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3-Amino-5-methylisoxazole is a significant intermediate compound that is formed during the biodegradation of sulfamethoxazole (SMX) by Pseudomonas psychrophila strain HA-4 and also during the photocatalytic degradation of SMX. It is characterized by its yellow crystalline powder, crystals, and chunks.

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  • 1072-67-9 Structure
  • Basic information

    1. Product Name: 3-Amino-5-methylisoxazole
    2. Synonyms: 3-Isoxazolamine,5-methyl-;3-Methyl-5-aminoisoxazole;5-Methyl-3-aminoisoxazole;5-methyl-3-isoxazolamin;5-Methyl-3-isoxazolamine;5-Methyl-3-iso-xazolamine;Isoxazole, 3-amino-5-methyl-;TIMTEC-BB SBB005553
    3. CAS NO:1072-67-9
    4. Molecular Formula: C4H6N2O
    5. Molecular Weight: 98.1
    6. EINECS: 214-013-6
    7. Product Categories: Oxazole&Isoxazole;Building Blocks;Heterocyclic Building Blocks;Isoxazoles;Amines;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Amines, Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
    8. Mol File: 1072-67-9.mol
  • Chemical Properties

    1. Melting Point: 59-61 °C(lit.)
    2. Boiling Point: 183.6°C (rough estimate)
    3. Flash Point: 96.5 °C
    4. Appearance: slightly yellow flakes
    5. Density: 1.1890 (rough estimate)
    6. Vapor Pressure: 0.0487mmHg at 25°C
    7. Refractive Index: 1.4327 (estimate)
    8. Storage Temp.: Refrigerator
    9. Solubility: soluble
    10. PKA: 2.40±0.10(Predicted)
    11. Water Solubility: soluble
    12. BRN: 108110
    13. CAS DataBase Reference: 3-Amino-5-methylisoxazole(CAS DataBase Reference)
    14. NIST Chemistry Reference: 3-Amino-5-methylisoxazole(1072-67-9)
    15. EPA Substance Registry System: 3-Amino-5-methylisoxazole(1072-67-9)
  • Safety Data

    1. Hazard Codes: Xi-F,Xi,F,Xn
    2. Statements: 5-36/37/38-11-36/37/38/5-20/21/22
    3. Safety Statements: 22-24/25-47-37/39-26-16-26/37/39/47-36
    4. WGK Germany: 3
    5. RTECS:
    6. F: 4.6
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1072-67-9(Hazardous Substances Data)

1072-67-9 Usage

Uses

Used in Pharmaceutical Synthesis:
3-Amino-5-methylisoxazole is used as a key intermediate in the synthesis of various pharmaceutical compounds, including naphtho[1,2-e][1,3]oxazines, a series of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones, which exhibit potential mosquito larvicidal activity. It is also utilized in the synthesis of hydroxylamines of sulfadiazine and sulfamethoxazole.
Used in Environmental Applications:
3-Amino-5-methylisoxazole serves as an impurity indicator in the degradation of sulfamethoxazole (SMX) in water. It is detected using a bioluminescence method during the application of electro-Fenton treatment, which helps in assessing the effectiveness of the treatment process in removing SMX from water sources.
Used in Research and Development:
As a major intermediate in the degradation of sulfamethoxazole, 3-Amino-5-methylisoxazole is also used in research and development to study the degradation pathways and mechanisms of SMX, as well as to develop more efficient methods for its removal from the environment.

Check Digit Verification of cas no

The CAS Registry Mumber 1072-67-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 2 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1072-67:
(6*1)+(5*0)+(4*7)+(3*2)+(2*6)+(1*7)=59
59 % 10 = 9
So 1072-67-9 is a valid CAS Registry Number.
InChI:InChI=1/C4H6N2O/c1-3-2-4(5)6-7-3/h2H,1H3,(H2,5,6)

1072-67-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Aldrich

  • (232270)  3-Amino-5-methylisoxazole  ≥97%

  • 1072-67-9

  • 232270-50G

  • 519.48CNY

  • Detail
  • USP

  • (1631533)  SulfamethoxazoleRelatedCompoundC  United States Pharmacopeia (USP) Reference Standard

  • 1072-67-9

  • 1631533-15MG

  • 14,500.98CNY

  • Detail

1072-67-9SDS

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 3-Amino-5-methylisoxazole

1.2 Other means of identification

Product number -
Other names 5-methyl-1,2-oxazol-3-amine

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:1072-67-9 SDS

1072-67-9Synthetic route

C11H13N3O2S

C11H13N3O2S

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

Conditions
ConditionsYield
Stage #1: C11H13N3O2S With hydroxylamine hydrochloride; potassium carbonate In water at 85℃; for 2h;
Stage #2: With hydrogenchloride In water for 1h;
80%
3-hydroxybutanenitrile
4368-06-3

