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13110-96-8

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13110-96-8 Usage

Preparation

Obtained by Fries rearrangement of 2-(acetyloxy)-benzoic acid (Aspirin) (1 mol) in the presence of aluminium chloride (3.3 mol), ? in nitrobenzene at r.t. for 1 h (36%) ; ? without solvent at 120–125° for 1 h (19%).

Synthesis Reference(s)

Journal of Medicinal Chemistry, 23, p. 738, 1980 DOI: 10.1021/jm00181a008

Check Digit Verification of cas no

The CAS Registry Mumber 13110-96-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,1,1 and 0 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 13110-96:
(7*1)+(6*3)+(5*1)+(4*1)+(3*0)+(2*9)+(1*6)=58
58 % 10 = 8
So 13110-96-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O4/c1-5(10)6-2-3-8(11)7(4-6)9(12)13/h2-4,11H,1H3,(H,12,13)/p-1

13110-96-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A11663)  5-Acetylsalicylic acid, 98+%   

  • 13110-96-8

  • 5g

  • 640.0CNY

  • Detail
  • Alfa Aesar

  • (A11663)  5-Acetylsalicylic acid, 98+%   

  • 13110-96-8

  • 25g

  • 2765.0CNY

  • Detail
  • Alfa Aesar

  • (A11663)  5-Acetylsalicylic acid, 98+%   

  • 13110-96-8

  • 100g

  • 8815.0CNY

  • Detail

13110-96-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Acetylsalicylic Acid

1.2 Other means of identification

Product number -
Other names 5-ACETYLSALICYLIC ACID

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13110-96-8 SDS

13110-96-8Synthetic route

3-acetylbenzoic acid
586-42-5

3-acetylbenzoic acid

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

Conditions
ConditionsYield
With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; under 3800.26 Torr; for 15h;85%
With oxygen; potassium acetate; p-benzoquinone; palladium diacetate In ISOPROPYLAMIDE at 115℃; under 3800.26 Torr; for 15h; Product distribution / selectivity;85%
aspirin
50-78-2

aspirin

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

Conditions
ConditionsYield
With aluminium trichloride In nitrobenzene for 1h;82%
With aluminum (III) chloride In neat (no solvent) at 120℃; for 0.333333h;78%
With aluminium trichloride; nitrobenzene at 60℃;
With aluminium trichloride; nitrobenzene
phenyl 2-acetoxybenzoate
134-55-4

phenyl 2-acetoxybenzoate

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

Conditions
ConditionsYield
With carbon disulfide; aluminium trichloride
estere metilico dell'acido 5-acetilsalicilico
16475-90-4

estere metilico dell'acido 5-acetilsalicilico

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

acetyl chloride
75-36-5

acetyl chloride

salicylic acid
69-72-7

salicylic acid

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

Conditions
ConditionsYield
With aluminium trichloride; nitrobenzene
With iron(III) chloride
iron(III) chloride
7705-08-0

iron(III) chloride

acetyl chloride
75-36-5

acetyl chloride

salicylic acid
69-72-7

salicylic acid

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

Conditions
ConditionsYield
at 110 - 115℃;
aluminium trichloride
7446-70-0

aluminium trichloride

nitrobenzene
98-95-3

nitrobenzene

aspirin
50-78-2

aspirin

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

Conditions
ConditionsYield
at 60℃;
carbon disulfide
75-15-0

carbon disulfide

aluminium trichloride
7446-70-0

aluminium trichloride

methyl acetylsalicylate
580-02-9

methyl acetylsalicylate

A

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

B

salicylic acid
69-72-7

salicylic acid

Conditions
ConditionsYield
anschliessendes Behandeln mit kaltem Wasser;
carbon disulfide
75-15-0

carbon disulfide

phenyl 2-acetoxybenzoate
134-55-4

phenyl 2-acetoxybenzoate

2 mol aluminium chloride

2 mol aluminium chloride

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

Conditions
ConditionsYield
anschliessend Behandeln mit kaltem Wasser;
carbon disulfide
75-15-0

carbon disulfide

aluminium trichloride
7446-70-0

aluminium trichloride

phenyl 2-acetoxybenzoate
134-55-4

phenyl 2-acetoxybenzoate

benzene
71-43-2

benzene

A

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

B

acetic acid
64-19-7

acetic acid

C

acetophenone
98-86-2

acetophenone

D

salicylic acid
69-72-7

salicylic acid

Conditions
ConditionsYield
anschliessend Behandeln mit kaltem Wasser;
aluminium trichloride
7446-70-0

aluminium trichloride

phenyl 2-acetoxybenzoate
134-55-4

phenyl 2-acetoxybenzoate

nitrobenzene
98-95-3

nitrobenzene

A

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

B

acetic acid
64-19-7

acetic acid

C

salicylic acid
69-72-7

salicylic acid

D

phenol
108-95-2

phenol

Conditions
ConditionsYield
anschliessend Behandeln mit kaltem Wasser;
methyl acetylsalicylate
580-02-9

methyl acetylsalicylate

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3; nitrobenzene
View Scheme
salicylic acid
69-72-7

salicylic acid

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: aluminum (III) chloride / neat (no solvent) / 0.33 h / 120 °C
View Scheme
methanol
67-56-1

methanol

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

estere metilico dell'acido 5-acetilsalicilico
16475-90-4

estere metilico dell'acido 5-acetilsalicilico

Conditions
ConditionsYield
With sulfuric acid for 24h; Heating;96%
With thionyl chloride at 65℃; for 24h; Inert atmosphere;
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

5-(3-(3-hydroxyphenyl)acryloyl)-2-hydroxybenzoic acid

5-(3-(3-hydroxyphenyl)acryloyl)-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Cooling;92%
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

2,4,6-trihydroxybenzaldehyde
487-70-7

2,4,6-trihydroxybenzaldehyde

C16H12O7

C16H12O7

Conditions
ConditionsYield
With sodium hydroxide In water Inert atmosphere; Reflux;87.8%
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

benzaldehyde
100-52-7

benzaldehyde

5-(3-phenylacryloyl)-2-hydroxybenzoic acid
33494-94-9

5-(3-phenylacryloyl)-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Cooling;86%
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

5-(3-(4-chlorophenyl)acryloyl)-2-hydroxybenzoic acid
33494-95-0

5-(3-(4-chlorophenyl)acryloyl)-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Cooling;86%
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

triphenylantimony dichloride
594-31-0, 34716-91-1, 20265-29-6

triphenylantimony dichloride

bis-(5-acetylsalicylato)triphenylantimony(V)

bis-(5-acetylsalicylato)triphenylantimony(V)

Conditions
ConditionsYield
Stage #1: 5-acetylsalicylic acid With sodium methylate In methanol at 20℃; for 1 - 2h; Inert atmosphere;
Stage #2: triphenylantimony dichloride In methanol at 20℃; for 24h; Inert atmosphere;
78%
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

5-(3-(4-bromophenyl)acryloyl)-2-hydroxybenzoic acid

5-(3-(4-bromophenyl)acryloyl)-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Cooling;74%
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

5-(3-(4-methoxyphenyl)acryloyl)-2-hydroxybenzoic acid
33494-96-1

5-(3-(4-methoxyphenyl)acryloyl)-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Cooling;73%
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

acetone
67-64-1

acetone

6-acetyl-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

6-acetyl-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Conditions
ConditionsYield
With trifluoroacetic acid; trifluoroacetic anhydride at 100℃; for 23h; Inert atmosphere; Cooling with ice;71%
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

5-bromoacetyl-2-hydroxy-benzoic acid
62423-71-6

5-bromoacetyl-2-hydroxy-benzoic acid

Conditions
ConditionsYield
With 1,4-dioxane dibromide In 1,4-dioxane; diethyl ether for 2h; Ambient temperature;69%
With copper(ll) bromide In ethyl acetate for 2.5h; Heating;
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

5-(3-(4-hydroxyphenyl)acryloyl)-2-hydroxybenzoic acid

5-(3-(4-hydroxyphenyl)acryloyl)-2-hydroxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Cooling;60%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

C16H12F3NO3

C16H12F3NO3

Conditions
ConditionsYield
With phosphorus trichloride In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 3h;41.2%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
5-methyl-indole-2,3-dione
608-05-9

5-methyl-indole-2,3-dione

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

2-(3-carboxy-4-hydroxy-phenyl)-6-methyl-quinoline-4-carboxylic acid

2-(3-carboxy-4-hydroxy-phenyl)-6-methyl-quinoline-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide
ethanol
64-17-5

ethanol

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

5-acetyl-2-hydroxybenzoic acid ethyl ester
16475-93-7

5-acetyl-2-hydroxybenzoic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

5-ethyl-2-hydroxy-benzoic acid
51-27-4

5-ethyl-2-hydroxy-benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

2-hydroxy-5-(1-hydroxyimino-ethyl)-benzoic acid

2-hydroxy-5-(1-hydroxyimino-ethyl)-benzoic acid

Conditions
ConditionsYield
With ethanol; hydroxylamine
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

