[ CAS No. 288-42-6 ]

Name: 288-42-6|Oxazole|98%
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Product Details of [ 288-42-6 ]

CAS No. :	288-42-6	MDL No. :	MFCD00009751
Formula :	C₃H₃NO	Boiling Point :	69.5°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	69.06 g/mol	Pubchem ID :	9255
Synonyms :

Safety of [ 288-42-6 ]

Signal Word:	Danger	Class:	3,8
Precautionary Statements:	P210-P233-P280-P370+P378-P303+P361+P353-P305+P351+P338+P310	UN#:	2924
Hazard Statements:	H225-H318	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 288-42-6 ]

Upstream synthesis route of [ 288-42-6 ]
Downstream synthetic route of [ 288-42-6 ]

[ 288-42-6 ] Synthesis Path-Upstream 1~5

1
[ 288-42-6 ]
[ 124-38-9 ]
[ 74-88-4 ]
[ 31698-88-1 ]

Reference： [1] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8858 - 8859

2
[ 288-42-6 ]
[ 68-12-2 ]
[ 65373-52-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: at 20℃;	At -78 °C, a solution of F-1 (800mg, 11.58mmol) in THF was treated with 1.6 M solution of n-BuLi in hexanes (7.2 mL, 11.58 mmol). The reaction was stirred for 1 hour, and then a solution of DMF (0.89 mmol, 1 1.58mmol) in THF (8 mL) was added. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was treated with MeOH, filtered through Dowex 50W x 8-200 resin (H⁺ form, 1 : 1 ratio to oxazole F-1), and washed with MeOH. The combined filtrate was concentrated to obtain the crude aldehyde F-2a, F-ia . This material was then purified by column chromatography (100-200 mesh silica gel, 2percent Et₂0/CH₂C1₂) to obtain the purified aldehyde (900mg, 80percent) as a light brown liquid (R_f = 0.7(2percent Et₂0/CH₂C1₂)). This product was used in the next step without any characterization.

Reference： [1] Patent: WO2011/35009, 2011, A1, . Location in patent: Page/Page column 45-46
[2] Patent: WO2008/61109, 2008, A2, . Location in patent: Page/Page column 62
[3] Patent: WO2005/102998, 2005, A1, . Location in patent: Page/Page column 31
[4] Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 316, p. 95 - 103

3
[ 288-42-6 ]
[ 4394-85-8 ]
[ 65373-52-6 ]

Reference： [1] Patent: EP1731513, 2006, A1, . Location in patent: Page/Page column 18
[2] Patent: WO2007/37010, 2007, A1, . Location in patent: Page/Page column 32-34

4
[ 288-42-6 ]
[ 68-12-2 ]
[ 130551-92-7 ]

Reference： [1] Patent: US2009/170907, 2009, A1, . Location in patent: Page/Page column 46

5
[ 288-42-6 ]
[ 78191-00-1 ]
[ 77311-07-0 ]

Reference： [1] Patent: WO2009/77990, 2009, A1, . Location in patent: Page/Page column 94

[ 288-42-6 ] Synthesis Path-Downstream 1~25

1
[ 23012-13-7 ]
[ 288-42-6 ]

Reference： [1]Heterocycles,2000,vol. 53,p. 1167 - 1170
[2]Journal of the Chemical Society,1947,p. 96,100
[3]Journal of Organic Chemistry,1999,vol. 64,p. 4995 - 4998

2
[ 288-42-6 ]
[ 95-89-6 ]
[ 141995-01-9 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 257 - 272

3
[ 288-42-6 ]
[ 116332-54-8 ]
(4-fluoro-phenyl)(oxazol-2-yl)methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 5828 - 5831

4
[ 288-42-6 ]
[ 104863-65-2 ]
[ 898758-21-9 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 5828 - 5831

5
[ 288-42-6 ]
[ 93683-65-9 ]
3-nitro-6-oxazol-2-ylpyridine-2-carbonitrile [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2567 - 2571

6
[ 288-42-6 ]
[ 118994-84-6 ]
[ 130551-90-5 ]