3-hydroxybutanenitrile

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

Conditions
ConditionsYield
Stage #1: 3-hydroxybutanenitrile With hydroxylamine hydrochloride; potassium carbonate In water at 20 - 60℃; for 3h;
Stage #2: With iron(III) chloride In toluene Reagent/catalyst; Temperature; Reflux;
77%
2-(5-methyl-1,2-oxazol-3-yl)-1H-isoindole-1,3(2H)-dione
91377-59-2

2-(5-methyl-1,2-oxazol-3-yl)-1H-isoindole-1,3(2H)-dione

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 3h; Heating;75.1%
cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

A

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

exo-3-(5-methylisoxazol-3-yl)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene 2 oxide

exo-3-(5-methylisoxazol-3-yl)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene 2 oxide

(1RS,2SR,4SR)-(2-oxo-2λ4-thia-3-azabicyclo[2.2.2]oct-5-en-3-yl)phosphonic acid diphenyl ester

(1RS,2SR,4SR)-(2-oxo-2λ4-thia-3-azabicyclo[2.2.2]oct-5-en-3-yl)phosphonic acid diphenyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 22h; hetero-Diels-Alder reaction;A n/a
B n/a
C 64%
(5-methyl-isoxazol-3-yl)-carbamic acid benzyl ester
100143-11-1

(5-methyl-isoxazol-3-yl)-carbamic acid benzyl ester

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

Conditions
ConditionsYield
With sodium hydroxide
(5-methyl-isoxazol-3-yl)-carbamic acid ethyl ester
92087-97-3

(5-methyl-isoxazol-3-yl)-carbamic acid ethyl ester

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

Conditions
ConditionsYield
With sodium hydroxide
but-2-enenitrile
4786-20-3

but-2-enenitrile

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

Conditions
ConditionsYield
(i) Br2, MeOH, (ii) aq. NaOH, NH2CONHOH; Multistep reaction;
(Z)-4-(5-Methyl-isoxazol-3-ylamino)-pent-3-en-2-one
106124-31-6

(Z)-4-(5-Methyl-isoxazol-3-ylamino)-pent-3-en-2-one

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 3h; Heating; Yield given;
sulfamethoxazole
723-46-6

sulfamethoxazole

A

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

B

C10H10ClN3O3S

C10H10ClN3O3S

C

4-amino-3-chloro-N-(5-methyl-isoxazol-3-yl)-benzenesulphonamide

4-amino-3-chloro-N-(5-methyl-isoxazol-3-yl)-benzenesulphonamide

Conditions
ConditionsYield
With sodium hypochlorite; borate buffer at 25℃; pH=9; Kinetics; Further Variations:; pH-values; Reagents; Solvents;
sulfamethoxazole
723-46-6

sulfamethoxazole

A

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

B

C10H13N3O4S

C10H13N3O4S

C

C10H13N3O5S

C10H13N3O5S

D

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide
29699-89-6

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide

Conditions
ConditionsYield
With hydrogenchloride; water; sodium chloride; sodium hydroxide pH=9.5; Catalytic behavior; Mechanism; Kinetics; pH-value; Reagent/catalyst; Inert atmosphere;
sulfamethoxazole
723-46-6

