[ CAS No. 1192-80-9 ] {[proInfo.proName]}

Name: 1192-80-9|3-(Chloromethyl)-5-methyl-1,2,4-oxadiazole|98%
Brand: Ambeed
SKU: A116661
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Quality Control of [ 1192-80-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1192-80-9 ]

CAS No. :	1192-80-9	MDL No. :	MFCD01809083
Formula :	C₄H₅ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZFYVXZGJPJTIPQ-UHFFFAOYSA-N
M.W :	132.55	Pubchem ID :	302157
Synonyms :

Calculated chemistry of [ 1192-80-9 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	29.03
TPSA :	38.92 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.72
Log Po/w (XLOGP3) :	0.96
Log Po/w (WLOGP) :	0.96
Log Po/w (MLOGP) :	-0.13
Log Po/w (SILICOS-IT) :	1.84
Consensus Log Po/w :	1.07

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.66
Solubility :	2.88 mg/ml ; 0.0217 mol/l
Class :	Very soluble
Log S (Ali) :	-1.36
Solubility :	5.72 mg/ml ; 0.0432 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.24
Solubility :	0.764 mg/ml ; 0.00577 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.33

Safety of [ 1192-80-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501	UN#:	3265
Hazard Statements:	H302-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1192-80-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1192-80-9 ]
Downstream synthetic route of [ 1192-80-9 ]

[ 1192-80-9 ] Synthesis Path-Upstream 1~4

1
[ 25977-23-5 ]
[ 1192-80-9 ]
[ 959406-40-7 ]

Reference： [1] Patent: US2017/298052, 2017, A1, . Location in patent: Paragraph 0887-0890
[2] Patent: US2017/291892, 2017, A1, . Location in patent: Paragraph 0842; 0843; 0844; 0845

2
[ 108-24-7 ]
[ 3272-96-6 ]
[ 1192-80-9 ]

Yield	Reaction Conditions	Operation in experiment
22.2%	at 20 - 130℃; for 3 h;	[2-CHLORO-N-HYDROXY-ACETAMIDINE] (217 mg, 2 mmol) was mixed with acetic anhydride (224.4 mg, 2.2 mmol) in dichloromethane (2 mL) at room temperature for 1 hour. Then DMF (1 mL) was added in and the reaction mixture was heated at [130 °C] for 2 h. The reaction was quenched with saturated sodium carbonate and extracted with ethyl acetate. The organic layer was dried and concentrated to give 59 mg (22.2percent) of the title compounds as a crude yellow oil, which could be used for the next step reaction without further purification. lH NMR [(CDC13),] 5 (ppm): 4. 51 (s, [2H),] 2.55 (s, 3H).

Reference： [1] Patent: WO2004/14902, 2004, A2, . Location in patent: Page 43
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2769 - 2772

3
[ 3272-96-6 ]
[ 1192-80-9 ]

Reference： [1] Patent: US5428047, 1995, A,

4
[ 108-24-7 ]
[ 3272-96-6 ]
[ 1192-80-9 ]

Reference： [1] Patent: WO2014/48065, 2014, A1, . Location in patent: Page/Page column 95

[ 1192-80-9 ] Synthesis Path-Downstream 1~30

1
[ 110-86-1 ]
[ 1192-80-9 ]
1-(5-methyl-[1,2,4]oxadiazol-3-ylmethyl)-pyridinium; chloride [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1979,vol. 16,p. 1477 - 1481

2
[ 108-24-7 ]
[ 3272-96-6 ]
[ 1192-80-9 ]

Yield	Reaction Conditions	Operation in experiment
22.2%	In DMF (N,N-dimethyl-formamide); dichloromethane; at 20 - 130℃; for 3h;	[2-CHLORO-N-HYDROXY-ACETAMIDINE] (217 mg, 2 mmol) was mixed with acetic anhydride (224.4 mg, 2.2 mmol) in dichloromethane (2 mL) at room temperature for 1 hour. Then DMF (1 mL) was added in and the reaction mixture was heated at [130 C] for 2 h. The reaction was quenched with saturated sodium carbonate and extracted with ethyl acetate. The organic layer was dried and concentrated to give 59 mg (22.2%) of the title compounds as a crude yellow oil, which could be used for the next step reaction without further purification. lH NMR [(CDC13),] 5 (ppm): 4. 51 (s, [2H),] 2.55 (s, 3H).

Reference： [1]Patent: WO2004/14902,2004,A2 .Location in patent: Page 43
[2]Journal of the Chemical Society. Perkin transactions I,1973,p. 2769 - 2772

3
[ 1192-80-9 ]
[ 603-35-0 ]
[ 51640-56-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1973,p. 2769 - 2772