Yield	Reaction Conditions	Operation in experiment
29%		A round bottom flask was charged with oxazole (476 mu^, 7.2 mmol) and THF (100 mL). The solution was cooled to -78 C. A solution of w-butyllithium (2.3 M in hexanes, 3.5 mL, 8.05 mmol) was added dropwise. After stirring at -78 C for 40 min, a solution of <strong>[118994-84-6]oxazole-4-carbaldehyde</strong> (773 mg, 7.96 mmol, in 8 mL THF) was added dropwise. The reaction was allowed to warm to room temperature. After 30 min, the reaction was quenched with sat NH4CI and extracted with CH2CI2 (3X). The organics were dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column (100% CH2Cl2 to 10% MeOH in CH2C12) and yielded bis(oxazol-4-yl)methanol (354 mg, 29%)as a light brown solid. NMR 400 MHz (CDC13) delta 7.93 (s, 2H), 7.73 (s, 2H), 5.87 (s, 1H), 3.52 (s, 1H). LCMS (ESI, m/z): 167 [M+H]+.
29%		Step 1: Preparation of bis(oxazol-4- l)methanol [00388] A round bottom flask was charged with oxazole (476 mu^, 7.2 mmol) and THF (100 mL). The solution was cooled to -78 C. A solution of w-butyllithium (2.3 M in hexanes, 3.5 mL, 8.05 mmol) was added dropwise. After stirring at -78 C for 40 min, a solution of <strong>[118994-84-6]oxazole-4-carbaldehyde</strong> (773 mg, 7.96 mmol, in 8 mL THF) was added dropwise. The reaction was allowed to warm to room temperature. After 30 min, the reaction was quenched with saturated NH4C1 and extracted with CH2C12 (3X). The organics were dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column (100% CH2Cl2 to 10% MeOH in CH2C12) and yielded bis(oxazol-4-yl)methanol (354 mg, 29%) as a light brown solid. XH NMR 400 MHz (CDC13) delta 7.93 (s, 2H), 7.73 (s, 2H), 5.87 (s, 1H), 3.52 (s, 1H). LCMS (ESI, m/z): 167.0 [M+H]+.
0.35 g (33.9%)	With n-butyllithium; In tetrahydrofuran; methanol; dichloromethane;	(d) To a solution of oxazole (0.4 ml (6.2 mmol) in 20 ml of THF cooled -78 C. under nitrogen was added 2.5M n-butyllithium (2.5 ml, 6.2 mmol). The mixture was stirred at -78 C. for 30 min and a solution of 4-oxazolylcarboxaldehyde (0.6 g, 6.2 mmol) in 25 ml of THF was added dropwise. The resulting mixture was warmed to room temperature and stirred overnight. The reaction mixture was quenched with a suspension of Dowex 50x2-200 (H+) in methanol (20 ml) and stirred for 30 min, filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in methylene chloride, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by chromatography on silica (5% methanol in MDC) to afford 0.35 g (33.9%) of 1,1-di(4-oxazolyl)-methanol.

0.35 g (33.9%)

With n-butyllithium; In tetrahydrofuran; methanol; dichloromethane;

(d) To a solution of oxazole (0.4 mL (6.2 mmol) in 20 mL of THE cooled to -78 C. under nitrogen was added 2.5M n-butyllithium (2.5 mL, 6.2 mmol). The mixture was stirred at -78 C. for 30 min and a solution of 4oxazolylcarboxaldehyde (0.6 g, 6.2 mmol) in 25 mL of THF was added dropwise. The resulting mixture was warmed to room temperature and stirred overnight. The reaction mixture was quenched with a suspension of Dowex 50*2-200 in methanol (20 mL) and stirred for 30 min, filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in methylene chloride, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by chromatography on silica (5% methanol in MDC) to afford 0.35 g (33.9%) of 1,1-di(4-oxazolyl)methanol.

Reference： [1]Patent: WO2013/103973,2013,A1 .Location in patent: Paragraph 00160
[2]Patent: WO2013/142307,2013,A1 .Location in patent: Paragraph 00388
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 9062 - 9084
[4]Patent: US5569655,1996,A
[5]Patent: US5554620,1996,A

Yield	Reaction Conditions	Operation in experiment
		4,6-dimethyl-5-pyrimidinol and 2,4,6-trimethyl-5-pyrimidinol are prepared according to the method of A. Dornow and H. Hell, Chem. Ber. 93, 1998-2001 (1960), in which 3-chloro-2,4-pentanedione are reacted with formamide or acetamide to give the corresponding oxazole which is heated with ammona under pressure to give the desired 5-pyrimidinol.

