[ CAS No. 59-49-4 ] {[proInfo.proName]}

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Quality Control of [ 59-49-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 59-49-4 ]

SDS Specification

Alternatived Products of [ 59-49-4 ]

Product Details of [ 59-49-4 ]

CAS No. :	59-49-4	MDL No. :	MFCD00005716
Formula :	C₇H₅NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ASSKVPFEZFQQNQ-UHFFFAOYSA-N
M.W :	135.12	Pubchem ID :	6043
Synonyms :	2-Benzoxazolone;1,3-Benzoxazol-2(3H)-one;2-Hydroxybenzoxazole	Chemical Name :	benzo[d]oxazol-2(3H)-one

Calculated chemistry of [ 59-49-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.03
TPSA :	46.26 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.33
Log Po/w (XLOGP3) :	1.86
Log Po/w (WLOGP) :	1.53
Log Po/w (MLOGP) :	0.78
Log Po/w (SILICOS-IT) :	1.46
Consensus Log Po/w :	1.39

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.52
Solubility :	0.412 mg/ml ; 0.00305 mol/l
Class :	Soluble
Log S (Ali) :	-2.45
Solubility :	0.476 mg/ml ; 0.00353 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.31
Solubility :	0.666 mg/ml ; 0.00493 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.35

Safety of [ 59-49-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302+H312+H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 59-49-4 ]

* 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 [ 59-49-4 ]
Downstream synthetic route of [ 59-49-4 ]

[ 59-49-4 ] Synthesis Path-Upstream 1~1

1
[ 59-49-4 ]
[ 62522-63-8 ]

Reference： [1] Chemistry of Heterocyclic Compounds, 2011, vol. 47, # 1, p. 90 - 95
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 20, p. 4875 - 4889
[3] Patent: CN107098846, 2017, A,

[ 59-49-4 ] Synthesis Path-Downstream 1~11

1
[ 59-49-4 ]
[ 19932-85-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With bromine; acetic acid; at 20℃; for 4h;	3H-1,3-Benzoxazol-2-one (5.00?g, 37.00?mmol) was dissolved in acetic acid (50?mL) and bromine (1.9?mL, 37.0?mmol) was added dropwise. The reaction mixture was stirred at 20?C for 4?h.The reaction mixture was poured onto ice and the precipitate was collected by filtration, washed with water and air-dried to give a pink powder (7.48?g, 34.8?mmol, 94%). Mp 191.6-192.3?C. 1H NMR (300?MHz, DMSOd6): δ 11.81 (s, 1H), 7.57 (dd, J?=?1.9?Hz, J?=?0.3?Hz, 1H), 7.30 (dd, J?=?8.3?Hz, J?=?1.9?Hz, 1H), 7.04 (dd, J?=?8.3?Hz, J?=?0.3?Hz, 1H). 13C NMR (75?MHz, DMSOd6): δ 154.5, 144.5, 130.3, 126.9, 113.5, 113.2, 111.7. LCMS m/z calc for [M?-?H]+: 211.9, 213.9, found: 211.8, 213.8.
94%		3H-1,3-Benzoxazol-2-one (5.00 g, 37.00 mmol) was dissolved in acetic acid (50 mL) and bromine (1.9 mL, 37.0 mmol) was added dropwise. The reaction mixture was stirred at20C for 4 h. The reaction mixture was poured onto ice and the precipitate was collected by filtration, washed with water and air-dried to give 1 as a pink powder (7.48 g, 94%). Mp 191.6C. 1H NMR (300 MHz), (5(ppm, DMSO-d6): 11.81 (s, 1H), 7.57 (dd, J= 1.9 Hz, J0.3 Hz, 1H), 7.30 (dd, J= 8.3 Hz, J= 1.9 Hz, 1H), 7.04 (dd, J 8.3 Hz, J 0.3 Hz, 1H).13C NMR (75 MHz), (5(ppm, DMSO-d6): 154.5, 144.5, 130.3, 126.9, 113.5, 113.2, 111.7.LCMS m/zcalc for [M-H]: 211.9, 213.9, found: 211.8, 213.8.
84%	With bromine; In dichloromethane; at 20℃; for 19.5h;	To a mixture of 3H-benzooxazol-2-one (20 g, 0.15 mol) in DCM (500 mL) was added bromine (8.34 mL, 0.16 mol). After stirring at room temperature for 19.5 h, the orange precipitate that had formed was filtered off and washed with DCM until the orange color was washed out. The filtrate was concentrated to approximately 33% of its original volume and filtered and washed as before. The combined solids weighed 28.36 g. 1H NMR indicated the product was clean albeit contained ca. 8-9% starting material meaning the true yield of product was 26.72 g, 84%.