sulfamethoxazole

A

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

B

benzenesulfonamide
98-10-2

benzenesulfonamide

C

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

D

N-((4-aminophenyl)sulfonyl)carbamimidic acid
547-44-4

N-((4-aminophenyl)sulfonyl)carbamimidic acid

E

3-hydroxybenzenesulfonamide
20759-40-4

3-hydroxybenzenesulfonamide

F

4-amino-N-(4-hydroxy-5-methylisoxazol-3-yl)benzenesulfonamide

4-amino-N-(4-hydroxy-5-methylisoxazol-3-yl)benzenesulfonamide

G

N-(4,5-dihydroxy-5-methyl-4,5-dihydroisoxazol-3-yl)-4-hydroxybenzenesulfonamide

N-(4,5-dihydroxy-5-methyl-4,5-dihydroisoxazol-3-yl)-4-hydroxybenzenesulfonamide

H

N-(4,5-dihydroxy-5-methyl-4,5-dihydroisoxazol-3-yl)benzenesulfonamide

N-(4,5-dihydroxy-5-methyl-4,5-dihydroisoxazol-3-yl)benzenesulfonamide

I

(Z)-N-((2-oxopropylidene)carbamoyl)methanesulfonamide

(Z)-N-((2-oxopropylidene)carbamoyl)methanesulfonamide

J

3,4-dihydroxy-N-(5-methylisoxazol-3-yl)benzenesulfonamide

3,4-dihydroxy-N-(5-methylisoxazol-3-yl)benzenesulfonamide

K

3,4-dihydroxy-N-(4-hydroxy-5-methylisoxazol-3-yl)benzenesulfonamide

3,4-dihydroxy-N-(4-hydroxy-5-methylisoxazol-3-yl)benzenesulfonamide

L

4-amino-3-hydroxy-N- (5-methylisoxazol-3-yl)benzenesulfonamide

4-amino-3-hydroxy-N- (5-methylisoxazol-3-yl)benzenesulfonamide

M

4-amino-3-hydroxy-N-(4-hydroxy-5-methylisoxazol-3-yl)benzenesulfonamide

4-amino-3-hydroxy-N-(4-hydroxy-5-methylisoxazol-3-yl)benzenesulfonamide

N

2-oxo-N-(phenylsulfonyl)acetimidamide

2-oxo-N-(phenylsulfonyl)acetimidamide

O

4-hydroxy-N-(5-methyl-3-isoxazolyl)benzenesulphonamide
141233-20-7

4-hydroxy-N-(5-methyl-3-isoxazolyl)benzenesulphonamide

P

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide
29699-89-6

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide

Q

phenol
108-95-2

phenol

Conditions
ConditionsYield
With AgBr-BaMoO4 composite photocatalyst In water for 1.25h; Kinetics; Reagent/catalyst; UV-irradiation;
sulfamethoxazole
723-46-6

sulfamethoxazole

A

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

B

5-methyl-3-nitrosoisoxazole
947619-95-6

5-methyl-3-nitrosoisoxazole

C

4-amino-3-hydroxy-N- (5-methylisoxazol-3-yl)benzenesulfonamide

4-amino-3-hydroxy-N- (5-methylisoxazol-3-yl)benzenesulfonamide

D

4-amino-3-hydroxy-N-(4-hydroxy-5-methylisoxazol-3-yl)benzenesulfonamide

4-amino-3-hydroxy-N-(4-hydroxy-5-methylisoxazol-3-yl)benzenesulfonamide

E

C4H8N2O

C4H8N2O

Conditions
ConditionsYield
With sodium sulfate In water pH=7; Kinetics; pH-value; Reagent/catalyst; Electrochemical reaction;
N1-acetylsulfamethoxazole
18607-98-2

N1-acetylsulfamethoxazole

A

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

B

5-methyl-3-nitrosoisoxazole
947619-95-6

5-methyl-3-nitrosoisoxazole

C

N-acetylsulfanilic acid
121-62-0

N-acetylsulfanilic acid

D

nitroso derivative of sulfamethoxazole
131549-85-4

nitroso derivative of sulfamethoxazole

E

Benzenesulfinic acid
618-41-7

Benzenesulfinic acid

F

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide
29699-89-6

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide

Conditions
ConditionsYield
With sodium sulfate In water pH=7; Kinetics; pH-value; Reagent/catalyst; Electrochemical reaction;
sulfamethoxazole
723-46-6

sulfamethoxazole

A

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

B

3-nitro-5-methylisoxazole
75079-82-2

3-nitro-5-methylisoxazole

C

5-methyl-3-nitrosoisoxazole
947619-95-6

5-methyl-3-nitrosoisoxazole

D

4-amino-3-hydroxy-N- (5-methylisoxazol-3-yl)benzenesulfonamide

4-amino-3-hydroxy-N- (5-methylisoxazol-3-yl)benzenesulfonamide

Conditions
ConditionsYield
With iron(III) sulfate; sodium hydrogensulfite at 25℃; pH=4; Kinetics; pH-value;
sulfamethoxazole
723-46-6

sulfamethoxazole

A

5-methylisoxazole
5765-44-6

5-methylisoxazole

B

5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

C

1-hydroxy-2-aminobenzene-5-sulfonic acid
2592-14-5

1-hydroxy-2-aminobenzene-5-sulfonic acid

D

C9H8N2O4S

C9H8N2O4S

E

4-hydroxy-N-(5-methyl-3-isoxazolyl)benzenesulphonamide
141233-20-7

4-hydroxy-N-(5-methyl-3-isoxazolyl)benzenesulphonamide

F

(5-methyl-1,2-oxazol-3-yl)sulfamic acid

(5-methyl-1,2-oxazol-3-yl)sulfamic acid

G

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide
29699-89-6

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide

Conditions
ConditionsYield
Stage #1: sulfamethoxazole With 0D/1D 50 wt.% AgI/MoO3 Z-scheme heterojunction composite In water for 0.5h; Darkness; Sonication;
Stage #2: In water pH=3.92; Kinetics; Catalytic behavior; Reagent/catalyst; Irradiation;
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

