493-53-8

Basic information

• Product Name: sodium O-acetylsalicylate
• Synonyms: sodium O-acetylsalicylate;2-(Acetyloxy)benzoic acid sodium salt;2-Acetyloxybenzoic acid sodium salt;sodium 2-acetoxy benzoate;sodium:2-acetyloxybenzoate
• CAS NO: 493-53-8
• Molecular Formula: C₉H₇O₄*Na
• Molecular Weight: 202.13925
• EINECS: 207-777-7
• Mol File: 493-53-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 218 °C
• Boiling Point: 321.4°Cat760mmHg
• Flash Point: 131.2°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.000124mmHg at 25°C
• CAS DataBase Reference: sodium O-acetylsalicylate(CAS DataBase Reference)
• NIST Chemistry Reference: sodium O-acetylsalicylate(493-53-8)
• EPA Substance Registry System: sodium O-acetylsalicylate(493-53-8)

Safety Data

• Hazardous Substances Data: 493-53-8(Hazardous Substances Data)

Usage

Description

Sodium O-acetylsalicylate, also known as the sodium salt of acetylsalicylic acid, is a chemical compound derived from acetylsalicylic acid. It possesses analgesic, antipyretic, anti-inflammatory, and antithrombotic properties, making it a versatile pharmaceutical agent.

Uses

Used in Pharmaceutical Industry:
Sodium O-acetylsalicylate is used as an analgesic for the relief of pain, as an antipyretic to reduce fever, and as an anti-inflammatory to alleviate inflammation. It is also utilized as an antithrombotic to prevent blood clot formation.
Used in Oncology:
Sodium O-acetylsalicylate is used as an anticancer agent, particularly against various types of cancer, including cervical, colorectal, lung, breast, colon, pancreas, prostate, and many others. It has been shown to prevent or inhibit tumor growth, making it a promising candidate for cancer treatment and prevention.
Used in Anti-Inflammatory Applications:
As an anti-inflammatory drug, sodium O-acetylsalicylate is widely used to treat conditions characterized by inflammation, such as arthritis, tendinitis, and other musculoskeletal disorders. Its ability to reduce inflammation and pain makes it a popular choice for managing these conditions.

InChI:InChI=1/C9H8O4.Na/c1-6(10)13-8-5-3-2-4-7(8)9(11)12;/h2-5H,1H3,(H,11,12);/q;+1/p-1

Synthetic route

aspirin (50-78-2) → sodium O-acetylsalicylate (493-53-8)

Conditions	Yield
With sodium hydrogencarbonate In water; isopropyl alcohol at 20℃; for 3h;	88%
With sodium hydride In N,N-dimethyl-formamide for 0.5h;
With sodium carbonate

aspirin (50-78-2) + sodium bi carbonate → sodium O-acetylsalicylate (493-53-8)

Conditions	Yield
With water

aspirin (50-78-2) + sodium carbonate → sodium O-acetylsalicylate (493-53-8)

Conditions	Yield
With acetic acid ester
With methanol
With methanol
With acetic acid ester

acetylsalicylic acid sodium salt + CuCl2 dihydrate + aspirin (50-78-2) → sodium O-acetylsalicylate (493-53-8)

Conditions	Yield
With sodium hydroxide In water
With sodium hydroxide In water

Ti(4+)*2OH(1-)*SO4(2-)=Ti(OH)2SO4 + sodium O-acetylsalicylate (493-53-8) → (OH)2Ti(IV)(acetylsalicylate)2 (294868-46-5)

Conditions	Yield
	92%

sodium acetate (127-09-3) + sodium O-acetylsalicylate (493-53-8) → 2-dipropylaminoethyl acetylsalicylate acetate

Conditions	Yield
Stage #1: 3-diethylamino-propyl bromide hydrobromide; sodium O-acetylsalicylate In chloroform for 0.5h; Stage #2: sodium acetate In chloroform for 2h; Product distribution / selectivity;	81.6%

sodium acetate (127-09-3) + 2-dipropylaminoethyl bromide hydrobromide (22511-39-3) + sodium O-acetylsalicylate (493-53-8) → 2-dipropylaminoethyl acetylsalicylate acetate

Conditions	Yield
Stage #1: 2-dipropylaminoethyl bromide hydrobromide; sodium O-acetylsalicylate In chloroform at 20℃; for 5h; Stage #2: sodium acetate In chloroform for 2h;	81.6%
Stage #1: 2-dipropylaminoethyl bromide hydrobromide; sodium O-acetylsalicylate In chloroform at 20℃; for 5h; Stage #2: sodium acetate In chloroform for 2h;	81.6%
Stage #1: 2-dipropylaminoethyl bromide hydrobromide; sodium O-acetylsalicylate In chloroform at 20℃; for 5h; Stage #2: sodium acetate In chloroform at 20℃; for 2h;

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + sodium O-acetylsalicylate (493-53-8) → [RuCl(κ2O-aspCO2)(η6-p-cymene)]

Conditions	Yield
In methanol at 20℃; for 2.5h; Schlenk technique; Inert atmosphere;	79%

bis(cyclopentadienyl)titanium dichloride (1271-19-8) + sodium O-acetylsalicylate (493-53-8) → (η(5)-cyclopentadienyl)2Ti(IV)(acetylsalicylate)2

Conditions	Yield
In benzene Na salt and Ti complex refluxed in benzene for 15 h; cooled to room temp., filtered, filtrate concd. in vac., petroleum ether added, placed in refrigerator overnight, filtered, dried in vac. desiccator over P4O10 for 30 h, elem. anal.;	78%
In benzene a mixt. of (η-C5H5)2TiCl2 and Na salt of the substituted benzoic acid in anhydrous benzene stirred at 30°C for 4 h; orange soln. filtered, concd., crystn. (refrigerator), recrystd. (benzene);	7%
In not given

dibutyltin chloride (683-18-1) + sodium O-acetylsalicylate (493-53-8) → nBu2Sn(acetylsalicylic acid(-H))2

Conditions	Yield
In ethanol Reflux;	74%

zinc perchlorate + sodium O-acetylsalicylate (493-53-8) + tris(N-benzyl-benzimidazol-2-ylmethyl)amine → [(N(CH2(C7H4N2(CH2C6H5)))3)ZnOCO(C6H4(OCOCH3))](1+)*ClO4(1-) = [(N(CH2(C7H4N2(CH2C6H5)))3)ZnOCO(C6H4(OCOCH3))](ClO4) (159665-24-4)

Conditions	Yield
In ethanol soln. of Na-salt and Zn(ClO4)2*6H2O added under stirring to a soln. of the amine; stirred for 4 days; concd. in vacuo, stored for 5 days at -25°C, ppt. washed (cold MeOH), dried in vacuo; elem. anal.;	72%

zinc perchlorate + sodium O-acetylsalicylate (493-53-8) + tris(N-methylbenzimidazol-2-ylmethyl)amine (82137-72-2) → [(N(CH2(C7H4N2(CH3)))3)ZnOCO(C6H4(OCOCH3))](1+)*ClO4(1-) = [(N(CH2(C7H4N2(CH3)))3)ZnOCO(C6H4(OCOCH3))](ClO4) (159694-94-7)

Conditions	Yield
In ethanol soln. of Na-salt and Zn(ClO4)2*6H2O added under stirring to a soln. of the amine; stirred for 4 days; concd. in vacuo, stored for 5 days at -25°C, ppt. washed (cold MeOH), dried in vacuo; elem. anal.;	51%

sodium O-acetylsalicylate (493-53-8) + O2-(chloromethyl)-1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (340728-86-1, 960231-74-7) → C14H17N3O6

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide at 25℃; for 24h;	46%

O2-(chloromethyl)-1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate (858135-02-1) + sodium O-acetylsalicylate (493-53-8) → C12H15N3O6

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide at 25℃; for 24h;	40%

zinc perchlorate + sodium O-acetylsalicylate (493-53-8) + N,N',N''-tris(2-benzimidazolylmethyl)amine (64019-57-4) → [(N(CH2(C7H5N2))3)ZnOCO(C6H4(OCOCH3))](1+)*ClO4(1-) = [(N(CH2(C7H5N2))3)ZnOCO(C6H4(OCOCH3))](ClO4) (159665-20-0)

Conditions	Yield
In ethanol soln. of Na-salt and Zn(ClO4)2*6H2O added under stirring to a soln. of the amine; stirred for 4 days; concd. in vacuo, stored for 5 days at -25°C, ppt. washed (cold MeOH), dried in vacuo; elem. anal.;	11%

2-chloroacetyl-10-phenoxyacetyl-10H-phenothiazine (58754-72-6) + sodium O-acetylsalicylate (493-53-8) → 2-acetoxy-benzoic acid 2-oxo-2-(10-phenoxyacetyl-10H-phenothiazin-2-yl)-ethyl ester (58754-58-8)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 1.5h;

10-chloroacetylphenothiazine (786-50-5) + sodium O-acetylsalicylate (493-53-8) → 2-acetoxy-benzoic acid 2-oxo-2-phenothiazin-10-yl-ethyl ester (58754-68-0)

Conditions	Yield
In N,N-dimethyl-formamide at 130℃; for 3h;

2-chloroacetylphenothiazine (5325-15-5) + sodium O-acetylsalicylate (493-53-8) → 2-acetoxy-benzoic acid 2-oxo-2-(10H-phenothiazin-2-yl)-ethyl ester (58754-59-9)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 1h;

sodium O-acetylsalicylate (493-53-8) + ethyl bromoacetate (105-36-2) → Acetylsalicyloylglykolsaeureethylester (50785-24-5)

Conditions	Yield
In water; acetone at 30 - 40℃; Rate constant;

sodium O-acetylsalicylate (493-53-8) → O-acetylsalicyloyl chloride (5538-51-2)

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 2.33333h;

sodium O-acetylsalicylate (493-53-8) → salicylic acid-(2-nitro-anilide) (37183-26-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 2.33 h / 0 - 20 °C 2: 84 percent / benzene / 16 h / Heating View Scheme

sodium O-acetylsalicylate (493-53-8) → N-(4-Chloro-2-nitro-phenyl)-2-hydroxy-benzamide (37399-40-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 2.33 h / 0 - 20 °C 2: 88 percent / benzene / 16 h / Heating View Scheme

sodium O-acetylsalicylate (493-53-8) → (1H-benzo[d][1,2,3]triazol-1-yl)(2-hydroxyphenyl)methanone (347370-91-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2 / 2.33 h / 0 - 20 °C 2: 84 percent / benzene / 16 h / Heating 3: 89 percent / H2 / Pd/C / acetic acid / 20 °C 4: 52 percent / aq. AcOH; NaNO2 / 2 h View Scheme

sodium O-acetylsalicylate (493-53-8) → (2-hydroxy-phenyl)-(5-methyl-benzotriazol-1-yl)-methanone

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2 / 2.33 h / 0 - 20 °C 2: 79 percent / benzene / 16 h / Heating 3: 96 percent / H2 / Pd/C / methanol / 20 °C 4: 96 percent / aq. AcOH; NaNO2 / 2 h View Scheme

sodium O-acetylsalicylate (493-53-8) → N-(4-chloro-2-aminophenyl)salicylamine (403599-67-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / 2.33 h / 0 - 20 °C 2: 88 percent / benzene / 16 h / Heating 3: 77 percent / H2 / Raney Ni / methanol / 20 °C View Scheme

sodium O-acetylsalicylate (493-53-8) → N-(4-methyl-2-aminophenyl)salicylamide (403599-66-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 / 2.33 h / 0 - 20 °C 2: 79 percent / benzene / 16 h / Heating 3: 96 percent / H2 / Pd/C / methanol / 20 °C View Scheme

sodium O-acetylsalicylate (493-53-8) → 2-hydroxy-N-(4-methyl-2-nitro-phenyl)-benzamide (403599-64-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 2.33 h / 0 - 20 °C 2: 79 percent / benzene / 16 h / Heating View Scheme

sodium O-acetylsalicylate (493-53-8) → (5-chloro-benzotriazol-1-yl)-(2-hydroxy-phenyl)-methanone

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2 / 2.33 h / 0 - 20 °C 2: 88 percent / benzene / 16 h / Heating 3: 77 percent / H2 / Raney Ni / methanol / 20 °C 4: 92 percent / aq. AcOH; NaNO2 / 2 h View Scheme

Upstream product

• 50-78-2 aspirin 

Downstream Products

• 5538-51-2 O-acetylsalicyloyl chloride 
• 58754-68-0 2-acetoxy-benzoic acid 2-oxo-2-phenothiazin-10-yl-ethyl ester 
• 58754-58-8 2-acetoxy-benzoic acid 2-oxo-2-(10-phenoxyacetyl-10H-phenothiazin-2-yl)-ethyl ester 
• 294868-46-5 (OH)2Ti(IV)(acetylsalicylate)2 
• 159694-94-7 [(N(CH₂(C₇H₄N₂(CH₃)))3)ZnOCO(C₆H₄(OCOCH₃))]⁽¹⁺⁾*ClO₄^(1-) = [(N(CH₂(C₇H₄N₂(CH₃)))3)ZnOCO(C₆H₄(OCOCH₃))](ClO₄) 
• 159665-24-4 [(N(CH₂(C₇H₄N₂(CH₂C₆H₅)))3)ZnOCO(C₆H₄(OCOCH₃))]⁽¹⁺⁾*ClO₄^(1-) = [(N(CH₂(C₇H₄N₂(CH₂C₆H₅)))3)ZnOCO(C₆H₄(OCOCH₃))](ClO₄) 
• 677324-58-2 C₃₉H₅₈O₆ 
• 677324-59-3 C₄₀H₆₀O₆ 
• 19283-97-7 1,3-propanediol bis-acetylsalicylate 
• 3679-66-1 N-(2-aminophenyl)salicylamide 
• 218930-32-6 2-hydroxy-N-(2-nitro-4-trifluoromethyl-phenyl)-benzamide 
• 403599-65-5 2-hydroxy-N-(3-nitro-biphenyl-4-yl)-benzamide 
• 403599-70-2 N-(2-aminobiphenyl)salicylamide 
• 403599-69-9 N-(4-trifluoromethyl-2-aminophenyl)salicylamide 

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