas 1 China 360 China Hong Kong 1 Europe 1 India 21 Japan 1 United Kingdom 2 United States 14 Global 401
Xunteng International Trading Co.,Limited
Tel
Country
China Hong Kong
ProdList
878
Advantage
55
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View Lastest Price from Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate manufacturers

HEBEI BRANT PHARMACEUTICAL CO.,LTD
Product
Ehtyl 2-(3-Formyl-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate 161798-01-2
Price
US $0.00-0.00/kg
Min. Order
2kg
Purity
99%
Supply Ability
20 tons
Release date
2025-07-04
Anhuyan (Hainan) Biotechnology Co., LTD
Product
Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate 161798-01-2
Price
US $0.00-0.00/kg
Min. Order
0.0001kg
Purity
99%
Supply Ability
2000000T
Release date
2025-06-16
Jinan Jianfeng Chemical Co., Ltd
Product
ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate 161798-01-2
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%min
Supply Ability
20ton
Release date
2024-08-09

161798-01-2, Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylateRelated Search:

Febuxostat Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate isopropyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate 2,2'-[4-(2-Methylpropoxy)-1,3-phenylene]bis[4-Methyl-5-thiazolecarboxylic Acid 5,5'-DiMethyl Ester Febuxostat Impurity 14 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid Febuxostat Impurity 6 2,2'-[4-(2-Methylpropoxy)-1,3-phenylene]bis[4-Methyl-5-thiazolecarboxylic Acid 2-[3-Carboxy-4-(2-Methylpropoxy)phenyl]-4-Methyl-5-thiazolecarboxylic Acid 2-(3-cyano-4-propoxyphenyl)-4-methylthiazole-5-carboxylic acid Febuxostat Impurity 8 4-(2-Methylpropoxy)-1,3-benzenedicarbothioaMide Ethyl 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate 3-Cyano-4-(2-methylpropoxy)benzenecarbothioamide Ethyl 2-(3-bromo-4-isobutoxyphenyl)- 4-methyl-5-thiazolecarboxylate 4-HYDROXYTHIOBENZAMIDE ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE ethyl 2-(4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate

  • ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
  • 2-(3-Formyl-4-hydroxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester
  • Thiazolecarboxylicacid,2-(3-forMyl-4-hydroxyphenyl)-4-Methyl-,ethylester
  • 5-carboxylato-1-ethyl-2-(3-forMyl-4-hydroxyphenyl)-4-Methyl-1H-1$l^{4},3-thiazol-1-yl
  • Ethyl 2-(3-forMyl-4-hydroxyphenyl)-4-Methyl-5-Thiazolecarboxylate
  • 5-carboxylato-1-ethyl-2-(3-forMyl-4-h
  • ETHYL 2-(3-FORMYL-4-HYDROXYPHENYL)-4-METHYL-1,3-THIAZOLE-5-CARBOXYLATE
  • Febuxostat-23
  • Febuxostat intermediate3
  • ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazo
  • 5-Thiazolecarboxylicacid, 2-(3-forMyl-4-hydroxyphenyl)-4-Methyl-, ethyl ester
  • 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
  • Febuxostat Impurity 1
  • Febuxostat PI-2
  • Ethyl 2-(3-formyl-4-hydroxyphenyl)
  • 2-(3-forMyl-4-hydroxyphenyl)-4-Methyl-5-Thiazolecarboxylicacid ethyl ester
  • Febuxostat Impurity Z17
  • ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-
  • -4-hydroxyphenyL
  • ethyl-2-(3-formyl-4-hydroxyphenyl)-4-methyl thiozole-5-carboxylate
  • Febuxostat intermediates，Ethyl 2-(3-formyl-4-hydroxyphenyl)-4- methylthiazole-5-carboxylate
  • Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate 2-
  • Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carbox...
  • Febuxostat Impurities1
  • Ethyl 2-(3- aldehyde -4- hydroxyphenyl) -4- methylthiazole -5- carboxylate
  • Ethyl 2-(3-formyl-4-hydroxypheip)-4-methylthiazole-5-carboxylate
  • 5-Thiazolecarboxylic acid, 2-(3-formyl-4-hydroxyphenyl)-4-methyl-, ethyl ester (9CI, ACI)
  • 2-(3-formyl-4-hydroxyphenyl)-4-methyl-5-Thiazolecarboxylic acid ethyl ester (9CI ACI)
  • 2-(3-formyl-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate
  • Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate（F3）
  • Ethyl 2-(3-formyl-4- hydroxyphenyl)-4-
  • 2-(3-formyl-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylat
  • 2- (3-aldehyde 4-hydroxyphenyl) -4-methylthiazole-5-carboxylic acid ethyl ester
  • cEthyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
  • Ehtyl 2-(3-Formyl-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate
  • Febuxostat Inter. (avoid the patent)
  • 161798-01-2
  • Febuxostat intermediate
  • 161798-01-2