8
[ 288-42-6 ]
[ 68-12-2 ]
[ 130551-92-7 ]

Yield	Reaction Conditions	Operation in experiment
		A. 1,3-Oxazol-2-ylmethanol To a solution of oxazole (0.66 mL, 10.0 mmol) in anh. THF (35 mL) at rt was added BH3.THF (10.0 mL of a 1.0M solution in THF, 10 mmol). The solution was stirred 1 h at rt, cooled to -78 C., and n-BuLi (4.40 mL of a 2.5M solution in hexanes, 11.0 mmol) was added dropwise over 5 min. The mixture was stirred 1 h 15 min at -78 C. and anh. DMF (0.85 mL, 11.0 mmol) was added dropwise. The mixture was gradually warmed to approx. -10 C. over 5 h, cooled to -78 C. and quenched by addition of 5% v/v HOAc/EtOH (35 mL). The cooling bath was removed, the mixture was stirred 18 h at rt and concentrated in vacuo. The residue was slurried in EtOAc and filtered through a coarse sinter. The filtrate was concentrated in vacuo and purified by flash chromatography (EtOAc/hexanes), affording 0.450 g of the title compound: 1H NMR (400 MHz, CDCl3) delta 7.64 (s, 1H), 7.09 (s, 1H), 4.75 (s, 2H), 4.55 (bs, 1H).

Reference： [1]Patent: US2009/170907,2009,A1 .Location in patent: Page/Page column 46

9
[ 288-42-6 ]
[ 623-00-7 ]
[ 87150-13-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4748 - 4760
[2]Tetrahedron,2009,vol. 65,p. 6348 - 6353

10
[ 288-42-6 ]
[ 38696-20-7 ]
[ 1217902-01-6 ]

Yield	Reaction Conditions	Operation in experiment
6%		Oxazole (124 mg, 1.8 mmol) was dissolved in stirring tetrahydrofuran (20 mL) under nitrogen at -78° C. and treated with n-butyllithium (2.0 M in cyclohexane, 1.1 mL, 2.2 mmol) maintaining internal temperature below -60° C. After stirring ten minutes, ZnCl2 (0.48 g, 3.5 mmol) was added portionwise. The cooling bath was removed and the solution was allowed to reach room temperature. Tetrakis(triphenylphosphine)palladium(0) (30 mg, 5 mole percent) and <strong>[38696-20-7]5-bromo-2-phenylpyrimidine</strong> (309 mg, 1.30 mmol) were added and the mixture heated at 60° C. for four hours. Solvent was removed under reduced pressure and the mixture partitioned between saturated aqueous ammonium chloride and ethyl acetate. The organic phase was retained and additional ethyl acetate extractions of the aqueous phase performed. The combined extracts were dried with anhydrous sodium sulfate, the solution filtered, and solvent removed under reduced pressure. Purification by silica gel flash chromatography (9:1 to 7:3 v/v hexane-ethyl acetate) through a 12-g Silicycle.(R). flash silica cartridge afforded the title compound as an off-white solid (17 mg, 6percent yield); Rf 0.66 with 3:1 v/v hexane-ethyl acetate; melting point 175-177° C.; 1H-NMR (300 MHz; DMSO-d6) delta 9.42 (s, 2H), 8.48 (dd, 2H), 8.41 (s, 1H), 7.56-7.62 (m, 3H), 7.54 (s, 1H); MS (ESI+) m/z 224 (M+1), (ESI-) m/z 222 (M-1); H-PGDS FPBA IC50: 7.8 muM.

Reference： [1]Patent: US2010/75990,2010,A1 .Location in patent: Page/Page column 43

11
[ 288-42-6 ]
[ 124-38-9 ]
[ 74-88-4 ]
[ 31698-88-1 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 8858 - 8859

12
[ 288-42-6 ]
[ 461-81-4 ]
[ 1239714-94-3 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3578 - 3581

13
[ 288-42-6 ]
[ 125872-95-9 ]
[ 1239714-96-5 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3578 - 3581

14
[ 288-42-6 ]
[ 38762-41-3 ]
[ 1079054-20-8 ]