2-hydroxy-5-(1-semicarbazono-ethyl)-benzoic acid
16475-98-2

2-hydroxy-5-(1-semicarbazono-ethyl)-benzoic acid

5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

Conditions
ConditionsYield
With calcium oxide bei der Destillation;
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

indole-2,3-dione
91-56-5

indole-2,3-dione

aristolochic acid
525-48-4

aristolochic acid

Conditions
ConditionsYield
With water; potassium carbonate
With calcium hydroxide; water
With potassium hydroxide
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

6-bromo-2-(3-carboxy-4-hydroxy-phenyl)-quinoline-4-carboxylic acid

6-bromo-2-(3-carboxy-4-hydroxy-phenyl)-quinoline-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

benzaldehyde
100-52-7

benzaldehyde

5-trans-cinnamoyl-2-hydroxy-benzoic acid
33494-94-9

5-trans-cinnamoyl-2-hydroxy-benzoic acid

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

salicylaldehyde
90-02-8

salicylaldehyde

2-hydroxy-5-(2-hydroxy-trans-cinnamoyl)-benzoic acid

2-hydroxy-5-(2-hydroxy-trans-cinnamoyl)-benzoic acid

Conditions
ConditionsYield
With potassium hydroxide
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

chloroacetic acid
79-11-8

chloroacetic acid

5-acetyl-2-carboxymethoxy-benzoic acid

5-acetyl-2-carboxymethoxy-benzoic acid

Conditions
ConditionsYield
With potassium hydroxide
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

phenylhydrazine
100-63-0

phenylhydrazine

2-hydroxy-5-(1-phenylhydrazono-ethyl)-benzoic acid
93733-65-4

2-hydroxy-5-(1-phenylhydrazono-ethyl)-benzoic acid

Conditions
ConditionsYield
With ethanol
5-acetylsalicylic acid
13110-96-8

5-acetylsalicylic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

3-carboxy-4-methoxy-acetophenone
68535-61-5

3-carboxy-4-methoxy-acetophenone

Conditions
ConditionsYield
With sodium hydroxide

13110-96-8Relevant articles and documents

Synthesis and biological evaluation of salicylic acid conjugated isoxazoline analogues on immune cell proliferation and angiogenesis

Puttaswamy, Naveen,Pavan Kumar,Al-Ghorbani, Mohammed,Vigneshwaran,Prabhakar,Khanum, Shaukath Ara

, p. 153 - 161 (2016/05/02)

Mitogenicity is the ability of the natural or synthetic compounds to induce cell division or proliferation. A series of salicylic acid derivatives containing isoxazoline moiety (8a-j) were synthesized and their immunopharmacological activities targeting lymphocyte proliferation and angiogenesis were evaluated. The compounds 8a-j mitogenicity were investigated on immunological cells that include human peripheral blood lymphocytes and murine splenocytes in-vitro. The results implicate that among the series of 8a-j, compound 8e showed a potent proliferative response on both human and murine lymphocytes. The proliferative index of the compound 8e was comparable to the reference mitogen Con A and mitogenecity is due to increased secretion IL-2. In-vivo CAM and rat corneal angiogenesis assays were performed to assess the compound's effect on endothelial cell migration and proliferation which inferred that 8e also induces the proliferation of endothelial cells. The study reports the synthetic immunostimulatory and pro-angiogenic activity of novel mitogen 8e which could be translated into new drug in future.

Pd(II)-catalyzed hydroxylation of arenes with 1 atm of O2 or air

Zhang, Yang-Hui,Yu, Jin-Quan

supporting information; experimental part, p. 14654 - 14655 (2010/01/06)

(Chemical Equation Presented) Pd(II)-catalyzed ortho-hydroxylation of variously substituted benzoic acids under 1 atm of O2 or air is achieved under nonacidic conditions. Extensive labeling studies support a direct oxygenation of aryl C-H bonds with molecular oxygen.

Synthesis and Structure-Activity Relationships among α-Adrenergic Receptor Agonists of the Phenylethanolamine Type

Leclerc, Gerard,Bizec, Jean Claude,Bieth, Nicole,Schwartz, Jean

, p. 738 - 744 (2007/10/02)

Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for α-adrenergic stimulant activity.In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, cyclohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups.The other series is meta hydroxylated with the para position substituted by the same groups.The influence of these groups upon the α-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine,norepinephrine, and norphenylephrine.It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental.The most active compound, α-(aminomethyl)-(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundreth the affinity and the same intrinsic activity as norepinephrine.

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