[ CAS No. 22514-58-5 ] {[proInfo.proName]}

Name: 22514-58-5|2-Bromobenzo[d]thiazole-6-carboxylic acid|95%
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SKU: A115257
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Quality Control of [ 22514-58-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 22514-58-5 ]

Product Details of [ 22514-58-5 ]

CAS No. :	22514-58-5	MDL No. :	MFCD09266217
Formula :	C₈H₄BrNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ICKXPLAJDFRFME-UHFFFAOYSA-N
M.W :	258.09	Pubchem ID :	45789628
Synonyms :

Calculated chemistry of [ 22514-58-5 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.28
TPSA :	78.43 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) :	-5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.71
Log Po/w (XLOGP3) :	2.85
Log Po/w (WLOGP) :	2.76
Log Po/w (MLOGP) :	1.77
Log Po/w (SILICOS-IT) :	3.16
Consensus Log Po/w :	2.45

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.68
Solubility :	0.0537 mg/ml ; 0.000208 mol/l
Class :	Soluble
Log S (Ali) :	-4.16
Solubility :	0.018 mg/ml ; 0.0000699 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.2
Solubility :	0.163 mg/ml ; 0.000632 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.17

Safety of [ 22514-58-5 ]

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 [ 22514-58-5 ]

* 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 [ 22514-58-5 ]
Downstream synthetic route of [ 22514-58-5 ]

[ 22514-58-5 ] Synthesis Path-Upstream 1~3

1
[ 66947-92-0 ]
[ 22514-58-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: With lithium hydroxide; water In tetrahydrofuran at 0 - 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran	2-Bromo-benzothiazole-6-carboxylic acid; [00105] To a solution of 2-bromo-benzothiazole-6-carboxylic acid methyl ester (1.256 g, 4.39 mmol) in THF (60 mL) and H₂O (20 mL) is added lithium hydroxide monohydrate (920 mg, 21.9 mmol) at 0 ⁰C. The mixture is stirred at rt overnight. The mixture is treated with IN HCl solution to adjust pH to 2 and extracted with ethyl acetate. The organic phase is washed with brine. The solvent is removed in vacuo and the crude product is used for next step without further purification. MS(ESI) m/z: 257.9 (M+l) ⁺.

Reference： [1] Patent: WO2008/124393, 2008, A1, . Location in patent: Page/Page column 33-34

2
[ 1024583-33-2 ]
[ 22514-58-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 7, p. 2324 - 2328

3
[ 22514-58-5 ]
[ 18107-18-1 ]
[ 1024583-33-2 ]

Reference： [1] Patent: US2011/152287, 2011, A1, . Location in patent: Page/Page column 21

[ 22514-58-5 ] Synthesis Path-Downstream 1~26

2
[ 22514-58-5 ]
[ 75-65-0 ]
[ 945400-88-4 ]

Yield	Reaction Conditions	Operation in experiment
	With diphenylphosphoranyl azide; triethylamine; at 80℃; for 4.0h;	Triethylamine (1.94 mL, 13.9 mmol) and diphenylphosphoryl azide (2.76 niL, 12.8 mmol) were added to a solution of 2-bromo-l,3-benzothiazole-6-carboxylic acid (3.0 g, 11.6 mmol) in tert-butanol (100 mL) and the reaction mixture was stirred at 80 0C for 4 h. The solvent was evaporated under reduced pressure and the residue was subjected to flash chromatography (Heptane/EtOAc gradient) to give tert-butyl (2-bromo-l,3-benzothiazol- 6-yl)carbamate (1.1 g) as a white solid. MS m/z (M+H) 329, 331.

Reference： [1]Patent: WO2007/86800,2007,A1 .Location in patent: Page/Page column 100