5-chlorosalicyclaldehyde
635-93-8

5-chlorosalicyclaldehyde

3-(2-hydroxy-8-chlorobenzylideneamino)-5-methylisoxazole
88812-64-0

3-(2-hydroxy-8-chlorobenzylideneamino)-5-methylisoxazole

Conditions
ConditionsYield
Reflux;100%
In ethanol for 2h; Reflux;88%
In ethanol Heating;
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

4-bromo-2-[(5-methyl-3-isoxazolyl)imino]methylphenol
88812-68-4

4-bromo-2-[(5-methyl-3-isoxazolyl)imino]methylphenol

Conditions
ConditionsYield
Reflux;100%
In ethanol for 2h; Reflux;95%
In ethanol Heating;
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

piperonal
120-57-0

piperonal

[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-(5-methyl-isoxazol-3-yl)-amine
88812-71-9

[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-(5-methyl-isoxazol-3-yl)-amine

Conditions
ConditionsYield
Heating;100%
In ethanol; chloroform
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

(5-Methyl-isoxazol-3-yl)-[1-p-tolyl-meth-(E)-ylidene]-amine
112633-38-2

(5-Methyl-isoxazol-3-yl)-[1-p-tolyl-meth-(E)-ylidene]-amine

Conditions
ConditionsYield
Heating;100%
With 1-methylimidazolium tetrafluoroborate at 30℃; for 0.25h;
In ethanol; chloroform
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

N-(4-chlorobenzylidene)-5-methylisoxazol-3-amine
88812-63-9

N-(4-chlorobenzylidene)-5-methylisoxazol-3-amine

Conditions
ConditionsYield
Heating;100%
With 1-methylimidazolium tetrafluoroborate at 30℃;
In ethanol; chloroform
In ethanol Reflux;
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

[1-(2-Chloro-phenyl)-meth-(E)-ylidene]-(5-methyl-isoxazol-3-yl)-amine
112633-41-7

[1-(2-Chloro-phenyl)-meth-(E)-ylidene]-(5-methyl-isoxazol-3-yl)-amine

Conditions
ConditionsYield
Heating;100%
With trimethylsilyl acetate; zinc(II) chloride In N,N-dimethyl-formamide at 100℃; for 8h;
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

(5-Methyl-isoxazol-3-yl)-[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amine
88812-66-2

(5-Methyl-isoxazol-3-yl)-[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amine

Conditions
ConditionsYield
Heating;100%
In ethanol; chloroform
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

(5-Methyl-isoxazol-3-yl)-[1-(4-nitro-phenyl)-meth-(Z)-ylidene]-amine
112633-39-3

(5-Methyl-isoxazol-3-yl)-[1-(4-nitro-phenyl)-meth-(Z)-ylidene]-amine

Conditions
ConditionsYield
Heating;100%
In ethanol; chloroform
With acetic acid In 1,2-dichloro-ethane at 60℃; for 1.5h;
With tert-butylisonitrile; phenylpropyolic acid In methanol at 20℃; for 24h;
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

benzaldehyde
100-52-7

benzaldehyde

N-benzylidene-5-methylisoxazol-3-amine
112633-37-1

N-benzylidene-5-methylisoxazol-3-amine

Conditions
ConditionsYield
Heating;100%
With 1-methylimidazolium tetrafluoroborate at 30℃; for 0.25h;
In ethanol; chloroform
With acetic acid In 1,2-dichloro-ethane at 60℃; for 1.5h;
With magnesium sulfate In ethanol at 20℃;
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-(5-methyl-isoxazol-3-yl)-amine
88812-69-5

[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-(5-methyl-isoxazol-3-yl)-amine

Conditions
ConditionsYield
Heating;100%
With piperidine In ethanol for 0.166667h; Reflux;76%
With 1-methylimidazolium tetrafluoroborate at 30℃;
In ethanol; chloroform
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

[1-(2,4-Dichloro-phenyl)-meth-(E)-ylidene]-(5-methyl-isoxazol-3-yl)-amine
112661-91-3

[1-(2,4-Dichloro-phenyl)-meth-(E)-ylidene]-(5-methyl-isoxazol-3-yl)-amine

Conditions
ConditionsYield
Heating;100%
In ethanol; chloroform
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

4-methoxy-2-[(5-methyl-3-isoxazolyl)imino]methylphenol
415715-07-0

4-methoxy-2-[(5-methyl-3-isoxazolyl)imino]methylphenol

Conditions
ConditionsYield
Reflux;100%
In ethanol for 2h; Reflux;90%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2-hydroxy-5-methylbenzaldehyde
613-84-3

