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556-08-1 Usage

Chemical Properties

white or off-white powder or crystals

Originator

4-Acetamidobenzoic acid ,ARIAC

Uses

Different sources of media describe the Uses of 556-08-1 differently. You can refer to the following data:
1. immune stimulant (component)
2. Acedoben is the acetylated derivative of p-aminobenzoic acid (PABA). Acedoben is a metabolite of the anesthetic Benzocaine (B202970).

Definition

ChEBI: A amidobenzoic acid that consists of benzoic acid bearing an acetamido substituent at position 4.

Manufacturing Process

Into a 2 L, 3-necked flask set in a tub and equipped with a stirrer, an air condenser (drying tube), thermometer, was placed 860 ml of water, 43.0 g of MgSO4 and 43.0 g of sodium acetate and heated on water bath. Into heated solution to 70°C stirring 43.0 g of N-p-tolylacetamide were added. Then 136.0 g of KMnO4 by small portions were added at 75°-80°C. The reaction mixture allow to stand for 6 h and stirring was continue till the solution became colorless. Hot solution was filtered and filtrate treated hydrochloric acid to slightly acidic pH. After that 44.0 g (85%) of p-acetoaminobenzoic acid was obtained as white precipitate, melting point 250°C.

Therapeutic Function

Antiviral

General Description

Needles or off-white powder.

Air & Water Reactions

Water insoluble.

Reactivity Profile

Simultaneously an amide and a carboxylic acid.

Fire Hazard

Flash point data for p-Acetylamino benzoic acid are not available; however, p-Acetylamino benzoic acid is probably combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 556-08-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 6 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 556-08:
(5*5)+(4*5)+(3*6)+(2*0)+(1*8)=71
71 % 10 = 1
So 556-08-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO3/c1-6(11)10-8-4-2-7(3-5-8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)/p-1

556-08-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (A12711)  4-Acetamidobenzoic acid, 98%   

  • 556-08-1

  • 50g

  • 417.0CNY

  • Detail
  • Alfa Aesar

  • (A12711)  4-Acetamidobenzoic acid, 98%   

  • 556-08-1

  • 250g

  • 1822.0CNY

  • Detail
  • Aldrich

  • (133337)  4-Acetamidobenzoicacid  98%

  • 556-08-1

  • 133337-25G

  • 409.50CNY

  • Detail

556-08-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-acetamidobenzoic acid

1.2 Other means of identification

Product number -
Other names p-Acetylamino-benzoic 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:556-08-1 SDS

556-08-1Synthetic route

acetic anhydride
108-24-7

acetic anhydride

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: acetic anhydride; 4-amino-benzoic acid With pyridine at 20℃; for 5h;
Stage #2: With hydrogenchloride In water pH=2 - 3;
Stage #3: In water
99%
With pyridine at 20℃; for 5h;99%
With formic acid at 55℃; under 450.045 Torr; for 2.66667h; Temperature; Pressure;96%
para-acetamidobenzaldehyde
122-85-0

para-acetamidobenzaldehyde

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In methanol; water; acetonitrile at 10℃; for 1h;98%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;98%
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube;90%
zinc diacetate
557-34-6

zinc diacetate

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
In acetic acid for 2.25h; Reflux; chemoselective reaction;98%
4-Methylacetanilide
103-89-9

4-Methylacetanilide

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 90℃; for 1h; Product distribution; Kinetics; var. concentration of reagents, var. temperature, var. time;97.9%
With potassium permanganate In water for 1.5h; Heating;70%
With cobalt(II) acetate; ozone; acetic acid at 95℃; for 10h; Kinetics;35.5%
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

acetyl chloride
75-36-5

acetyl chloride

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3h; Heating;91%
With silica gel at 20℃; for 2.5h; Green chemistry; chemoselective reaction;82%
With pyridine
With triethylamine In tetrahydrofuran at 20℃;
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

acetic acid
64-19-7

acetic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
at 150℃; microwave irradiation;91%
With magnesia In neat (no solvent) at 70℃; for 0.583333h; Green chemistry; chemoselective reaction;91%
With aluminum oxide at 70℃; for 0.5h; Neat (no solvent);88%
With zinc(II) acetate dihydrate for 0.1h; Microwave irradiation; Sealed tube; chemoselective reaction;81%
With hydrazine hydrate for 4h; Heating;59%
acetic anhydride
108-24-7

acetic anhydride

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

acetic acid
64-19-7

acetic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
for 0.25h; Reflux;90%
carbon dioxide
124-38-9

carbon dioxide

4-acetamidophenyl sulfurofluoridate
16704-37-3

4-acetamidophenyl sulfurofluoridate

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox;83%
4-acetylamino-benzoic acid allyl ester

