[ CAS No. 22876-22-8 ] {[proInfo.proName]}

Name: 22876-22-8|5-Methylbenzo[d]oxazole-2(3H)-thione|98%
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SKU: A165857
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Quality Control of [ 22876-22-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 22876-22-8 ]

CAS No. :	22876-22-8	MDL No. :	MFCD00052492
Formula :	C₈H₇NOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SSWZUOXLFTXIEZ-UHFFFAOYSA-N
M.W :	165.21	Pubchem ID :	710258
Synonyms :

Calculated chemistry of [ 22876-22-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.36
TPSA :	61.02 Å²

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) :	-5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.96
Log Po/w (XLOGP3) :	2.1
Log Po/w (WLOGP) :	2.8
Log Po/w (MLOGP) :	1.23
Log Po/w (SILICOS-IT) :	3.95
Consensus Log Po/w :	2.41

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.79
Solubility :	0.266 mg/ml ; 0.00161 mol/l
Class :	Soluble
Log S (Ali) :	-3.01
Solubility :	0.161 mg/ml ; 0.000973 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.4
Solubility :	0.0653 mg/ml ; 0.000395 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.36

Safety of [ 22876-22-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 22876-22-8 ]

* 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 [ 22876-22-8 ]

[ 22876-22-8 ] Synthesis Path-Downstream 1~75

1
[ 50609-01-3 ]
[ 22876-22-8 ]
[ 38519-93-6 ]

Reference： [1]Journal of medicinal chemistry,1972,vol. 15,p. 523 - 529

2
[ 103-71-9 ]
[ 103-72-0 ]
[ 79558-91-1 ]
[ 22876-22-8 ]
[ 102-08-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1518 - 1524

3
[ 103-72-0 ]
[ 95-84-1 ]
[ 79558-91-1 ]
[ 22876-22-8 ]
[ 102-08-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1518 - 1524

4
[ 79558-90-0 ]
[ 22876-22-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1518 - 1524

5
[ 79558-91-1 ]
[ 79558-93-3 ]
[ 22876-22-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1518 - 1524

6
[ 75-15-0 ]
[ 95-84-1 ]
[ 22876-22-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide; In ethanol; for 10h;Reflux;	In a 100ml round bottom one neck flask was chargedwith 2.20g (20 mmol) of o-aminophenol and 40 ml ofabsolute ethanol was added and the contents were stirred for15 minutes. In the meanwhile, 2.0g (29 mmol) of potassiumhydroxide pellets was powdered and transferred into the flask followed by 15 ml of carbon disulfide. The mixturewas refluxed for 8- 10 hours when a grayish yellow coloredprecipitate appeared. The contents were cooled to roomtemperature and the solvent was rotary evaporated to yield asolid product. This product was carefully transferred into abeaker and 75 ml of water was added when a clear solutionresulted. The clear solution was acidified by adding aceticacid when a precipitate appeared. The precipitate was filteredand then washed with 3x50 ml of water and dried in vacuumover night. A light yellowish powder was obtained: yield2.3g, (yield 77%).

Reference： [1]Letters in Organic Chemistry,2010,vol. 7,p. 519 - 527
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 913 - 923
[3]Chemical and Pharmaceutical Bulletin,1998,vol. 46,p. 445 - 451
[4]Journal of Medicinal Chemistry,1998,vol. 41,p. 3015 - 3021
[5]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3515 - 3523
[6]Indian Journal of Heterocyclic Chemistry,2010,vol. 20,p. 121 - 124
[7]Archiv der Pharmazie,2019,vol. 352
[8]Archiv der Pharmazie,2019,vol. 352

7
[ 140-89-6 ]
[ 95-84-1 ]
[ 22876-22-8 ]

Yield	Reaction Conditions	Operation in experiment
96%		Compound 22: A mixture of potassium ethyl xanthate (16.0 g, 0.1 mol) and 2-amino-4-methylphenol (12.3 g, 0.1 mol) was dissolved in absolute ethanol (150 mL). The mixture was stirred at reflux overnight. After cooling, the reaction solvent was evaporated under reduced pressure. The resultant residue was dissolved in water (200 mL) and treated with HOAc to pH to 5. The resultant solid was filtered and dried to afford 5-methyl-2-mercaptobenzoxazole (16.0 g, 96% yield).