2-hydroxy-5-methylbenzaldehyde

4-methyl-2-[(5-methyl-3-isoxazolyl)imino]methylphenol
326878-69-7

4-methyl-2-[(5-methyl-3-isoxazolyl)imino]methylphenol

Conditions
ConditionsYield
Reflux;100%
In ethanol for 2h; Reflux;90%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

salicylaldehyde
90-02-8

salicylaldehyde

2-((5-methylisoxazol-3-ylimino)methyl)phenol
112633-43-9

2-((5-methylisoxazol-3-ylimino)methyl)phenol

Conditions
ConditionsYield
Reflux;100%
In ethanol for 2h; Reflux;95%
In methanol Reflux;82%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

3,5-Dibromosalicylaldehyde
90-59-5

3,5-Dibromosalicylaldehyde

C11H8Br2N2O2
116808-16-3

C11H8Br2N2O2

Conditions
ConditionsYield
Reflux;100%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

3,5-dichlorosalicyclaldehyde
90-60-8

3,5-dichlorosalicyclaldehyde

C11H8Cl2N2O2
88812-65-1

C11H8Cl2N2O2

Conditions
ConditionsYield
Reflux;100%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

1,3-diisopropyl-2-(5-methylisoxazol-3-yl)guanidine

1,3-diisopropyl-2-(5-methylisoxazol-3-yl)guanidine

Conditions
ConditionsYield
[{Me2Si(C5Me4)(NPh)}Y(CH2SiMe3)(thf)2] In tetrahydrofuran at 20℃; for 1h;99%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

mercaptoacetic acid
68-11-1

mercaptoacetic acid

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

4-(3-(5-methylisoxazol-3-yl)-4-oxothiazolidin-2-yl)benzonitrile
1610829-08-7

4-(3-(5-methylisoxazol-3-yl)-4-oxothiazolidin-2-yl)benzonitrile

Conditions
ConditionsYield
In toluene Reflux; Dean-Stark;98.7%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

C21H17FN2O3
1380601-72-8

C21H17FN2O3

Conditions
ConditionsYield
at 80℃; for 0.5h; Neat (no solvent);98%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

(1,1,1-trifluoro-2-(trifluoromethyl)-but-2-yl)isocyanate
312932-31-3

(1,1,1-trifluoro-2-(trifluoromethyl)-but-2-yl)isocyanate

1-[1,1-bis(trifluoromethyl)propyl]-3-(5-methylisoxazol-3-yl)urea
355829-46-8

1-[1,1-bis(trifluoromethyl)propyl]-3-(5-methylisoxazol-3-yl)urea

Conditions
ConditionsYield
In diethyl ether at 20℃; for 4h;98%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide
29699-89-6

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide

Conditions
ConditionsYield
With pyridine at 20℃; for 5h;97%
95%
With pyridine at 0℃; for 2h; Inert atmosphere;90%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

C12H12ClN3O
1338361-28-6

C12H12ClN3O

1-(3,4-dimethylphenyl)-5-methyl-N-(5-methylisoxazol-3-yl)-1H-1,2,3-triazole-4-carboxamide
915910-20-2

1-(3,4-dimethylphenyl)-5-methyl-N-(5-methylisoxazol-3-yl)-1H-1,2,3-triazole-4-carboxamide

Conditions
ConditionsYield
With triethylamine In acetonitrile at 70℃;97%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

bromobenzene
108-86-1

bromobenzene

3-anilino-5-methylisoxazole
71854-24-5

3-anilino-5-methylisoxazole

Conditions
ConditionsYield
With [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; tert-butyl XPhos In tert-butyl alcohol at 20℃; for 2h; Inert atmosphere;97%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1-[(5-methylisoxazol-3-ylamino)(4-nitrophenyl)methyl]naphthalene-2,7-diol
1380601-75-1

1-[(5-methylisoxazol-3-ylamino)(4-nitrophenyl)methyl]naphthalene-2,7-diol

Conditions
ConditionsYield
at 80℃; for 0.5h; Neat (no solvent);97%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

1H-indol-2-ylcarboxaldehyde
19005-93-7

1H-indol-2-ylcarboxaldehyde

N-((1H-indol-2-yl)methylene)-5-methylisoxazol-3-amine

N-((1H-indol-2-yl)methylene)-5-methylisoxazol-3-amine

Conditions
ConditionsYield
With acetic acid In methanol at 30℃; for 0.2h; Temperature; Sonication;97%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2,4,6-trimethoxybenzaldehyde
830-79-5

2,4,6-trimethoxybenzaldehyde

N-(2,4,6-trimethoxybenzylidene)-5-methylisoxazol-3-amine

N-(2,4,6-trimethoxybenzylidene)-5-methylisoxazol-3-amine

Conditions
ConditionsYield
With acetic acid In methanol at 30℃; for 0.2h; Temperature; Sonication;97%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2,6-difluorobenzaldehyde
437-81-0

