2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole supplier

Name
2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole
EINECS
CAS No. 723286-98-4
Article Data25
CAS DataBase
Density 1.556 g/cm³
Solubility
Melting Point
Formula C₄H₂ClF₃N₂O
Boiling Point 144.323 °C at 760 mmHg
Molecular Weight 186.521
Flash Point 41.085 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5-(Trifluoromethyl)-2-(chloromethyl)-1,3,4-oxadiazole;
PSA 38.92000
LogP 1.82720

Synthetic route

: 762240-99-3
N'-(2-chloroacetyl)trifluoroacetohydrazide

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

Conditions

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

: 407-25-0
trifluoroacetic anhydride

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

Conditions

Conditions	Yield
In dichloromethane at 20℃;	49%

: 1538-08-5
2,2,2-trifluoroacetohydrazide

: 79-04-9
chloroacetyl chloride

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

Conditions

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℃;

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 37164-19-5
ethylene-d4-diamine

: C6H5(2)H4F3N4O

Conditions

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

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 107-15-3
ethylenediamine

: 763105-70-0
2,2,2-trifluoro-N’-[(2Z)-piperazin-2-ylidene]acetohydrazide

Conditions

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%

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 109-81-9
N-methyl-ethane-1,2-diamine

: 763105-73-3, 849944-46-3
2,2,2-trifluoro-N'-[(2Z)-4-methylpiperazin-2-ylidene]acetohydrazide

Conditions

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

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 4152-09-4
N-benzylethylenediamine

: 763105-74-4, 849944-48-5
N'-[(2Z)-4-benzylpiperazin-2-ylidene]-2,2,2-trifluoroacetohydrazide

Conditions

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

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 83-67-0
theobromine /

: 3,7-dimethyl-1-((5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione

Conditions

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

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 811-93-8
1,1-dimethylethylenediamine

: 723286-97-3
5,5-dimethyl-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

Conditions

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;

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 111-92-2
dibutylamine

: dibutyl-(5-trifluoromethyl-[1,3,4]oxadiazol-2-ylmethyl)-amine

Conditions

Conditions	Yield
In methanol at -40℃;

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 15967-72-3
(S)-1,2-diaminopropane

: 24424-99-5
di-tert-butyl dicarbonate

A: 1013657-13-0
tert-butyl (5S)-5-methyl-3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate

B: 1013657-14-1
tert-butyl (6S)-6-methyl-3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate

Conditions

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

...Expand

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 78-90-0, 6852-78-4, 10424-38-1, 15967-72-3
(R)-1,2-diaminopropane

: 24424-99-5
di-tert-butyl dicarbonate

A: 1013656-80-8
tert-butyl (5R)-5-methyl-3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate

B: 1013656-81-9
tert-butyl (6R)-6-methyl-3-(trifluoromethyl)-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate

Conditions

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.;

...Expand

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 140-89-6
potassium ethyl xanthogenate

: O-ethyl S-[(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)methyl]xanthate

Conditions

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

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 1308375-93-0
{(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

: C34H36F7N7O5

Conditions

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

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 42869-47-6
6-bromo-2-methyl-1H-imidazo[4,5-b]pyridine

: 2-((6-bromo-2-methyl-1H-imidazo[4,5-b]pyridin-1-yl)methyl)-5-(trifluoromethyl)-1,3,4-oxadiazole

Conditions

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

: 723286-98-4
2-trifluoromethyl-1,3,4-oxadiazol-5-ylmethyl chloride

: 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

Conditions	Yield
With caesium carbonate In acetonitrile

2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole Specification

The 2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole, with the CAS registry number 723286-98-4, is also known as 1,3,4-Oxadiazole, 2-(chloromethyl)-5-(trifluoromethyl)-. It belongs to the product categories of Heterocyclic Compounds; Heterocycles; Intermediates; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C₄H₂ClF₃N₂O and molecular weight is 186.52. What's more, its IUPAC name is the same with its product name. It can be used as sitagliptin intermediate and an anti-hypertensive agent for the treatment of diabetes and hypertension.

Physical properties about 2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole are: (1)ACD/LogP: -0.023; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.02; (4)ACD/LogD (pH 7.4): -0.02; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 23.13; (8)ACD/KOC (pH 7.4): 23.13; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 38.92 Å²; (13)Index of Refraction: 1.406; (14)Molar Refractivity: 29.481 cm³; (15)Molar Volume: 119.881 cm³; (16)Polarizability: 11.687×10^-24cm³; (17)Surface Tension: 30.62 dyne/cm; (18)Density: 1.556 g/cm³; (19)Flash Point: 41.085 °C; (20)Enthalpy of Vaporization: 36.567 kJ/mol; (21)Boiling Point: 144.323 °C at 760 mmHg; (22)Vapour Pressure: 6.44 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: FC(F)(F)c1nnc(o1)CCl
(2) InChI: InChI=1S/C4H2ClF3N2O/c5-1-2-9-10-3(11-2)4(6,7)8/h1H2
(3) InChIKey: GPXSXZGMVOSWMN-UHFFFAOYSA-N

Product Name

2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole

Synthetic route

2-Chloromethyl-5-trifluoromethyl-[1,3,4]oxadiazole Specification

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