723286-98-4

Basic information

• Product Name: 2-CHLOROMETHYL-5-TRIFLUOROMETHYL-[1,3,4]OXADIAZOLE
• Synonyms: 2-CHLOROMETHYL-5-TRIFLUOROMETHYL-[1,3,4]OXADIAZOLE;5-(Trifluoromethyl)-2-(chloromethyl)-1,3,4-oxadiazole;1,3,4-Oxadiazole, 2-(chlo...;1,3,4-Oxadiazole, 2-(chloroMethyl)-5-(trifluoroMethyl)-;2-Chloromethyl-5-trifluoromethyl trifluoromethyl -[1,3,4]oxadiazole
• CAS NO: 723286-98-4
• Molecular Formula: C₄H₂ClF₃N₂O
• Molecular Weight: 186.5196896
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 723286-98-4.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 144.323 °C at 760 mmHg
• Flash Point: 41.085 °C
• Appearance: /
• Density: 1.556 g/cm³
• Vapor Pressure: 6.44mmHg at 25°C
• Refractive Index: 1.406
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Soluble), Methanol (Sparingly)
• PKA: -8.11±0.44(Predicted)
• CAS DataBase Reference: 2-CHLOROMETHYL-5-TRIFLUOROMETHYL-[1,3,4]OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROMETHYL-5-TRIFLUOROMETHYL-[1,3,4]OXADIAZOLE(723286-98-4)
• EPA Substance Registry System: 2-CHLOROMETHYL-5-TRIFLUOROMETHYL-[1,3,4]OXADIAZOLE(723286-98-4)

Safety Data

• Hazardous Substances Data: 723286-98-4(Hazardous Substances Data)

Usage

Description

2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole is a chemical compound characterized by its yellow liquid appearance. It is a derivative of the oxadiazole family, which is known for its diverse range of applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole is used as an intermediate in the synthesis of Sitagliptin, a medication that is particularly effective in the treatment of diabetes and hypertension. Its role in the pharmaceutical industry is crucial for the development of drugs that can help manage and treat these prevalent health conditions.
Used in Chemical Synthesis:
As a versatile chemical intermediate, 2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole can be utilized in the synthesis of various other compounds, contributing to the advancement of chemical research and development. Its unique properties make it a valuable building block for creating new molecules with potential applications in different fields.

InChI:InChI=1/C4H2ClF3N2O/c5-1-2-9-10-3(11-2)4(6,7)8/h1H2

Synthetic route

N'-(2-chloroacetyl)trifluoroacetohydrazide (762240-99-3) → 2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-ethane at 80 - 85℃; Reagent/catalyst; Temperature;	90.2%
With trichlorophosphate In acetonitrile at 100℃; Temperature;	87.73%
With trichlorophosphate In acetonitrile at 80℃; for 24h;	86%

5-chloromethyltetrazole + trifluoroacetic anhydride (407-25-0) → 2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4)

Conditions	Yield
In dichloromethane at 20℃;	49%

2,2,2-trifluoroacetohydrazide (1538-08-5) + chloroacetyl chloride (79-04-9) → 2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4)

Conditions	Yield
Stage #1: 2,2,2-trifluoroacetohydrazide; chloroacetyl chloride With triethylamine In acetonitrile at -5 - 5℃; for 3h; Stage #2: With trichlorophosphate In acetonitrile at 0 - 85℃;

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + ethylene-d4-diamine (37164-19-5) → C6H5(2)H4F3N4O

Conditions	Yield
With oxazepine In methanol at -20 - -10℃; for 2h;	80.44%

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + ethylenediamine (107-15-3) → 2,2,2-trifluoro-N’-[(2Z)-piperazin-2-ylidene]acetohydrazide (763105-70-0)

Conditions	Yield
In methanol at -20℃; for 1h;	74%
In methanol; ethanol at -20 - -5℃; for 2h;	72%
In methanol at -20℃; for 1h;	72%

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + N-methyl-ethane-1,2-diamine (109-81-9) → 2,2,2-trifluoro-N'-[(2Z)-4-methylpiperazin-2-ylidene]acetohydrazide (763105-73-3, 849944-46-3)

Conditions	Yield
In methanol at -20℃; for 1h;	74%

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + N-benzylethylenediamine (4152-09-4) → N'-[(2Z)-4-benzylpiperazin-2-ylidene]-2,2,2-trifluoroacetohydrazide (763105-74-4, 849944-48-5)

Conditions	Yield
In methanol at -20℃; for 1h;	67%

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + theobromine / (83-67-0) → 3,7-dimethyl-1-((5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 120℃; for 3h;	34%

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + 1,1-dimethylethylenediamine (811-93-8) → 5,5-dimethyl-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (723286-97-3)

Conditions	Yield
Stage #1: 2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride; 1,1-dimethylethylenediamine With N-ethyl-N,N-diisopropylamine In methanol at 0 - 20℃; for 2.5h; Stage #2: With superphosphoric acid at 110℃; for 18h; Further stages.;	8%
Stage #1: 2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride; 1,1-dimethylethylenediamine With N-ethyl-N,N-diisopropylamine In methanol at 0 - 20℃; for 2.5h; Stage #2: With superphosphoric acid at 110℃; for 18h;

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + dibutylamine (111-92-2) → dibutyl-(5-trifluoromethyl-[1,3,4]oxadiazol-2-ylmethyl)-amine

Conditions	Yield
In methanol at -40℃;

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + (S)-1,2-diaminopropane (15967-72-3) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (5S)-5-methyl-3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate (1013657-13-0) + tert-butyl (6S)-6-methyl-3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate (1013657-14-1)

Conditions	Yield
Stage #1: 2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride; (S)-1,2-diaminopropane With N-ethyl-N,N-diisopropylamine In methanol for 22h; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; for 1h; Further stages.;	A 103 mg B 243 mg

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + (R)-1,2-diaminopropane (78-90-0, 6852-78-4, 10424-38-1, 15967-72-3) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (5R)-5-methyl-3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate (1013656-80-8) + tert-butyl (6R)-6-methyl-3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate (1013656-81-9)

Conditions	Yield
Stage #1: 2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride; (R)-1,2-diaminopropane With N-ethyl-N,N-diisopropylamine In methanol for 22h; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; for 1h; Further stages.;

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + potassium ethyl xanthogenate (140-89-6) → O-ethyl S-[(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)methyl]xanthate

Conditions	Yield
In acetone at 0℃; for 1h;

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + {(R)-2-[3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-5-piperazin-1-yl-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (1308375-93-0) → C34H36F7N7O5

Conditions	Yield
With potassium carbonate In acetonitrile at 20 - 60℃; for 3h;

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + 6-bromo-2-methyl-1H-imidazo[4,5-b]pyridine (42869-47-6) → 2-((6-bromo-2-methyl-1H-imidazo[4,5-b]pyridin-1-yl)methyl)-5-(trifluoromethyl)-1,3,4-oxadiazole

Conditions	Yield
Stage #1: 6-bromo-2-methyl-1H-imidazo[4,5-b]pyridine With potassium tert-butylate In tetrahydrofuran at 45℃; for 0.5h; Stage #2: 2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 45℃; for 1h;	0.094 g

2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride (723286-98-4) + tert-butyl (5S)-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate → tert-butyl (5S)-3-oxo-2-{[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]methyl}-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate

Conditions	Yield
With caesium carbonate In acetonitrile

Upstream product

• 762240-99-3 N'-(2-chloroacetyl)trifluoroacetohydrazide 
• 407-25-0 trifluoroacetic anhydride 
• 1538-08-5 2,2,2-trifluoroacetohydrazide 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 763105-70-0 2,2,2-trifluoro-N’-[(2Z)-piperazin-2-ylidene]acetohydrazide 
• 763105-74-4 N'-[(2Z)-4-benzylpiperazin-2-ylidene]-2,2,2-trifluoroacetohydrazide 
• 723286-97-3 5,5-dimethyl-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine 

Relevant articles and documents

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