5-Acetylsalicylamide supplier

Name
5-Acetylsalicylamide
EINECS 254-830-5
CAS No. 40187-51-7
Article Data6
CAS DataBase
Density 1.297 g/cm³
Solubility
Melting Point 220-222 °C(lit.)
Formula C₉H₉NO₃
Boiling Point 376.3 °C at 760 mmHg
Molecular Weight 179.175
Flash Point 181.4 °C
Transport Information
Appearance cream to beige powder
Safety 26-36-37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms 5-Acetyl-2-hydroxy-benzamide;Benzamide, 5-acetyl-2-hydroxy-;
PSA 80.39000
LogP 1.39400

Synthetic route

: 75-36-5
acetyl chloride

: 65-45-2
salicylamide

: 40187-51-7
5-acetylsalicylamide

Conditions

Conditions	Yield
With aluminum (III) chloride In nitromethane; dichloromethane at 0 - 20℃; Friedel-Crafts Acylation;	95%
With aluminum (III) chloride; sodium chloride at 140℃; for 0.666667h; Temperature; Reagent/catalyst;	92.2%
Stage #1: salicylamide With aluminum (III) chloride; sodium chloride In water at 180℃; for 3h; Stage #2: acetyl chloride In water at 180℃; for 4h;	88.5%
With aluminium trichloride

: 5663-71-8
O-acetylsalicylamide

: 40187-51-7
5-acetylsalicylamide

Conditions

Conditions	Yield
With aluminium trichloride

: (3-Carbamoyl-4-hydroxy-benzyl)-carbamic acid tert-butyl ester

: 40187-51-7
5-acetylsalicylamide

: 40187-51-7
5-acetylsalicylamide

: 2550-36-9
(bromomethylcyclohexane)

: 189393-76-8
5-acetyl-2-(cyclohexylmethoxy)benzamide

Conditions

Conditions	Yield
Stage #1: 5-acetylsalicylamide With caesium carbonate In methanol; water for 0.5h; Metallation; Stage #2: Cyclohexylmethyl bromide In N,N-dimethyl-formamide at 90℃; for 42h; Alkylation;	98%

: 40187-51-7
5-acetylsalicylamide

: 100-39-0
benzyl bromide

: 75637-30-8
5-acetyl-2-(phenylmethoxy)benzamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	98%
With potassium carbonate In acetonitrile Reflux;	98%
With sodium methylate In methanol	80%

: 40187-51-7
5-acetylsalicylamide

: 54209-84-6
5-acetylbenzo[d]oxazol-2(3H)-one

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; potassium hydroxide In methanol at 0℃; for 1.08333h; Hofmann Rearrangement;	89%

: 40187-51-7
5-acetylsalicylamide

: 459-57-4
4-fluorobenzaldehyde

: (E)-5-(3-(4-fluorophenyl)acryloyl)-2-hydroxybenzamide

Conditions

Conditions	Yield
With thionyl chloride In ethanol at 25℃; for 14h;	83%
With thionyl chloride In ethanol at 25℃; for 24h; Claisen-Schmidt Condensation;

: 40187-51-7
5-acetylsalicylamide

: 73866-23-6
5-(2-bromoacetyl)-2-hydroxybenzamide

Conditions

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;

: 40187-51-7
5-acetylsalicylamide

: 77-76-9
2,2-dimethoxy-propane

: 142167-24-6
6-Acetyl-2,2-dimethyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetone Heating;	36%

: 40187-51-7
5-acetylsalicylamide

: 106-93-4
ethylene dibromide

: C11H12BrNO3

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In ethyl acetate Reflux;	35%

: 40187-51-7
5-acetylsalicylamide

: 100-44-7
benzyl chloride

: 75637-30-8
5-acetyl-2-(phenylmethoxy)benzamide

Conditions

Conditions	Yield
With sodium methylate 1.) DMF, 2.) DMF, heating, 7 h; Yield given. Multistep reaction;

: 358-23-6
trifluoromethylsulfonic anhydride

: 40187-51-7
5-acetylsalicylamide

: trifluoro-methanesulfonic acid 4-acetyl-2-carbamoyl-phenyl ester

Conditions

Conditions	Yield
With triethylamine at -40℃;

: 40187-51-7
5-acetylsalicylamide

: 343339-00-4
4-(2-furyl)-3-(carboxamido)phenyl-1-ethanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / -40 °C 2: Pd(PPh3)4; LiCl / dioxane / 110 °C View Scheme

: 40187-51-7
5-acetylsalicylamide

: 343339-01-5
1-[4-(2-furyl)3-(carboxamido)phenyl]-4,4,4-trifluoro-1,3-butanedione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / -40 °C 2: Pd(PPh3)4; LiCl / dioxane / 110 °C 3: NaOMe / 1,2-dimethoxy-ethane / 20 °C View Scheme

