[ CAS No. 288-42-6 ] {[proInfo.proName]}

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Quality Control of [ 288-42-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 288-42-6 ]

SDS Specification

Alternatived Products of [ 288-42-6 ]

Product Citations

Surveying the scope of aromatic decarboxylations catalyzed by prenylated-flavin dependent enzymes

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. Faraday Discuss.,2024,252,208-222. DOI: 10.1039/D4FD00006D PubMed ID: 38837123

Abstract: The prenylated-flavin mononucleotide-dependent

Purchased from AmBeed: class="">27916-43-4 ; class="">2438-05-3 ; class="">501-89-3 ; class="">42287-94-5 ; class="">776-79-4 ; class="">53473-36-2 ; class="">7251-61-8 ; class="">42287-97-8 ; class="">1621-91-6 ; class="">37718-11-9 ; class="">288-13-1 ; class="">86-73-7 ; class="">104-53-0 ; class="">2018-90-8 ; class="">87-66-1 ; class="span_more span_less">135-19-3 ; class="span_more span_less">1664-57-9 ; class="span_more span_less">289-80-5 ; class="span_more span_less">693-95-8 ; class="span_more span_less">55-22-1 ; class="span_more span_less">102-93-2 ; class="span_more span_less">1477-50-5 ; class="span_more span_less">1632-76-4 ; class="span_more span_less">4780-79-4 ; class="span_more span_less">16642-79-8 ; class="span_more span_less">3581-89-3 ; class="span_more span_less">501-97-3 ; class="span_more span_less">771-50-6 ; class="span_more span_less">98-98-6 ; class="span_more span_less">619-64-7 ; class="span_more span_less">100-51-6 ; class="span_more span_less">402-45-9 ; class="span_more span_less">59-67-6 ; class="span_more span_less">93-60-7 ; class="span_more span_less">273-53-0 ; class="span_more span_less">2084-13-1 ; class="span_more span_less">51-17-2 ; class="span_more span_less">2459-09-8 ; class="span_more span_less">2459-07-6 ; class="span_more span_less">95-16-9 ; class="span_more span_less">459-31-4 ; class="span_more span_less">90-05-1 ; class="span_more span_less">150-76-5 ; class="span_more span_less">103-25-3 ; class="span_more span_less">271-44-3 ; class="span_more span_less">6293-56-7 ; class="span_more span_less">2550-26-7 ; class="span_more span_less">288-32-4 ; class="span_more span_less">501-52-0 ; class="span_more span_less">2001-32-3 ; class="span_more span_less">1592-38-7 ; class="span_more span_less">95-15-8 ; class="span_more span_less">91-19-0 ; class="span_more span_less">1122-61-8 ; class="span_more span_less">3724-19-4 ; class="span_more span_less">20173-24-4 ; class="span_more span_less">118-31-0 ; class="span_more span_less">6125-24-2 ; class="span_more span_less">60-12-8 ; class="span_more span_less">90-15-3 ; class="span_more span_less">120-72-9 ; class="span_more span_less">822-36-6 ; class="span_more span_less">288-47-1 ; class="span_more span_less">288-42-6 ; class="span_more span_less">2038-57-5 ; class="span_more span_less">38628-51-2 ; class="span_more span_less">1929-29-9 ; class="span_more span_less">15009-91-3 ; class="span_more span_less">1505-50-6 ; class="span_more span_less">581-40-8 ; class="span_more span_less">616-47-7 ; class="span_more span_less">1571-33-1 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Product Details of [ 288-42-6 ]

CAS No. :	288-42-6	MDL No. :	MFCD00009751
Formula :	C₃H₃NO	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	ZCQWOFVYLHDMMC-UHFFFAOYSA-N
M.W :	69.06	Pubchem ID :	9255
Synonyms :

Calculated chemistry of [ 288-42-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	5
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	16.5
TPSA :	26.03 ?2

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) :	-6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.12
Log Po/w (WLOGP) :	0.67
Log Po/w (MLOGP) :	-0.92
Log Po/w (SILICOS-IT) :	1.23
Consensus Log Po/w :	0.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.08
Solubility :	5.69 mg/ml ; 0.0825 mol/l
Class :	Very soluble
Log S (Ali) :	-0.22
Solubility :	41.4 mg/ml ; 0.599 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.09
Solubility :	5.6 mg/ml ; 0.0811 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

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 ]