Yield	Reaction Conditions	Operation in experiment
37%	With potassium carbonate; Trimethylacetic acid;palladium diacetate; catacxium A; In ISOPROPYLAMIDE; at 110℃;	Preparation 94: 2-Chloro-4-(oxazol-5-yl)aniline; [00264] Palladium acetate (5.4mg, 0.024mmol) was added to a solution of 4-bromo-2- chloroaniline (0.1 g, 0.484mmol), oxazole (0.064mL, 0.969mmol), di(1 -adamantyl)-/> butylphosphine (0.017g, 0.048mmol), pivalic acid (0.020g, 0.194mmol) and potassium carbonate (0.201 g, 1 .453mmol) in DMA (2.4ml_). The reaction mixture was heated at 1 10 C overnight before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to give the title product as a white solid (35mg, 37%). 1 H NMR (500 MHz, CDCI3): delta 4.25 (br s, 2H), 6.82 (d, J = 8.3Hz, 1 H), 7.20 (s, 1 H), 7.38 (dd, J = 8.3, 2.0Hz, 1 H), 7.58 (d, J = 2.0Hz, 1 H), 7.87 (s, 1 H).LC (Method B)-MS (ESI, m/z) fR 2.47 min, 195 [(M+H+), 100%].
37%	With palladium diacetate; potassium carbonate; catacxium A; Trimethylacetic acid; In N,N-dimethyl acetamide; at 110℃;	Preparation 94 2-Chloro-4-(oxazol-5-yl)aniline Palladium acetate (5.4 mg, 0.024 mmol) was added to a solution of 4-bromo-2-chloroaniline (0.1 g, 0.484 mmol), oxazole (0.064 mL, 0.969 mmol), di(1-adamantyl)-n-butylphosphine (0.017 g, 0.048 mmol), pivalic acid (0.020 g, 0.194 mmol) and potassium carbonate (0.201 g, 1.453 mmol) in DMA (2.4 mL). The reaction mixture was heated at 110 C. overnight before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to give the title product as a white solid (35 mg, 37%). 1H NMR (500 MHz, CDCl3): delta 4.25 (br s, 2H), 6.82 (d, J=8.3 Hz, 1H), 7.20 (s, 1H), 7.38 (dd, J=8.3, 2.0 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H), 7.87 (s, 1H). LC (Method B)-MS (ESI, m/z) tR 2.47 min, 195 [(M+H+), 100%].

Reference： [1]Patent: WO2012/123745,2012,A1 .Location in patent: Page/Page column 94
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 10045 - 10065
[3]Patent: US2013/345181,2013,A1 .Location in patent: Paragraph 0702-0703

15
[ 288-42-6 ]
[ 106-41-2 ]
[ 1128-71-8 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 5621 - 5630

16
[ 288-42-6 ]
[ 586-78-7 ]
[ 1014-23-9 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4748 - 4760
[2]European Journal of Organic Chemistry,2013,p. 5621 - 5630

17
[ 288-42-6 ]
[ 1158098-73-7 ]
C₁₀H₁₆N₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 36 5-Chloro-4-cyclopropylmethoxy-pyridine-2-carboxylic acid (3-oxazol-2-yl-oxetan-3- yl)-amide To a solution of oxazole (217 mg, 3.14 mmol) in 8mL dry THF under argon at room temperature was added BH3.THF (3.14 ml, 3.14 mmol), the reaction mixture was stirred at room temperature for 15 minutes, cooled down to -75 C followed by slow addition of BuLi (1.96 ml, 3.14 mmol). The resulting reaction mixture was stirred at -75C for 30 minutes and a solution of <strong>[1158098-73-7]2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide</strong> (CAN 1158098-73-7, 0.5 g, 2.85 mmol) in 4mL dry THF was added. The reaction mixture was stirred at -75C for 30minutes, then the reaction was let to warm up to room temperature and was stirred for 1 hour. The reaction was quenched by addition of lmL of an aqueous solution 7N ammoniun chloride and reaction mixture was stirred for 15 minutes. The mixture was diluted with ethylacetate, poured into a separatory funnel and extracted with water. The organic phase was collected, dried over sodium sulfate and evaporated down to dryness to give a yellow oil. The crude material was used without any further purification. To a solution of the former crude oil (697 mg, 2.85 mmol) in methanol (9 ml) cooled down to 0C was added a 4.0M solution of hydrochloric acid in dioxane (2.14 ml, 8.56 mmol). The reaction mixture was stirred at 0C for 1 hour. The reaction mixture was concentrated in vacuo, the residue was dissolved in diethyl ether and a precipitate formed. The suspension was stored in the fridge for 2 hours and then precipitate was collected by filtration. The collected solid was dried under high vaccum for 2 hours to give a crude yellow solid which was used without any purification. The crude solid was used to synthesize the title compound in analogy to Example 24d, using 5-Chloro-4- cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 4a) as starting material and could be isolated (15 mg, 39%) as white solid; MS (ESI, m/z): 350.5 (M+H+).

Reference： [1]Patent: WO2014/86805,2014,A1 .Location in patent: Page/Page column 65-66

18
[ 288-42-6 ]
[ 50638-46-5 ]
2-(2-chloro-4-methoxyphenyl)oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium tert-butylate; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere;	A mixture of 1 -bromo-2-chloro-4-methoxybenzene (1.5 g, 6.8 mmol), oxazole (878 mg, 12.7 mmol), /-BuOK (1.52 g, 13.5 mmol) and tetrakis (1.56 g, 1.35 mmol) in dioxane (10 mL) was heated to 100C under N2 atmosphere for 4 hr. After cooling to r.t., the reaction mixture was concentrated under reduced pressure to give the crude product which was purified by flash chromatography (silica gel, 0 to 25% EA in PE) to afford 2-(2-chloro-4-methoxyphenyl)oxazole (40) (600 mg, 42 % yield) as a yellow solid. LC-MS (ESI): mlz (M+l) 210.0.

Reference： [1]Patent: WO2016/4272,2016,A1 .Location in patent: Paragraph 00597

19
[ 288-42-6 ]
[ 51554-95-1 ]
2-(4-pentylphenyl)oxazole [ No CAS ]

Reference： [1]MedChemComm,2016,vol. 7,p. 1952 - 1956

20
[ 288-42-6 ]
[ 19063-56-0 ]
7-(oxazol-2-yl)-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With copper(l) iodide; palladium diacetate; In N,N-dimethyl-formamide; at 20 - 140℃; for 1.5h;Inert atmosphere; Sealed tube; Microwave irradiation;	General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel).

Reference： [1]Synlett,2018,vol. 29,p. 2412 - 2416

21
[ 288-42-6 ]
[ 623-00-7 ]
4-(oxazol-2-yl)benzonitrile [ No CAS ]
[ 87150-13-8 ]
[ 55368-59-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4748 - 4760

22
[ 156780-52-8 ]
[ 288-42-6 ]
[ 623-00-7 ]
4-(2-(4-methoxyphenyl)oxazol-5-yl)benzonitrile [ No CAS ]
[ 87150-13-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4748 - 4760

23
[ 288-42-6 ]
[ 623-00-7 ]
[ 87150-13-8 ]
4-(oxazol-2-yl)benzonitrile [ No CAS ]
[ 55368-59-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4748 - 4760

24
[ 288-42-6 ]
[ 577-19-5 ]
[ 89808-75-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4748 - 4760

25
[ 288-42-6 ]
[ 916792-13-7 ]
2-fluoro-5-methyl-4-(oxazol-2-yl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With n-butyllithium; zinc(II) chloride; In tetrahydrofuran; hexane; at -70 - 60℃;Inert atmosphere;	a) 2-Fluoro-5-methyl-4-(oxazol-2-yl)benzonitrile I64 To a solution of oxazole (90 mg, 1.31 mmol) in THF (10 ml.) at -70 C under N2 was added n-BuLi (2.5 M solution in hexane, 1.1 ml_, 2.66 mmol) and the mixture was stirred for 10 min. Solid ZnCI2 (380 mg, 2.79 mmol) was added and the mixture was allowed to warm to RT. 4-Bromo-2-fluoro-5-methylbenzonitrile (200 mg, 0.93 mmol) was added and the mixture was heated at 60 C overnight. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (Pet. ether/EtOAc 10/1) to give the title compound (50 mg, 27%) as a white solid. LCMS-D: Rt2.51 min; m/z 203.0 [M+H]+.

Reference： [1]Patent: WO2019/243491,2019,A1 .Location in patent: Page/Page column 93-94

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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
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
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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. 288-42-6 ]

Quality Control of [ 288-42-6 ]

Related Doc. of [ 288-42-6 ]

Product Details of [ 288-42-6 ]

Safety of [ 288-42-6 ]

Application In Synthesis of [ 288-42-6 ]

[ 288-42-6 ] Synthesis Path-Upstream 1~5

[ 288-42-6 ] Synthesis Path-Downstream 1~25

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry