22876-16-0|6-Methylbenzo[d]oxazol-2(3H)-one| Ambeed

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Quality Control of [ 22876-16-0 ] Purity: 98% SDS Specification

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Product Details of [ 22876-16-0 ]

CAS No. :	22876-16-0
Formula :	C₈H₇NO₂
M.W :	149.15
SMILES Code :	O=C1OC2=CC(C)=CC=C2N1
MDL No. :	MFCD02090051
InChI Key :	SAQACWOVZKNHSB-UHFFFAOYSA-N
Pubchem ID :	322634

Safety of [ 22876-16-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 22876-16-0 ]

* 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.

Downstream synthetic route of [ 22876-16-0 ]

[ 22876-16-0 ] Synthesis Path-Downstream 1~35

1
O-acetyl-N-(2-hydroxy-4-methyl-benzoyl)-hydroxylamine [ No CAS ]
[ 22876-16-0 ]

References: [1]Roczniki Chemii,1954,vol. 28,p. 549,554, 555.
Chem.Abstr.,1956,p. 305.

2
[ 158671-29-5 ]
[ 60100-09-6 ]
[ 22876-16-0 ]

References: [1]Roczniki Chemii,1954,vol. 28,p. 549,554, 555.
Chem.Abstr.,1956,p. 305.

3
[ 131761-56-3 ]
[ 22876-16-0 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 1788 - 1800.

4
(2-Hydroxy-4-methyl-phenyl)-carbamic acid phenyl ester [ No CAS ]
[ 22876-16-0 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1937 - 1939.

5
[ 2835-98-5 ]
[ 530-62-1 ]
[ 22876-16-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	In acetonitrile; at 23 - 70℃;	To a solution of 2-amino-5-methylphenol (777 mg, 6.32 mmol) in acetonitrile (27 mL) at 23 C. was added 1,1'-carbonyldiimidazole (3.07 g, 18.9 mmol) and the reaction mixture was heated to 70 C., and stirred overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate (150 mL) and H2O (100 mL). The organic layer was separated and washed with brine (100 mL), dried (MgSO4) and concentrated to yield the crude product which was purified by silica gel column chromatography (20-50% EtOAc in hexanes) to yield 6-methyl-3H-benzooxazol-2-one (853 mg, 90%).
	In dichloromethane; at 20℃; for 24h;Inert atmosphere;	General procedure: To a solution of the corresponding 2-amino phenol (1 equiv.) in dry dichloromethane was added 1,1’,-dicarbonyldiimidazole (1.1 equiv) and stirred at ambient temperature under a nitrogen atmosphere for 24 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3x). The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The benzoxazolone residue was purified by silica gel chromatography.

References: [1]Patent: US2006/211603,2006,A1 .Location in patent: Page/Page column 69.
[2]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1545 - 1547.
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4689 - 4693.
[4]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272.

6
[ 22876-16-0 ]
[ 76513-69-4 ]
6-Methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzooxazol-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924.

7
[ 1440-61-5 ]
[ 22876-16-0 ]
6-methyl-3-(2-morpholin-4-yl-2-oxo-ethyl)-3H-benzooxazol-2-one [ No CAS ]

References: [1]Il Farmaco,1998,vol. 53,p. 80 - 84.

8
[ 22876-16-0 ]
[ 96-34-4 ]
(6-methyl-2-oxo-benzooxazol-3-yl)-acetic acid methyl ester [ No CAS ]

References: [1]Il Farmaco,1998,vol. 53,p. 80 - 84.

9
[ 22876-16-0 ]
[ 79-11-8 ]
(6-methyl-2-oxobenzooxazol-3-yl)acetic acid [ No CAS ]

References: [1]Il Farmaco,1998,vol. 53,p. 80 - 84.

10
[ 22876-16-0 ]
[ 2315-36-8 ]
N,N-diethyl-2-(6-methyl-2-oxo-benzooxazol-3-yl)-acetamide [ No CAS ]

References: [1]Il Farmaco,1998,vol. 53,p. 80 - 84.

11
[ 22876-16-0 ]
[ 77-78-1 ]
[ 33178-83-5 ]

References: [1]Heterocycles,1999,vol. 51,p. 1929 - 1943.

12
[ 2835-98-5 ]
[ 57-13-6 ]
[ 22876-16-0 ]

References: [1]Heterocycles,1999,vol. 51,p. 1929 - 1943.
[2]Arzneimittel-Forschung/Drug Research,2012,vol. 62,p. 330 - 334.

