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5467-64-1

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5467-64-1 Usage

Synthesis

The synthesis of?2-AMINOPHENOL-N,O-DIACETATE is as follows:The substrate (alcohol, phenol or amine; 1.0 mmol) was treated with Ac2O (2.0 mmol) in the presence of P(4-VPH)ClO4?(50 mg) at room temperature under solvent-free conditions and magnetic stirring. After completion of the reaction as indicated by TLC, the mixture was diluted with Et2O (25 ml) and the catalyst allowed to settle down. The supernatant ethereal solution was decanted off, the catalyst washed with Et2O (2 ml) and the combined ethereal solution concentrated under vacuum to afford the product, identical(mp, IR,?1H and?13C NMR, and GC-MS) to an authentic sample of acetylated product. The recovered catalyst was dried at 50 °C under vacuum for 2 h. The recovered catalyst, after drying, was reused for four more consecutive acetylation reactions of benzyl alcohol (1.0 mmol) affording 96, 96, 94, and 94% yields.

Check Digit Verification of cas no

The CAS Registry Mumber 5467-64-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,6 and 7 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5467-64:
(6*5)+(5*4)+(4*6)+(3*7)+(2*6)+(1*4)=111
111 % 10 = 1
So 5467-64-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H11NO3/c1-7(12)11-9-5-3-4-6-10(9)14-8(2)13/h3-6H,1-2H3,(H,11,12)

5467-64-1SDS

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 (2-acetamidophenyl) acetate

1.2 Other means of identification

Product number -
Other names 1-Acetoxy-2-acetylamino-benzol

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:5467-64-1 SDS

5467-64-1Synthetic route

acetic anhydride
108-24-7

acetic anhydride

2-amino-phenol
95-55-6

2-amino-phenol

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
With sulfuric acid In methanol for 4h; Concentration; Reflux; Large scale;99.1%
With poly(N-vinylimidazole) In neat (no solvent) at 20℃; for 0.0666667h; Green chemistry;98%
With succinimide-N-sulfonic acid In neat (no solvent) at 20℃; for 0.0333333h; Mechanism;98%
acetic acid
64-19-7

acetic acid

2-amino-phenol
95-55-6

2-amino-phenol

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
With poly(4-vinylpyridine) perchlorate In neat (no solvent) at 20℃; for 0.2h;98%
acetic anhydride
108-24-7

acetic anhydride

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
Stage #1: 2-hydroxynitrobenzene With sodium tetrahydroborate; water In neat (no solvent) at 20℃; for 0.0166667h;
Stage #2: acetic anhydride In neat (no solvent) at 40℃; for 0.0666667h; Reagent/catalyst;
92%
With sodium tetrahydroborate at 60℃; for 0.183333h;91%
Stage #1: 2-hydroxynitrobenzene In water for 0.0833333h;
Stage #2: With sodium tetrahydroborate In water at 65℃; for 0.0833333h;
Stage #3: acetic anhydride In water at 65℃; for 0.0333333h; Catalytic behavior;
90%
acetyl chloride
75-36-5

acetyl chloride

2-(acetylamino)phenol
614-80-2

2-(acetylamino)phenol

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
With pyridine In acetonitrile for 0.0833333h; Ambient temperature;91%
sulfuric acid at 80℃; for 0.25h;
C10H11NO3
1262859-22-2

C10H11NO3

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
With iodine In acetonitrile for 3h; Beckmann rearrangement; Reflux;90%
N,N,O-Triacetyl-2-aminophenol
59130-68-6

N,N,O-Triacetyl-2-aminophenol

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
With acetic acid for 3h; Heating;87%
acetic acid
64-19-7

acetic acid

Acetanilid
103-84-4

Acetanilid

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
With potassium peroxomonosulphate; palladium diacetate In 1,2-dichloro-ethane at 100℃; for 48h;77%
With ammonium peroxydisulfate; palladium diacetate; trifluoroacetic acid at 20℃; for 24h;67%
With ammonium peroxydisulfate; C20H16F6N2O6Pd2 at 20℃; for 24h;62%
With ammonium peroxydisulfate; silver hexafluoroantimonate; [RhCl2(p-cymene)]2 In 1,2-dichloro-ethane at 100℃; for 24h; Inert atmosphere; regioselective reaction;56%
2-aminophenyl acetate
82833-70-3

2-aminophenyl acetate

A

2-methyl-1,3-benzoxazole
95-21-6

2-methyl-1,3-benzoxazole

B

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

C

2-(acetylamino)phenol
614-80-2

2-(acetylamino)phenol

Conditions
ConditionsYield
With acetic acid at 138℃; for 3h;A 41%
B 0.5%
C 3.6%
sodium acetate
127-09-3

sodium acetate

2-aminophenol hydrochloride
51-19-4

2-aminophenol hydrochloride

acetic anhydride
108-24-7

acetic anhydride

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

2-aminophenol hydrochloride
51-19-4

2-aminophenol hydrochloride

acetic anhydride
108-24-7

acetic anhydride

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

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

acetic anhydride

ethyl acetate
141-78-6

ethyl acetate

2-amino-phenol
95-55-6

2-amino-phenol

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

acetic anhydride
108-24-7

acetic anhydride

2-(acetylamino)phenol
614-80-2

2-(acetylamino)phenol

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
With sodium hydroxide
2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
With acetic anhydride; nickel Hydrogenation;
Multi-step reaction with 2 steps
1: tin(II) chloride dihdyrate; choline chloride / 80 °C
2: sodium acetate / water / 0.17 h / Heating
View Scheme
2-benzylideneaminophenyl acetate

2-benzylideneaminophenyl acetate

A

2-methyl-1,3-benzoxazole
95-21-6

2-methyl-1,3-benzoxazole

B

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

C

2-(acetylamino)phenol
614-80-2

2-(acetylamino)phenol

Conditions
ConditionsYield
With sulfuric acid 2.) light petroleum; Yield given. Multistep reaction. Yields of byproduct given;
With sulfuric acid 2.) light petroleum, R.T.; Yield given. Multistep reaction. Yields of byproduct given;
acetic acid
64-19-7

acetic acid

Phenyl azide
622-37-7

Phenyl azide

A

1,3-dihydro-2H-azepin-2-one
2183-86-0

1,3-dihydro-2H-azepin-2-one

B

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

C

4-acetoxyacetanilide
2623-33-8

4-acetoxyacetanilide

D

2-(acetylamino)phenol
614-80-2

2-(acetylamino)phenol

Conditions
ConditionsYield
at 25℃; Irradiation; Further byproducts given;A 39.2 % Turnov.
B 5.6 % Turnov.
C 12.2 % Turnov.
D 7.9 % Turnov.
Phenyl azide
622-37-7

Phenyl azide

A

1,3-dihydro-2H-azepin-2-one
2183-86-0

1,3-dihydro-2H-azepin-2-one

B

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

C

4-acetoxyacetanilide
2623-33-8

4-acetoxyacetanilide

D

2-(acetylamino)phenol
614-80-2

2-(acetylamino)phenol

Conditions
ConditionsYield
With acetic acid at 25℃; for 72h; Irradiation; Further byproducts given;A 39.2 % Turnov.
B 5.6 % Turnov.
C 12.2 % Turnov.
D 7.9 % Turnov.
1,2-Benzochinon-monophenylthioimin
41772-20-7

1,2-Benzochinon-monophenylthioimin

acetic anhydride
108-24-7

acetic anhydride

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
With pyridine; acetic acid; zinc
acetic acid
64-19-7

acetic acid

Phenyl azide
622-37-7

Phenyl azide

A

2-methyl-1,3-benzoxazole
95-21-6

2-methyl-1,3-benzoxazole

B

1,3-dihydro-2H-azepin-2-one
2183-86-0

1,3-dihydro-2H-azepin-2-one

C

4-acetaminophenol
103-90-2

4-acetaminophenol

D

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

E

4-acetoxyacetanilide
2623-33-8

4-acetoxyacetanilide

F

2-(acetylamino)phenol
614-80-2

2-(acetylamino)phenol

G

PhNHAc, PhN=NPh

PhNHAc, PhN=NPh

Conditions
ConditionsYield
at 25℃; Product distribution; Mechanism; Irradiation; var. of solvent, further thermolysis;A 4.2 % Chromat.
B 39.2 % Chromat.
C 2.3 % Chromat.
D 6.5 % Chromat.
E 12.2 % Chromat.
F 7.9 % Chromat.
G n/a
acetic anhydride
108-24-7

acetic anhydride

2-aminophenyl acetate
82833-70-3

2-aminophenyl acetate

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

Conditions
ConditionsYield
In dichloromethane at 20℃;
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

2-methyl-1,3-benzoxazole
95-21-6

2-methyl-1,3-benzoxazole

Conditions
ConditionsYield
With acetic acid at 138℃; for 6h;94.5%
at 210℃;
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

3'-Amino-2'-hydroxyacetophenone
70977-72-9

3'-Amino-2'-hydroxyacetophenone

Conditions
ConditionsYield
With titanium tetrachloride In 1-methyl-pyrrolidin-2-one at 120℃; for 3h; Catalytic behavior; Concentration; Fries Phenol Ester Rearrangement; Large scale;87%
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

2-(acetylamino)phenol
614-80-2

2-(acetylamino)phenol

Conditions
ConditionsYield
In water at 25℃; trypsin, O.1 M phosphate buffer, pH 8.0;85%
With sodium hydroxide
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

2-Acetamido-5-chlorophenyl acetate
139399-68-1

2-Acetamido-5-chlorophenyl acetate

Conditions
ConditionsYield
With N-chloro-succinimide; acetic acid for 120h; Ambient temperature;81%
With chloroform; chlorine
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

2-methylbenzo[d]oxazol-4-yl acetate

2-methylbenzo[d]oxazol-4-yl acetate

Conditions
ConditionsYield
With dipotassium peroxodisulfate; trifluorormethanesulfonic acid; palladium diacetate; acetic acid In N,N-dimethyl-formamide at 100℃; for 24h; Reagent/catalyst; Sealed tube;68%
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

2-Acetamido-5-bromophenyl Acetate
91715-77-4

2-Acetamido-5-bromophenyl Acetate

Conditions
ConditionsYield
With N-Bromosuccinimide In acetic acid Ambient temperature;67%
With N-Bromosuccinimide; acetic acid Ambient temperature;
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

A

2-methyl-1,3-benzoxazole
95-21-6

2-methyl-1,3-benzoxazole

B

2-(acetylamino)phenol
614-80-2

2-(acetylamino)phenol

Conditions
ConditionsYield
In ethanol; acetic acid Product distribution; Heating;A 39%
B 45%
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

di(1H-benzotriazol-1-yl) sulfoxide
88348-79-2

di(1H-benzotriazol-1-yl) sulfoxide

1-[N-(o-acetoxyphenyl)acetimidoyl]-1H-benzotriazole

1-[N-(o-acetoxyphenyl)acetimidoyl]-1H-benzotriazole

Conditions
ConditionsYield
45%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

2-Amino-5-benzhydryl-phenol

2-Amino-5-benzhydryl-phenol

Conditions
ConditionsYield
With sulfuric acid; acetic acid und Erhitzen des Reaktionsprodukts mit wss.H2SO4;
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

1-<3-(acetylamino)-4-hydroxyphenyl>ethanone
74896-30-3

1-<3-(acetylamino)-4-hydroxyphenyl>ethanone

Conditions
ConditionsYield
With aluminium trichloride
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

A

1-acetoxy-2-acetylamino-3-nitro-benzene
69194-51-0

1-acetoxy-2-acetylamino-3-nitro-benzene

B

2-acetoxy-1-acetylamino-4-nitro-benzene
304667-95-6

2-acetoxy-1-acetylamino-4-nitro-benzene

Conditions
ConditionsYield
With nitric acid; acetic anhydride
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

2-acetoxy-1-acetylamino-4-nitro-benzene
304667-95-6

2-acetoxy-1-acetylamino-4-nitro-benzene

Conditions
ConditionsYield
With nitric acid
durch Nitrierung;
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

acetic acid-(2-hydroxy-3,5-dinitro-anilide)
5422-72-0

acetic acid-(2-hydroxy-3,5-dinitro-anilide)

Conditions
ConditionsYield
durch Nitrieren;
bei der Nitrierung;
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

benzoyl chloride
98-88-4

benzoyl chloride

1-acetoxy-2-(acetyl-benzoyl-amino)-benzene

1-acetoxy-2-(acetyl-benzoyl-amino)-benzene

Conditions
ConditionsYield
With pyridine
2-acetamidophenyl acetate
5467-64-1

2-acetamidophenyl acetate

A

3-acetamido-4-hydroxybenzenesulfonyl chloride

3-acetamido-4-hydroxybenzenesulfonyl chloride

B

4-acetamido-3-hydroxybenzenesulfonyl chloride

4-acetamido-3-hydroxybenzenesulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid In chloroform at 50 - 60℃; for 2h; Yield given. Yields of byproduct given;