6
[ 1192-80-9 ]
[ 17231-95-7 ]
3-(2,3-dichloro-phenylthiomethyl)-5-methyl-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Example 7 3-(2,3-Dichloro-phenylthiomethyl)-5-methyl-1,2,4-oxadiazole STR23 7.0 g (39.1 mmol) of 2,3-dichloro-thiophenol are introduced into 50 ml of absolute tetrahydrofuran, the mixture is treated with 1.2 g (0.039 mmol) of 80% sodium hydride dispersion in portions and stirred for 2 hours at reflux temperature. The mixture is subsequently treated with 4.5 g (33.9 mmol) of <strong>[1192-80-9]3-chloromethyl-5-methyl-1,2,4-oxadiazole</strong> at room temperature and stirred until the reaction is complete (approximately 10 to 15 hours). The sodium chloride which has precipitated is subsequently separated off and the entire batch is concentrated in vacuo. The crude product which remains can be chromatographed over a silica gel column (silica gel 60-Merck, particle size: 0.040 to 0.063 mm) using toluene as the eluent. 3.8 g (36.5% of theory) of 3-(2,3-dichlorophenylthiomethyl)-5-methyl-1,2,4-oxadiazole are obtained. M.p.: 66 to 68 C. 1 H-NMR (CDCl3), delta, ppm): 2.57 (s, 3H, hetarom. H); 4.17 (s, 2H, --CH2 --S--); 7.13-7.36 (m, 3H, arom. H)

Reference： [1]Patent: US5428047,1995,A

7
[ 3272-96-6 ]
[ 1192-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bicarbonate; acetic anhydride; In ethyl acetate;	54.6 g (0.5 mol) of chloroacetamide oxime are introduced into 96 ml of acetic anhydride and the mixture is stirred for 2 hours at 120 to 130 C. The entire batch is subsequently concentrated in vacuo, neutralised using sodium hydrogen carbonate and extracted using ethyl acetate. The organic phase is dried over magnesium sulphate, the solvent is distilled off, and the oily residue is distilled in vacuo. 27.3 g (41.2% of theory) of 3-chloromethyl-5-methyl-1,2,4-oxadiazole are obtained. B.p.12mbar: 60 to 75 C. 1 H-NMR (CDCl3, delta, ppm): 2.63 (s, 3H, --CH3); 4.59 (s, 2H, --CH2 --Cl)

Reference： [1]Patent: US5428047,1995,A

8
[ 1192-80-9 ]
[ 81721-86-0 ]
[ 120101-64-6 ]

Yield	Reaction Conditions	Operation in experiment
	In water; ethyl acetate;	STR89 A mixture of 7-nitro-2H-1,4-benzoxazin-3(4H)-one (3.88 g) (this compound can be obtained by a process shown in J. Chem. Soc., 1928, p. 3046, or Synthesis, 1982, p. 986), potassium carbonate (3.1 g) and acetonitrile (80 ml) was prepared. To this mixture was dropwise added <strong>[1192-80-9]3-chloromethyl-5-methyl-1,2,4-oxadiazole</strong> (2.92 g) at a temperature of 40 to 50 C. The reaction mixture was continuously stirred under refluxing for 4 hours, and then cooled. After that, the solvent was distilled off under a reduced pressure, and the residue was admixed with ethyl acetate (150 ml) and water (50 ml). The organic layer was separated, washed with a 5% aqueous potassium hydroxide solution, with water and then with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure, and the residue thus obtained was recrystallized from toluene, so that the aimed compound, i.e. 4-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-7-nitro-2H-1,4-benzoxazin-3-(4H)-one (3.22 g) was obtained. m.p. 182-183 C.

Reference： [1]Patent: US4902335,1990,A

9
[ 1192-80-9 ]
[ 3485-82-3 ]
7-[(5-methyl-1,2,4-oxadiazol-3-yl)-methyl]-theophylline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.2%		g. 20.2 g. of theophylline-sodium, 300 cm3 isopropyl alcohol and 13.2 g. of <strong>[1192-80-9]3-chloromethyl-5-methyl-1,2,4-oxadiazole</strong> are heated under stirring for 10 hours. After processing 20.5 g. (74.2% yield) of 7-(5-methyl-1,2,4-oxadiazol-3-yl)-methyl-theophylline are obtained. M.p.: 134-135 C.

Reference： [1]Patent: US4565817,1986,A

10
[ 1192-80-9 ]
[ 156-57-0 ]
2-[(5-methyl-1,2,4-oxadiazol-3-yl)methylthio]ethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol;	A. 2-[(5-Methyl-1,2,4-oxadiazol-3-yl)methylthio]ethylamine Cysteamine hydrochloride (3.03 g; 26.7 mmoles) was added in several portions over a period of 10 minutes to a stirred solution of sodium methylate (2.89 g; 53.4 mmoles) in 50 ml of methanol at 0. After stirring for 70 minutes at 0, a solution of <strong>[1192-80-9]3-chloromethyl-5-methyl-1,2,4-oxadiazole</strong> (3.54 g; 26.7 mmoles) in 15 ml of methanol was added dropwise over a period of 15 minutes, and the reaction mixture was allowed to stir at ambient temperature for 16 hours. The mixture was filtered, evaporated and redissolved in isopropyl alcohol, then filtered and evaporated under reduced pressure to give the title compound (5.64 g) as a yellow oil. The NMR spectrum (60 MHz) in CDCl3 gave the following resonances delta: 3.77 (s, 2H); 2.77 (m, 4H); 2.63 (s, 3H).

