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546-88-3

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546-88-3 Usage

Description

Acetohydroxamic acid is a potent, non-competitive and irreversible inhibitor of bacterial urease (Ki≈lO-7M). This enzyme, which is widely distributed in plants and bacteria, but not in mammalian cells, catalyzes the decomposition of urea to ammonia. Elevated urinary ammonia levels can reduce the antibacterial effectiveness of a number of agents. Thus, acetohydroxamic acid is useful as adjunctive therapy to decrease urinary ammonia and alkalinity in patients with chronic urea-splitting urinary infection. Such infections are a leading cause of recurring complications and death in paraplegics.

Chemical Properties

White Crystalline Solid

Originator

Research Organics; Baylor Unk. (USA)

Uses

Different sources of media describe the Uses of 546-88-3 differently. You can refer to the following data:
1. Acetohydroxamic acid is a potent inhibitor of bacterial urease activity and reduces urinary ammonia levels. 2-Acetohydroxamic acid loaded floating microspheres forms an efficient drug delivery system for the treatment of Helicobacter pylori.Acetohydroxamic acid was used:to study the mechanism of complexation of iron (III) with acetohydroxamic acid.to study the inhibitory mechanism of lansoprazole and omeprazole on Helicobacter pyloni.in urease inhibition studies.for in situ generation of nitrosocarbonylmethane as a Diels-Alder dienophile.Used in urease inhibition studies and for in situ generation of nitrosocarbonylmethane as a Diels-Alder dienophile.
2. A urease inhibitor. Used in the synthesis
3. Urease inhibitorAcetohydroxamic acid acts as a drug, as an inhibitor of bacterial and plant urease, which is used for urinary tract infections. It is also used in organic synthesis. It acts as an antiurolithic and antibacterial agent. It is involved in the study of complexation of iron(III) with acetohydroxamic acid as well as in the inhibition study of lansoprazole and omeprazole on Helicobacter pyloni. It plays an important role in the insitu generation of nitrosocarbonylmethane as a Diels-Alder dienophile. In addition to this, it is used in the treatment of kidney stones and urinary tract infections.

Manufacturing Process

3 Methods of producing of acetohydroxamic acid: 1. Ethyl acetic acid ether was treated with hydroxylamine and acetohydroxamic acid was obtained. 2. Acetohydroxamic acid was obtained in the result of reaction of acetamide with hydroxylamine. 3. Acetohydroxamic acid was obtained by treatment of acetaldehyde with nitrohydroxylamine.

Brand name

Lithostat (Mission).

Therapeutic Function

Urease inhibitor

General Description

Acetohydroxamic acid is a potent inhibitor of bacterial urease activity and reduces urinary ammonia levels. 2-Acetohydroxamic acid loaded floating microspheres forms an efficient drug delivery system for the treatment of Helicobacter pylori.

Side effects

Get emergency medical help if you have any of these signs of an allergic reaction: hives; difficulty breathing; swelling of your face, lips, tongue, or throat.Call your doctor at once if you have:pounding heartbeats or fluttering in your chest;signs of a blood clot in your leg --pain, swelling, warmth, or redness in one or both legs;signs of a red blood cell disorder --pale or yellowed skin, dark colored urine, fever, confusion or weakness.Common side effects may include:headache during the first 2 days of treatment;skin rash, warmth, tingling or redness (especially if you drink alcohol while taking acetohydroxamic acid);upset stomach, nausea, loss of appetite;depressed mood;anxiety, tremors, nervousness;hair loss.

Safety Profile

Moderately toxic by intraperitonealroute. An experimental teratogen. Other experimentalreproductive effects. Mutation data reported. When heatedto decomposition it emits toxic fumes of NOx.

Veterinary Drugs and Treatments

Acetohydroxamic acid can be used in dogs as adjunctive therapy in some cases of recurrent urolithiasis or in the treatment of persistent urinary tract infections caused by the following bacteria: E. coli, Klebsiella, Morganella morganii, Staphylococci spp., and Pseudomonas aeruginosa. Adverse effects limit its usefulness.

