• Name

  METHYL 5-ACETYLSALICYLATE

• EINECS 240-532-2
• CAS No. 16475-90-4
• Article Data18
• CAS DataBase
• Density 1.234 g/cm³
• Solubility
• Melting Point 62-64 °C(lit.)
• Formula C₁₀H₁₀O₄
• Boiling Point 345.4 °C at 760 mmHg
• Molecular Weight 194.187
• Flash Point 138 °C
• Transport Information
• Appearance white to light yellow-orange crystalline powder
• Safety 26-36
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Xi
• Synonyms 5-Acetyl-2-hydroxybenzoic acidmethyl ester;Salicylicacid, 5-acetyl-, methyl ester (6CI,7CI,8CI);Methyl 3-acetyl-6-hydroxybenzoate;Methyl5-acetyl-2-hydroxybenzoate;NSC 67867;Methyl2-hydroxy-5-acetylbenzoate;5-Acetylsalicylic acid methyl ester;
• PSA 63.60000
• LogP 1.38140

Synthetic route

67-56-1

methanol

13110-96-8

5-acetylsalicylic acid

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With sulfuric acid for 24h; Heating;	96%
With thionyl chloride at 65℃; for 24h; Inert atmosphere;

2-acetoxy-5-acetyl-benzoic acid methyl ester

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With ytterbium(III) triflate In isopropyl alcohol for 20h; Deacetylation; Heating;	95%

108-24-7

acetic anhydride

119-36-8

methyl salicylate

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane for 3h; Friedel-Crafts reaction;	93%
With aluminum (III) chloride In dichloromethane at -5 - 10℃; for 20h; Inert atmosphere;	83.3%
With aluminum (III) chloride In nitrobenzene at 120 - 180℃; for 0.133333h; Temperature; Time; Pressure; Friedel-Crafts Acylation; Microwave irradiation;	100 %Chromat.

5-acetyl-2-(3-methyl-but-2-enyloxy)-benzoic acid methyl ester

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With ytterbium(III) triflate In nitromethane for 1h; Ambient temperature;	74%

72554-64-4

3-acetyl-3',3'-dicyano-5-methoxycarbonylxanthyrone

A

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

B

99-93-4

4-Hydroxyacetophenone

Conditions

Conditions	Yield
With water for 3h; Product distribution; Heating; other xanthyrones;	A 41% B 16%

72554-63-3

3-acetyl-3'-cyano-3',5-bismethoxycarbonylxanthyrone

A

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

B

99-93-4

4-Hydroxyacetophenone

Conditions

Conditions	Yield
With water for 3h; Product distribution; Heating; other xanthyrones;	A 41% B 16%

64-19-7

acetic acid

119-36-8

methyl salicylate

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With PPA at 80℃; for 2h;	20%

580-02-9

methyl acetylsalicylate

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With aluminium trichloride; nitrobenzene

606-45-1

2-methoxybenzoic acid methyl ester

75-36-5

acetyl chloride

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With carbon disulfide; aluminium trichloride

74823-33-9, 78075-03-3

3'-acetyl-3,5,5'-trismethoxycarbonylglaucyrone

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With water for 3h; Product distribution; Heating; other glaucyrones;

75-36-5

acetyl chloride

119-36-8

methyl salicylate

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With aluminium trichloride In 1,1,2,2-tetrachloroethylene
In 1,1,2,2-tetrachloroethylene

36256-45-8

3-carbomethoxy-4-hydroxy-α-bromoacetophenone

A

2-Hydroxy-5-((R)-1-hydroxy-ethyl)-benzoic acid methyl ester

B

methyl 5-(2-bromo-1-hydroxyethyl)-2-hydroxybenzoate

C

(R)-methyl 5-(2-bromo-1-hydroxyethyl)-2-hydroxybenzoate

D

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
With sodium formate; cetyltrimethylammonim bromide; sodium dodecyl-sulfate; (R,R)-TsDPEN; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 28℃; for 5h; Title compound not separated from byproducts;

...Expand

50-78-2

aspirin

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / AlCl3 / nitrobenzene / 1 h 2: 96 percent / H2SO4 / 24 h / Heating View Scheme

127-18-4

1,1,2,2-tetrachloroethylene

75-36-5

acetyl chloride

119-36-8

methyl salicylate

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions

Conditions	Yield
aluminium chloride	40 g (43%)