Reference： [1]Patent: US4471122,1984,A

11
[ 1192-80-9 ]
[ 24549-06-2 ]
[ 74704-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;	PREPARATION OF THE STARTING MATERIAL (II-2) STR88 13 g (0.1 mol) of <strong>[1192-80-9]3-chloromethyl-5-methyl-1,2,4-oxadiazole</strong> were added dropwise to a mixture of 27 g (0.2 mol) of 2-ethyl-6-methyl-aniline and 13.8 g (0.1 mol) of potassium carbonate at 100 C., while stirring. The reaction mixture was subsequently stirred at 100 C. for 6 hours and then poured onto water. The mixture was extracted with methylene chloride and the organic phase was dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The residue was distilled under a high vacuum. 5.2 g (22.5% of theory) of 2-ethyl-6-methyl-N-(5'-methyl-1',2',4'-oxadiazol-3'-yl-methyl)-aniline of boiling point 132 C./0.2 mm Hg and with a melting point of 54-55 C. were obtained.

Reference： [1]Patent: US4338119,1982,A

12
[ 1192-80-9 ]
[ 208580-23-8 ]
[ 1258213-54-5 ]

Yield	Reaction Conditions	Operation in experiment
89.13%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 2h;	Intermediate 51Ethyl 7-bromo-1-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylateTo a stirred solution of <strong>[208580-23-8]ethyl 7-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate</strong> (Intermediate 55, 3.5 g, 11.82 mmol) in dry dimethylformamide (40 mL), potassium carbonate (4.90 g, 85.47 mM) was added and stirred at room temperature. To the above reaction mixture 3-chloromethyl-5-methyl-1,2,4-oxadiazole (3.5 mL, 26.60 mmol) was added and the mixture was stirred at 80 C. for 2 h. After the completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to dryness. The residue was triturated with petroleum ether (40 mL) to obtain solid compound which was filtered and dried to afford 4.1 g (89.13%) of ethyl 7-bromo-1-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate as pale brown solid.1H NMR (400 MHz, DMSO-d6): delta 1.29 (t, 3H), 2.50 (s, 3H), 4.22-4.27 (q, 2H), 5.89 (s, 2H), 7.63-7.65 (m, 1H), 7.97 (d, 1H), 8.12-8.14 (d, 1H), 8.85 (s, 1H).LC-MS: m/z 392.1 (M+H).

Reference： [1]Patent: US2010/317624,2010,A1 .Location in patent: Page/Page column 61

13
[ 1192-80-9 ]
[ 1402428-39-0 ]
[ 1426825-55-9 ]

Yield	Reaction Conditions	Operation in experiment
		Scheme 4 CI Step 1 CI Step 1 A solution of 0.103 g (0.205 mmol) of compound 6, 0.004 g (0.10 mmol) of sodium borohydride, and 0.057 g (0.41 mmol) of potassium carbonate in 2.1 mL of methanol was stirred at room temperature for 20 min. To this solution was added 0.054 g (0.41 mmol) of compound 12, and the reaction was stirred for 1 h. After this time, the reaction was quenched with 10 mL of saturated aqueous ammonium chloride and extracted with three 10 mL of methylene chloride. The combined organics were dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the crude product 13 which was used directly without further purification: MS: Calcd. for C24H23ClF2N2Na05S2 (MNa+), m/z = 579.1; found 579.1. Retention time: 2.31 min.

Reference： [1]Patent: WO2013/36464,2013,A1 .Location in patent: Page/Page column 21; 22

14
[ 1192-80-9 ]
1-(4-methoxybenzyl)-5,6,7,8-tetrahydropyrazolo[3,4-b]azepin-4(1H)-one [ No CAS ]
[ 1448437-87-3 ]

Yield	Reaction Conditions	Operation in experiment
61%		Under N2, to a solution of l-(4-methoxybenzyl)- 5,6,7,8-tetrahydropyrazolo[3,4-]azepin-4(lH)-one (0.50 g, 1.84 mmol) in THF (15 mL) were added consecutively 15-crown-5 (0.61 g, 2.76 mmol), NaOtBu (0.35 g, 3.69 mmol) and after stirring for 10 min, 3-(chloromethyl)-5-methyl-l,2,4-oxadiazole (0.37 g, 2.76 mmol). The mixture was stirred at reflux for 2 h. The reaction was quenched with water and the mixture was diluted with EtOAc. The separated aqueous layer was extracted with EtOAc. The organic layers were combined, dried over MgS04, filtered and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel using yclohexane/EtOAc (100:0 to 30:70) as eluent to afford the title compound (410 mg, 61%). UPLC-MS (Ml): RT = 0.82 min; MS m/z ES+= 368.3.
61%		1-(4-Methoxybenzyl)-8-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-5,6,7,8-tetrahydro pyrazolo[3,4-b]azepin-4(1H)-one According to Scheme 3, Step 1: Under N2, to a solution of 1-(4-methoxybenzyl)-5,6,7,8-tetrahydropyrazolo[3,4-b]azepin-4(1H)-one (0.50 g, 1.84 mmol) in THF (15 mL) were added consecutively 15-crown-5 (0.61 g, 2.76 mmol), NaOtBu (0.35 g, 3.69 mmol) and after stirring for 10 min, <strong>[1192-80-9]3-(chloromethyl)-5-methyl-1,2,4-oxadiazole</strong> (0.37 g, 2.76 mmol). The mixture was stirred at reflux for 2 h. The reaction was quenched with water and the mixture was diluted with EtOAc. The separated aqueous layer was extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel using yclohexane/EtOAc (100:0 to 30:70) as eluent to afford the title compound (410 mg, 61%). UPLC-MS (M1): RT=0.82 min; MS m/z ES+=368.3.