3
[ 22514-58-5 ]
C₈H₃BrClNOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 20 - 60℃; for 1.5h;	2-Bromo-l,3-benzothiazole-6-carboxylic acid (100 mg, 0.39 mmol) and thionyl chloride (2 mL) were mixted and stirred at rt for 1 h then at 60 0C for 30 min. The mixture was <n="100"/>concentrated under reduced pressure and the residue was dissolved in CHCl3 (3 niL). This solution was added dropwise to NH3 (ca. 7 N in MeOH, 5 mL) at 0 0C. The mixture was stirred at rt for 1 h before it was concentrated under reduced pressure. The crude product was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc and the organic phase was dried (Na2SO4) and concentrated to give the the product (77 mg) as a white solid. MS m/z (M+H) 213, (M-H) 211.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; for 3.0h;Cooling with ice;	STEP A: <strong>[22514-58-5]2-Bromo-6-benzothiazolecarboxylic acid</strong> (496.0 mg, 192 mmol) was suspended in dichloromethane (15 mL), cooled in ice bath, then treated with 2M oxalyl chloride in dichloromethane (2 mL, 4 mmol) and 1 drop of dimethylformamide. The resulting homogenous mixture was stirred for 3 h, then concentrated to a solid. The solid was dissolved in dichloromethane (20 mL), the resulting solution was cooled in an ice bath, then treated with diisopropylethylamine (0.45 mL, 2.58 mmol) and 4-aminoveratole (323.9 mg, 2.11 mmol). The resulting mixture was stirred overnight at room temperature, then diluted with dichloromethane, washed with water, washed with brine, dried over sodium sulfate, filtered and concentrated to yield 2-bromo-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide as a brown solid. 1HNMR (DMSO-d6) delta 10.3 (s, 1H), 8.69 (s, 1H), 8.10 (s, 2H), 7.47 (d, J=2.23 Hz, 1H), 7.37-7.33 (m, 1H), 6.94 (d, J=8.73 Hz, 1H), 3.76 (s, 3H), 3.75 (s, 3H). MS MH+=393.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1.0h;	2-Chloro-benzothiazole-6-carboxylic acid r2-methyl-5-(3-trifluoromethyl-benzoylamino)- phenyll -amide[0100] To a solution of <strong>[22514-58-5]2-bromo-benzothiazole-6-carboxylic acid</strong> (984 mg, 3.81 mmol) in CH2Cl2 (40 mL) is added DMF (70 muL) and oxalyl chloride (6.6 mL, 76 mmol). After the addition is complete, the reaction is stirred at rt for an additional hour. After solvent removal in vacuo, the crude product is used without further purification. The corresponding acetyl chloride <n="36"/>is dissolved in 20 mL CH2Cl2. The solution is added via cannula to a solution of N-(3-amino-4- methyl-phenyl)-3-trifluoromethyl-benzamide (1.12 g, 3.81 mmol) and diisopropanylethylamine (1.65 mL, 9.52 mmol) in 40 mL CH2Cl2 at 0 0C over 30 min. The mixture is stirred at rt for 1 h. The mixture is extracted with ethyl acetate. The organic phase is washed with saturated nuaHCU3 solution and brine. The solvent is removed in vacuo and the crude product is purified by recrystallization (hexane:CH2Cl2/10:l) to give 2-chloro-benzothiazole-6-carboxylic acid [2- methyl-5-(3-trifluoromethyl-benzoylamino)-phenyl]-amide. 1H NMR (400 MHz, DMSO) delta 10.50 (s, IH), 10.12 (s, IH), 8.75 (s, IH), 8.30 (s, IH), 8.26 (d, IH), 8.13 (s, 2H), 7.97 (d, IH), 7.87 (d, IH), 7.78 (d, IH), 7.61 (dd, IH), 7.29 (d, IH), 2.24 (s, 3H). MS(ESI) m/z: 490.1 (M+ 1)

Reference： [1]Patent: WO2007/86800,2007,A1 .Location in patent: Page/Page column 98-99
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2324 - 2328
[3]Patent: US2011/152287,2011,A1 .Location in patent: Page/Page column 18
[4]Patent: WO2008/124393,2008,A1 .Location in patent: Page/Page column 33; 34-35

4
[ 1024583-33-2 ]
[ 22514-58-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2324 - 2328

5
[ 66947-92-0 ]
[ 22514-58-5 ]

Yield	Reaction Conditions	Operation in experiment
99%		2-Bromo-benzothiazole-6-carboxylic acid; [00105] To a solution of 2-bromo-benzothiazole-6-carboxylic acid methyl ester (1.256 g, 4.39 mmol) in THF (60 mL) and H2O (20 mL) is added lithium hydroxide monohydrate (920 mg, 21.9 mmol) at 0 0C. The mixture is stirred at rt overnight. The mixture is treated with IN HCl solution to adjust pH to 2 and extracted with ethyl acetate. The organic phase is washed with brine. The solvent is removed in vacuo and the crude product is used for next step without further purification. MS(ESI) m/z: 257.9 (M+l) +.

Reference： [1]Patent: WO2008/124393,2008,A1 .Location in patent: Page/Page column 33-34

6
[ 22514-58-5 ]
[ 18107-18-1 ]
[ 1024583-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane; at 20℃;Cooling with ice;	STEP A: <strong>[22514-58-5]2-Bromo-6-benzothiazolecarboxylic acid</strong> (0.500 g, 1.94 mmol) was suspended in dichloromethane/methanol (12 ml, 6:1) and cooled to 0 C. with an ice-water bath. Then, 2M (trimethylsilyl)diazomethane (2.91 ml, 5.81 mmol) was added dropwise over 5 min. The resulting mixture was warmed to room temperature and stirred at room temperature for 2 hrs. The resulting mixture was concentrated in vacuo to yield methyl 2-bromobenzo[d]thiazole-6-carboxylate. 1HNMR (CDCl3) delta 8.55 (s, 1H), 8.15 (d, J=8.6 Hz, 1H), 8.02 (d, J=8.6 Hz, 1H), 3.07 (s, 3H).

Reference： [1]Patent: US2011/152287,2011,A1 .Location in patent: Page/Page column 21

7
[ 22514-58-5 ]
[ 1312762-76-7 ]