70%	With N-Bromosuccinimide; In acetic acid; at 20℃; for 72h;	Step 1: N-Bromosuccinimide (26.6 g, 0.15 mol) was added to a stirred solution of 2-benzoxazolinone (20.0 g, 0.15 mol) in glacial acetic acid (220 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into H2O (1.2 L), and the white solid that formed was collected. Recrystallization from hot EtOH (300 mL) gave bromide 1 (22.1 g, 70%) as an off-white solid: mp 190-195 C.; IR (KBr): 3278, 1779, 1736, 1623 cm?1; 1H NMR (300 MHz, CD3OD): ?7.41 (d, J=2 Hz, 1H), 7.32 (dd, J=5, 2 Hz, 1H), 6.99 (d, J=5 Hz, 1H); CI MS (methane) (m/z): 215 [M+H]+.
31%	With N-Bromosuccinimide; In acetonitrile; at -15 - 20℃;	Preparation of 6-Bromo-3H-benzoxazol-2-one. To a stirred suspension of 3H-benzoxazol-2-one (1.35 g, 10 mmol) in acetonitrile (23 ML) at -15 C. was added portionwise NBS (2.00 g, 11.0 mmol).Following complete addition of NBS the mixture was stirred at -15 to 0 C. for 3 h then allowed to warm to ambient temperature and stirred overnight.The solvent was evaporated in vacuo and the residue was partitioned between CH2Cl2/H2O precipitating the intermediate title compound, 6-bromo-3H-benzoxazol-2-one, (0.67 g, 31%) as a brown solid. 1HNMR(CDCl3) δ 7.0 (1H, d), 7.15 (1H.,d), 7.3 (1H, s), 11.9 (1H, s).
	With bromine; In dichloromethane; at 20℃; for 19.5h;	To a mixture of 3H-benzooxazol-2-one (20 g, 0.15 mol) in DCM (500 mL) was added bromine (8.34 mL, 0.16 mol). After stirring at room temperature for 19.5 h, the orange precipitate that had formed was filtered off and washed with DCM until the orange color was washed out. The filtrate was concentrated to approximately 33% of its original volume and filtered and washed as before. The combined solids weighed 28.36 g and contained ca. 8-9% starting material.
	With N-Bromosuccinimide; In water; acetic acid;	Step 1: To a solution of benzoxazolinone (20 g, 0.148 mol) in 220 mL glacial acetic acid was added N-bromosuccinimide (NBS, 26.36 g, 0.148 mol), and the reaction mixture was stirred at room temperature for 63 hours before pouring into 1500 mL water. The precipitated product was washed thoroughly with water upon collection and recrystallized from EtOH to give 6-bromo-3H-benzoxazol-2-one (9) (25.09 g, 79%): Theory: C, 39.28; H, 1.88; N, 6.54; Br, 37.33. Found: C, 39.36; H, 2.02; N, 6.36; Br, 37.43. MP 192-194 C.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 159,p. 104 - 125
[2]Patent: WO2020/11848,2020,A1 .Location in patent: Page/Page column 38; 41-42
[3]Patent: US6372933,2002,B1 .Location in patent: Page column 5 - 6
[4]Patent: US2008/138413,2008,A1 .Location in patent: Page/Page column 22
[5]Monatshefte fur Chemie,2011,vol. 142,p. 67 - 80
[6]Patent: EP1251128,2002,A1 .Location in patent: Page 38
[7]Patent: US2003/236252,2003,A1 .Location in patent: Page 14
[8]Monatshefte fur Chemie,1993,vol. 124,p. 367 - 380
[9]Patent: US2003/225127,2003,A1 .Location in patent: Page 10
[10]Journal fur praktische Chemie (Leipzig 1954),1888,vol. <2> 37,p. 28 Anm. 1, 31, 38, 46
[11]Journal of the Chemical Society,1934,p. 1186,1190
[12]Collection of Czechoslovak Chemical Communications,1979,vol. 44,p. 1790 - 1798
[13]Patent: WO2006/86705,2006,A1 .Location in patent: Page/Page column 84
[14]Acta poloniae pharmaceutica,2013,vol. 70,p. 245 - 253
[15]European Journal of Medicinal Chemistry,2015,vol. 92,p. 575 - 582
[16]Patent: US2003/18021,2003,A1
[17]ChemMedChem,2018,vol. 13,p. 2522 - 2529