Reference： [1]Patent: WO2013/107862,2013,A1 .Location in patent: Page/Page column 67; 68
[2]Patent: US2014/349994,2014,A1 .Location in patent: Paragraph 0575; 0576

15
[ 1192-80-9 ]
[ 1523412-59-0 ]
[ 1523404-27-4 ]

Reference： [1]Patent: WO2013/190510,2013,A2 .Location in patent: Page/Page column 133

16
[ 1192-80-9 ]
[ 1523413-55-9 ]
[ 1523408-89-0 ]

Reference： [1]Patent: WO2013/190510,2013,A2 .Location in patent: Page/Page column 184

17
[ 108-24-7 ]
[ 3272-96-6 ]
[ 1192-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	at 125℃; for 2h;	Step 2: 2-Chloro-N-hydroxyethanimidamide (0.2 g) was added to Ac20 (132.6 g) and the mixture was stirred for 2 hours at 125C. The reaction mixture was neutralized using sodium carbonate and extracted with EtOAc (2 L). The organic layer was dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to afford 3-(chloromethyl)-5- methyl- 1,2,4-oxadiazole. 1H NMR (300 MHz, CDC13) delta 2.62 (s, 3 H), 4.58 (s, 2 H).

Reference： [1]Patent: WO2014/48065,2014,A1 .Location in patent: Page/Page column 95

18
[ 1192-80-9 ]
[ 1172111-81-7 ]
tert-butyl methyl((2S,3S)-3-((5-methyl-1,2,4-oxadiazol-3-yl)methoxy)-2-(naphthalen-2-yl)-3-phenylpropyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26.8%		To an ice-cooled stirred suspension of the sodium hydride (75 mg, 1.88 mmol) in 2.5 mL DMF was added drop- wise a solution of Compound No. 8a (210 mg, 0.54 mmol) in 0.75 mL DMF. After stirring for 30 minutes at 0C, a solution of 3- (chloi methyl)-5-methyl-l,2,4-oxadiazole (140 mg, 1.06 mmol) in DMF (0.5 mL)) was added. The resulting mixture was allowed to gradually warm to 25C over 4 hours, was diluted with ether (30 mL), was washed with water and brine, was aqueous back-extracted with ether. The organics were combined, dried, and concentrated to give crude product. This product was subjected to ISCO automated flashchromatography, eluting with a 0-50% EtOAc/hexanes gradient to give purified tert- butyl methyl((25',35)-3-((5-methyl-l,2,4-oxadiazol-3-yl)methoxy)-2-(naphthalen-2- yl)-3-phenylpropyl)carbamate (70.0 mg, 26.8 %).

Reference： [1]Patent: WO2014/159251,2014,A2 .Location in patent: Page/Page column 131-132

19
[ 1192-80-9 ]
[ 1523412-61-4 ]
[ 1523404-56-9 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 376 - 400

20
[ 1192-80-9 ]
3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol [ No CAS ]
5-{4-cyclobutyl-2-fluoro-3-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl}pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; acetonitrile; at 80℃;	General procedure: To a 5 mL vial containing a stir bar, 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (50 mg, 0.19 mmol) and 4-fluorobenzonitrile (26 mg, 0.21 mmol) were added Cs2CO3(96 mg, 0.29 mmol) and 0.55 mL DMSO. The resultant mixture was stirred at 80 Celsius for approximately 15 hours. The mixture was cooled to room temperature and then passed through a syringe filter. The filtrate was subjected to FCC to give the title compound (36 mg, 52%). The title compound was prepared using conditions similar to those described in Example 101 using acetonitrile with 10% DMF as the solvent and <strong>[1192-80-9]3-(chloromethyl)-5-methyl-1,2,4-oxadiazole</strong>. MS (ESI): mass calcd. for C18H18FN5O2, 355.14; m/z found, 356.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.51-8.46 (m, 1H), 8.09 (d, J=1.4, 1H), 7.61 (m, 1H), 7.16 (d, J=8.2, 1H), 5.15 (s, 2H), 4.72 (s, 2H), 3.91-3.79 (m, 1H), 2.65 (s, 3H), 2.39-2.27 (m, 2H), 2.20-1.96 (m, 3H), 1.92-1.79 (m, 1H).