Yield	Reaction Conditions	Operation in experiment
73%	With cesium fluoride; In diethylene glycol dimethyl ether; at 100℃; for 20h;Glovebox; Schlenk technique;	General procedure: In a glove box, add o-phenylenediamine (1mmol), CsF (2mol), and diglyme (3mL) to a 10ml Schlenk bottle, and replace the air with CO2; connect the Schlenk bottle with a CO2 balloon, and then PMHS (4.5 mmol) was poured into a reaction bottle using a syringe, and the mixture was placed in an oil bath and stirred at 100 C for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, and then poured into 30 mL of H2O to immediately obtain a large amount of precipitate. Then, a large amount of solid powder was obtained by suction filtration. The solid powder was washed with n-hexane (3 × 5 mL) to remove unreacted raw materials, and then ethyl acetate (3 × 10 mL) Wash the solid powder. The ethyl acetate layer was collected, dried over anhydrous magnesium sulfate, and then subjected to vacuum rotary evaporation to obtain a pure product with an isolated yield of 95%.
		3.38 6-Methyl-3H-benzooxazol-2-one (86KK20c) 2-Hydroxy-4-methylanilin (0.145 g, 1.17 mmol) and carbonyldiimidazole (0.250 g, 1.54 mmol) were reacted according to GP6 to give the crude title compound (86KK20d).

14
[ 700-38-9 ]
[ 201230-82-2 ]
[ 22876-16-0 ]

References: [1]European Journal of Organic Chemistry,2005,p. 1675 - 1679.

15
[ 22876-16-0 ]
[ 139487-08-4 ]

References: [1]Heterocycles,1999,vol. 51,p. 1929 - 1943.

16
[ 22876-16-0 ]
[ 245095-53-8 ]

References: [1]Heterocycles,1999,vol. 51,p. 1929 - 1943.

17
[ 22876-16-0 ]
(3-methyl-2-oxo-2,3-dihydro-benzooxazol-6-yl)-acetyl chloride [ No CAS ]

References: [1]Heterocycles,1999,vol. 51,p. 1929 - 1943.

18
[ 22876-16-0 ]
[ 245095-56-1 ]

References: [1]Heterocycles,1999,vol. 51,p. 1929 - 1943.

19
[ 22876-16-0 ]
3-methyl-N-(4,6-dimethylpyridin-2-yl)-2(3H)-(benzoxazolinon-6-yl)methylcarboxamide [ No CAS ]

References: [1]Heterocycles,1999,vol. 51,p. 1929 - 1943.

20
[ 22876-16-0 ]
[ 187275-00-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924.

21
[ 22876-16-0 ]
(4R,5S,6S,7R)-1,3-Bis-benzooxazol-6-ylmethyl-4,7-dibenzyl-5,6-dihydroxy-[1,3]diazepan-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924.

22
[ 22876-16-0 ]
(4R,5S,6S,7R)-1,3-Bis-(2-amino-benzooxazol-6-ylmethyl)-4,7-dibenzyl-5,6-dihydroxy-[1,3]diazepan-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924.

23
[ 22876-16-0 ]
(3aS,4R,8R,8aS)-4,8-Dibenzyl-2,2-dimethyl-5,7-bis-(2-oxo-2,3-dihydro-benzooxazol-6-ylmethyl)-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924.

24
[ 22876-16-0 ]
C₃₅H₃₂N₄O₇ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924.

25
[ 22876-16-0 ]
(4R,5S,6S,7R)-4,7-Dibenzyl-5,6-dihydroxy-1,3-bis-(2-thioxo-2,3-dihydro-benzooxazol-6-ylmethyl)-[1,3]diazepan-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924.

26
[ 22876-16-0 ]
(3aS,4R,8R,8aS)-4,8-Dibenzyl-2,2-dimethyl-5,7-bis-[2-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-2,3-dihydro-benzooxazol-6-ylmethyl]-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2919 - 2924.

27
[ 2835-98-5 ]
[ 22876-16-0 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1937 - 1939.

28
[ 700-38-9 ]
[ 22876-16-0 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1545 - 1547.

29
[ 75-44-5 ]
[ 22876-16-0 ]
[ 26825-92-3 ]
[ 83475-45-0 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; In chlorhydrate de methyl-5 orthoaminophenol-1,2; N,N-dimethyl-formamide; mineral oil;	EXAMPLE 5 8-(6-Methyl-2-oxo-benzoxazolin-3-yl)-caprylic acid methyl ester The product is produced as described in example 1 from 3.6 g. of NaH (of 80% suspension in mineral oil), 19.9 g. of <strong>[22876-16-0]6-methylbenzoxazolin-2-one</strong> (produced in usual manners by subjecting 2-amino-5-methyl-phenol-hydrochloride to reaction with phosgene), 240 cc. of DMF, 28.4 g. of 8-bromo caprylic acid methyl ester and 3.6 g. NaJ. Yield: 31.1 g. (oil). IR (film): 1780 and 1740 cm-1.

References: [1]Patent: US4377695,1983,A .

30
[ 22876-16-0 ]
[ 123-62-6 ]
[ 1158182-72-9 ]

References: [1]Tetrahedron,2009,vol. 65,p. 3704 - 3710.

31
C₁₉H₂₁NO₅ [ No CAS ]
[ 22876-16-0 ]

References: [1]Organic Letters,2010,vol. 12,p. 812 - 815.