Check Digit Verification of cas no

The CAS Registry Mumber 546-88-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 6 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 546-88:
(5*5)+(4*4)+(3*6)+(2*8)+(1*8)=83
83 % 10 = 3
So 546-88-3 is a valid CAS Registry Number.
InChI:InChI=1/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)

546-88-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L01569)  Acetohydroxamic acid, 98%   

  • 546-88-3

  • 1g

  • 193.0CNY

  • Detail
  • Alfa Aesar

  • (L01569)  Acetohydroxamic acid, 98%   

  • 546-88-3

  • 5g

  • 467.0CNY

  • Detail
  • Alfa Aesar

  • (L01569)  Acetohydroxamic acid, 98%   

  • 546-88-3

  • 25g

  • 1937.0CNY

  • Detail
  • USP

  • (1006506)  Acetohydroxamicacid  United States Pharmacopeia (USP) Reference Standard

  • 546-88-3

  • 1006506-200MG

  • 4,662.45CNY

  • Detail
  • Aldrich

  • (159034)  Acetohydroxamicacid  98%

  • 546-88-3

  • 159034-5G

  • 644.67CNY

  • Detail
  • Aldrich

  • (159034)  Acetohydroxamicacid  98%

  • 546-88-3

  • 159034-10G

  • 1,132.56CNY

  • Detail
  • Aldrich

  • (159034)  Acetohydroxamicacid  98%

  • 546-88-3

  • 159034-50G

  • 4,130.10CNY

  • Detail

546-88-3SDS

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 acetohydroxamic acid

1.2 Other means of identification

Product number -
Other names N-acetylhydroxylamine

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:546-88-3 SDS

546-88-3Synthetic route

ethyl acetate
141-78-6

ethyl acetate

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With hydroxyammonium sulfate; sodium ethanolate In ethanol at 25℃; for 2h; Concentration;97.1%
With hydroxylamine hydrochloride; sodium hydroxide In methanol; water at 40℃; for 3h; Concentration; Reagent/catalyst; Temperature; Solvent; Large scale;84.6%
With hydroxylamine; sodium ethanolate
acetamide
60-35-5

acetamide

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With hydrogenchloride; iron(III) chloride; amidase from Pseudomonas aeruginosa strain L10; hydroxylamine; cetyltrimethylammonium bromide In octanol; n-heptane; water for 0.5h; aq. buffer; Enzymatic reaction;92%
With hydroxylamine; amidase from Brevibacterium sp. R312 Mechanism; further reagent concentration: 100mM;
With hydroxylamine hydrochloride
C12H21NO6

C12H21NO6

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0℃; for 18h;80.1%
Nitroethane
79-24-3

Nitroethane

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With selenium(IV) oxide; triethylamine In dichloromethane 1.) 0-10 deg C, 10 min. 2.) 20 deg C, 30 min. 3.) reflux, 1h;66%
Geschwindigkeit;
acetic anhydride
108-24-7

acetic anhydride

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With hydroxylamine monohydrate In water at 20 - 80℃;55%
With hydroxylamine hydrochloride
With hydroxylamine hydrochloride
hydroxylamine succinic acid salt
869669-06-7

hydroxylamine succinic acid salt

acetic acid
64-19-7

acetic acid

A

1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
for 10 - 15h; Product distribution / selectivity; Heating / reflux;A 54.4%
B 3.7%
Ketene
463-51-4

Ketene

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With diethyl ether; hydroxylamine
Acetaldehyde oxime
107-29-9

Acetaldehyde oxime

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With caro's acid
N-(1-nitroso-ethylidene)-hydroxylamine
3354-65-2

N-(1-nitroso-ethylidene)-hydroxylamine

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With acetic acid
ethyl acetylcarbamate
2597-54-8

ethyl acetylcarbamate

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With methanol; hydroxylamine at 40 - 50℃;
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With hydrogenchloride
N-hydroxy-acetamide oxime
2282-80-6

N-hydroxy-acetamide oxime

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With sodium hydroxide
N-acetoxyacetamide
7340-09-2

N-acetoxyacetamide

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With sodium carbonate
N-acetoxyacetamide
7340-09-2

N-acetoxyacetamide

A

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
Zerfaellung;
sodium acetate
127-09-3

sodium acetate

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With adenylpyrophosphate; pigeon's liverextract; hydroxylamine
With acetylcholine esterase; hydroxylamine at 37℃; bei pH 7.1;
2,4,6-trimethyl-hexahydro-[1,3,5]triazine; trihydrate
58052-80-5, 76231-37-3

