32326-25-3

Basic information

• Product Name: 3-Amino-5-methoxyisoxazole
• Synonyms: 3-Amino-5-methoxyisoxazole;5-methoxyisoxazol-3-amine;3-AMINE-5-METHOXYISOXAZOLE;3-Amino-5-methoxisoxazole;5-Methoxy-1,2-oxazol-3-aMine;5-Methoxy-isoxazol-3-ylamine
• CAS NO: 32326-25-3
• Molecular Formula: C₄H₆N₂O₂
• Molecular Weight: 114.10264
• Mol File: 32326-25-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 282°C
• Flash Point: 124°C
• Appearance: /
• Density: 1.243
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.85±0.10(Predicted)
• CAS DataBase Reference: 3-Amino-5-methoxyisoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-5-methoxyisoxazole(32326-25-3)
• EPA Substance Registry System: 3-Amino-5-methoxyisoxazole(32326-25-3)

Safety Data

• Hazardous Substances Data: 32326-25-3(Hazardous Substances Data)

Usage

Uses

5-Methoxyisoxazol-3-amine is a useful reactant in the synthesis of pyrazolidine derivatives and 1-substituted tetrazoles via cyclization of amines.

Synthetic route

1-cyano-2,2-bis(methoxy)ethylene (15732-02-2) → 3-amino-5-methoxyisoxazole (32326-25-3)

Conditions	Yield
With sodium hydroxide; hydroxylamine hydrochloride In methanol at 45 - 60℃; for 7h;	75%
With sodium hydroxide; hydroxylamine hydrochloride In methanol; water	70.6%

orthoformic acid triethyl ester (122-51-0) + 3-amino-5-methoxyisoxazole (32326-25-3) → 5-methoxy-3-(1H-tetrazol-1-yl)isoxazole

Conditions	Yield
With sodium azide In neat (no solvent) at 90℃; for 0.666667h; Reagent/catalyst; Green chemistry;	91%

C20H20F3NO4S + 3-amino-5-methoxyisoxazole (32326-25-3) → 1-(2-(5-methoxyisoxazol-3-yl-amino)ethyl)-7-(trifluoromethyl)-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

Conditions	Yield
With potassium hydrogencarbonate In methanol for 8h; Reflux;	88%

potassium thioacyanate (333-20-0) + methyl chloroformate (79-22-1) + 3-amino-5-methoxyisoxazole (32326-25-3) → (5-methoxycarbonylamino-[1,2,4]thiadiazol-3-yl)-acetic acid methyl ester (149196-71-4)

Conditions	Yield
In acetonitrile 1.) 70 deg C, 30 min; 2.) 5 deg C, 10 min then 20 deg C, 15 min;	86%
1.) MeCN, 70 deg C, 30 min, 2.) MeCN, a) 5 deg C, 10 min, b) RT, 15 min; Yield given. Multistep reaction;

potassium thioacyanate (333-20-0) + chloroformic acid ethyl ester (541-41-3) + 3-amino-5-methoxyisoxazole (32326-25-3) → methyl 2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (150215-07-9)

Conditions	Yield
In acetonitrile 1.) 70 deg C, 30 min; 2.) 5 deg C, 10 min then 20 deg C, 15 min;	83%
1.) MeCN, 70 deg C, 30 min, 2.) MeCN, a) 5 deg C, 10 min, b) RT, 15 min; Yield given. Multistep reaction;

methyl chloroformate (79-22-1) + 3-amino-5-methoxyisoxazole (32326-25-3) → (5-methoxycarbonylamino-[1,2,4]thiadiazol-3-yl)-acetic acid methyl ester (149196-71-4)

Conditions	Yield
In acetonitrile	80.6%

chloroformic acid ethyl ester (541-41-3) + 3-amino-5-methoxyisoxazole (32326-25-3) → methyl 2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (150215-07-9)

Conditions	Yield
In acetonitrile	78.9%

potassium thioacyanate (333-20-0) + phenyl chloroformate (1885-14-9) + 3-amino-5-methoxyisoxazole (32326-25-3) → methyl 2-(5-phenoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (150215-08-0)

Conditions	Yield
In acetonitrile 1.) 70 deg C, 30 min; 2.) 5 deg C, 10 min then 20 deg C, 15 min;	60%
1.) MeCN, 70 deg C, 30 min, 2.) MeCN, a) 5 deg C, 10 min, b) RT, 15 min; Yield given. Multistep reaction;

Benzoyl isothiocyanate (532-55-8) + 3-amino-5-methoxyisoxazole (32326-25-3) → methyl 2-(5-phenylcarbonylamino-1,2,4-thiadiazol-3-yl)acetate

Conditions	Yield
In tetrahydrofuran; ethanol	57.7%

phenyl chloroformate (1885-14-9) + 3-amino-5-methoxyisoxazole (32326-25-3) → methyl 2-(5-phenoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (150215-08-0)

Conditions	Yield
In acetonitrile	57.4%

potassium thioacyanate (333-20-0) + benzyl chloroformate (501-53-1) + 3-amino-5-methoxyisoxazole (32326-25-3) → methyl 2-(5-benzyloxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (150215-09-1)

Conditions	Yield
In acetonitrile 1.) 70 deg C, 30 min; 2.) 5 deg C, 10 min then 20 deg C, 15 min;	40%
1.) MeCN, 70 deg C, 30 min, 2.) MeCN, a) 5 deg C, 10 min, b) RT, 15 min; Yield given. Multistep reaction;

benzyl chloroformate (501-53-1) + 3-amino-5-methoxyisoxazole (32326-25-3) → methyl 2-(5-benzyloxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate (150215-09-1)

Conditions	Yield
In acetonitrile	24.9%

[2-methyl-1-(pyrazolidine-1-carbonyl)-butyl]-carbamic acid tert-butyl ester + phosgene (75-44-5) + 3-amino-5-methoxyisoxazole (32326-25-3) → {1-[2-(5-methoxy-isoxazol-3-ylcarbamoyl)-pyrazolidine-1-carbonyl]-2-methyl-butyl}-carbamic acid tert-butyl ester

Conditions	Yield
With pyridine In dichloromethane; toluene at 20℃;

methyl chloroformate (79-22-1) + 3-amino-5-methoxyisoxazole (32326-25-3) → [5-Amino-3-(1,2,4-thiadiazole)]acetic acid, methyl ester

Conditions	Yield
In tetrahydrofuran; water

Upstream product

• 15732-02-2 1-cyano-2,2-bis(methoxy)ethylene 

Downstream Products

• 150215-08-0 methyl 2-(5-phenoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate 
• 150215-09-1 methyl 2-(5-benzyloxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate 
• 150215-07-9 methyl 2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetate 

Relevant articles and documents

Process for preparing 1,2,4-thiadiazole derivatives

An improved process for the production of 5-amino-1,2,4-thiadiazol-3-yl-(2-(lower)-alkoxyimino)acetic acids starting from 5-substituted- or unsubstituted-3-amino-isoxazole compounds is disclosed herein. The title compounds are useful as acylating agents for the production of 7-acylaminocephalosporins.