56563-01-0

Basic information

• Product Name: ETHYL 2-(1H-1,2,4-TRIAZOL-1-YL)ACETATE
• Synonyms: ETHYL 2-(1H-1,2,4-TRIAZOL-1-YL)ACETATE;ETHYL-2-(1H-1,2,4-TRIAZOLE-1-YL)ACETATE;ETHYL 2-(1H-1,2,4-TRIAZOLE-1-YL)ACETIC ACID;Ethyl 1H-1,2,4-triazol-1-ylacetate
• CAS NO: 56563-01-0
• Molecular Formula: C₆H₉N₃O₂
• Molecular Weight: 155.15
• Mol File: 56563-01-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 277.5 °C at 760 mmHg
• Flash Point: 121.7 °C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 0.0045mmHg at 25°C
• Refractive Index: 1.556
• PKA: 2.29±0.10(Predicted)
• CAS DataBase Reference: ETHYL 2-(1H-1,2,4-TRIAZOL-1-YL)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-(1H-1,2,4-TRIAZOL-1-YL)ACETATE(56563-01-0)
• EPA Substance Registry System: ETHYL 2-(1H-1,2,4-TRIAZOL-1-YL)ACETATE(56563-01-0)

Safety Data

• Hazardous Substances Data: 56563-01-0(Hazardous Substances Data)

Usage

General Description

ETHYL 2-(1H-1,2,4-TRIAZOL-1-YL)ACETATE is a chemical compound with the molecular formula C6H8N4O2. It is a colorless liquid with a fruity odor, commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. It is also used as a solvent and in the production of other chemicals. ETHYL 2-(1H-1,2,4-TRIAZOL-1-YL)ACETATE is a stable compound under normal conditions, but should be handled with care as it can cause skin and eye irritation. It is important to follow safety precautions and handle this chemical in a well-ventilated area.

InChI:InChI=1/C6H9N3O2/c1-2-11-6(10)3-9-5-7-4-8-9/h4-5H,2-3H2,1H3

Synthetic route

1,2,4-Triazole (288-88-0) + chloroacetic acid ethyl ester (105-39-5) → ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0)

Conditions	Yield
With potassium carbonate In 1,4-dioxane for 6h; Heating;	84%
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetone at 50 - 55℃; for 4h;	76%
With sodium hydroxide In N,N-dimethyl-formamide for 1h; Ambient temperature;	70%
With sodium ethanolate In ethanol at 70℃; for 12h; sealed tube;	69%

1,2,4-Triazole (288-88-0) + chloroacetic acid ethyl ester (105-39-5) → ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + ethyl 4H-1,2,4-triazol-4-yl-acetate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0 - 20℃; Alkylation;	A 69% B n/a

1,2,4-Triazole (288-88-0) + ethyl bromoacetate (105-36-2) → ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	65%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	65%
With potassium carbonate In N,N-dimethyl-formamide for 16h;	56%
With sodium ethanolate

1,2,4-Triazole (288-88-0) + ethyl bromoacetate (105-36-2) → ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + ethyl 4H-1,2,4-triazol-4-yl-acetate

Conditions	Yield
With sodium ethanolate 1.) EtOH, RT, 2 h, 2.) EtOH, overnight; Yield given. Multistep reaction;
With sodium ethanolate 1.) EtOH, RT, 2 h, 2.) EtOH, overnight; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1,2,4-Triazole (288-88-0) + α-bromoacetophenone (70-11-1) → ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0)

Conditions	Yield
With ethanol; sodium Yield given. Multistep reaction;

sodium triazole (41253-21-8) + ethyl bromoacetate (105-36-2) → ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0)

Conditions	Yield
In N,N-dimethyl-formamide at -10 - 20℃; for 20h;

2-(1H-1,2,4-triazol-1-yl)acetic acid (28711-29-7) + ethanol (64-17-5) → ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0)

Conditions	Yield
With hydrogenchloride at 20℃;

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + formic acid ethyl ester (109-94-4) → Sodium; (E)-2-ethoxycarbonyl-2-[1,2,4]triazol-1-yl-ethenolate (82248-27-9)

Conditions	Yield
With sodium In ethanol; toluene at 31℃; for 2h;	98.5%

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → 2-(1H-1,2,4-triazol-1-yl)acetohydrazide (56563-02-1)

Conditions	Yield
With hydrazine hydrate for 5h; Reflux;	94%
With hydrazine hydrate In 1,4-dioxane for 5h; Heating;	82%
With hydrazine hydrate In ethanol for 24h; Ambient temperature;	71%

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + aniline (62-53-3) → α-(1,2,4-triazole-1-yl)-N-phenylacetamide (154221-24-6)

Conditions	Yield
In ethanol for 15h; Heating;	82%

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + benzylamine (100-46-9) → N-Benzyl-2-[1,2,4]triazol-1-yl-acetamide (156097-78-8)

Conditions	Yield
In ethanol for 15h; Heating;	81%

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + thiosemicarbazide (79-19-6) → (N1-1,2,4-triazolylacetyl)-thiosemicarbazide (503524-74-1)

Conditions	Yield
In 1,4-dioxane for 7h; Heating;	81%

propylamine (107-10-8) + ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → N-Propyl-2-[1,2,4]triazol-1-yl-acetamide (156097-77-7)

Conditions	Yield
In ethanol for 15h; Heating;	78%

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + α-bromoacetophenone (70-11-1) → (1-N-carbethoxymethylene-4-N-phenacyl)-1,2,4-triazolium bromide (133593-04-1)

Conditions	Yield
In acetone Heating;	77%
In acetone

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + hydroxylamine O-picryl ether (38100-34-4) → 4-amino-1-ethoxycarbonylmethyl-1,2,4-triazolium picrate

Conditions	Yield
In dichloromethane at 20℃;	76%

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + 4-Nitrophenacyl bromide (99-81-0) → (1-N-carbethoxymethylene-4-N-p-nitrophenacyl)-1,2,4-triazolium bromide (133593-05-2)

Conditions	Yield
In acetone Heating;	67%
In acetone

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → 2-(1H-1,2,4-triazol-1-yl)acetic acid (28711-29-7)

Conditions	Yield
With sodium hydroxide In methanol for 0.25h; Ambient temperature;	63%
With hydrogenchloride In water at 95℃; for 16h;	62%
With hydrogenchloride at 95℃; for 16h;	62%
With hydrogenchloride; water

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + 1-bromomethyl-4-bromobenzene (589-15-1) → ethyl 3-(4-bromophenyl)-2-(1H-1,2,4-triazol-1-yl)propanoate (501031-47-6)

Conditions	Yield
Stage #1: ethyl 2-(1H-1,2,4-triazol-1-yl)acetate With lithium diisopropyl amide In diethyl ether; hexane at -20℃; Inert atmosphere; Stage #2: 1-bromomethyl-4-bromobenzene In diethyl ether; hexane at -20 - 20℃; Inert atmosphere;	21%

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → 1-(2-hydroxyethyl)-1H-1,2,4-triazole (3273-14-1)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → 2-[1,2,4]triazol-1-yl-acetamide (63190-93-2)

Conditions	Yield
With methanol; ammonia

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → C6H7(2)H2N3O2

Conditions	Yield
With [(2)H6]acetone; water-d2; triethylamine for 53h; Ambient temperature;

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + benzyl bromide (100-39-0) → 4-benzyl-1-ethoxycarbonylmethyl-1H-[1,2,4]triazol-4-ium; bromide

Conditions	Yield
In acetone at 20℃; for 168000h; Alkylation;

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) + phenyl isothiocyanate (103-72-0) → 4-phenyl-3-(1,2,4-triazol-1-ylmethyl)-1,2,4-triazoline-5-thione

Conditions	Yield
With sodium hydroxide; hydrazine In water

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → C18H17N5O2S

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 168000 h / 20 °C 2: K2CO3 / CHCl3; ethanol / 168000 h / 20 °C View Scheme

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → C18H16N4O3S

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 168000 h / 20 °C 2: 28 percent / K2CO3 / CHCl3; ethanol / 168000 h / 20 °C View Scheme

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → C19H19N3O5

Conditions	Yield
Multi-step reaction with 3 steps 1: acetone / 168000 h / 20 °C 2: K2CO3 / CHCl3; ethanol / 168000 h / 20 °C 3: 30 percent / xylene / 24 h / Heating View Scheme

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → C18H17N5O2S

Conditions	Yield
Multi-step reaction with 3 steps 1: acetone / 168000 h / 20 °C 2: K2CO3 / CHCl3; ethanol / 168000 h / 20 °C 3: 35 percent / xylene / 24 h / Heating View Scheme

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → C21H25N3O6

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 168000 h / 20 °C 2: K2CO3 / CHCl3; ethanol / 168000 h / 20 °C View Scheme

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → C14H15N3O3

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / acetone / Heating 2: aq. K2CO3 / CH2Cl2 / 0.33 h View Scheme

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → C14H14N4O5

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / acetone / Heating 2: aq. K2CO3 / CH2Cl2 / 0.33 h View Scheme

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → 1-carbethoxymethylene, benzoyl 2,4,6-trinitrophenyl 4-triazolium-methylide

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / acetone / Heating 2: Et3N / CH2Cl2 / Ambient temperature View Scheme

ethyl 2-(1H-1,2,4-triazol-1-yl)acetate (56563-01-0) → 1-carbethoxymethylene, p-nitrobenzoyl 2,4,6-trinitrophenyl 4-triazolium-methylide

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / acetone / Heating 2: Et3N / CH2Cl2 / Ambient temperature View Scheme

Upstream product

• 41253-21-8 sodium triazole 
• 105-36-2 ethyl bromoacetate 
• 28711-29-7 2-(1H-1,2,4-triazol-1-yl)acetic acid 
• 64-17-5 ethanol 
• 288-88-0 1,2,4-Triazole 
• 105-39-5 chloroacetic acid ethyl ester 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 154221-24-6 α-(1,2,4-triazole-1-yl)-N-phenylacetamide 
• 156097-78-8 N-Benzyl-2-[1,2,4]triazol-1-yl-acetamide 
• 82248-31-5 (Z)-3-Benzyloxy-2-[1,2,4]triazol-1-yl-acrylic acid ethyl ester 
• 82248-32-6 (Z)-3-(4-Chloro-benzyloxy)-2-[1,2,4]triazol-1-yl-acrylic acid ethyl ester 
• 82248-33-7 (Z)-3-(3-Phenoxy-benzyloxy)-2-[1,2,4]triazol-1-yl-acrylic acid ethyl ester 
• 1109216-77-4 C₁₃H₁₃Cl₂N₃O₂ 
• 501031-47-6 ethyl 3-(4-bromophenyl)-2-(1H-1,2,4-triazol-1-yl)propanoate 
• 56563-02-1 2-(1H-1,2,4-triazol-1-yl)acetohydrazide 
• 133593-04-1 (1-N-carbethoxymethylene-4-N-phenacyl)-1,2,4-triazolium bromide 
• 133593-05-2 (1-N-carbethoxymethylene-4-N-p-nitrophenacyl)-1,2,4-triazolium bromide 
• 63190-93-2 2-[1,2,4]triazol-1-yl-acetamide 
• 28711-29-7 2-(1H-1,2,4-triazol-1-yl)acetic acid 

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