73866-23-6

Basic information

• Product Name: 5-Bromoacetyl salicylamide
• Synonyms: 5-(bromoacetyl)-2-hydroxy-benzamid;5-(BROMOACETYL)-2-HYDROXYBENZAMIDE;5-BROMO ACETYL SALICYAMIDE;5-(BROMOACETYL)SALICYLAMIDE;5-Bromoacetylsalicylicamide;5-(2-Bromoacetyl)-2-hydroxybenzamide;5-Bromoacetyl-2-hydroy benzamide;BenzaMide,5-(2-broMoacetyl)-2-hydroxy-
• CAS NO: 73866-23-6
• Molecular Formula: C₉H₈BrNO₃
• Molecular Weight: 258.07
• EINECS: 277-626-8
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;(intermediate of labetalol)
• Mol File: 73866-23-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 200-210°C
• Boiling Point: 420.2 °C at 760 mmHg
• Flash Point: 207.9 °C
• Appearance: /
• Density: 1.705 g/cm³
• Vapor Pressure: 1.18E-07mmHg at 25°C
• Refractive Index: 1.644
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.13±0.20(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: 5-Bromoacetyl salicylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromoacetyl salicylamide(73866-23-6)
• EPA Substance Registry System: 5-Bromoacetyl salicylamide(73866-23-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• RTECS: CV2365900
• Hazardous Substances Data: 73866-23-6(Hazardous Substances Data)

Usage

Chemical Properties

Class white light yellow powder

Uses

5-Bromoacetyl-2-hydroxybenzamide is a reagent used in the synthesis of bisthiazole derivatives and novel 7-methylguanine derivatives targeting influenza polymerase binding domains.

InChI:InChI=1/C9H8BrNO3/c10-4-8(13)5-1-2-7(12)6(3-5)9(11)14/h1-3,12H,4H2,(H2,11,14)

Synthetic route

5-acetylsalicylamide (40187-51-7) → 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6)

Conditions	Yield
With hydrogen bromide; bromine In ethyl acetate at 5 - 10℃; for 18h;	69.4%
With phenyltrimethylammonium tribromide In methanol; dichloromethane at 20℃;	29%
Stage #1: 5-acetylsalicylamide With copper(I) bromide In ethyl acetate under 760.014 Torr; Inert atmosphere; Stage #2: under 760.014 Torr;

C8H11N3O2S2 + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 2-hydroxy-5-{2-[methyl-(4-sulfamoylphenyl)amino]thiazol-4-yl}benzamide

Conditions	Yield
In ethanol for 2h; Reflux;	98%

C13H17N3O2S + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 3-[4-(3-carbamoyl-4-hydroxyphenyl)thiazol-2-ylamino]pyrrolidine-1-carboxylic acid benzyl ester

Conditions	Yield
In ethanol for 2h; Reflux;	95%

5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 5-(Dihydroxyacetyl)-2-hydroxybenzamide

Conditions	Yield
In water; dimethyl sulfoxide; isopropyl alcohol	92%

1-(2-bromo-5-methoxybenzoyl)thiosemicarbazide (286440-10-6) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → BrCH3OC6H3CON2H2C3HNSC6H3OHCONH2

Conditions	Yield
In ethanol for 10h; Heating;	90%

5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) + thioacetamide (62-55-5) → 2-hydroxy-5-(2-methylthiazol-4-yl)benzamide (1067911-23-2)

Conditions	Yield
In ethanol for 2h; Reflux; Inert atmosphere;	90%

C12H13N3OS (1116152-03-4) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → C21H18N4O3S (1116151-78-0)

Conditions	Yield
In ethanol for 6h; Reflux;	88%

C11H11N3OS (1116152-04-5) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → C20H16N4O3S (1116151-82-6)

Conditions	Yield
In ethanol for 6h; Reflux;	87%

C11H10ClN3OS (1116152-05-6) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → C20H15ClN4O3S (1116151-86-0)

Conditions	Yield
In ethanol for 6h; Reflux;	87%

2-(4-chlorophenoxymethyl)benzathiamide (1019391-35-5) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 4-(3-carboxamido-4-hydroxyphenyl)-2-[(4-chlorophenoxymethyl)phenyl]-[1,3]-thiazole (1397689-13-2)

Conditions	Yield
In ethanol for 4h; Reflux;	86%

2,3,5-trichlorobenzaldehyde thiosemicarbazone (1018688-24-8) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → C17H11Cl3N4O2S (1018688-17-9)

Conditions	Yield
In methanol for 4h; Heating;	85%

4-amino-5-(2,3,5-trichlorophenyl)-4H-[1,2,4]triazole-3-thiol (1029491-80-2) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 6-(3-carbamoyl-4-hydroxyphenyl)-3-(2,3,5-trichlorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (1029492-05-4)

Conditions	Yield
In ethanol Heating;	85%

C15H15NOS (1017025-76-1) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 4-(3-carboxamido-4-hydroxyphenyl)-2-[(2-methylphenoxymethyl)phenyl]-[1,3]-thiazole (1397689-10-9)

Conditions	Yield
In ethanol for 4h; Reflux;	85%

(Z)-5-(4-hydroxyphenylmethylene)-2,4-thiazolidinedione (103788-60-9) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → (Z)-5-(2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetyl)-2-hydroxybenzamide (1228763-96-9)

Conditions	Yield
Stage #1: (Z)-5-(4-hydroxyphenylmethylene)-2,4-thiazolidinedione With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: 5-(2-bromoacetyl)-2-hydroxybenzamide In N,N-dimethyl-formamide at 20℃; for 4h;	84%