2
[ 59-49-4 ]
[ 50-00-0 ]
[ 615-55-4 ]
3-(3,4-dibromo-anilinomethyl)-3<i>H</i>-benzooxazol-2-one [ No CAS ]

Reference： [1]Chemische Berichte,1961,vol. 94,p. 2209 - 2217

3
[ 59-49-4 ]
[ 50-00-0 ]
[ 29608-05-7 ]
[ 108176-83-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 877 - 879

4
[ 59-49-4 ]
[ 2991-28-8 ]
[ 230628-46-3 ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 112 - 115
[2]Il Farmaco,2002,vol. 57,p. 535 - 538
[3]Arzneimittel-Forschung/Drug Research,2003,vol. 53,p. 114 - 120

5
[ 59-49-4 ]
N-(t-butoxy)-4-hydroxypiperidine [ No CAS ]
[ 1972-28-7 ]
[ 162045-53-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	(i) 1,1-Dimethylethyl 4-(2-oxo-1,3-benzoxazol-3(2H)-yl)piperidine-1-carboxylate 2-Benzoxazolinone (1 g) was added to a cooled solution of triphenylphoshine (2.13 g) and diethylazodicarboxylate (1.28 ml) in dry tetrahydrofuran (20 ml). After 10 min at 0 C., N-(t-butoxy)-4-hydroxypiperidine (1.63 g) (Tetrahedron Letters, 1996, 6439-6442) was added portionwise. The reaction mixture was stirred at room temperature for 16 h. The solution was diluted with water, extracted with ethyl acetate, dried and evaporated under reduced pressure. Purification was by chromatography eluding with (1:2) diethylether/isohexane. Yield 0.5 g as an oil.

Reference： [1]Patent: US2003/40513,2003,A1

6
[ 59-49-4 ]
[ 77-48-5 ]
[ 19932-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluorormethanesulfonic acid; In dichloromethane; ethyl acetate;	EXAMPLE 251A 6-bromo-1,3-benzoxazol-2(3H)-one A mixture of 2-benzoxazolinone (3.00 g, 22.2 mmol), 1,3-dibromo-5,5-dimethylhydantoin (3.49 g, 12.2 mmol), and trifluoromethanesulfonic acid (5.00 g, 33.3 mmol) in dichloromethane (100 mL) at room temperature was protected from light, stirred for 1 hour, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product.
	With trifluorormethanesulfonic acid; In dichloromethane; ethyl acetate;	Example 251A 6-bromo-1,3-benzoxazol-2(3H)-one A mixture of 2-benzoxazolinone (3.00 g, 22.2 mmol), 1,3-dibromo-5,5-dimethylhydantoin (3.49 g, 12.2 mmol), and trifluoromethanesulfonic acid (5.00 g, 33.3 mmol) in dichloromethane (100 mL) at room temperature was protected from light, stirred for 1 hour, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product.

Reference： [1]Patent: US2002/55631,2002,A1
[2]Patent: US2002/86887,2002,A1

7
[ 59-49-4 ]
[ 131184-73-1 ]
[ 1194551-82-0 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 5154 - 5157

