5304-34-7

Basic information

• Product Name: N-PHENACYLTHIAZOLIUM BROMIDE
• Synonyms: N-PHENACYLTHIAZOLIUM BROMIDE;3-Phenacylthiazoliumbromide;ThiazoliuM,3-(2-oxo-2-phenylethyl)-, broMide (1:1)
• CAS NO: 5304-34-7
• Molecular Formula: Br*C₁₁H₁₀NOS
• Molecular Weight: 284.17
• Mol File: 5304-34-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-PHENACYLTHIAZOLIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-PHENACYLTHIAZOLIUM BROMIDE(5304-34-7)
• EPA Substance Registry System: N-PHENACYLTHIAZOLIUM BROMIDE(5304-34-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 5304-34-7(Hazardous Substances Data)

Usage

General Description

N-Phenacylthiazolium bromide is a chemical compound that has been used as a reactant in chemical synthesis, particularly in the preparation of various thiazolium salts. It is a quaternary ammonium compound with a thiazolium ring, and its bromide salt form is often used to initiate the oxidative cyclization of 2'-deoxyadenosine to form 2'-deoxyisoguanosine, which has potential anti-cancer properties. Additionally, N-phenacylthiazolium bromide has been studied for its potential application in fluorescent imaging and photodynamic therapy due to its unique photophysical properties. Overall, this chemical compound has shown promise in a variety of research applications, particularly in the fields of organic chemistry and biomedical sciences.

InChI:InChI=1/C11H10NOS.BrH/c13-11(8-12-6-7-14-9-12)10-4-2-1-3-5-10;/h1-7,9H,8H2;1H/q+1;/p-1

Synthetic route

1,3-thiazole (288-47-1) + α-bromoacetophenone (70-11-1) → 2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7)

Conditions	Yield
In methanol for 3h; Reflux; Inert atmosphere;	51%
In benzene for 4h; Heating;	42%

N-p-tolylphenylmaleimide (1631-28-3) + 2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → (5S,5aS,8aS,8bR)-5-Benzoyl-7-p-tolyl-5,5a,8a,8b-tetrahydro-pyrrolo[3',4':3,4]pyrrolo[2,1-b]thiazole-6,8-dione

Conditions	Yield
With triethylamine In dichloromethane for 0.166667h; Ambient temperature;	97%

3-(2,3-diphenyl-2-cyclopropenylidene)-2,4-pentanedione (15104-20-8) + 2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → C31H25NO3S (82735-59-9)

Conditions	Yield
With triethylamine In tetrahydrofuran 1.) rt, 2 h; 2) reflux, 2 h;	93%

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → 3-(2-Hydroxy-2-phenyl-ethyl)-thiazol-3-ium; bromide

Conditions	Yield
With sodium tetrahydroborate In water Ambient temperature;	76%

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) + dimethylfumarate (624-49-7) → (5R,6R,7S,7aS)-5-Benzoyl-5,6,7,7a-tetrahydro-pyrrolo[2,1-b]thiazole-6,7-dicarboxylic acid dimethyl ester + (5R,6S,7R,7aS)-5-Benzoyl-5,6,7,7a-tetrahydro-pyrrolo[2,1-b]thiazole-6,7-dicarboxylic acid dimethyl ester

Conditions	Yield
With triethylamine In chloroform for 0.166667h; Ambient temperature; Title compound not separated from byproducts;	A 50% B 50%

(E)-1-(4-methylphenyl)-3-phenyl-2-propen-1-one (14802-30-3) + 2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → ((5R,6R,7R,7aR)-5-Benzoyl-6-phenyl-5,6,7,7a-tetrahydro-pyrrolo[2,1-b]thiazol-7-yl)-p-tolyl-methanone

Conditions	Yield
With triethylamine CHCl3, r.t., 14 h; Yield given. Multistep reaction;

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) + 2-oxopropanal (78-98-8) → 5-benzoyl-6,7-dihydroxy-7-methyl-6,7-dihydro-5H-pyrrolo[2,1-b]thiazol-4-ylium

Conditions	Yield
With phosphate buffer In water at 37℃; for 24h; pH=7.4;

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → 3-((E)-Styryl)-thiazol-3-ium; bromide

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / NaBH4 / H2O / Ambient temperature 2: 73 percent / benzoyl chloride / 190 - 200 °C View Scheme

2-(3-thiazolium)-1-phenylethanone bromide (5304-34-7) → Thiazolo[2,3-a]isoquinolin-4-ylium; bromide

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent / NaBH4 / H2O / Ambient temperature 2: 73 percent / benzoyl chloride / 190 - 200 °C 3: I2 / methanol / Ambient temperature; Irradiation View Scheme

Upstream product

• 288-47-1 1,3-thiazole 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 82735-59-9 C₃₁H₂₅NO₃S 

Relevant articles and documents

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