: 40187-51-7
5-acetylsalicylamide

: 2-furan-2-yl-5-[2-(5-methanesulfonyl-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Et3N / -40 °C 2: Pd(PPh3)4; LiCl / dioxane / 110 °C 3: NaOMe / 1,2-dimethoxy-ethane / 20 °C 4: ethanol / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 2-furan-2-yl-5-[1-(5-methanesulfonyl-pyridin-2-yl)-5-trifluoromethyl-1H-pyrazol-3-yl]-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Et3N / -40 °C 2: Pd(PPh3)4; LiCl / dioxane / 110 °C 3: NaOMe / 1,2-dimethoxy-ethane / 20 °C 4: ethanol / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 2-hydroxy-5-(1,3-thiazol-5-yl)-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 36 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 799280-24-3
2-hydroxy-5-(2-methyl-thiazol-5-yl)-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 75 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 799280-23-2
5-(2-amino-thiazol-5-yl)-2-hydroxy-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 65 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 2-hydroxy-5-(2-isopropyl-1,3-thiazol-5-yl)-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 46 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 5-(2-methyl-thiazol-5-yl)-2-propoxy-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 75 percent / ethanol / 6 h / Heating 3: 90 percent / potassium carbonate / dimethylformamide / 60 °C View Scheme

: 40187-51-7
5-acetylsalicylamide

: 5-(2-amino-thiazol-5-yl)-2-propoxy-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 65 percent / ethanol / 6 h / Heating 3: 92 percent / potassium carbonate / dimethylformamide / 60 °C View Scheme

: 40187-51-7
5-acetylsalicylamide

: 2-butoxy-5-(2-methyl-thiazol-5-yl)-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 75 percent / ethanol / 6 h / Heating 3: 94 percent / potassium carbonate / dimethylformamide / 60 °C View Scheme

: 40187-51-7
5-acetylsalicylamide

: 2-hydroxy-5-[2-(pyridin-2-ylamino)-thiazol-5-yl]-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 57 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 799280-05-0
2-hydroxy-5-(2-phenylamino-thiazol-5-yl)-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 65 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 2-hydroxy-5-(2-o-tolylamino-thiazol-5-yl)-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 62 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 799280-07-2
2-hydroxy-5-(2-p-tolylamino-thiazol-5-yl)-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 61 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 799280-09-4
5-[2-(3-chloro-phenylamino)-thiazol-5-yl]-2-hydroxy-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 52 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 5-(2-phenylamino-thiazol-5-yl)-2-propoxy-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 65 percent / ethanol / 6 h / Heating 3: 95 percent / potassium carbonate / dimethylformamide / 60 °C View Scheme

: 40187-51-7
5-acetylsalicylamide

: 5-[2-(4-chloro-phenylamino)-thiazol-5-yl]-2-hydroxy-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 49 percent / ethanol / 6 h / Heating View Scheme

: 40187-51-7
5-acetylsalicylamide

: 2-hydroxy-5-[2-(6-methyl-pyridin-2-ylamino)-thiazol-5-yl]-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.4 percent / HBr; bromine / ethyl acetate / 18 h / 5 - 10 °C 2: 68 percent / ethanol / 6 h / Heating View Scheme

5-Acetylsalicylamide Specification

The CAS register number of 5-Acetylsalicylamide is 40187-51-7. The IUPAC name is 5-acetyl-2-hydroxybenzamide. In addition, the molecular formula is C₉H₉NO₃ and the molecular weight is 179.17. It also can be called as benzamide, 5-acetyl-2-hydroxy-. What's more, it belongs to the classes of Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts. Besides, it should be stored in sealed container, and put them in a cool and dry place.

Physical properties about 5-Acetylsalicylamide are: (1)ACD/LogP: 1.63; (2)ACD/LogD (pH 5.5): 1.58; (3)ACD/LogD (pH 7.4): 0.63; (4)ACD/BCF (pH 5.5): 9.15; (5)ACD/BCF (pH 7.4): 1.01; (6)ACD/KOC (pH 5.5): 164.52; (7)ACD/KOC (pH 7.4): 18.22; (8)#H bond acceptors: 4; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 46.61Å²; (12)Index of Refraction: 1.597; (13)Molar Refractivity: 47.09 cm³; (14)Molar Volume: 138 cm³; (15)Polarizability: 18.66x10^-24cm³; (16)Surface Tension: 58.4 dyne/cm; (18)Density: 1.297 g/cm³; (19)Flash Point: 181.4 °C; (19)Enthalpy of Vaporization: 64.84 kJ/mol; (20)Boiling Point: 376.3 °C at 760 mmHg; (21)Vapour Pressure: 3.38E-06 mmHg at 25°C.

Uses of 5-Acetylsalicylamide: this chemical can be used as pharmaceutical intermediates. In addition, it can be used to produce 6-acetyl-2,2-dimethyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one with 2,2-dimethoxy-propane. This reaction will need reagent p-TsOH*H₂O and solvent acetone. The yield is about 36% by heating.

5-Acetylsalicylamide can be used to produce 6-acetyl-2,2-dimethyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one with 2,2-dimethoxy-propane

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1cc(ccc1O)C(=O)C)N
(2)InChI: InChI=1/C9H9NO3/c1-5(11)6-2-3-8(12)7(4-6)9(10)13/h2-4,12H,1H3,(H2,10,13)
(3)InChIKey: LWAQTCWTCCNHJR-UHFFFAOYAA

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	1700mg/kg (1700mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR	Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 39, 1990.

Product Name

5-Acetylsalicylamide

Synthetic route

5-Acetylsalicylamide Specification

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