8
[ 59-49-4 ]
[ 459-04-1 ]
3-(2-(4-fluorophenyl)acetyl)benzo[d]oxazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine; In tetrahydrofuran; at 70℃; for 6h;	General procedure: To a solution of 4a or 4b (1mol equiv.) in anhydrous THF was added TEA (3mol equiv.). The mixture was added drop wise the solution of acyl chlorides (1.1mol equiv.) in anhydrous THF at 0C and stirred at 70C for 6h. The water was added to quench the reaction. The mitxure was extracted with ethyl acetate to afford the crude product that was purified by flash column chromatography on silica gel to yield the target products.4.1.6.1 3-(2-(4-Fluorophenyl)acetyl)benzo[d]oxazol-2(3H)-one (9a) (0050) White solid. Yield 86%. Mp 180-182C. 1H NMR (300MHz, DMSO-d6): δ(ppm) 7.98-7.89 (m, 1H), 7.50-7.41 (m, 1H), 7.41-7.28 (m, 4H), 7.24-7.14 (m, 2H), 4.41 (s, 2H). MS (EI): m/z 272.2 [M+H]+. IR (KBr): 3067, 1796, 1721, 1601, 1514, 1248cm-1.
86%	With triethylamine; In tetrahydrofuran; water; at 70℃; for 6h;Cooling with ice;	A solution of 1a (0.10 g, 0.74 mmol) was dissolved in 10 mL of dry tetrahydrofuran,Triethylamine (0.22 g, 2.22 mmol) was added to the acid,No addition of p-fluorophenyl acetyl chloride to the ice bathWater tetrahydrofuran solution (0.15 g, 0.89 mmol)Drop the reaction temperature will rise to room temperature,Heated to 70 C,Reaction 6h,The reaction was quenched with 10 mL of water and extracted with ethyl acetate (3 x 7 mL). Column chromatography (Petroleum ether: ethyl acetate = 10: 1) to give 0.17 g of a white solid, 86% yield, mp 180-182 C.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 138,p. 199 - 211
[2]Patent: CN106905256,2017,A .Location in patent: Paragraph 0169; 0170; 0171; 0172

9
[ 59-49-4 ]
[ 3621-82-7 ]

Yield	Reaction Conditions	Operation in experiment
68.3%	With pyridine; chlorine; trichlorophosphate; at 100℃; for 5h;	In a reactor equipped with exhaust gas absorption, 27.0 g of benzoxazolone (molecular weight 135.1, 0.20 mol) was added, 150.0 g of phosphorus oxychloride (molecular weight 153.3, 0.98 mol), 79.1 g of pyridine (molecular weight 79.1, 1.0 mol), Stir and heat to about 100 ° C, Passing chlorine gas reaction, About 5g of chlorine gas is introduced every hour. Chlorine gas is about 5h, sampling and testing, 6-chlorobenzoxazolone content is less than 1percent as the end of the reaction; Atmospheric distillation, Removing the remaining phosphorus oxychloride; Vacuum distillation, Heating temperature is about 120 °C, Oil pump decompression, The degree of vacuum is 1~3Kpa, The product was isolated 25.7 g, White crystal, The yield is 68.3percent. The qualitative content is 99percent.

Reference： [1]Patent: CN109553588,2019,A .Location in patent: Paragraph 0044; 0045
[2]Patent: CN108794421,2018,A

10
[ 17641-08-6 ]
[ 59-49-4 ]
N-(3-methoxyphenyl)-2-(2-oxobenzo[d]oxazol-3(2H)-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: To a stirred suspension of benzo [d]oxazol-2(3H)-one derivative,or benzimidazole, or 2H-benzo [b] [1,4]oxazin-3(4H)-one(1.0 mmol), anhydrous K2CO3 (1.2 mmol) was added in the DMFsolvent for 20 min at 70 C. Then bromoacetylated 1a-1f or 2a-2c(1.3 mmol) and TBAI (0.1 mmol) were added simultaneously. Thereaction was stirred and heated for 4 h. After completion, themixture was extracted with EtOAc/H2O three times. The combinedorganic layers were washed with brine, dried over anhydrousNa2SO4, filtered and concentrated under reduced pressure. Thecrude product was purified by silica gel column chromatographyeluting with EtOAc/PE (3:1e8:1) to afford compounds B01-B29,C01-C03.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 182

11
[ 603-87-2 ]
[ 59-49-4 ]

Reference： [1]Patent: CN110156712,2019,A

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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. 59-49-4 ] {[proInfo.proName]}

Quality Control of [ 59-49-4 ]

Related Doc. of [ 59-49-4 ]

Product Details of [ 59-49-4 ]

Calculated chemistry of [ 59-49-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 59-49-4 ]

Application In Synthesis of [ 59-49-4 ]

[ 59-49-4 ] Synthesis Path-Upstream 1~1

[ 59-49-4 ] Synthesis Path-Downstream 1~11

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry