Methyl 1,2,4-triazole-3-carboxylate supplier

Name
Methyl 1,2,4-triazole-3-carboxylate
EINECS 480-470-5
CAS No. 4928-88-5
Article Data8
CAS DataBase
Density 1.38 g/cm³
Solubility
Melting Point 196-199 °C(lit.)
Formula C₄H₅N₃O₂
Boiling Point 283.9 °C at 760 mmHg
Molecular Weight 127.103
Flash Point 125.5 °C
Transport Information
Appearance white crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1H-1,2,4-Triazole-3-carboxylicacid, methyl ester (9CI);s-Triazole-3-carboxylic acid, methyl ester (7CI,8CI);3-Methoxycarbonyl-1,2,4-triazole;Methyl1H-1,2,4-triazole-3-carboxylate;
PSA 67.87000
LogP -0.40870

Synthetic route

: 67-56-1
methanol

: 4928-87-4
1,2,4-triazole-3-carboxylic acid

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With thionyl chloride at 0 - 65℃; for 3h;	97%
With thionyl chloride at 10 - 20℃;	80%
With hydrogenchloride

: 67-56-1
methanol

: 124-41-4
sodium methylate

: C3H2Cl3N3

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
at 50℃; for 3h;	91.2%

...Expand

: 3641-14-3
5-amino-1H-[1,2,4]-triazole-3-carboxylic acid methyl ester

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With sodium hypophosphite; phosphoric acid; sodium nitrite In water at 0 - 20℃; for 1h; Reagent/catalyst; Temperature;	75%

: 67-56-1
methanol

: 26663-10-5
monopotassium salt of 1,2,4-triazole-3,5-dicarboxylic acid

A: 26663-15-0
dimethyl 1H-1,2,4-triazole-3,5-dicarboxylate

B: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With hydrogenchloride at 0℃; for 2h;	A 17% B 15%

...Expand

: 67-56-1
methanol

: 3641-08-5
1,2,4-triazole-3-carboxamide

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 4h;

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 13035-61-5
1,2,3,5-tetraacetylribose

: 57198-04-6, 39925-10-5
1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol	95%
With toluene-4-sulfonic acid In ethanol	92%
With toluene-4-sulfonic acid In 2-methyl-propan-1-ol	92%

: 930-68-7
cyclohexenone

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: methyl 1-(3-oxocyclohexyl)-1H-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In acetonitrile at 23℃; for 1h; Michael Addition;	95%

: 1,2,3-tri-O-acetyl-α,β-D-ribofuranose-5-[phenylbis(isoamyl-L-aspartyl)]phosphate

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 1-(methyl 1H-1,2,4-triazole-3-carboxylate-1-yl)-2',3'-di-O-acetyl-β-D-ribofuranose-5-[phenylbis(isoamyl-L-aspartyl)]phosphate

Conditions

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane at 20℃; for 24h; Vorbrueggen Nucleoside Synthesis; diastereoselective reaction;	92%

: 108-91-8
cyclohexylamine

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: N-cyclohexyl-1H-1,2,4-triazole-3-carboxamide

Conditions

Conditions	Yield
With trimethylaluminum In toluene at 0℃; for 9h; Inert atmosphere; Reflux;	92%

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 21732-98-9
1H-[1,2,4]triazole-3-carboxylic acid hydrazide

Conditions

Conditions	Yield
With hydrazine hydrate In methanol for 24h; Reflux;	91%

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 13035-61-5
1,2,3,5-tetraacetylribose

: 38934-69-9
methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With methanol; sodium iodide at 65℃; for 1h; Reagent/catalyst;	90%
With trifluorormethanesulfonic acid at 55℃; for 1h; Microwave irradiation;	246.92 g

: 105-39-5
chloroacetic acid ethyl ester

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: methyl 1-(2-ethoxy-2-oxoethyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 24h;	89%

: 352-13-6
4-flourophenylmagnesium bromide

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: bis(4-fluorophenyl)(1H-1,2,4-triazol-3-yl)methanol