2,4,6-trimethyl-hexahydro-[1,3,5]triazine; trihydrate

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With caro's acid
ethylamine
75-04-7

ethylamine

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With caro's acid
piloty's acid
599-71-3

piloty's acid

acetaldehyde
75-07-0

acetaldehyde

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With alkali
acetaldehyde
75-07-0

acetaldehyde

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With water; hydroxylamine; dihydrogen peroxide
diethylamine
109-89-7

diethylamine

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With dihydrogen peroxide
With potassium permanganate
With oxygen; copper
N-Acetylimidazole
2466-76-4

N-Acetylimidazole

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With hydroxylamine hydrochloride
ethyl thioacetate
625-60-5

ethyl thioacetate

A

(O-carboxymethyl)hydroxylamine
19479-87-9

(O-carboxymethyl)hydroxylamine

B

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With hydroxylamine In methanol; water at 30℃; Mechanism; Product distribution; different buffers (pH-s);
With hydroxylamine In methanol; water at 30℃;
(E)-acetonitrolic acid
600-26-0

(E)-acetonitrolic acid

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With water; hydroxide at 55℃; Rate constant; diff. pH;;
N-acetyl-O-(p-nitrobenzoyl)hydroxylamine
123206-53-1

N-acetyl-O-(p-nitrobenzoyl)hydroxylamine

A

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With sodium borate buffer In water; acetonitrile at 55℃; Rate constant; Thermodynamic data; Mechanism; various pH; ΔH(excit.), ΔS(excit.);
acetic acid
64-19-7

acetic acid

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With hydroxylamine In water at 37℃; for 16h; Product distribution; pH = 5.2; effect of metal ions and organic phosphates on hydroxamate formation;
With hydroxylamine; amidase from Brevibacterium sp. R312
With hydroxylamine; 1,1'-carbonyldiimidazole
Stage #1: acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃;
Stage #2: With hydroxylamine hydrochloride In tetrahydrofuran; dichloromethane at 20℃;
C16H20O14(4-)*4C4H12N(1+)*C2H5NO2
109667-44-9

C16H20O14(4-)*4C4H12N(1+)*C2H5NO2

A

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With water-d2 In 1,4-dioxane at 50℃; for 3.7h; Product distribution; Rate constant;
tris(trimethylsilyl)hydroxylamine
21023-20-1

tris(trimethylsilyl)hydroxylamine

acetyl chloride
75-36-5

acetyl chloride

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With ethanol 1.) 20 deg C, 12 h; 2.) 20 deg C, 3 h; Yield given. Multistep reaction;
acetyl chloride
75-36-5

acetyl chloride

A

(O-carboxymethyl)hydroxylamine
19479-87-9

(O-carboxymethyl)hydroxylamine

B

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
With hydroxylamine In 1,4-dioxane; water at 22℃; Rate constant; Product distribution; pH=7.26; different hydroxylamine and AcCl concentrations and pH;
potassium hexafluoridotechnetate(IV)

potassium hexafluoridotechnetate(IV)

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

[tetramminefluoronitrosyltechnetium(I)]4[hexafluoridotechnetate(IV)][HF2]2

[tetramminefluoronitrosyltechnetium(I)]4[hexafluoridotechnetate(IV)][HF2]2

Conditions
ConditionsYield
In hydrogen fluoride; water for 0.5h; liquid HF;100%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

[Zr(acetohydroxamate acid)4]

[Zr(acetohydroxamate acid)4]

Conditions
ConditionsYield
In methanol at 75℃; for 15h; Inert atmosphere; Schlenk technique;100%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
pH=7.3; Electrochemical reaction;98%
With hydrogen cation In 1,4-dioxane at 35℃; Kinetics; Further Variations:; Solvents;
With water; nitric acid; iron(III) Kinetics; Acid hydrolysis;
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
942428-83-3