32
[ 22876-16-0 ]
[ 100-39-0 ]
[ 1208448-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 45℃;Inert atmosphere;	To a solution of <strong>[22876-16-0]6-methylbenzo[d]oxazol-2(3H)-one</strong> (300 mg, 1.98 mmol) and K2CO3 (668 mg, 4.95 mmol) in DMF was added benzyl bromide (375 mg, 2.1 mmol) at 45 0C and the reaction was stirred under nitrogen atmosphere for 5 h. The reaction mixture was poured into ice water and the precipitate was filtered, washed with n-hexane and dried under vacuum to give compound 2 (250 mg, 50%) as a white solid.

References: [1]Patent: WO2010/21693,2010,A2 .Location in patent: Page/Page column 33; 34.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5811 - 5814.

33
[ 32315-10-9 ]
[ 2835-98-5 ]
[ 22876-16-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine; In tetrahydrofuran; at 0 - 20℃;	A solution of triphosgene (1.93g, 6.5mmol) in anhydrous THF (40mL) was added to a solution of 2-amino-5-methylphenol (10g, 8.1mmol) and Et3N (2.3mL) in anhydrous THF (40mL) at 0C. The resulting solution was stirred at room temperature (RT) for overnight and was diluted with water (10mL). After 30min, the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (50mL×3). The combined organic layer was washed by saturated sodium chloride solution for three times, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 6-methylbenzo[d]oxazol-2(3H)-one as an off-white solid. Yield 83% (1.93g). MS (ESI): 150.1 [M+H]+
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃;Inert atmosphere;	Synthesis of 3-benzyl-6-methyl-3H-benzooxazol-2-one (2)A solution of 2-amino-5-methyl-phenol (1.0 gm, 8.1 mmol) in CH2Cl2 (30 ml) was cooled to 0 0C. Triphosgene (721 mg, 2.43 mmol) was added followed by diisopropylethylamine (7.0 ml, 17.6 mmol) and the reaction mixture was stirred under nitrogen atmosphere for 2 h. The reaction mixture was washed with water and brine. The organic phase was dried over anhydrous MgSO4 and evaporated under vacuum. The crude product 6- methylbenzo[d]oxazol-2(3H)-one was used for the next step without any purification.

References: [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 191 - 200.
[2]Patent: WO2010/21693,2010,A2 .Location in patent: Page/Page column 33-34.

34
[ 22876-16-0 ]
[ 5437-45-6 ]
[ 910322-62-2 ]

Yield	Reaction Conditions	Operation in experiment
57%		To a portion of <strong>[22876-16-0]6-methyl-3H-benzooxazol-2-one</strong> (450 mg, 3.02 mmol) in DMF (10 mL) at 23 C. was added K2CO3 (900 mg, 6.51 mmol), and the reaction mixture was stirred for 30 min. Benzyl-2-bromoacetate (909 μL, 5.74 mmol) was slowly added to the reaction mixture, while stirring. After 17 h, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with 1.0 N HCl (100 mL), saturate aqueous NaHCO3 (100 mL), then brine (100 mL), and then was dried (Na2SO4) and concentrated to yield the crude product that was purified by silica gel column chromatography (20-50% EtOAc in hexanes) to afford (6-methyl-2-oxobenzooxazol-3-yl)acetic acid benzyl ester (512 mg, 57%).

References: [1]Patent: US2006/211603,2006,A1 .Location in patent: Page/Page column 69.

35
[ 22876-16-0 ]
[ 874-98-6 ]
[ 1246928-35-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5811 - 5814.

Historical Records

Technical Information

• Acyl Group Substitution • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 22876-16-0 ]

Amides

A983390 [22876-15-9]

5-Methylbenzo[d]oxazol-2(3H)-one

Similarity: 0.96

A485911 [54903-15-0]

2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carbaldehyde

Similarity: 0.95

A575134 [93771-18-7]

6-Ethylbenzo[d]oxazol-2(3H)-one

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A661203 [808114-07-0]

6-Methyl-3-phenylbenzo[d]oxazol-2(3H)-one

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A889572 [151254-40-9]

5-Ethylbenzo[d]oxazol-2(3H)-one

Similarity: 0.91

Related Parent Nucleus of
[ 22876-16-0 ]

Benzoxazoles

A983390 [22876-15-9]

5-Methylbenzo[d]oxazol-2(3H)-one

Similarity: 0.96

A485911 [54903-15-0]

2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carbaldehyde

Similarity: 0.95

A575134 [93771-18-7]

6-Ethylbenzo[d]oxazol-2(3H)-one

Similarity: 0.95

A661203 [808114-07-0]

6-Methyl-3-phenylbenzo[d]oxazol-2(3H)-one

Similarity: 0.93

A889572 [151254-40-9]

5-Ethylbenzo[d]oxazol-2(3H)-one

Similarity: 0.91

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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.: 22876-16-0

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