Reference： [1]Patent: US2014/221310,2014,A1 .Location in patent: Paragraph 0365; 0366; 0303; 0304

21
[ 1192-80-9 ]
[ 5466-88-6 ]
4-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 1821 - 1836

22
[ 1192-80-9 ]
[ 623-33-6 ]
ethyl 2-[(5-methyl-1,2,4-oxadiazol-3-yl)methylamino]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; sodium iodide; In acetonitrile; at 0 - 20℃;	Step 1 Synthesis of Ethyl 2-[[(5-Methyl-1,2,4-oxadiazol-3-yl)methylamino]acetate (0508) Glycine ethyl ester hydrochloride (105 mg, 0.754 mmol) was dissolved in acetonitrile (10 mL), and potassium carbonate (313 mg, 2.26 mmol) was added thereto. After the mixture was cooled to 0 C., <strong>[1192-80-9]3-(chloromethyl)-5-methyl-1,2,4-oxadiazole</strong> (100 mg, 0.754 mmol) diluted with acetonitrile (1 mL) and sodium iodide (113 mg, 0.754 mmol) were added thereto. While the temperature was being gradually returned to room temperature, the mixture was stirred overnight. After insoluble matters were separated by filtration, the filtrate was concentrated under reduced pressure to obtain a crude product of Step 1. (0509) Yield: 272 mg (0510) MS (ESI) m/z 200 [M+H]+

Reference： [1]Patent: US2016/46592,2016,A1 .Location in patent: Paragraph 0508; 0509; 0510

23
[ 1192-80-9 ]
2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6'-methyl-5'-(trifluoromethyl)-[2,3-bipyridin]-6-yl)acetamide [ No CAS ]
2-(3-methyl-1-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6'-methyl-5'-(trifluoromethyl)-[2,3'-bipyridin]-6-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29.5%	With potassium carbonate; In N,N-dimethyl-formamide; at 55℃; for 18h;Inert atmosphere;	2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6?-methyl-5?-(trifluoromethyl)-[2,3- bipyridin]-6-yl)acetamide (50 mg, 0.109 mmol) and potassium carbonate (25 mg, 0.327 mmol) were combined in DMF (3 mL) then <strong>[1192-80-9]3-(chloromethyl)-5-methyl-1,2,4-oxadiazole</strong> (16 mg, 0.120 mmol) was added. The reaction was heated at 55oC for 18 h, cooled to RT then concentrated to a residue which was purified by chromatography eluted with MeOH/DCM (1:99 to 3:97) to give 2- (3-methyl-1-((5-methyl-1,2,4-oxadiazol-3-yl)methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)- N-(6?-methyl-5?-(trifluoromethyl)-[2,3?-bipyridin]-6-yl)acetamide (18 mg, 29.5% yield) as a light tan solid.1H NMR (CDCl3) delta: 9.26 (brd s, 1H), 9.14 (s, 1H), 8.47 (s, 1H), 8.08 (brd s, 1H), 7.84-7.75 (m, 2H), 7.54 (d, J = 8 Hz, 1H), 5.35 (s, 2H), 5.16 (s, 2H) 3.62 (s, 3H), 2.77 (s, 3H), 2.47 (s, 3H). LCMS: MH+ 556 and TR = 2.962 min.

Reference： [1]Patent: WO2016/44792,2016,A1 .Location in patent: Page/Page column 303; 304

24
[ 1192-80-9 ]
6-(5-chloro-2-[(2,4-dimethoxyphenyl)methyl](oxan-4-yl)amino}pyrimidin-4-yl)-2,3-dihydro-1H-isoindol-1-one [ No CAS ]
6-(5-chloro-2-[(2,4-dimethoxyphenyl)methyl](oxan-4-yl)amino}pyrimidin-4-yl)-2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-2,3-dihydro-1H-isoindol-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20℃; for 22h;	Preparation 66: 6-(5-chloro-2-[(2,4-dimethoxyphenyl)methyl](oxan-4-yl)amino}pyrimidin- 4-yl)-2-[(5-methyl-1 ,2,4-oxadiazol-3-yl)methyl]-2,3-dihydro-1 H-isoindol-1-one (1588) (1589) A solution of 6-(5-chloro-2-[(2,4-dimethoxyphenyl)methyl](oxan-4-yl)amino}pyrimidin-4-yl)-2,3- dihydro-1 H-isoindol-1-one (50 mg, 0.10 mmol) in THF (0.5 mL) was cooled to -78 C and treated with a lithium bis(trimethylsilyl)amide (1 M in THF, 0.15 mL, 0.15 mmol). The solution was stirred for 30 min, then treated with 3-(chloromethyl)-5-methyl-1 ,2,4-oxadiazole (20 mg, 0.15 mmol), and the mixture allowed to warm to RT and stirred for 18 h. A further portion of lithium bis(trimethylsilyl)amide (1 M in THF, 0.15 mL, 0.15 mmol) was added and the reaction was stirred for 10 min, before 3-(chloromethyl)-5-methyl-1 ,2,4-oxadiazole (10 mg, 0.075 mmol) was added and the mixture stirred for 4 h. The mixture was treated with tetrabutylammonium iodide (3 mg, 0.008 mmol) and stirred for 3 days. Brine (5 mL) was added and the mixture was extracted with ethyl acetate (3x5 mL). The combined organic phases were washed with brine (5 mL), dried (Na2S04) and concentrated. Purification by chromatography (S1O2, 10-100% ethyl acetate in iso-hexane) gave the title compound (1 1 mg, 0.015 mmol, 15 %) as a yellow glass. LC-MS: [M+H]+ =591.

Reference： [1]Patent: WO2017/68412,2017,A1 .Location in patent: Page/Page column 210

25
[ 1192-80-9 ]
(1S,3'R,6'R,7'S,8'E,12'R)-6-chloro-7'-hydroxy-12'-methyl-3,4-dihydro-2H,15'H-spiro[naphthalene-1,22'-[20]oxa[13]thia[1,14]diazatetracyclo[14.7.2.0³'⁶.0¹⁹'²⁴]pentacosa[8,16,18,24]tetraen]-15'-one 13',13'-dioxide [ No CAS ]
(1S,3’R,6’R,7’S,8’E,12’R)-6-chloro-12'-methyl-7'-((5-methyl-1,2,4-oxadiazol-3-yl)methoxy)-3,4-dihydro-2H,15’H-spiro[naphthalene-1,22'-[20]oxa[13]thia[1,14]diazatetracyclo[14.7.2.03,6.019,24]pentacosa[8,16,18,24]tetraen]-15'-one-13',13’-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		To a 2 rnL vial was added sodium hydride, 60% dispersion in mineral oil (2.0 mg, 0.049 mmol) and (1 S,3?R.6R,7S,8E, 12R)-6-chloro-7-hydroxv-12-methyl-3,4-dihvdro-2H, I 5H-spiro[naphthalene- 1,22-[20Ioxa[1 3]thia[ I, 14]diazatetracycio[14.7.2.036.0?9?24Ipentacosa[8, 16,1 8,24Itetrae n]-15-one 13,13-dioxide (Example 404, Step 1) (5.7 mg. 9.7 pmol) in TI-IF (0.33 ml) at ambient temperature. The reaction mixture was stirred for 5 mm, and then 3-(chloromethvi)-5-methyi- 1 ,2,4-oxadiazole (3.9 rng, 0.029 mmoi) was added.The reaction mixture was stirred at ambient temperature for I 7h. The reaction mixture was diluted with MeOI-I. filtered and purified by I-iPLC (5% to 95% MeCN/H20 with 0.1% TFA) to give the title product, (2,6 mg, 39%). 1H NMR (500 MHz, CDC13) oe 7.95 (s, 1H). 7.70 (d, J8.6 Hz, 1H), 7.19 (dci, J8.6, 2.2 Hz, 1H), 7.09 (ci, J2.2 Hz, 1H), 6,92 (d,J8.i Hz. 1H), 6.87 (dd,J8.i, 2,0 Hz, 1H),6.80 (d, J1.7 Hz, IH), 5.88 (ddd, J15.2, ).3 3.9 Hz, IH), 5.61 (dd, J15.4, 9.0 Hz, 11:1), 4.57 (d, J:::i3, 2 Hz, IH), 4.45 (d, J:::13,2 Hz, il-i), 434-422 (m, IH),4.07 (q, J=12. 1 Hz, 2H), 3.93 (dd, .J9.0, 3.4 Hz, 1H), 3.83 (d, J=14.9 Hz, 1H),3.72 (d, J=14.4 Hz, IH), 3.22 (d, J=14.2 Hz, 1H), 2.98 (dcl, J=15.3, 10.4 Hz, 1H),2.85-2.70 (m, 2H), 2.63 (s, 31-1), 2.60-2.51 (in, 11-1), 2.44-2.21 (m, 31-1), 2.09-1.91(4H. in), 1.91-1,74 (31-1, rn). 1.70-1.62 (in, 11-1), 1.60 (d, .J::6.8 FIz. 3H). 139 (t, J=13.0 Hz, 1H): MS (ES) m/z [M÷H] = 680.8.

Reference： [1]Patent: WO2017/147410,2017,A1 .Location in patent: Page/Page column 1417; 1418