* 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 [ 288-42-6 ]
Downstream synthetic route of [ 288-42-6 ]

[ 288-42-6 ] Synthesis Path-Upstream 1~2

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 ]
[ 130551-92-7 ]

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

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

1
[ 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

2
[ 288-42-6 ]
[ 1461-22-9 ]
[ 145214-05-7 ]

Yield	Reaction Conditions	Operation in experiment
99%		[00443] To a solution of oxazole (4 g, 57.92 mmol) in THE (40 mL) -78 C under a nitrogen atmosphere was added dropwise n-BuLi (26 mL, 63.71 mmol). The reaction mixture was stirred for 15 min, ;.hen //-Bu SnCI (20 g, 61.81 mmol) was added slowly. The reaction mixture was stirred for 1 hour and then concentrated in vacuo to afford the title compound (20.7 g, 99%) as a deep pink oil which was used directly without further purification. NMR (400 MHz, CDCi): d 7.85 (s, 111), 7.19 (s, 111), 1.62 - 1.59 (m, Oi l). 1.37 - 1.32 (m, 1211), 0.93 - 0 90 (m, 9H).
77%		To a solution of oxazole (500 mg, 7.25 mmol) in THF (15 mL) at -78 C under N2 was added n-BuLi (2.5 M solution in hexanes, 2.9 mL, 7.32 mmol) dropwise and the mixture was stirred at -78 C for 30 min. Tributylchlorostannane (1.96 mL, 7.25 mmol) was then added and the mixture was allowed to warm to room temperature and stirred for 1 h. The solvent was removed under reduced pressure and residue was taken up in hexanes (50 mL). The resulting precipitate was removed by filtration and the filtrate was concentrated under reduced pressure to give the title compound I39 (2.0 g, 77%) as colourless oil. 1H NMR (400 MHz, DMSO-de) d 8.20 (s, 1H), 7.20 (s, 1H), 1.59 - 1.49 (m, 6H), 1.31 - 1.26 (m, 6H), 1.16 - 1.10 (m, 6H), 0.83 (t, J = 7.3 Hz, 9H).
77%		a) 2-(Tributylstannyl)oxazole I84 To a solution of oxazole (500 mg, 7.25 mmol) in THF (15 mL) at -78 C under N2 was added n-BuLi (2.5 M solution in hexanes, 2.9 mL, 7.32 mmol) dropwise and the mixture was stirred at -78 C for 30 min. Tributylchlorostannane (1.96 mL, 7.25 mmol) was then added and the mixture was allowed to warm to RT and stirred for 1 h. The solvent was removed under reduced pressure and residue was taken up in hexanes (50 mL). The resulting precipitate was removed by filtration and the filtrate was concentrated under reduced pressure to give the title compound (2.0 g, 77%) as colorless oil. NMR (400 MHz, DMSO -cfe) d 8.20 (s, 1H), 7.20 (s, 1H), 1.59 - 1.49 (m, 6H), 1.31 - 1.26 (m, 6H), 1.16 - 1.10 (m, 6H), 0.83 (t, J = 7.3 Hz, 9H).