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

2,3,4,6-tetra-O-acetyl-1-O-acetylhydroxamoyl-β-D-glucopyranose

2,3,4,6-tetra-O-acetyl-1-O-acetylhydroxamoyl-β-D-glucopyranose

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20 - 20℃;97%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

phenylstannic acid

phenylstannic acid

[CH3C(O)NHOSnC6H5(O)]2
75503-60-5

[CH3C(O)NHOSnC6H5(O)]2

Conditions
ConditionsYield
In benzene C6H5SnO1.5 and ligand was reacted in 1:1 molar ratio; water was removed azeotropically, solvent was removed, solid was dried at reduced pressure, elem. anal.;97%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

(R)-1-chloro-1-(3-trifluoromethylphenyl)ethane
208196-20-7

(R)-1-chloro-1-(3-trifluoromethylphenyl)ethane

(S)-O-{1-(3-trifluoromethylphenyl)ethyl}-acetohydroxamate
208196-02-5

(S)-O-{1-(3-trifluoromethylphenyl)ethyl}-acetohydroxamate

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In ethanol; water96.8%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

6β,14β-(N-acetylepoxyimino)-6,14-dihydrothebaine
51029-23-3

6β,14β-(N-acetylepoxyimino)-6,14-dihydrothebaine

Conditions
ConditionsYield
With tetraethylammonium metaperiodate In ethyl acetate at 0℃; for 1h; pH 6;96%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

9,10-dimethylanthracene
781-43-1

9,10-dimethylanthracene

10-(1-oxoethyl)-9,10-dihydro-9,10-dimethyl-10,9-(epoxyimino)anthracene
51029-28-8

10-(1-oxoethyl)-9,10-dihydro-9,10-dimethyl-10,9-(epoxyimino)anthracene

Conditions
ConditionsYield
With tetrapropylammonium periodate In chloroform; N,N-dimethyl-formamide at 5 - 15℃;95%
With tetraethylammonium metaperiodate In dichloromethane at 0 - 5℃; for 1h;1.6 g
With tert-butylammonium metaperiodate In chloroform; N,N-dimethyl-formamide at 0 - 20℃; for 3h;
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

N-acetyl-2-oxa-3-azabicyclo<2.2.2>oct-5-ene
77803-76-0

N-acetyl-2-oxa-3-azabicyclo<2.2.2>oct-5-ene

Conditions
ConditionsYield
Stage #1: acetylhydroxamic acid; cyclohexa-1,3-diene With tetrakis(tetrabutylammonium)decatungstate(VI); oxygen; sodium hydrogencarbonate In water; acetonitrile for 1h; Sealed tube; Irradiation;
Stage #2: In water; acetonitrile at 20℃; for 2h; Sealed tube; Darkness;
95%
With sodium periodate In methanol at 20℃; hetero-Diels-Alder cycloaddition;68%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

2-aminoacetophenone
551-93-9

2-aminoacetophenone

2,4-dimethylquinazoline 3-oxide
1837-71-4

2,4-dimethylquinazoline 3-oxide

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate In toluene at 110℃; for 6h; Reagent/catalyst; Solvent;95%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

2-fluoro-6-methoxybenzonitrile
94088-46-7

2-fluoro-6-methoxybenzonitrile

4-methoxy-3-amino-1,2-benzisoxazole
177995-40-3

4-methoxy-3-amino-1,2-benzisoxazole

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide94%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

carbon monoxide
201230-82-2

carbon monoxide

17-iodo-4-aza-4-methylandrost-16-en-3-one

17-iodo-4-aza-4-methylandrost-16-en-3-one

N-((4aR,4bS,6aS,9aS,9bS,11aS)-1,4a,6a-Trimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carbonyloxy)-acetamide

N-((4aR,4bS,6aS,9aS,9bS,11aS)-1,4a,6a-Trimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carbonyloxy)-acetamide

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 60℃; Carbonylation; addition;94%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

malononitrile
109-77-3

malononitrile

2-acetyl-5-amino-3-(2-bromophenyl)-2,3-dihydroisoxazole-4-carbonitrile

2-acetyl-5-amino-3-(2-bromophenyl)-2,3-dihydroisoxazole-4-carbonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 8h;93%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