4-acetylamino-benzoic acid allyl ester

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: 4-acetylamino-benzoic acid allyl ester With sodium tetrahydroborate In dimethyl sulfoxide at 20℃;
Stage #2: With hydrogenchloride; water In dimethyl sulfoxide for 0.5h; chemoselective reaction;
81%
With iodine; dimethyl sulfoxide for 0.5h; Heating;78%
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

thioacetic acid
507-09-5

thioacetic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate In methanol at 20℃; for 0.0833333h;79%
4-(1-(hydroxyimino)ethyl)benzoic acid
91004-29-4

4-(1-(hydroxyimino)ethyl)benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: 4-(1-(hydroxyimino)ethyl)benzoic acid With fluorosulfonyl fluoride; triethylamine In acetonitrile at 20℃; for 1h; Beckmann Rearrangement;
Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; Beckmann Rearrangement;
79%
acetic acid
64-19-7

acetic acid

4-Methylacetanilide
103-89-9

4-Methylacetanilide

A

N-<4-(bromomethyl)phenyl>acetamide
66047-05-0

N-<4-(bromomethyl)phenyl>acetamide

B

para-acetamidobenzaldehyde
122-85-0

para-acetamidobenzaldehyde

C

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With ozone; potassium bromide; cobalt(II) acetate at 95℃; Kinetics; Further Variations:; Reagents; Catalysts;A n/a
B n/a
C 75%
acetamide
60-35-5

acetamide

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With graphene oxide at 150℃; for 24h;71%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

(4-acetylaminophenyl)boronic acid
101251-09-6

(4-acetylaminophenyl)boronic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: tert-butylisonitrile; (4-acetylaminophenyl)boronic acid With copper diacetate; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24h; Molecular sieve; Sealed tube;
Stage #2: With water In N,N-dimethyl-formamide Molecular sieve; Sealed tube;
70%
mono-O-acetyl maleic hydrazide
15456-83-4

mono-O-acetyl maleic hydrazide

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 70 - 80℃; for 4h;68%
2,4,6-triacetyloxy-1,3,5-triazine
13483-16-4

2,4,6-triacetyloxy-1,3,5-triazine

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
at 25℃; for 0.166667h; neat (no solvent);66%
4-Ethynyl-benzoic acid
10602-00-3

4-Ethynyl-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With trimethylsilylazide; silver carbonate; trifluoroacetic acid In water; 1,2-dichloro-ethane at 60℃; for 12h; Schlenk technique; Inert atmosphere;64%
With (triphenylphosphine)gold(I) chloride; trimethylsilylazide; water; silver carbonate; trifluoroacetic acid In 1,2-dichloro-ethane at 60℃; Schlenk technique; Inert atmosphere;52%
carbon dioxide
124-38-9

carbon dioxide

sodium 4-acetamidobenzenesulfonate
6034-54-4

sodium 4-acetamidobenzenesulfonate

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; sodium p-acetaminobenzenesulfonate With copper(l) iodide; potassium tert-butylate; o-phenanthroline In dimethyl sulfoxide at 140℃; under 760.051 Torr; for 12h; Schlenk technique;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide Schlenk technique;
63%
carbon monoxide
201230-82-2

carbon monoxide

4-(acetylamino)benzenediazonium tetrafluoroborate

4-(acetylamino)benzenediazonium tetrafluoroborate

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With Ru(2,2'-bipyridine)3Cl2·6H2O; water In acetonitrile at 20℃; under 37503.8 Torr; for 16h; Autoclave; Irradiation;63%
zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
for 0.4h; Microwave irradiation; Sealed tube; chemoselective reaction;51%
sodium benzoate
532-32-1

sodium benzoate

ethyl acetate
141-78-6

ethyl acetate

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
sodium methylate In ethylene glycol at 75 - 135℃; for 26h; Conversion of starting material;48%
N-[4-(chloroacetyl)phenyl]acetamide
140-49-8

N-[4-(chloroacetyl)phenyl]acetamide

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With potassium permanganate
acetic acid-[4-(trans-2-chloro-vinyl)-anilide]
99058-20-5

acetic acid-[4-(trans-2-chloro-vinyl)-anilide]

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With potassium permanganate; acetone
acetic acid-(4-trichloroacetyl-anilide)
103501-31-1

acetic acid-(4-trichloroacetyl-anilide)