5467-64-1Relevant articles and documents

Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water

Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein

, p. 3289 - 3312 (2021/05/11)

Developing and/or modifying fundamental chemical reactions using chemical industry-favorite heterogeneous recoverable catalytic systems in the water solvent is very important. In this paper, we developed convenient, green, and efficient approaches for the chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes in the presence of the recoverable heterogeneous carbon-supported palladium (Pd/C) catalytic system in water. The utilize of the simple, effective, and recoverable catalyst and also using of water as an entirely green solvent along with relatively short reaction times and good-to-excellent yields of the desired products are some of the noticeable features of the presented synthetic protocols. Graphic abstract: [Figure not available: see fulltext.].

The immobilized Cu nanoparticles on magnetic montmorillonite (MMT?Fe3O4?Cu): As an efficient and reusable nanocatalyst for reduction and reductive-acetylation of nitroarenes with NaBH4

Zeynizadeh, Behzad,Rahmani, Soleiman,Tizhoush, Hengameh

, (2019/11/28)

In this study, the immobilization of copper nanoparticles on superparamagnetic montmorillonite, MMT?Fe3O4?Cu, was studied. Magnetically nanoparticles (MNPs) of iron oxide (Fe3O4) were primarily prepared by a chemical co-precipitation method. Next, the prepared Fe3O4 MNPs were intercalated within the interlamellar spaces and external surface of sodium-exchanged montmorillonite. Finally, Cu NPs were immobilized on magnetic montmorillonite by a simply mixing of an aqueous solution of CuCl2·2H2O with MMT?Fe3O4 followed by the reduction with NaBH4. Characterization of MMT?Fe3O4 clay system represented that through the immobilization of Fe3O4 MNPs, disordered-layers structure of MMT was easily reorganized to an ordered-layers arrangement. The synthesized composite systems were characterized using FT-IR, SEM, EDX, XRD, VSM, BET and ICP-OES analyses. SEM analysis exhibited that dispersion of Cu NPs, with the size distribution of 15–25 nm, on the surface of magnetic clay was taken place perfectly. BET surface analysis indicated that after the immobilization of Fe3O4 and Cu species, the surface area and total pore volume of MMT?Fe3O4?Cu system was decreased. Next, the Cu-clay nanocomposite system showed a perfect catalytic activity towards reduction of nitroarenes to anilines as well as reductive-acetylation of nitroarenes to acetanilides using NaBH4 and Ac2O in water as a green and economic solvent. The copper magnetic clay catalyst can be easily separated from the reaction mixture by an external magnetic field and reused for six consecutive cycles without the significant loss of its catalytic activity.

The immobilized Ni(II)-thiourea complex on silica-layered copper ferrite: A novel and reusable nanocatalyst for one-pot reductive-acetylation of nitroarenes

Zeynizadeh, Behzad,Shokri, Zahra,Hasanpour Galehban, Morteza

, (2019/01/16)

In this study, magnetically nanoparticles of CuFe2O4@SiO2@PTMS@Tu@Ni(II) as novel and reusable catalyst were prepared. Synthesis of the Ni (II)-nanocatalyst was carried out through the complexation of Ni(OAc)2·4H2O with the immobilized thiourea on silica-layered CuFe2O4. The prepared nanocomposite system was then characterized using SEM, EDX, XRD, VSM, ICP-OES, Raman, UV–Vis and FT-IR analyses. Catalytic activity of the Ni(II)-CuFe2O4 system was investigated towards rapid reduction of aromatic nitro compounds to arylamines with sodium borohydride as well as one-pot reductive-acetylation of nitroarenes to acetanilides with NaBH4/Ac2O system without the isolation of intermediate arylamines. All reactions were carried out in H2O within 3–7?min to afford the products arylamines/acetanilides in high to excellent yields. Reusability of the Ni(II)-nanocatalyst was examined for seven consecutive cycles without the significant loss of the catalytic activity.

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