2-Chloro-5-methyl-Δ4-1,3,4,2-dioxazaphospholine
125419-21-8

2-Chloro-5-methyl-Δ4-1,3,4,2-dioxazaphospholine

Conditions
ConditionsYield
With phosphorus trichloride 1) 0.5 h, 40 deg C; 2) 1 h, 20 deg C;92%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

carbon monoxide
201230-82-2

carbon monoxide

17-iodoandrost-16-ene

17-iodoandrost-16-ene

N-((5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonyloxy)-acetamide

N-((5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonyloxy)-acetamide

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 60℃; Carbonylation; addition;92%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

malononitrile
109-77-3

malononitrile

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

2-acetyl-5-amino-3-cyclohexyl-2,3-dihydroisoxazole-4-carbonitrile

2-acetyl-5-amino-3-cyclohexyl-2,3-dihydroisoxazole-4-carbonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 8h;92%
4-Trifluoromethylbenzaldehyde
455-19-6

4-Trifluoromethylbenzaldehyde

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

malononitrile
109-77-3

malononitrile

2-acetyl-5-amino-3-(4-(trifluoromethyl)phenyl)-2,3-dihydroisoxazole-4-carbonitrile

2-acetyl-5-amino-3-(4-(trifluoromethyl)phenyl)-2,3-dihydroisoxazole-4-carbonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 7h;92%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

malononitrile
109-77-3

malononitrile

2-acetyl-5-amino-3-(4-nitrophenyl)-2,3-dihydroisoxazole-4-carbonitrile

2-acetyl-5-amino-3-(4-nitrophenyl)-2,3-dihydroisoxazole-4-carbonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 8h; Solvent;92%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

phenyltin triisopropoxide
65332-72-1

phenyltin triisopropoxide

tris(acetohydroxamato)phenyltin(IV)
75503-56-9

tris(acetohydroxamato)phenyltin(IV)

Conditions
ConditionsYield
In tetrahydrofuran acetohydroxamic acid was allowed to react with C6H5Sn(OCH(CH3)2)3 in 3:1 molar ratio in refluxing THF; filtered, dried at 50°C/1 Hgmm for 1 h, elem. anal.;91%
chloroform
67-66-3

chloroform

acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

[bis(5-tert-butyl-3-methylpyrazol-2-yl)acetato](methyl)zinc(II)
502627-50-1

[bis(5-tert-butyl-3-methylpyrazol-2-yl)acetato](methyl)zinc(II)

[bis(5-tert-butyl-3-methylpyrazol-2-yl)acetato](acetohydroxamato)zinc(II) * 0.25 CHCl3

[bis(5-tert-butyl-3-methylpyrazol-2-yl)acetato](acetohydroxamato)zinc(II) * 0.25 CHCl3

Conditions
ConditionsYield
In acetonitrile soln. of Zn complex in MeCN treated with solid CH3CONHOH, stirred for 2 h; concd. under reduced pressure, ppt. filtered off, washed with Et2O and dried in vacuo, crystn. from CHCl3; elem. anal.;91%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

benzaldehyde
100-52-7

benzaldehyde

malononitrile
109-77-3

malononitrile

2-acetyl-5-amino-3-phenyl-2,3-dihydroisoxazole-4-carbonitrile

2-acetyl-5-amino-3-phenyl-2,3-dihydroisoxazole-4-carbonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 6h;91%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

malononitrile
109-77-3

malononitrile

2-acetyl-5-amino-3-p-tolyl-2,3-dihydroisoxazole-4-carbonitrile

2-acetyl-5-amino-3-p-tolyl-2,3-dihydroisoxazole-4-carbonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 6h;91%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

2-chloro-8-{4-(trifluoromethyl)phenoxy}quinoline-5-carbonitrile

2-chloro-8-{4-(trifluoromethyl)phenoxy}quinoline-5-carbonitrile

2-hydroxy-8-{4-(trifluoromethyl)phenoxy}quinoline-5-carbonitrile

2-hydroxy-8-{4-(trifluoromethyl)phenoxy}quinoline-5-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 2h;91%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

(+)-ethyl (3aR,7aS)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-4-carboxylate
1185040-54-3

(+)-ethyl (3aR,7aS)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-4-carboxylate

(1R,2S,6S,7S)-9-acetyl-4,4-dimethyl-3,5,8-trioxa-9-aza-tricyclo[5.2.2.0.2.6]undec-10-ene-7-carboxylic acid ethyl ester
1173701-23-9