Reference： [1]Patent: US2011/224269,2011,A1 .Location in patent: Page/Page column 21
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 1617 - 1625
[3]Journal of Medicinal Chemistry,1988,vol. 31,p. 1719 - 1728
[4]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4689 - 4693

8
[ 22876-22-8 ]
[ 3770-60-3 ]

Yield	Reaction Conditions	Operation in experiment
58%	With thionyl chloride;N,N-dimethyl-formamide; at 20℃; for 0.5h;	Subsequently, the <strong>[22876-22-8]5-methyl-2-mercaptobenzoxazole</strong> (6.2 g, 38 mmol) was dissolved in thionyl chloride (36.9 mL) and 2.79 mL of DMF was added. The reaction mixture was then stirred at r.t. for 30 min. The solvent was removed under reduced pressure and to the residue was added toluene (2*60 mL) followed by evaporation each time to remove excess SOCl2 via an azetrope. The resultant crude product was dissolved in ethyl acetate (100 mL),washed with water (100 mL) and dried over Na2SO4. Evaporation of ethyl acetate gave crude 22 which was purified by silica-gel column chromatography (eluent: petroleum ether) to provide pure 2-chloro-5-methylbenzoxazole, compound 22, (3.5 g, 58%).
	With phosphorus pentachloride; sodium carbonate; In dichloromethane; trichlorophosphate;	To a suspension of <strong>[22876-22-8]5-methylbenzo[d]oxazole-2-thiol</strong> (1.0 g, 6.1 mmol.) in POCl3 (11.7 g, 76.4 mmol.) at room temperature was added PCl5 (1.9 g, 9.15 mmol.) along with CH2Cl2 (10 mL). After 4 h of stirring at room temperature, the reaction mixture was concentrated to remove excess POCl3, and the residue was treated with Na2CO3 solution until ~pH 8 was reached. The aqueous phase was extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered and concentrated to afford 2-chloro-5-methylbenzo[d]oxazole (1.1 g crude product) which was used without further purification. MS (ESI) m/e (M+H+) 168.

Reference： [1]Patent: US2011/224269,2011,A1 .Location in patent: Page/Page column 21
[2]Journal of Medicinal Chemistry,1988,vol. 31,p. 1719 - 1728
[3]Journal of Medicinal Chemistry,1994,vol. 37,p. 913 - 923
[4]Chemical and Pharmaceutical Bulletin,1998,vol. 46,p. 445 - 451
[5]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3515 - 3523
[6]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4689 - 4693
[7]Patent: US2009/269305,2009,A1

9
[ 22876-22-8 ]
[ 933945-38-1 ]

Reference： [1]Archiv der Pharmazie,1997,vol. 330,p. 169 - 172
[2]Journal of Medicinal Chemistry,1988,vol. 31,p. 1719 - 1728