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0 - 20℃; Grignard Reaction; Inert atmosphere;	89%

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 39925-12-7
methyl 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol	85%

: 144490-03-9
1,2,3,5-tetra-O-acetyl-β-L-ribofuranose

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

A: 263708-15-2
methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-5-carboxylate

B: 206269-26-3
methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With Bis(p-nitrophenyl) phosphate at 165 - 175℃; for 0.416667h; Condensation;	A 11% B 84%

...Expand

: 76-83-5
trityl chloride

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 151607-70-4
1-trityl-1H-[1,2,4]triazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In methanol; N,N-dimethyl-formamide	84%
With triethylamine In N,N-dimethyl-formamide	84%
With triethylamine In DMF (N,N-dimethyl-formamide) at 25℃; for 96h;	84%

: 95-64-7
4-amino-o-xylene

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: N-(3,4-dimethylphenyl)-1H-1,2,4-triazole-3-carboxamide

Conditions

Conditions	Yield
With trimethylaluminum In toluene at 0℃; for 9h; Inert atmosphere; Reflux;	83%

: 28708-32-9
1,2,3,5-tetra-O-acetyl-D-ribofuranose

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 57198-04-6, 39925-10-5
1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With iodine at 100 - 115℃; for 3h; Temperature;	82%
tin(IV) chloride In dichloromethane at 5 - 20℃; for 2h; Heating / reflux;

: 444019-07-2
1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-D-ribofuranose

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

A: 1065271-43-3
1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester

B: 1065271-44-4
2-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With Bis(p-nitrophenyl) phosphate at 165℃; for 1.5h;	A 81% B 3%

...Expand

: 769-92-6
4-tert-Butylaniline

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: N-(4-(tert-butyl)phenyl)-1H-1,2,4-triazole-3-carboxamide

Conditions

Conditions	Yield
With trimethylaluminum In toluene at 0℃; for 9h; Inert atmosphere; Reflux;	81%

: (2R,3R,4R,5R)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-2,3,4-triyl tribenzoate

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 1254180-64-7
methyl 1-(2-methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃; for 3h;	80%

: 201287-82-3
1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyle

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: methyl 1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With Bis(p-nitrophenyl) phosphate at 165 - 175℃; for 0.416667h; Condensation;	79%

: 645-15-8
Bis(p-nitrophenyl) phosphate

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 13035-61-5
1,2,3,5-tetraacetylribose

: 57198-04-6, 39925-10-5
1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
In cyclohexane; benzene	77.8%

...Expand

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 13035-61-5
1,2,3,5-tetraacetylribose

: 36791-04-5
ribavirin

Conditions

Conditions	Yield
With Bis(p-nitrophenyl) phosphate at 80 - 147℃; for 0.833333h; Temperature; Large scale;	77.1%

: 170079-20-6
1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-L-erythro-pentofuranose

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 263708-28-7
methyl 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With Bis(p-nitrophenyl) phosphate at 165 - 175℃; for 0.416667h; Condensation;	77%

: 659722-55-1
1,2,3,5-tetra-O-acetyl-α-L-ribofuranose

: 144490-03-9
1,2,3,5-tetra-O-acetyl-β-L-ribofuranose

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 206269-26-3
methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1,2,3,5-tetra-O-acetyl-α-L-ribofuranose; 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose; methyl 1H-1,2,4-triazole-3-carboxylate With acetic anhydride In dichloromethane at 90 - 120℃; under 22.5023 Torr; for 1.33333h; Stage #2: With trifluorormethanesulfonic acid at 110 - 120℃; for 4h;	75.1%

...Expand

: 41295-55-0
4-(chloromethyl)-7-methoxy-2H-chromen-2-one

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: methyl 1-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: methyl 1H-1,2,4-triazole-3-carboxylate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 4-(chloromethyl)-7-methoxy-2H-chromen-2-one In N,N-dimethyl-formamide at 80℃;	75%