(1R,2S,6S,7S)-9-acetyl-4,4-dimethyl-3,5,8-trioxa-9-aza-tricyclo[5.2.2.0.2.6]undec-10-ene-7-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium periodate In methanol at 20℃; hetero-Diels-Alder cycloaddition;90%
With sodium periodate In methanol; water at 20℃; for 16.0833h;
With sodium periodate In methanol at 20℃; for 16.2h; Diels-Alder cycloaddition; Inert atmosphere; regioselective reaction;5.65 g
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

Cyclohepta-1,3-diene
876938-53-3

Cyclohepta-1,3-diene

C9H13NO2

C9H13NO2

Conditions
ConditionsYield
With sodium periodate In methanol at 20℃; hetero-Diels-Alder cycloaddition;90%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

hexanal
66-25-1

hexanal

malononitrile
109-77-3

malononitrile

2-acetyl-5-amino-3-pentyl-2,3-dihydroisoxazole-4-carbonitrile

2-acetyl-5-amino-3-pentyl-2,3-dihydroisoxazole-4-carbonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 7h;90%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

1-bromo-4-(bromomethyl)-2-(trifluoromethyl)benzene
1159512-68-1

1-bromo-4-(bromomethyl)-2-(trifluoromethyl)benzene

N-((4-bromo-3-(trifluoromethyl)benzyl)oxy)acetamide

N-((4-bromo-3-(trifluoromethyl)benzyl)oxy)acetamide

Conditions
ConditionsYield
Stage #1: acetylhydroxamic acid With potassium carbonate In tetrahydrofuran at 20℃; for 1h;
Stage #2: 1-bromo-4-(bromomethyl)-2-(trifluoromethyl)benzene In tetrahydrofuran at 20℃;
89.2%
acetylhydroxamic acid
546-88-3

acetylhydroxamic acid

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

3-acetyl-2-oxa-3-azabicyclo[2.2.1]hept-5-ene
78607-56-4

3-acetyl-2-oxa-3-azabicyclo[2.2.1]hept-5-ene

Conditions
ConditionsYield
With sodium periodate In methanol at 20℃; hetero-Diels-Alder cycloaddition;89%
With 2,6-bis(2-oxazolinyl)pyr Ru(II)-pyr-2,6-dicarboxylate; dihydrogen peroxide In tetrahydrofuran; water at 0 - 20℃; for 2h;84%
Stage #1: acetylhydroxamic acid; cyclopenta-1,3-diene With tetrakis(tetrabutylammonium)decatungstate(VI); oxygen; sodium hydrogencarbonate In water; acetonitrile for 1h; Sealed tube; Irradiation;
Stage #2: In water; acetonitrile at 20℃; for 2h; Sealed tube; Darkness;
84%
With tetraethylammonium metaperiodate In dichloromethane at 0℃; for 0.75h;70%

546-88-3Relevant articles and documents

Munson,Connors

, p. 1979,1980-1984 (1972)

N-O Bond Fission as the Rate-Determining Step in the Aqueous Conversion of N-Peptidyl-O-(p-nitrobenzoyl)hydroxylamines to p-Nitrobenzoic Acid and Peptidylhydroxamic Acids

Demuth, Hans-Ulrich,Fischer, G.,Barth, A.,Schowen, R. L.

, p. 5880 - 5883 (1989)

N-Acetyl-, N-alanyl-alanyl-, N-alanyl-prolyl-, and N-Boc-alanyl-prolyl-O-(p-nitrobenzoyl) hydroxylamines, compounds that are mechanism-based irreversible inactivators of some proteolytic enzymes, are degraded in aqueous buffers at neutral pH to p-nitrobenzoic acid and either the corresponding N-acylhydroxamic acid or products of its further degradation such as the diketopiperazine.At neutral pH, the reactants exist as the monoanion, as a result of the acidity of the -CO-NH-O- linkage.The p-nitrobenzoic acid formed in a mixture of 50percent H2(18)O and 50percent H2(16)O contains less than 2percent (18)O, which shows that nucleophilic attack of water at the ester carbonyl is not occuring in the degradation.The decomposition of the N-alanyl-prolyl derivative, labeled with (15)N at the N-O nitrogen, exhibits a kinetic isotope effect k14/k15 = 1.092 +/- 0.056, suggesting that N-O fission is occuring in the rate-determining step of the degradation.Kinetic solvent isotope effects of 1.02-1.15 are inconsistent with an expectation of factors around 2 or greater for spontaneous hydrolysis of the ester linkage.All derivatives have ΔH* = 24-27 kcal/mol and ΔS* = +4-7 eu, consistent with unimolecular fission of the substrate N-O to generate p-nitrobenzoate ion and the acyl nitrene.The nitrene must suffer nucleophilic attack at nitrogen very rapidly, producing the hydroxamic acid as the initial product.In the peptide derivatives, further reaction to the cyclized products results.