2,6-difluorobenzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-(2,6-difluorophenyl)-3-(5-methylisoxazol-3-yl)thiazolidin-4-one
1350308-04-1

2-(2,6-difluorophenyl)-3-(5-methylisoxazol-3-yl)thiazolidin-4-one

Conditions
ConditionsYield
In toluene Reflux;96.7%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2,6-dichlorobenzaldehyde
83-38-5

2,6-dichlorobenzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

2-(2,6-dichlorophenyl)-3-(5-methylisoxazol-3-yl)thiazolidin-4-one
1350308-03-0

2-(2,6-dichlorophenyl)-3-(5-methylisoxazol-3-yl)thiazolidin-4-one

Conditions
ConditionsYield
In toluene Reflux;96.5%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

ethyl N-(5-methylisoxazol-3-yl)acetimidate

ethyl N-(5-methylisoxazol-3-yl)acetimidate

Conditions
ConditionsYield
for 1.5h; Heating;96%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

ethyl (ethoxymethylene)cyanoacetate
94-05-3

ethyl (ethoxymethylene)cyanoacetate

ethyl 2-cyano-3-(5-methylisoxazol-3-ylamino)acrylate
219619-78-0

ethyl 2-cyano-3-(5-methylisoxazol-3-ylamino)acrylate

Conditions
ConditionsYield
In ethanol for 1.5h; Reflux;96%

1072-67-9Related news

Rapid degradation of sulphamethoxazole and the further transformation of 3-Amino-5-methylisoxazole (cas 1072-67-9) in a microbial fuel cell07/25/2019

Sulphamethoxazole (SMX) is extensively used in humans and livestock, but its appearance in natural water raises environmental concerns. This study demonstrated that SMX and its degradation product, 3-amino-5-methylisoxazole (3A5MI), could be effectively degraded in microbial fuel cell (MFC) reac...detailed

1072-67-9Relevant articles and documents

Insight into sulfamethoxazole degradation, mechanism, and pathways by AgBr-BaMoO4 composite photocatalyst

Ray, Schindra Kumar,Dhakal, Dipesh,Lee, Soo Wohn

, p. 686 - 695 (2018)

A composite photocatalyst, AgBr-BaMoO4 was fabricated by two step method; microwave hydrothermal and precipitation-deposition. The as prepared photocatalyst samples were characterized by various techniques. The facet coupling was seen between the (204) plane of BaMoO4 and (200)/(222) planes of AgBr on the basis of XRD/HRTEM analysis. The pharmaceutical pollutant, sulfamethoxazole was adopted to investigate the photocatalytic performances of samples under UV–vis irradiation. The AgBr-BaMoO4 composite degraded the aqueous sulfamethoxazole drug in UV–vis light about 64% within 75 min, which was attributed to efficient separation of photogenerated electron–hole pairs across the interface between Ag/AgBr and BaMoO4. The multi-electron induced oxygen reduced reaction (ORR) was observed. The radical trapping experiment indicates that OH? has major role for sulfamethoxazole degradation. The four successive photodegradation of sulfamethoxazole in UV–vis light indicates the stability of composite photocatalyst. Furthermore, the three different degradation pathways were designed on the basis of retention time and molecular masses of 18 degraded organic fragments that was confirmed by high-performance liquid chromatography photodiode array (HPLC-PDA) and high resolution-quadruple time of flight electrospray ionization mass spectroscopy (HR-QTOF ESI/MS) techniques. The total organic carbon (TOC) analysis suggested the mineralization of SMZ by composite photocatalyst. This study not only demonstrates the enhancement of photocatalytic performance of wide band gap semiconductor by making composite with narrow band gap semiconductor but also detail degradation pathways and mechanisms of sulfamethoxazole.

Effects of water environmental factors on the photocatalytic degradation of sulfamethoxazole by AgI/UiO-66 composite under visible light irradiation

Wang, Chao,Xue, Yao,Wang, Peifang,Ao, Yanhui

, p. 314 - 322 (2018)

