[ CAS No. 32137-76-1 ] {[proInfo.proName]}

Name: 32137-76-1|Ethyl 1,3-benzothiazole-2-carboxylate|98%
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3d Animation Molecule Structure of 32137-76-1

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COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 32137-76-1 ]

Product Details of [ 32137-76-1 ]

CAS No. :	32137-76-1	MDL No. :	MFCD00848360
Formula :	C₁₀H₉NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VLQLCEXNNGQELL-UHFFFAOYSA-N
M.W :	207.25	Pubchem ID :	640708
Synonyms :

Calculated chemistry of [ 32137-76-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.71
TPSA :	67.43 Å²

Pharmacokinetics

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

Lipophilicity

Log Po/w (iLOGP) :	2.57
Log Po/w (XLOGP3) :	2.49
Log Po/w (WLOGP) :	2.47
Log Po/w (MLOGP) :	1.65
Log Po/w (SILICOS-IT) :	3.29
Consensus Log Po/w :	2.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.97
Solubility :	0.221 mg/ml ; 0.00107 mol/l
Class :	Soluble
Log S (Ali) :	-3.55
Solubility :	0.0583 mg/ml ; 0.000281 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.46
Solubility :	0.0724 mg/ml ; 0.000349 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.42

Safety of [ 32137-76-1 ]

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

Application In Synthesis of [ 32137-76-1 ]

* 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 [ 32137-76-1 ]
Downstream synthetic route of [ 32137-76-1 ]

[ 32137-76-1 ] Synthesis Path-Upstream 1~3

1
[ 515-84-4 ]
[ 126507-54-8 ]
[ 615-20-3 ]
[ 32137-76-1 ]

Reference： [1] Journal of Organometallic Chemistry, 1999, vol. 588, # 2, p. 155 - 159

2
[ 32137-76-1 ]
[ 37859-43-1 ]

Reference： [1] Tetrahedron, 1988, vol. 44, # 7, p. 2021 - 2032

3
[ 32137-76-1 ]
[ 7724-12-1 ]

Reference： [1] Patent: US2011/224442, 2011, A1,
[2] Patent: US2011/224442, 2011, A1,
[3] Patent: US2011/224442, 2011, A1,

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Yield	Reaction Conditions	Operation in experiment
90%	In ethanol;Reflux;	A solution of hydrazine hydrate (22 mmol) and <strong>[32137-76-1]ethyl benzo[d]thiazole-2-carboxylate</strong> (10 mmol) in absolute ethanol (50 mL)was refluxed for 1 h. The solid formed was filtered off and washedwith ethanol, dried and crystallization from ethanol afforded benzo[d]thiazole-2-carbohydrazide (4c) as pale yellow crystals in 90%yield, mp = 175-176 C [lit.80 mp. 175-176 C]; 1H NMR (CDCl3+ DMSO-d6, 400 MHz): d 7.99 (ddd, J = 8.0, 1.6, 0.4 Hz, 1H), 7.95(ddd, J = 8.0, 1.6, 0.4 Hz, 1H), 7.48 (td, J = 7.2, 1.6 Hz, 1H); 7.43(td, J = 7.2, 1.6 Hz, 1H); 13C NMR (CDCl3 + DMSO-d6, 100 MHz): d163.07, 159.09, 153.11, 136.28, 126.91, 126.76, 124.22 and122.51 ppm. ESI mass (m/z) 193.8 [M+H]+ (calculated exact mass193.0); CAS number: 28891-34-1.
90%	With hydrazine hydrate; In ethanol; for 1h;Reflux;	An ethanol solution (50 mL) in which hydrazine hydrate (22 mmol) and ethylbenzo [d] thiazole-2-carboxylate (10 mmol; 4f) were dissolved was refluxed for 1 hour. The resulting solid was filtered, washed with ethanol and dried. Crystallization with ethanol gave pale yellow crystals of benzo [d] thiazole-2-carbohydrazide (4c) in 90% yield.
89.1%	With hydrazine hydrate; In ethanol; for 6h;Reflux;	To a 250 mL round bottom flask was added <strong>[32137-76-1]ethyl benzothiazole-2-carboxylate</strong> (1.0363 g, 5.0 mmol). 20 mL ethanol and 2 mL hydrazine hydrate were added followed by heating the solution to reflux for 6 hours. The reaction mixture was cooled to room temperature and solid precipitate was filtered, collected, and recrystallized in ethanol to yield benzo[d]thiazole-2-carbohydrazide (943.4 mg, 89.1% yield).