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide; In ethanol; at 90℃;	General procedure: To a solution of KOH (4.75g, 84.8mmol) in EtOH (lOOmL) were added 2-amino-4-(trifluoromethyl)phenol (5g, 28.25mmol) and CS2 (5.llmL, 84.8mmol) at rt. The reaction mixture was refluxed overnight. The TLC showed the reaction to be complete. The solvent was removed under reduced pressure to give crude residue. The residue was acidified with iN HCI (100 mL) and extracted with EtOAc (3xlOOmL). The organic layer was washed with brine (lOOmL), dried (Na2SO4), filtered and concentrated under reduced pressure to afford 5- (trifluoromethyl)benzo[d]oxazole-2-thiol as an off white solid. Yield: 5.2 g (85%); 1H NMR (400 MHz, DMSO-d6): 14.25 (bs, 1H), 7.72 (d, J = 8.4 Hz, 1H), 7.64 (d, J = 8.4 Hz, 1 H), 7.51 (5, 1 H); MS (ESI-) for CHNOS m/z 217.94 [M-H].
		INVENTIVE EXAMPLE 17 2-(4-Methyl-1-piperazinyl)-5-methylbenzoxazole Phosphorus pentachloride (227 mg) was dissolved in anhydrous toluene (3 ml), the resulting solution was mixed with 2-mercapto-5-methylbenzoxazole (150 mg) which has been obtained in the same manner as described in Reference Example 1, and the mixture was then stirred with heating at 100 C. for 2 hours.
		EXAMPLE 2A A general procedure for the preparation of 2-mercaptobenzoxazoles (from the corresponding 2-aminophenol) is illustrated by the following preparation of 2-mercapto-5-methylbenzoxazole. To a brown solution of 2-amino-5-methylphenol (5 g) in 2M NaOH (80 cm3) stirring at the ambient temperature was added carbon disulphide and the reaction mixture was stirred for 5 days. The solution was acidified to pH 4 by the addition of concentrated hydrochloric acid, causing formation of a beige precipitate. The precipitate was filtered and dried by suction to give the title product as a free flowing beige powder (4.06 g). 1 H NMR (DMSO): delta13.9 (1H,br s); 7.5(1H,d); 7.18(1H,d); 7.15(1H,s); 2.49(3H,s) ppm.

11
[ 22876-22-8 ]
3-MeO-C₆H₄CH₂-halide [ No CAS ]
2-(3-methoxy-benzylsulfanyl)-5-methyl-benzooxazole [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1997,vol. 7,p. 151 - 167

12
[ 75-15-0 ]
[ 95-84-1 ]
[ 22876-22-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In neat (no solvent) at 40℃; for 0.5h;	General procedure: The basic procedure for preparing all products was similar. Taking the entry 1 inTable 2 as an example: 1a (2 mmol) and [DBUH][OAc] (1 mL) were added to a 10mLflask and stirred at room temperature. After 30 minutes, adding 5mL water into theflask dispersed the solid product, which could be separated by filtration. The solid wasrecrystallized from an ethyl acetate and petroleum ether mixture (v/v, 1/1) to get 2a.The aqueous residue was evaporated under vacuum at 50C for 8 h and reused in thenext run. All the products were known compounds, and the characteristic data accordedwith the relevant literature.
90%	In ethanol; water at 80℃; for 8h; Cooling with ice; Alkaline conditions;
54%	Stage #1: carbon disulfide; 3-amino-4-hydroxytoluene With potassium carbonate In ethanol for 2h; Heating; Stage #2: With dihydrogen peroxide In ethanol for 1h; Further stages.;

	With potassium hydroxide In methanol; water
	With potassium hydroxide In ethanol for 18h; Heating / reflux;	9.1 To a solution of 2-amino-p-cresol (1.81 g, 0.015 mol) and KOH (1.2 eq. 0.99 g) in 30 mL of EtOH was added methanedithione (18 mL). The resulting mixture was heated to reflux for 18 h. Upon cooling, the volatiles were removed in vacuo and the residue was partitioned between EtOAc and 18 mL of 1N HCl. The organic layer was separated, washed with water, dried over sodium sulfate, and concentrated to give 1.2 g of 5-methyl-3H-benzooxazole-2-thione: (M+H)+=165.