It is necessary to find visible light responsive photocatalysts for rapid and simple degradation of organic pollutants in water environment. In this work, a visible light responsive composite photocatalyst AgI/UiO-66 was prepared by an in situ growth method. Sulfamethoxazole (SMZ) antibiotic was selected as the target contaminant to probe the photocatalytic performance of the as-prepared AgI/UiO-66 composite under visible light irradiation. The results showed that the photocatalytic performance of the AgI/UiO-66 composite enhanced significantly compared to pure AgI. The effects of typical environment factors (i.e. pH, inorganic salt ions and common anions) on the degradation of SMZ were evaluated extensively. Results showed that the investigated pH (5.2, 7.0, 9.5) had no apparent effect on the photocatalytic degradation of SMZ except pH 2.5, at which the degradation rate of SMZ decreased significantly. In addition, inorganic salt ions and Cl?, HCO3? and SO42? anions in water exhibited no apparent effect on the degradation of SMZ. The effect of water matrix on the degradation of SMZ was also investigated. In the river water, the removal efficiency of SMZ was reduced compared with the cleaner water matrix. The capture experiments of radicals confirmed that superoxide radicals ([rad]O2?) and hydroxyl radicals ([rad]OH) were the main active species for the photocatalytic degradation of SMZ in the present work. Finally, the tentative degradation pathways of SMZ were proposed based on the intermediates analysis.

Transformation of the antibacterial agent sulfamethoxazole in reactions with chlorine: Kinetics, mechanisms, and pathways

Dodd, Michael C.,Huang, Ching-Hua

, p. 5607 - 5615 (2004)

Sulfamethoxazole (SMX) - a member of the sulfonamide antibacterial class - has beenfrequently detected in municipal wastewater and surface water bodies in recent years. Kinetics, mechanisms, and products of SMX in reactions with free chlorine (HOCl/OCl-) were studied in detail to evaluate the effect of chlorination processes on the fate of sulfonamides in municipal wastewaters and affected drinking waters. Direct reactions of free available chlorine (FAC) with SMX were quite rapid. A half-life of 23 s was measured under pseudo-first-order conditions ([FAC]0 = 20 μM (1.4 mg/L) and [SMX]0 = 2 μM) at pH 7 and 25°C in buffered reagent water. In contrast, a half-life of 38 h was determined for reactions with combined chlorine (NH2Cl, NHCl2) under similar conditions. Free chlorine reaction rates were first-order in both substrate and oxidant, with specific second-order rate constants of 1.1 × 103 and 2.4 × 103 M -1 s-1 for SMX neutral and anionic species, respectively. Investigations with substructure model compounds and identification of reaction products verified that chlorine directly attacks the SMX aniline-nitrogen, resulting in (i) halogenation of the SMX aniline moiety to yield a ring-chlorinated product at sub-stoichiometric FAC concentrations (i.e., [FAC]0:[SMX]0 ≤ 1) or (ii) rupture of the SMX sulfonamide moiety in the presence of stoichiometric excess of FAC to yield 3-amino-5-methylisoxazole, SO42- (via SO2), and N-chloro-p-benzoquinoneimine. Reaction ii represents an unexpected aromatic amine chlorination mechanism that has not previously been evaluated in great detail. Experiments conducted in wastewater and drinking water matrixes appeared to validate measured reaction kinetics for SMX, indicating that SMX and likely other sulfonamide antibacterials should generally undergo substantial transformation during disinfection of such waters with free chlorine residuals.

0D/1D AgI/MoO3 Z-scheme heterojunction photocatalyst: Highly efficient visible-light-driven photocatalyst for sulfamethoxazole degradation

Xu, Jing,Chen, Juan,Ao, Yanhui,Wang, Peifang

supporting information, p. 3226 - 3230 (2021/05/29)

Low dimension nano photocatalysts show great potential in the field of treating contaminated water for their large surface area and size effect. In this study, a 0D/1D AgI/MoO3 Z-scheme photocatalyst with striking photocatalytic performance was constructed successfully. The one-dimensional MoO3 nanobelts were prepared by a simple hydrothermal method, and then it was modified by AgI nanoparticles in a handy deposition approach. When choosing sulfamethoxazole (SMZ) as the target contaminant, the rate constant value of the optimal 0D/1D AgI/MoO3 composite could hit up to 0.13 min?1, which is nearly 22.4 times and 32.5 times as that of pure MoO3 (0.0058 min?1) and AgI (0.0040 min?1), respectively. A series of detailed characterizations give evidences that the charge transfer in the composite followed Z scheme mechanism. Therefore, efficient separation/transfer and the remained high redox activity of photogenerated carriers played a vital role in the sharply enhanced photocatalytic properties. The possible degradation pathways of SMZ were proposed based on the intermediates detected by high-performance liquid chromatography-mass spectrometry (HPLC-MS). Meanwhile, the magnificent cyclic stability makes the material a promising material in the practical application.

Insights into the electrochemical degradation of sulfamethoxazole and its metabolite by Ti/SnO2-Sb/Er-PbO2 anode

Wang, Yanping,Zhou, Chengzhi,Wu, Jinhua,Niu, Junfeng

supporting information, p. 2673 - 2677 (2020/06/01)

Electrochemical degradation of sulfamethoxazole (SMX) and its metabolite acetyl-sulfamethoxazole (Ac-SMX) by Ti/SnO2-Sb/Er-PbO2 were investigated. Results indicated that the electrochemical degradation of SMX and Ac-SMX followed pseu

Preparation method 3 -amino -5 -alkyl isoxazole

-

Paragraph 0024-0025; 0028; 0029-0030; 0033, (2020/06/05)

The invention discloses a preparation method of 3-amino-5-alkyl isoxazole, realizes preparation through two steps and belongs to the technical field of organic chemistry. By starting from easily obtained aldehyde, after the addition with acetonitrile under the existence of metal alkali, an intermediate of hydroxy nitrile is obtained; then, the hydroxy nitrile reacts with hydroxylamine; ring closing reaction is performed under the existence of Lewis acid; after autoxidation, the 3-amino-5-alkyl isoxazole is obtained. The raw materials in the reaction process are very commons; chloroform or tetrachloromethane in a traditional method is avoided; potential industrial amplification prospects are realized.

A simple Fe3+/bisulfite system for rapid degradation of sulfamethoxazole

Fu, Yongsheng,Liu, Yiqing,Wang, Guangsheng,Wang, Hongbin,Wang, Shixiang

, p. 30162 - 30168 (2020/09/03)

Sulfate radical (SO4-) based oxidation technologies have been widely used in the remediation of antibiotic-containing wastewater. Activated persulfates are efficient reagents for achieving SO4-, but the storage and transportation of concentrated persulfates present associated safety issues. In this study, bisulfite (BS) was used as an alternative precursor for replacing persulfates, and a simple advanced oxidation system (Fe3+/BS) for generating SO4- and hydroxyl radical (HO) was formulated and evaluated for removing sulfamethoxazole (SMX) from contaminated water. The initial pH, dosages of Fe3+ and BS, as well as the water matrix were investigated to improve the SMX degradation. The results indicated that 1 μmol L-1 SMX was completely removed within 5 min at optimum initial pH of 4.0, Fe3+ dosage of 10 μmol L-1, BS dosage of 100 μmol L-1 and temperature of 25 °C. The presence of HCO3- and natural organic matter (NOM) showed obviously negative effects on SMX degradation, while Cu2+ could slightly promote the degradation of SMX if its concentration was in an appropriate range (~1 μmol L-1). Scavenger quenching experiments confirmed the presence of SO4- and HO, which resulted in efficient SMX degradation in the Fe3+/BS system. During the radical chain reactions, Fe2+ and Fe3+ could be converted into each other to form self-circulation in this system. The degradation pathway of SMX by Fe3+/BS was proposed including hydroxylation and bond cleavage.

Preparation method for 3-amino-5-methylisoxazole

-

Paragraph 0027; 0035; 0043, (2018/04/03)

The invention discloses a preparation method for 3-amino-5-methylisooxazole, belonging to the technical field of organic chemistry. The preparation method is completed through three steps: with an easily-available raw material namely ethyl acetate as a starting material, carrying out a reaction with acetonitrile in the presence of an alkali metal so as to form acetyl acetonitrile, then carrying out a reaction with p-toluenesulfonhydrazide so as to form hydrazone, and carrying out a ring closing reaction with hydroxylamine under an alkaline condition so as to obtain the 3-amino-5-methylisoxazole. According to the invention, raw materials in the reactions are common; chloroform or carbon tetrachloride in a traditional method are avoided; and analogous isomers of the 3-amino-5-methylisoxazoleare not detected in the reaction process.

Preparation and evaluation of N-sulfinyl dienophiles for asymmetric hetero-Diels-Alder reactions

Endeshaw, Molla Mellese,Hansen, Lars K.,Gautun, Odd R.

, p. 149 - 154 (2008/09/20)

(Chemical Equation Presented) A series of N-sulfinyl dienophiles 1c-i has been screened in asymmetric hetero-Diels-Alder reactions using chiral bis(oxazoline)copper(II) and -zinc(II) triflates. The survey pointed out N-sulfine 1c (R = P(=O)(OPh)2) as the most promising N-sulfine regarding yield and stereoselectivity (up to 97% ee). The relative configurations, and in one case the absolute configuration, of the HDA adducts were established by X-ray analysis.

Isoxazolyl enaminones

-

, (2008/06/13)

An oxazolyl enaminone is provided having the formula: STR1 wherein R1 is selected from the group consisting of a branched or unbranched alkyl groups containing from 1 to 4 carbon atoms and R2 is selected from the group consisting of a branched or unbranched alkyl group containing from 1 to 4 carbon atoms, a chloro group, a trifluoromethyl group and a trifluoromethoxy group. Also provided are pharmaceutically accepatable salts and isomers of the above, and pharmaceutical compositions containing the same.

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