1-[(7-nitro-1H-indol-2-yl)carbonyl]thiosemicarbazide (948914-04-3) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 2-hydroxy-5-{2-[N'-(7-nitro-1H-indole-2-carbonyl)-hydrazino]-thiazol-4-yl}-benzamide

Conditions	Yield
In methanol Heating;	83%

4-amino-6-(4-methylthiobenzyl)-3-mercapto-1,2,4-triazin-5(4H)-one (956431-06-4) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → C20H19N5O4S2

Conditions	Yield
With sodium acetate In ethanol; N,N-dimethyl-formamide at 20℃; for 4h;	82%

2,3,5-trichlorobenzenecarbothiamide (1018688-04-4) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → C16H9Cl3N2O2S (1018688-09-9)

Conditions	Yield
In methanol for 4h; Heating;	82%

4-amino-5-[4-(methylsulfonyl)benzyl]-2,4-dihydro-3H-[1,2,4]-triazole-3-thione (1394240-72-2) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 2-hydroxy-5-{3-[4-(methylsulfonyl)benzyl]-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl}benzamide (1394240-81-3)

Conditions	Yield
In ethanol at 80℃; for 5h;	82%

2-(3-methylphenoxymethyl)benzathiamide (1017040-86-6) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → C24H20N2O3S (1397689-11-0)

Conditions	Yield
In ethanol for 4h; Reflux;	82%

1-[(6-nitro-1H-indol-2-yl)carbonyl]thiosemicarbazide (948914-03-2) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 2-hydroxy-5-{2-[N'-(6-nitro-1H-indole-2-carbonyl)-hydrazino]-thiazol-4-yl}-benzamide

Conditions	Yield
In methanol Heating;	81%

5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) + 2-mercapto-6-methylpyrimidin-4(3H)-one (56-04-2) → 2-hydroxy-5-(2-((4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)thio)acetyl)benzamide

Conditions	Yield
Stage #1: 2-mercapto-6-methylpyrimidin-4(3H)-one With potassium hydroxide In methanol at 22 - 25℃; under 760.014 Torr; for 0.25h; Inert atmosphere; Stage #2: 5-(2-bromoacetyl)-2-hydroxybenzamide In methanol at 22 - 25℃; under 760.014 Torr; for 12h; Inert atmosphere;	80%

2-(4-methylphenoxymethyl)benzathiamide (1016836-45-5) + 5-(2-bromoacetyl)-2-hydroxybenzamide (73866-23-6) → 4-(3-carboxamido-4-hydroxyphenyl)-2-[(4-methylphenoxymethyl)phenyl]-[1,3]-thiazole (1397689-12-1)

Conditions	Yield
In ethanol for 4h; Reflux;	78%

Upstream product

• 40187-51-7 5-acetylsalicylamide 

Downstream Products

• 799280-07-2 2-hydroxy-5-(2-p-tolylamino-thiazol-5-yl)-benzamide 
• 799280-09-4 5-[2-(3-chloro-phenylamino)-thiazol-5-yl]-2-hydroxy-benzamide 
• 799280-05-0 2-hydroxy-5-(2-phenylamino-thiazol-5-yl)-benzamide 
• 799280-23-2 5-(2-amino-thiazol-5-yl)-2-hydroxy-benzamide 
• 799280-24-3 2-hydroxy-5-(2-methyl-thiazol-5-yl)-benzamide 

Relevant articles and documents

Novel Aryl-Substituted Pyrimidones as Inhibitors of 3-Mercaptopyruvate Sulfurtransferase with Antiproliferative Efficacy in Colon Cancer

The enzyme 3-mercaptopyruvate sulfurtransferase (3-MST) is one of the more recently identified mammalian sources of H2S. A recent study identified several novel 3-MST inhibitors with micromolar potency. Among those, (2-[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]-1-(naphthalen-1-yl)ethan-1-one) or HMPSNE was found to be the most potent and selective. We now took the central core of this compound and modified the pyrimidone and the arylketone sides independently. A 63-compound library was synthesized; compounds were tested for H2S generation from recombinant 3-MST in vitro. Active compounds were subsequently tested to elucidate their potency and selectivity. Computer modeling studies have delineated some of the key structural features necessary for binding to the 3-MST's active site. Six novel 3-MST inhibitors were tested in cell-based assays: they exerted inhibitory effects in murine MC38 and CT26 colon cancer cell proliferation; the antiproliferative effect of the compound with the highest potency and best cell-based activity (1b) was also confirmed on the growth of MC38 tumors in mice.

Synthesis of some new 5-(2-substituted-1,3-thiazol-5-yl)-2-hydroxy benzamides and their 2-alkoxy derivatives as possible antifungal agents

The 2-hydroxy-5-(1,3-thiazol-5-yl) benzamide (4a), 5-(2-amino-1, 3-thiazol-5-yl)-2-hydroxy benzamide (4b), 2-hydroxy-5-(2-alkyl-1,3-Thiazol-5-yl) benzamide (4c and 4d), 5-{2-[(N-substituted aryl)amino]-1,3-thiazol-5-yl}2- hydroxy benzamides (6a-j) were prepared by reacting 5-(bromoacetyl) salicylamide (2) with thiourea, thioformamide, thioalkylamide (3c-d) and substituted thioureas (5a-j) in absolute ethanol. These compounds were converted to 5-(2-substituted-1,3-thiazol-5-yl)-2-alkoxybenzamides and 5-(2-N-(substituted aryl)-1,3-thiazol-5-yl)-2-alkoxy benzamides (8a-g) by reacting with n-alkylbromides (7a-b) in presence of a base. The newly synthesized compounds were characterized by IR, 1H-NMR and mass spectral data. Compounds were also screened for their antifungal activity.