	With n-butyllithium; In tetrahydrofuran; hexane;	A. 2-tributylstannyloxazole A solution of 1.00 g (14.5 mmol) of oxazole in 25 ml of THF at -78 C. was treated with 10.2 ml (14.6 mmol) of 1.43M butyllithium in hexane. After stirring for 30 minutes, an addition of 3.93 ml (14.5 mmol) of tributyltin chloride was made, and the solution was allowed to warm to room temperature. Stirring was continued for another hour after which most of the solvents were evaporated in vacuo. The resulting residue was taken up in 50 ml of hexane, and the resulting precipitate was separated by filtration through filtercel. Evaporation of the solvent from the filtrate provided 5.13 g of a colorless oil which was identified by NMR as the 2-stannyl derivative plus a small amount of tetrabutylstannane.
	With n-butyllithium; In tetrahydrofuran; hexane;	A. 2 -tributylstannyloxazole A solution of 1.00 g (14.5 mmol) of oxazole in 25 ml of THF at -78 C. was treated with 10.2 ml (14.6 mmol) of 1.43M butyllithium in hexane. After stirring for 30 minutes, an addition of 3.93 ml (14.5 mmol) of tributyltin chloride was made, and the solution was allowed to warm to room temperature. Stirring was continued for another hour after which most of the solvents were evaporated in vacuo. The resulting residue was taken up in 50 ml of hexane, and the resulting precipitate was separated by filtration through filtercel. Evaporation of the solvent from the filtrate provided 5.13 g of a colorless oil which was identified by NMR as the 2-stannyl derivative plus a small amount of tetrabutylstannane.
		To a cooled (-65oC) solution OF OXAZOLE (0.54 g) in THF (100 mL) is added drop-wise, a solution of 1.5 M nBuLi in pentane (5.7 mL) over a 5-minute period. The resulting solution is stirred for 35 minutes at-65oC at which time, a solution of tributyltin chloride (2.4 mL) in THF (10 mL) is added drop-wise, and the resulting solution is allowed to warm to 0oC. Several drops of water are added, and the solvent removed in vacuo to give 2- (TRIBUTYLSTANNYL)-1, 3-oxazole that is taken up in ET2O, washed with saturated KF, brine, dried (NA2S04), and concentrated to give an oil that is carried crude.
		Step H (2): Preparation of methyl 3-((i?)-2-(methoxymethyl)pyrrolidine- l-carbonyl)-5-(oxazol-2-yl)benzoate.; To a solution of oxazole (2.0 g, 29.0 mmol) in THF (30 mL) was added r?-butyl lithium (2.0 M solution in cyclohexanes, 16 mL, 31.9 mmol) at -780C slowly. The reaction mixture was stirred at -780C for 1.2 h, then tributylstannyl chloride (5.0 g, 15.4 mmol) was added. The reaction mixture was warmed up to rt over 3 h. Hexanes (200 mL) was added and the EPO <DP n="45"/>mixture was washed with H2O, dried over Na2SO4 and concentrated under vacuum to give 5.6 g of the 2-(tributylstannyl)oxazole ready for use.

Reference： [1]Patent: WO2021/108483,2021,A1 .Location in patent: Paragraph 00442-00443
[2]Patent: WO2020/2587,2020,A1 .Location in patent: Page/Page column 72-73
[3]Patent: WO2019/243491,2019,A1 .Location in patent: Page/Page column 103-104
[4]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1005 - 1009
[5]Patent: US5347013,1994,A
[6]Patent: US5364856,1994,A
[7]Patent: WO2004/85433,2004,A2 .Location in patent: Page 63; 65-66
[8]Patent: WO2006/99352,2006,A1 .Location in patent: Page/Page column 43-44

3
[ 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

4
[ 288-42-6 ]
[ 108-86-1 ]
[ 1006-68-4 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3578 - 3581
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4748 - 4760
[3]European Journal of Organic Chemistry,2015,vol. 2015,p. 56 - 59

5
[ 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

6
[ 288-42-6 ]
[ 10485-09-3 ]
C₁₂H₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; nixantphos; In tetrahydrofuran; at 25℃; for 24h;Glovebox; Inert atmosphere;	General procedure: An oven-dried 10 mL reaction vial equipped with a stir bar was charged with azole heterocycles (1, 0.2 mmol, 1.0 equiv) and alkenyl bromides (2, 0.30 mmol, 1.5 equiv) in a glove box under a nitrogen atmosphere. A solution of catalytic Pd2(dba)3 (9.15 mg, 0.01 mmol, 5 mol%) and NiXantphos (11.03 mg, 0.02 mmol, 10 mol%) was stirred in 1 mL of dry tetrahydrofuran (THF) for 2 h at room temperature. Then, t-BuONa (57.7 mg, 0.6 mmol, 3.0 equiv) and reagent mixed with catalyst were added to the reaction mixture. And thenthe vial was capped. According to the temperature requirements for different products, some vials were stirred in the glove box for 24 h, but others were removed from the glove box, and stirred for 24 h at 70 or 150 . The reaction mixture was quenched with three drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of silica. The pad was rinsed with ethyl acetate (15-25 mL), and the combined solutions were concentrated in vacuo. The crude material was loaded onto a deactivated silica gel column and purified by flash chromatography to afford the desired product.

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 68 - 71

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Technical Information

? Arndt-Eistert Homologation ? Hunsdiecker-Borodin Reaction ? Passerini Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction

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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

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

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[ CAS No. 288-42-6 ] {[proInfo.proName]}

Quality Control of [ 288-42-6 ]

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[ 288-42-6 ] Synthesis Path-Upstream 1~2

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

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