...Expand

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

100-39-0

benzyl bromide

27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 85℃; for 9h;	100%
With potassium carbonate In acetonitrile at 75℃; for 16h;	100%
With potassium carbonate In acetonitrile for 24h;	96.6%

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

107-21-1

ethylene glycol

467429-12-5

2-[4-hydroxy-3-(methoxycarbonyl)phenyl]-2-methyl-1,3-dioxolane

Conditions

Conditions	Yield
With Triisopropoxymethan; cerium triflate In hexane at 25℃; for 2h;	99%
With toluene-4-sulfonic acid In toluene for 16h; Heating;	91%

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

66654-06-6

1-(4'-hydroxy-3'-methoxycarbonylphenyl)ethanol

Conditions

Conditions	Yield
With CdS(x)Se(1-x) x:0-1;; cesium acetate; para-thiocresol In toluene for 10h; Sealed tube; Inert atmosphere; Irradiation;	99%
With sodium tetrahydroborate; boric acid for 1.5h;	60 % Chromat.

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

100-44-7

benzyl chloride

27475-09-8

5-acetyl-2-benzyloxybenzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 50 - 65℃; for 2h;	98.5%
With sodium carbonate In N,N-dimethyl-formamide at 110 - 115℃; for 2h;	84.7%
With sodium In ethanol for 30h; Heating;	55%
With sodium carbonate; sodium iodide In acetonitrile for 16h; Heating / reflux;	55%
With potassium carbonate

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

504-63-2

trimethyleneglycol

1171247-80-5

2-[4-hydroxy-3-(methoxycarbonyl)phenyl]-2-methyl-1,3-dioxane

Conditions

Conditions	Yield
With Triisopropoxymethan; cerium triflate In hexane at 25℃; for 2h;	98%

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

heptyl halide

heptyl halide

1373427-92-9

methyl 5-acetyl-2-heptyloxybenzoate

Conditions

Conditions	Yield
Stage #1: estere metilico dell'acido 5-acetilsalicilico With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: heptyl halide In N,N-dimethyl-formamide at 50℃; for 5h;	97.6%

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

methyl halide

methyl halide

39971-36-3

5-acetyl-2-methoxybenzoic acid methyl ester

Conditions

Conditions	Yield
Stage #1: estere metilico dell'acido 5-acetilsalicilico With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: methyl halide In N,N-dimethyl-formamide at 50℃; for 5h;	97%

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

74-88-4

methyl iodide

39971-36-3

5-acetyl-2-methoxybenzoic acid methyl ester

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide	96.5%
With sodium carbonate In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 3h;	96.5%
With sodium carbonate In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 3h;	96.5%

358-23-6

trifluoromethylsulfonic anhydride

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

343338-97-6

5-acetyl-2-(trifluoro-methyl-sulfonyloxy)-benzoic acid,methyl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 0.5h;	96%
With pyridine In dichloromethane at 0℃; for 0.833333h;	96%
With triethylamine at -40℃;
With 2,6-dimethylpyridine; dmap In dichloromethane at -30 - 20℃; for 3h;

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

hexyl halide

hexyl halide

1373427-91-8

methyl 5-acetyl-2-hexyloxybenzoate

Conditions

Conditions	Yield
Stage #1: estere metilico dell'acido 5-acetilsalicilico With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: hexyl halide In N,N-dimethyl-formamide at 50℃; for 5h;	95.9%

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

octyl halide

octyl halide

1373427-93-0

methyl 5-acetyl-2-octyloxybenzoate

Conditions

Conditions	Yield
Stage #1: estere metilico dell'acido 5-acetilsalicilico With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: octyl halide In N,N-dimethyl-formamide at 50℃; for 5h;	93.5%

16475-90-4

estere metilico dell'acido 5-acetilsalicilico

butyl halide

butyl halide

methyl 5-acetyl-2-butoxybenzoate

Conditions

Conditions	Yield
Stage #1: estere metilico dell'acido 5-acetilsalicilico With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: butyl halide In N,N-dimethyl-formamide at 50℃; for 5h;	92%

Methyl 5-acetylsalicylate Chemical Properties

Methyl 5-acetylsalicylate Uses

Methyl 5-acetylsalicylate Safety Profile