Yield	Reaction Conditions	Operation in experiment
	With KNO3; In sulfuric acid;	EXAMPLE 5 Synthesis of ethyl 6-nitrobenzothiazole-2-carboxylate (7) Ethyl 6-nitrobenzothiazole-2-carboxylate was synthesized from <strong>[32137-76-1]ethyl benzothiazole-2-carboxylate</strong> according to the following reaction scheme. In particular, commercially available <strong>[32137-76-1]ethyl benzothiazole-2-carboxylate</strong> 6 (24.1 mmol, 5.0 g) was suspended in 22 ml conc. H2SO4 at 0 C. At 10 C. KNO3 (26.4 mmol, 26 g) was added portionwise over 30 min to the stifling solution, not to exceed 15 C. Color of reaction changed from bright green/yellow to yellow over time. The reaction warmed from 25 C. to 40 C. for an additional 30 min. When the temperature of the reaction was decreased, the solution was poured over ice/water). The precipitate forming in solution was collected via glass frit vacuum filtration to yield a light yellow solid 7. Resultant solid 7 was additionally washed with water, extracted into EtOAc, and concentrated in vacuo. Agilent HPLC displayed partial conversion to the crude product at ~10.0 min with a peak at ~9.9 min corresponding to the starting material. Attempts to purify the product were made using gravity silica column chromatography (4 Hexane: 1 EtOAc) to yield a yellow solid (~10% yield).
	With sulfuric acid; potassium nitrate; at 10 - 40℃; for 1h;	Example 5Synthesis of ethyl 6-nitrobenzothiazole-2-carboxylate (7)Ethyl 6-nitrobenzothiazole-2-carboxylate was synthesized from <strong>[32137-76-1]ethyl benzothiazole-2-carboxylate</strong> according to the following reaction scheme. In particular, commercially available <strong>[32137-76-1]ethyl benzothiazole-2-carboxylate</strong> 6 (24.1 mmol, 5.0 g) was suspended in 22 ml conc. H2SO4 at 0 C. At 10 C. KNO3 (26.4 mmol, 2.6 g) was added portionwise over 30 min to the stifling solution, not to exceed 15 C. Color of reaction changed from bright green/yellow to yellow over time. The reaction warmed from 25 C. to 40 C. for an additional 30 min. When the temperature of the reaction was decreased, the solution was poured over ice/water). The precipitate forming in solution was collected via glass frit vacuum filtration to yield a light yellow solid 7.Resultant solid 7 was additionally washed with water, extracted into EtOAc, and concentrated in vacuo. Agilent HPLC displayed partial conversion to the crude product at 10.0 min with a peak at 9.9 min corresponding to the starting material. Attempts to purify the product were made using gravity silica column chromatography (4 Hexane: 1 EtOAc) to yield a yellow solid (10% yield). Compound 7 was identified with LC/MS spectroscopic analysis as illustrated in FIG. 16.

Yield	Reaction Conditions	Operation in experiment
98%	With lithium hydroxide; In tetrahydrofuran; water; at 0 - 10℃; for 0.5h;	To the solution of 2 (207mg, 1mmol) in 22 THF (0.5mL) at 10C was added 107 LiOH·H2O (42mg, 1mmol, 1equiv) in 99 water (2mL) and stirred magnetically for 30min followed by drop wise addition of dil. 108 HCl (1N) until precipitation occurred. The precipitate was filtered and dried under rotary vacuum evaporation (24 psi) to afford 19 5a in 98% yield, identical (spectral data) with an authentic sample [12]. 4.1.4 19 Benzo[d]thiazole-2-carboxylic acid (5a) (0024) Yield: 175mg, 98% (white solid), mp 104-108C. IR (KBr) nu: 1708cm-1. 1H NMR (400MHz, DMSO-D6): delta (ppm): 9.43 (s, 1H), 8.19 (d, J=8.52Hz, 1H), 8.12 (d, J=8.44Hz, 1H), 7.57 (dt, J=1.16, 8.2Hz, 1H), 7.51 (dt, J=1.2, 8.08Hz, 1H). 13C NMR (100MHz, DMSO-D6): delta (ppm): 161.43, 159.98, 152.97, 136.26, 127.47, 127.15, 124.68, 122.99; MS (APCI) m/z 180 (M+H) +
87.57%	With water; sodium hydroxide; In tetrahydrofuran; at 20℃; for 2h;	Weigh 1.40g (6.76mmol)Ethyl benzothiazole-2-carboxylate in a 100 mL round bottom bottle,Add 15 mL of tetrahydrofuran,Add 4.05 mL (8.11 mmol) with stirring at room temperatureAqueous sodium hydroxide solution (2M),After stirring the reaction for 2 hours,The reaction was monitored by TLC (PE: EA = 5:1). Adjust the pH to 2 with 2M hydrochloric acid,After dilution with water, suction filtration gave a white solid.After drying, the product was obtained in 1.06 g (5.92 mmol).The yield was 87.57%.
81%	With water; sodium hydroxide; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	To a solution of A (10 g, 48 mmol) in THF (50 mL) at 0C under nitrogen was added aq.NaOH (72ml, 2M, 145 mmol). Reaction mixture was stirred at room temperature for 30-120min, monitored by TLC. Mixture was acidified with aq.HCl (6M) to pH=3-4, and precipitate filtered to give 1 (7 g, 81%) as a white solid.

81.4%	With sodium hydroxide; In tetrahydrofuran; methanol; water; for 4h;Reflux;	Ethyl benzothiazole-2-carboxylate 4a (4.8 mmol) was refluxedfor 4 h along with 1 g NaOH in a mixture of methanol (22 mL),water(9 mL) and THF (11 mL). After completion of the ester hydrolysis,the organic solvents were evaporated under reduced pressure andthe aqueous solution was extracted with DCM. The organic phasewas discarded while the aqueous phase was acidified to pH 3 using1 N HCl, extracted with EtOAc twice and the combined organicphases were passed over anhydrous MgSO4. Evaporating theorganic solvent under reduced pressure afforded the pure desiredacid 4b. Yellow solid (81.4%); mp: 103e104; 1H NMR (d): (400 MHz,CDCl3) d 9.09 (s, 1H), 8.20 (d, J 8.0 Hz, 1H), 7.99 (d, J 8.5 Hz, 1H),7.60e7.46 (m, 2H) [45].
	With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20℃; for 4h;	Suspension of <strong>[32137-76-1]ethyl benzothiazole-2-carboxylate</strong> (0.1 m) and lithium hydroxide monohydrate (0.12 m) in THF:water (2:1) was stirred for 4 h at RT. After completion of the reaction (confirmed by TLC), it was extracted with ethyl acetate.The aqueous layer was acidified by adding 2 N HCl to obtain white precipitate, which was extracted by filtering and dried. M.p.: 147-148 C.

[ CAS No. 32137-76-1 ] {[proInfo.proName]}

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