Reference： [1]Li, Wei-wei; Zheng, Hui [Organic Preparations and Procedures International, 2019, vol. 51, # 2, p. 175 - 181]
[2]Varun, Begur Vasanthkumar; Prabhu, Kandikere Ramaiah [Journal of Organic Chemistry, 2014, vol. 79, # 20, p. 9655 - 9668]
[3]Singh; Singh, Pallavi; Singh, Shweta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 10, p. 1666 - 1671]
[4]Nakao, Kazuya; Asao, Masaaki; Shirai, Hiroki; Saito, Kiyoshi; Moriya, Tamon; Iwata, Hiroshi; Matsumoto, Mamoru; Matsuoka, Yuzo; Shimizu, Ryo [Medicinal Chemistry Research, 1999, vol. 9, # 7-8, p. 631 - 642]
[5]Current Patent Assignee: ROCHE HOLDING AG - US2005/90504, 2005, A1 Location in patent: Page/Page column 16

13
[ 10254-07-6 ]
[ 22876-22-8 ]
N-benzhydryl-2-(5-methyl-benzooxazol-2-ylsulfanyl)-acetamide [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2004,vol. 179,p. 2183 - 2188

14
[ 22876-22-8 ]
[ 50772-54-8 ]
N-(4,5-dimethyl-thiazol-2-yl)-2-(5-methyl-benzooxazol-2-ylsulfanyl)-acetamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2004,vol. 39,p. 267 - 272

15
[ 60442-41-3 ]
[ 22876-22-8 ]
2-[2-(5-methyl-benzooxazol-2-ylsulfanyl)-acetylamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2005,vol. 180,p. 1841 - 1848

16
[ 22876-22-8 ]
C₂₈H₃₀N₂O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4689 - 4693

17
[ 119-33-5 ]
[ 22876-22-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3515 - 3523

18
[ 22876-22-8 ]
[ 199292-78-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3515 - 3523
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 3015 - 3021
[3]Chemical and Pharmaceutical Bulletin,1998,vol. 46,p. 445 - 451

19
[ 22876-22-8 ]
3-MeO-C₆H₄CH₂-halide [ No CAS ]
XT₅₃₃ [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1997,vol. 7,p. 151 - 167

20
[ 22876-22-8 ]
3-MeO-C₆H₄CH₂-halide [ No CAS ]
2-(3-methoxy-phenylmethanesulfonyl)-5-methyl-benzooxazole [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1997,vol. 7,p. 151 - 167

21
[ 22876-22-8 ]
picolinic acid N¹-2-(5-methylbenzoxazolyl)amidrazone [ No CAS ]

Reference： [1]Archiv der Pharmazie,1997,vol. 330,p. 169 - 172

22
[ 22876-22-8 ]
(2-Cyclohexyl-1-pyridin-3-yl-ethyl)-(5-methyl-benzooxazol-2-yl)-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 913 - 923

23
[ 22876-22-8 ]
(2-Cyclohexyl-1-pyridin-4-yl-ethyl)-(5-methyl-benzooxazol-2-yl)-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 913 - 923

24
[ 22876-22-8 ]
(R,S)-N-<2-cyclohexyl-1-(2-pyridynyl)ethyl>-5-methyl-2-benzoxazolamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 913 - 923

25
[ 22876-22-8 ]
ontazolast [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 913 - 923

26
[ 22876-22-8 ]
BIRM-270 [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 913 - 923

27
[ 22876-22-8 ]
[ 93794-10-6 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1719 - 1728

28
[ 22876-22-8 ]
[ 114997-44-3 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1719 - 1728

29
[ 22876-22-8 ]
[ 114997-50-1 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1719 - 1728

30
[ 95-84-1 ]
[ 22876-22-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1518 - 1524
[2]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1518 - 1524