Activation and Orientation by Receptor-Substrate Binding. The Case of Acyl Transfer from O-Acetylhydroxylamine

Lehn, Jean-Marie,Nishiya, Takako

, p. 215 - 218 (1987)

The strong binding ability of the receptor molecule 1 induces complexation of O-acetylhydroxylamine and of hydroxylamine in their protonated forms; as a result, subsequent reaction of bound CH3COONH3+ becomes fast and selective, giving only acetic acid with a rate enhancement by a factor of about 30.

Bamberger,Seligman

, p. 3885 (1902)

Hydroxamic acids. II. Kinetics and mechanisms of hydroxyaminolysis of succinimide.

Notari

, p. 1064 - 1068 (1969)

-

Novel fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety: Design, synthesis, crystal structure and biological evaluation

Dai, Peng,Jiao, Jian,Wang, Qing-Qing,Zhang, Shu-Guang,Zhang, Wei-Hua

, (2021/06/28)

A series of fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety have been designed, synthesized and evaluated for their antifungal activity. All the target compounds were determined by1H-NMR,13C-NMR, FTIR and HR-MS spectra. The single-crystal structures of compounds 4e, 4h, 5h and 6c were further confirmed using X-ray diffraction. The antifungal activities against Botrytis cinerea (B. cinerea), Alternaria solani (A. solani), Gibberella zeae (G. zeae), Rhizoctorzia solani (R. solani), Colletotrichum orbiculare (C. orbiculare) and Alternaria alternata (A. alternata) were evaluated in vitro. The preliminary bioassays showed that some of the designed compounds displayed the promising antifungal activities against the above tested fungi. Strikingly, the target compounds 5f and 6h exhibited outstanding antifungal activity against B. cinerea at 100 μg/mL, with the corresponding inhibition rates reached 90.1 and 85.0%, which were better than the positive control Osthole (83.6%) and Azoxystrobin (46.5%). The compound 5f was identified as the promising fungicide candidate against B. cinerea with the EC50 values of 5.75 μg/mL, which was obviously better than Osthole (33.20 μg/mL) and Azoxystrobin (64.95 μg/mL). Meanwhile, the compound 5f showed remarkable antifungal activities against R. solani with the EC50 values of 28.96 μg/mL, which was better than Osthole (67.18 μg/mL) and equivalent to Azoxystrobin (21.34 μg/mL). The results provide a significant foundation for the search of novel fluorinated 7-hydroxycoumarin derivatives with good antifungal activity.

Synthetic method for acetylhydroxylamine

-

Paragraph 0026-0029, (2021/08/06)

The invention provides a synthesis method for acetylhydroxylamine. The method adopts a two-step method to synthesize acetylhydroxylamine, a first micro-channel reactor and a second micro-channel reactor are used for replacing a traditional reaction bottle. The complete dissolution concentration of hydroxylamine hydrochloride in water is 42%, and 30% sodium hydroxide solution is prepared. The hydroxylamine hydrochloride aqueous solution and the sodium hydroxide aqueous solution are simultaneously fed into a first micro-channel reactor by using different metering pumps to react, the reaction temperature is controlled to be 20-25 DEG C, reaction liquid is collected, the obtained reaction liquid and ethyl acetate are simultaneously fed into a second micro-channel reactor to react, the reaction temperature is controlled to be 30-35 DEG C, and after the reaction is finished, distilling is conducted to obtain acetylhydroxylamine. The synthetic method of acetylhydroxylamine is improved, the raw materials are simple, the reaction is easy to control, the process is simple, waste is few, the total yield can reach 98%, and the synthetic method is suitable for industrial production.

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