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide
acetic anhydride
108-24-7

acetic anhydride

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With water; tin(ll) chloride; iron(II) chloride
With copper(l) chloride; tin(ll) chloride
Ketene
463-51-4

Ketene

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With water
N-acetylacetamide
625-77-4

N-acetylacetamide

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With perchloric acid
sodium acetate
127-09-3

sodium acetate

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With acetic acid
sodium acetate
127-09-3

sodium acetate

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

acetic acid
64-19-7

acetic acid

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

4-nitrophenol acetate
830-03-5

4-nitrophenol acetate

A

p-nitrophenolate
14609-74-6

p-nitrophenolate

B

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

Conditions
ConditionsYield
With borate buffer; azoniacyclophane CP66 In 1,4-dioxane at 25℃; Rate constant;
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

potassium 4-acetamidobenzoate
1086406-22-5

potassium 4-acetamidobenzoate

Conditions
ConditionsYield
With potassium tert-butylate In ethanol at 20℃; for 3h;97%
With potassium tert-butylate In ethanol at 20℃; Inert atmosphere;97%
edoxaban

edoxaban

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

C24H30ClN7O4S*C9H9NO3

C24H30ClN7O4S*C9H9NO3

Conditions
ConditionsYield
In acetonitrile at 60℃; for 5h;97%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

thiophenol
108-98-5

thiophenol

4-Acetylamino-thiobenzoic acid S-phenyl ester
75839-79-1

4-Acetylamino-thiobenzoic acid S-phenyl ester

Conditions
ConditionsYield
With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature;96%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

α-bromoacetophenone
70-11-1

α-bromoacetophenone

4-Acetylamino-benzoic acid 2-oxo-2-phenyl-ethyl ester

4-Acetylamino-benzoic acid 2-oxo-2-phenyl-ethyl ester

Conditions
ConditionsYield
With water; sodium carbonate In ethanol for 2h; Heating;96%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

4-acetamidobenzoyl fluoride

4-acetamidobenzoyl fluoride

Conditions
ConditionsYield
With tetramethylammonium trifluoromethanethiolate In acetonitrile at 20℃; for 1.5h;96%
With sodium fluoride; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate at 20℃; for 24h; Inert atmosphere;71%
With potassium 2-(difluoro(trifluoromethoxy)methoxy)-2,2-difluoroacetate In acetonitrile at 80℃; for 1h; Schlenk technique; Sealed tube; Inert atmosphere;65%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

2-methylallyl 4-acetamidobenzoate

2-methylallyl 4-acetamidobenzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;96%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

para-acetamidobenzaldehyde
122-85-0

para-acetamidobenzaldehyde

Conditions
ConditionsYield
With 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation;94%
With palladium(II) acetylacetonate; hydrogen; 2,2-dimethylpropanoic anhydride; dicyclohexylphenylphosphine In tetrahydrofuran at 80℃; under 3750.38 Torr; for 20h; Inert atmosphere;91%
With potassium phosphate; sodium hypophosphite; 2,2-dimethylpropanoic anhydride; palladium diacetate; tricyclohexylphosphine In tetrahydrofuran at 60℃; for 16h;69%
With glycerol-3-Phosphate Dehydrogenase; D-glucose; NADP+; Nocardia PPTase; Segniliparus CAR; ATP; coenzyme A; magnesium chloride In dimethyl sulfoxide at 35℃; for 16h; pH=9; Enzymatic reaction;
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

tegaserod
1044642-88-7

tegaserod

3-(5-methoxy-1H-indol-3-ylmethylene)-N-pentylcarbazimidamide acetamidobenzoate

3-(5-methoxy-1H-indol-3-ylmethylene)-N-pentylcarbazimidamide acetamidobenzoate

Conditions
ConditionsYield
In ethanol at 25 - 65℃; for 20h;93.5%
tert-butyldimethylsilyl cyanide
56522-24-8

tert-butyldimethylsilyl cyanide

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

C15H23NO3Si
103202-03-5

C15H23NO3Si

Conditions
ConditionsYield
at 80℃; for 0.0833333h;93%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

dimethyl dicarbonate
4525-33-1

dimethyl dicarbonate

methyl 4-acetamidobenzoate
17012-22-5

methyl 4-acetamidobenzoate

Conditions
ConditionsYield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;93%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

4-acetylamino-3-iodo-benzoic acid
190071-24-0

4-acetylamino-3-iodo-benzoic acid

Conditions
ConditionsYield
With sodium percarbonate; sulfuric acid; iodine; acetic anhydride; acetic acid at 45 - 50℃; for 2h;92%
With sodium periodate; sulfuric acid; potassium iodide at 25 - 30℃; for 1h;65%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

benzene
71-43-2

benzene

N-(4-benzoylphenyl)acetamide
4834-61-1

N-(4-benzoylphenyl)acetamide

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; tris(methyl salicylate)phoshate ester at 20℃; for 0.333333h; chemoselective reaction;92%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

(4-acetaminophenyl)-[4-(4-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyridine-5-yl]-methanone
213461-22-4

(4-acetaminophenyl)-[4-(4-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyridine-5-yl]-methanone

Conditions
ConditionsYield
Stage #1: p-(acetylamino)benzoic acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine In N,N-dimethyl-formamide at 20℃;
91%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

4-methoxycarbonyl aniline
619-45-4

4-methoxycarbonyl aniline

C16H14N2O4

C16H14N2O4

Conditions
ConditionsYield
Stage #1: p-(acetylamino)benzoic acid; 4-methoxycarbonyl aniline With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 60℃; for 24h;
Stage #2: With ethanol; water; lithium hydroxide In tetrahydrofuran at 70℃; for 12h;
91%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With pepsin immobilized on terephthalaldehyde functionalized chitosan magnetic nanoparticle In acetonitrile at 20℃; for 48h; pH=2;90%
With ammonium bromide; ethylenediamine at 70℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent);81%
With hydrogenchloride
With ethanol at 60℃; Acidic conditions;
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 4-acetamidobenzoate
17012-22-5

methyl 4-acetamidobenzoate

Conditions
ConditionsYield
With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction;90%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

tert–butyl (2–aminophenyl)carbamate
146651-75-4

tert–butyl (2–aminophenyl)carbamate

tert-butyl (2-(4-acetamidobenzamido)phenyl)carbamate
1299346-13-6

tert-butyl (2-(4-acetamidobenzamido)phenyl)carbamate

Conditions
ConditionsYield
With pyridine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate at 23℃; for 48h; Product distribution / selectivity;90%
With pyridine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate at 23℃; for 48h;90%
With pyridine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In methanol at 23℃; for 48h; Reagent/catalyst; Solvent; Time;90%
potassium thioacyanate
333-20-0

potassium thioacyanate

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

4-acetamidobenzoyl isothiocyanate

4-acetamidobenzoyl isothiocyanate

Conditions
ConditionsYield
Stage #1: p-(acetylamino)benzoic acid With trichloroisocyanuric acid; triphenylphosphine In toluene at 0℃; for 0.25h;
Stage #2: potassium thioacyanate In toluene at 0 - 20℃; for 1.5h;
90%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

4-Acetylamino-benzenecarboperoxoic acid tert-butyl ester
93915-79-8

4-Acetylamino-benzenecarboperoxoic acid tert-butyl ester

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide 0 deg C, 1.5 h; RT, 2 h;88%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

2-hydroxy-5-nitroaniline
99-57-0

2-hydroxy-5-nitroaniline

N-(4-(5-nitrobenzo[d]oxazol-2-yl)phenyl)acetamide

N-(4-(5-nitrobenzo[d]oxazol-2-yl)phenyl)acetamide

Conditions
ConditionsYield
With polyphosphoric acid at 60℃; for 6h; Temperature;87.72%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

dibenzyl dicarbonate
31139-36-3

dibenzyl dicarbonate

4-acetylamino-benzoic acid benzyl ester

4-acetylamino-benzoic acid benzyl ester

Conditions
ConditionsYield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;87%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

benzylamine
100-46-9

benzylamine

4-acetamido-N-benzylbenzamide

4-acetamido-N-benzylbenzamide

Conditions
ConditionsYield
Stage #1: p-(acetylamino)benzoic acid With N-chlorobenzotriazole; triphenylphosphine In dichloromethane for 0.25h;
Stage #2: benzylamine With triethylamine In dichloromethane at 20℃; for 0.666667h;
87%
p-(acetylamino)benzoic acid
556-08-1

p-(acetylamino)benzoic acid

phenylboronic acid
98-80-6

phenylboronic acid

N-(4-benzoylphenyl)acetamide
4834-61-1

N-(4-benzoylphenyl)acetamide

Conditions
ConditionsYield
Stage #1: p-(acetylamino)benzoic acid With di(succinimido) carbonate; sodium carbonate; tricyclohexylphosphine; palladium(II) hexafluoroacetylacetonate In tetrahydrofuran at 60℃;
Stage #2: phenylboronic acid In tetrahydrofuran at 60℃; for 20h; Further stages.;
86%
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triphenylphosphine In tetrahydrofuran; water at 60℃; for 16h;85%
With 2,2-dimethylpropanoic anhydride; triphenylphosphine In tetrahydrofuran; water at 60℃; for 16h;85%
With P(p-CH3OC6H4)3; water; dimethyl dicarbonate; palladium diacetate In tetrahydrofuran at 50℃; for 16h;69%

556-08-1Relevant articles and documents

Interaction of human arylamine n-acetyltransferase 1 with different nanomaterials

Deng, Zhou J.,Butcher, Neville J.,Mortimer, Gysell M.,Jia, Zhongfan,Monteiro, Michael J.,Martin, Darren J.,Minchin, Rodney F.

, p. 377 - 383 (2014)

Humans are exposed to nanoparticles in the environment as well as those in nanomaterials developed for biomedical applications. However, the safety and biologic effects of many nanoparticles remain to be elucidated. Over the past decade, our understanding of the interaction of proteins with various nanomaterials has grown. The protein corona can determine not only how nanoparticles interact with cells but also their biologic effects and toxicity. In this study, we describe the effects that several different classes of nanoparticles exert on the enzymatic activity of the cytosolic protein human arylamine N-acetyltransferase 1 (NAT1), a drug-metabolizing enzyme widely distributed in the body that is also responsible for the activation and detoxification of known carcinogens. We investigated three metal oxides (zinc oxide, titanium dioxide, and silicon dioxide), two synthetic clay nanoparticles (layered double hydroxide and layered silicate nanoparticles), and a self-assembling thermoresponsive polymeric nanoparticle that differ in size and surface characteristics. We found that the different nanoparticles induced very different responses, ranging from inhibition to marked enhancement of enzyme activity. The layered silicates did not directly inactivate NAT1, but was found to enhance substrate-dependent inhibition. These differing effects demonstrate the multiplicity of nanoparticle-protein interactions and suggest that enzyme activity may be compromised in organs exposed to nanoparticles, such as the lungs or reticulo-endothelial system. Copyright

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

Han, Min Su,Jang, Mingyeong,Lim, Taeho,Park, Byoung Yong

, p. 910 - 919 (2022/01/20)

In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4′-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

Paracetamol and other acetanilide analogs as inter-molecular hydrogen bonding assisted diamagnetic CEST MRI contrast agents

Chakraborty, Subhayan,Peruncheralathan,Ghosh, Arindam

, p. 6526 - 6534 (2021/02/21)

Paracetamol and a few other acetanilide derivatives are reported as a special class of diamagnetic Chemical Exchange Saturation Transfer (diaCEST) MRI contrast agents, that exhibit contrast only when the molecules form inter-molecular hydrogen bonding mediated molecular chains or sheets. Without the protection of the hydrogen bonding their contrast producing labile proton exchanges too quickly with the solvent to produce any appreciable contrast. Through a number of variable temperature experiments we demonstrate that under the conditions when the hydrogen bond network breaks and the high exchange returns back, the contrast drops quickly. The well-known analgesic drug paracetamol shows 12% contrast at a concentration of 15 mM at physiological conditions. With the proven safety track-record for human consumption and appreciable physiological contrast, paracetamol shows promise as a diaCEST agent forin vivostudies.

Synthetic method of 4-(5-nitrobenzo [d] oxazole-2-yl) aniline

-

Paragraph 0025-0029; 0044; 0045; 0048; 0049; 0052; 0053, (2020/05/01)

The invention discloses a synthetic method of 4-(5-nitrobenzo [d] oxazole-2-yl) aniline. The method comprises the following steps: mixing a substrate p-aminobenzoic acid with a reaction solvent; raising the temperature to a reaction temperature of 70-100 DEG C while stirring; dropping acetic anhydride after dissolution of the substrate, reacting for 0.5-1.5 hours after dropwise adding and then performing post-treatment of the reaction liquid to obtain p-acetaminobenzoic acid; mixing the p-acetaminobenzoic acid with 2-amino-4-nitrophenol and polyphosphoric acid, heating to 50-120 DEG C while stirring, carrying out a constant temperature reaction for 2-7 h and then performing post-treatment of the reaction liquid to obtain N-(4-(5-nitrobenzo [d] oxazole-2-yl) phenyl) acetamide; and mixing the N-(4-(5-nitrobenzo [d] oxazole-2-yl) phenyl) acetamide with the reaction solvent, heating to 80-110 DEG C while stirring and reacting for 3-5 h and then performing post-treatment of the reaction liquid to obtain the target product. The reaction process parameters are easy to control, the energy consumption is low, the yield is good, the purity is high and the industrial feasibility is high.

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