26
[ 1192-80-9 ]
methyl N-((1S,3’R,6’R,7’S,8’E,12’R)-6-chloro-12’-methyl-13',13'-dioxido-15'-oxo-3,4-dihydro-2Hspiro[naphthalene-1,22’-[20]oxa[13]thia[1,14]diazatetracyclo[14.7.2.03,6.019,24]pentacosa[8,16,18,24]tetraen]-7'-yl)glycinate trifluoroacetic acid [ No CAS ]
(1S,3’R,6'R,7’S,8’E,12’R)-7'-(bis((5-methyl-1,2,4-oxadiazol-3-yl)methyl)amino)-6-chloro-12'-methyl-3,4-dihydro-2H,15’H-spiro[naphthalene-1,22’-[20]oxa[13]thia[1,14]diazatetracyclo[14.7.2.03,6.019,24]pentacosa[8,16,18,24]tetraen]-15'-one-13',13'-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a 2 mL vial was added N,N-diisopropylethyl amine (5.38 il, 0.031 mmol) and (1 S,3R,6?R.7S,8E, I 2R)-6-chloro- 12-methyi-7?-amino-3,4-dihydro- ZR, 1 5H-spiro[naphthalene- 1,22?-[20]oxa[ l3ithia[i, l4idiazatetracycio[14. 7.2.03?6.0?924]pentacosa[8, 16,1 8,24]tetrae ni-IS-one 13,13-dioxide trifluoroacetate from Example 599. step 8 (6.0 rng, 10 imoi) in MeCN (0.34 ml) at ambient temperature. The reaction mixture was stirred for 5 mm, and then 3-(chiorornethyl)-5-rnethyi-1,2,4-oxadiazoie (4.1 rng, 0.031 rnmoi) was added. The reaction mixture was stirred at 70 C for 16 h. Thesolution was diluted with MeOH. filtered and purified by FIPLC (5% to 95%MeCN/H20 with 0.1% TFA) to give the dialkylated product. ?H NMR (500 MHz,CDCI3) d 7.86 (, I H), 7.69 (d, J8.6 Hz, I H), 7.18 (dd, J=8.4, 2.3 Hz, I H),7.09 (d. j:::22 FIz, 11-1), 6.94 - 6.89 (in, 11-1), 6.87 - 6.82 (in, 11-1), 6.74 (d, J:::j,5Hz, 1 H), 5.83 -5.74(m, 1 5.63 (dd,Ji4.9, 8.8 Hz, I H),4.23 -4.15 (m, I H), 412- 392 (ni. 6 H), 3.80 (d, J:::15,9 Hz, 1 H), 3.71 (d. J:::13,7 Hz, I H). 343(d,J9.8 Hz, I H), 3.20 (d,J=139 Hz, I H), 2.98 (dd,J=15.5, 10.4Hz, 1 H), 285- 2.73 (rn, 2 H), 2.72 - 2.65 (rn, 1 H), 2.63 (s, 6 H), 2.32 (t, J=8.2 Hz, 2 H), 2.21(ci, J=16.1 Hz, 1 1-1), 2.07- 1.89 (rn, 5 H), 1.88 1.67 (rn, 4H), 1.58 (d. J=6.8 Hz,3 H), 1.38 (t. J:::i2,3 Hz, 1 H): MS (ESI) m/z 775.8 [M+H].

Reference： [1]Patent: WO2017/147410,2017,A1 .Location in patent: Page/Page column 1416; 1417

27
[ 25977-23-5 ]
[ 1192-80-9 ]
[ 959406-40-7 ]

Yield	Reaction Conditions	Operation in experiment
		Under argon, 0.95 g (7.91 mmol, 95% purity) of (5-methyl-1,2,4-oxadiazol-3-yl)methanol and 1.43 ml (10.28 mmol, 1.3 eq.) of triethylamine were dissolved in 11 ml of DMF and cooled to 0 C. At this temperature, 0.796 ml (10.28 mmol, 1.3 eq.) of methanesulphonyl chloride was added dropwise and the mixture was stirred at 0 C. for 1 h. 1.92 g (22.14 mmol, 2.8 eq.) of lithium bromide were then added, and the mixture was stirred at 0 C. for 1 h. The reaction mixture was admixed with 60 ml of water and 15 g of sodium chloride and extracted four times with diethyl ether. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated. The residue was purified by means of Biotage-Isolera (eluent: dichloromethane, then dichloromethane/methanol 20:1). Yield: 610 mg (43% of theory) (0889) LC/MS [Method 9]: Rt=2.80 min; MS (ESIneg): m/z=175 (M-H)-, (0890) LC/MS [Method 9]: Rt=2.31 min; MS (ESIpos): m/z=133 (M+H)+.
		[0843] Under argon, 0.95 g (7.91 mmol) of (5-methyl-i, 2,4-oxadiazol-3-yl)methanol and 1.43 ml (10.28 mmol, 1.3 eq.) of triethylamine were dissolved in ii ml of DMF and cooled to 0 C. At this temperature, 0.796 ml (10.28 mmol, 1.3 eq.) of methanesulphonyl chloride was added dropwise and the mixture was stirred at 00 C. for 1 h. 1.92 g (22.14 mmol, 2.8 eq.) of lithium bromide were then added, and the mixture was stirred at 00 C. for 1 h. The reaction mixture was admixed with 60 ml of water and 15 g of sodium chloride and extracted four times with diethyl ethet The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated. The residue was purified by means of normal phase flash chromatography (eluent: dichloromethane, then dichloromethane/methanol 20:1). Yield: 610 mg (43% of theory)j0844] LC/MS [Method 9]: R=2.80 mm; MS (ESIneg):m1z175 (M-H)-,10845] LC/MS [Method 9]: R=2.3i mm; MS (ESIpos):m1z133 (M+H).

Reference： [1]Patent: US2017/298052,2017,A1 .Location in patent: Paragraph 0887-0890
[2]Patent: US2017/291892,2017,A1 .Location in patent: Paragraph 0842; 0843; 0844; 0845

28
[ 1192-80-9 ]
[ 790667-99-1 ]
tert-butyl (2S,4S)-2-methyl-4-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate; In acetonitrile; at 5 - 20℃;	3-(Chloromethyl)-5-methyl-1,2,4-oxadiazole (43.5 g, 301 mmol) is added to a solution of tert-butyl (2S,4S)-4-hydroxy-2-methyl-piperidine-1-carboxylate (29.5 g, 137 mmol) in acetonitrile (590 mL) at room temperature. The reaction mixture is stirred in an ice-water bath and sodium tert-butoxide (54.3 g, 548 mmol) is added in portions over 10 minutes, maintaining an internal temperature below 10 C. The reaction mixture is stirred in an ice-water bath at an internal temperature of 5 C. for 9 hours, then is warmed slowly to room temperature and is stirred overnight. The reaction mixture is cooled in an ice-water bath and saturated aqueous ammonium chloride solution (200 mL) is added over 5 minutes, maintaining an internal temperature below 10 C. during the addition. The mixture is then diluted with water (100 mL) and warmed to room temperature. The mixture is extracted with methyl tert-butyl ether (2*300 mL) and the combined organics are washed with brine (300 mL). The combined organics are dried over sodium sulfate, filtered and concentrated to give a residue. The residue is passed quickly through a pad of silica gel (300 g) eluting with methyl tert-butyl ether (1 L) and the filtrate is concentrated to give the title compound (46.5 g, 109%). MS m/z 334.0 (M+Na).
	With sodium t-butanolate; In acetonitrile; at 5 - 20℃;	3-(Chloromethyl)-5-methyl-l,2,4-oxadiazole (43.5 g, 301 mmol) is added to a solution of tert-butyl (2S,4S)-4-hydroxy-2-methyl-piperidine-l-carboxylate (29.5 g, 137 mmol) in acetonitrile (590 mL) at room temperature. The reaction mixture is stirred in an ice-water bath and sodium tert-butoxide (54.3 g, 548 mmol) is added in portions over 10 minutes, maintaining an internal temperature below 10 C. The reaction mixture is stirred in an ice-water bath at an internal temperature of 5 C for 9 hours, then is warmed slowly to room temperature and is stirred overnight. The reaction mixture is cooled in an ice- water bath and saturated aqueous ammonium chloride solution (200 mL) is added over 5 minutes, maintaining an internal temperature below 10 C during the addition. The mixture is then diluted with water (100 mL) and warmed to room temperature. The mixture is extracted with methyl tert-butyl ether (2 x 300 mL) and the combined organics are washed with brine (300 mL). The combined organics are dried over sodium sulfate, filtered and concentrated to give a residue. The residue is passed quickly through a pad of silica gel (300 g) eluting with methyl tert-butyl ether (1 L) and the filtrate is concentrated to give the title compound (46.5 g, 109%). MS m/z 334.0 (M+Na).

Reference： [1]Patent: US2018/215751,2018,A1 .Location in patent: Paragraph 0050; 0052
[2]Patent: WO2020/28141,2020,A1 .Location in patent: Page/Page column 14

29
[ 1192-80-9 ]
[ 42869-47-6 ]
3-((6-bromo-2-methyl-1H-imidazo[4,5-b]pyridin-1-yl)methyl)-5-methyl-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.43 g	With tetra-(n-butyl)ammonium iodide; potassium hydroxide; In tetrahydrofuran; at 60℃; for 2h;Inert atmosphere;	Potassium hydroxide (1.270 g) was added to a mixture of <strong>[42869-47-6]6-bromo-2-methyl-1H-imidazo[4,5-b]pyridine</strong> (1.600 g), 3-(chloromethyl)-5-methyl-1,2,4-oxadiazole (1 g), TBAI (2.79 g) and THF (10 mL) at 60C. The mixture was stirred under a nitrogen atmosphere at 60C for 2 hours. The mixture was poured into water at room temperature, and extracted with ethyl acetate. The organic layer was washed with water and a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (0.430 g). 1H NMR (300 MHz, DMSO-d6) delta2.54 (3H, s), 2.60 (3H, s), 5.73 (2H, s), 8.33 (1H, d, J = 2.2 Hz), 8.43 (1H, d, J = 2.2 Hz).

Reference： [1]Patent: EP3450436,2019,A1 .Location in patent: Paragraph 0451

30
[ 1192-80-9 ]
[ 269410-08-4 ]
5-methyl-3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃;Inert atmosphere;	Pyrazole-4-boronic acid pinacol ester (106 mg, 0.535 mmol), 3-(chloromethyl)-5- methyl-1,2,4-oxadiazole (145 mg, 1.07 mmol) and potassium carbonate (142 mg, 1.03 mmol) were added in vial under nitrogen. Anhydrous DMF (1.5 mL) was then added and the reaction mixture was heated to 50 C overnight. The remaining salts were filtered off and after evaporation of the volatiles under reduced pressure, the title product was used onto the next step (69 mg, 47%).

Reference： [1]Patent: WO2019/74962,2019,A1 .Location in patent: Paragraph 0160; 0184

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P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1192-80-9 ] {[proInfo.proName]}

Quality Control of [ 1192-80-9 ]

Related Doc. of [ 1192-80-9 ]

Product Details of [ 1192-80-9 ]

Calculated chemistry of [ 1192-80-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1192-80-9 ]

Application In Synthesis of [ 1192-80-9 ]

[ 1192-80-9 ] Synthesis Path-Upstream 1~4

[ 1192-80-9 ] Synthesis Path-Downstream 1~30

Related Functional Groups of [ 1192-80-9 ]

Chlorides

Related Parent Nucleus of [ 1192-80-9 ]

Oxadiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1192-80-9 ]

Related Parent Nucleus of
[ 1192-80-9 ]