: 74-89-5
methylamine

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: N-methyl-1H-1,2,4-triazole-3-carboxamide

Conditions

Conditions	Yield
In methanol for 1h; Reflux;	73%

: 145828-13-3
α-D-1,3,5-tri-O-benzoyl-2-O-[3-(trifluoromethyl)benzoyl]ribofuranose

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 1384470-92-1
methyl 1-((2R,3R,4R,5R)-4-(benzoyloxy)-5-((benzoyloxy)methyl)-3-((3-(trifluoromethyl)benzoyl)oxy)tetrahydrofuran-2-yl)-1H-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 120℃; for 15h; Microwave irradiation; regioselective reaction;	72%

: 659722-55-1
1,2,3,5-tetra-O-acetyl-α-L-ribofuranose

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 206269-26-3
methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1,2,3,5-tetra-O-acetyl-α-L-ribofuranose; methyl 1H-1,2,4-triazole-3-carboxylate In acetic acid methyl ester at 90℃; Stage #2: With trifluorormethanesulfonic acid In acetic acid methyl ester at 115℃; under 22.5023 Torr; for 4h;	70%
With trifluorormethanesulfonic acid In acetic acid methyl ester at 90 - 115℃; under 22.5023 Torr; for 4h;	70%

: 915694-38-1
(3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: methyl 1-((3aR,3bR,4aS,5R,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-yl)-1H-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: methyl 1H-1,2,4-triazole-3-carboxylate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Stage #2: (3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol In tetrahydrofuran at 20℃;	68%

: 144490-03-9
1,2,3,5-tetra-O-acetyl-β-L-ribofuranose

: 4928-88-5
methyl 1H-1,2,4-triazole-3-carboxylate

: 206269-26-3
methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

Conditions

Conditions	Yield
With Bis(p-nitrophenyl) phosphate at 160 - 165℃; for 0.416667h;	66%

Methyl 1,2,4-triazole-3-carboxylate Specification

The 1H-1,2,4-Triazole-5-carboxylicacid, methyl ester, with the CAS registry number 4928-88-5, has the systematic name of methyl 1H-1,2,4-triazole-5-carboxylate. It belongs to the following product categories: Aromatic Esters; Building Blocks; Heterocyclic Building Blocks; Triazoles. And the molecular formula of the chemical is C₄H₅N₃O₂.

The physical properties of 1H-1,2,4-Triazole-5-carboxylicacid, methyl ester are as followings: (1)ACD/LogP: -0.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.66; (4)ACD/LogD (pH 7.4): -0.77; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 10.34; (8)ACD/KOC (pH 7.4): 8.16; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 57.01 Å²; (13)Index of Refraction: 1.534; (14)Molar Refractivity: 28.64 cm³; (15)Molar Volume: 92 cm³; (16)Polarizability: 11.35×10^-24cm³; (17)Surface Tension: 63.5 dyne/cm; (18)Density: 1.38 g/cm³; (19)Flash Point: 125.5 °C; (20)Enthalpy of Vaporization: 52.29 kJ/mol; (21)Boiling Point: 283.9 °C at 760 mmHg; (22)Vapour Pressure: 0.00307 mmHg at 25°C.

Uses of 1H-1,2,4-Triazole-5-carboxylicacid, methyl ester: It can react with 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-L-erythro-pentofuranose to produce methyl 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-b-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate. This reaction will need reagent bis(p-nitrophenyl)phosphate. The reaction time is 25 minutes with temperature of 77°C, and the yield is about 92%.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)c1ncnn1
(2)InChI: InChI=1/C4H5N3O2/c1-9-4(8)3-5-2-6-7-3/h2H,1H3,(H,5,6,7)
(3)InChIKey: QMPFMODFBNEYJH-UHFFFAOYAX

Product Name

Methyl 1,2,4-triazole-3-carboxylate

Synthetic route

Methyl 1,2,4-triazole-3-carboxylate Specification

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