31
[ 110-85-0 ]
[ 22876-22-8 ]
5-methyl-2-(piperazin-1-yl)benzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In toluene; at 150℃; for 16h;	In a 100ml round bottom flask was placed 0.604g (4mmol) of benzoxazole and 0.688g (8 mmol) of anhydrouspiperazine or substituted piperazine derivative. 50 ml of drytoluene was added to this mixture and the contents werestirred and refluxed over an oil bath maintained at 150C for16-18 hours. After this period, the mixture was cooled andthe solvent was rotary evaporated and the residue wassubjected to column chromatography over silica gel usingmethanol/methylene chloride (20/80) to furnish the titledcompounds.
	With phosphorus pentachloride; sodium hydrogencarbonate; In toluene;	INVENTIVE EXAMPLE 9 5-Methyl-2-(1-piperazinyl)benzoxazole A 100 mg portion of <strong>[22876-22-8]5-methyl-2-mercaptobenzoxazole</strong> was suspended in 20 ml of anhydrous toluene, and the suspension was mixed with 150 mg of phosphorus pentachloride and heated under reflux for 1 hour. The reaction solution was cooled in an ice bath and, with stirring, 500 mg of piperazine was added thereto. After 30 minutes of stirring, the ice bath was removed to carry out 1 hour of stirring at room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution, and then the water layer was washed with ethyl acetate and concentrated under a reduced pressure. Thereafter, the thus obtained mixture was purified by an LH-20 gel column chromatography (chloroform:methanol=1:1) to obtain the title compound (40 mg) in white color. 1 H-NMR (DCl) delta values: 2.39 (3 H, s), 3.35 (4 H, t), 4.05 (4 H, t), 3.75 (2 H, d), 7.12 (1 H, d), 7.24 (1 H, s), 7.39 (1 H, s); MS (EI): m/z 217 (M+)

Reference： [1]Letters in Organic Chemistry,2010,vol. 7,p. 519 - 527
[2]Patent: US6037342,2000,A

32
[ 4318-37-0 ]
[ 22876-22-8 ]
[ 199292-96-1 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform;	INVENTIVE EXAMPLE 35 5-Methyl-2-(4-methyl-1-homopiperazinyl)benzoxazole 5-Methyl-2-mercaptobenzoxazole (200 mg) was dissolved in chloroform (20 ml), N-methylhomopiperazine (1.24 ml) was added dropwise to the solution and then the mixture was stirred with heating for 2 days. After evaporation of the solvent, the thus obtained mixture was purified by a silica gel column chromatography (methylene chloride:methanol=10:1) to obtain the title compound 5-methyl-2-(4-methyl-1-homopiperazinyl)benzoxazole (124 mg).

Reference： [1]Patent: US6037342,2000,A

33
[ 72336-24-4 ]
[ 22876-22-8 ]
[ 445260-71-9 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2007,vol. 182,p. 639 - 646

34
[ 140-89-6 ]
[ 95-84-1 ]
2-Thiol Benzoxazole [ No CAS ]
[ 22876-22-8 ]

Yield	Reaction Conditions	Operation in experiment
92.3%	With acetic acid; In ethanol; water;	General Procedure for Preparing 2-Thiol Benzoxazole or Benzothiazole Intermediates: Potassium ethyl xanthate (4.4 g, 27.5 mmol.) was added to solution of 2-amino-4-methyl-phenol (2 g, 16.2 mmol.) in ethanol (40 mL). The reaction mixture was heated at reflux for 4 h then allowed to cool to rt. Upon cooling to rt the mixture was concentrated and the resulting residue was dissolved in water. Acetic acid was added until pH=5 and a white solid precipitated from the solution. The solid was collected by filtration, washed with water and dried to afford 5-methylbenzo[d]oxazole-2-thiol as a powder (2.4 g, 92.3%) which was used without further purification. MS (ESI) m/e (M+H+) 166.

Reference： [1]Patent: US2009/269305,2009,A1

35
[ 623-24-5 ]
[ 22876-22-8 ]
[ 1220709-72-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 1617 - 1625

36
[ 1237542-32-3 ]
[ 22876-22-8 ]
[ 1237542-35-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 3320 - 3328

37
[ 22876-22-8 ]
[ 1334386-29-6 ]

Reference： [1]Patent: US2011/224269,2011,A1

38
[ 22876-22-8 ]
[ 1334386-00-3 ]

Reference： [1]Patent: US2011/224269,2011,A1

39
[ 22876-22-8 ]
[ 1334386-01-4 ]

Reference： [1]Patent: US2011/224269,2011,A1

40
[ 105-39-5 ]
[ 22876-22-8 ]
[ 682330-60-5 ]