[ CAS No. 36341-25-0 ] {[proInfo.proName]}

Name: 36341-25-0|4-(Benzo[d]thiazol-2-yl)-2-methoxyphenol|98%
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SKU: A139850
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Quality Control of [ 36341-25-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 36341-25-0 ]

SDS Specification

Alternatived Products of [ 36341-25-0 ]

Product Details of [ 36341-25-0 ]

CAS No. :	36341-25-0	MDL No. :	MFCD00030231
Formula :	C₁₄H₁₁NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KRVBOHJNAFQFPW-UHFFFAOYSA-N
M.W :	257.31	Pubchem ID :	3155228
Synonyms :

Calculated chemistry of [ 36341-25-0 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.07
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	73.57
TPSA :	70.59 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.87
Log Po/w (XLOGP3) :	3.88
Log Po/w (WLOGP) :	3.68
Log Po/w (MLOGP) :	2.32
Log Po/w (SILICOS-IT) :	4.17
Consensus Log Po/w :	3.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.36
Solubility :	0.0111 mg/ml ; 0.0000432 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.06
Solubility :	0.00224 mg/ml ; 0.00000871 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.04
Solubility :	0.00233 mg/ml ; 0.00000906 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 36341-25-0 ]

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 [ 36341-25-0 ]

* 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.

Upstream synthesis route of [ 36341-25-0 ]
Downstream synthetic route of [ 36341-25-0 ]

[ 36341-25-0 ] Synthesis Path-Upstream 1~8

1
[ 121-33-5 ]
[ 137-07-5 ]
[ 36341-25-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With cadmium sulphide In methanol at 20℃; for 0.416667 h; Irradiation	General procedure: In the experimental procedure for catalytic reaction, amixture of aldehyde (3 mmol), 2-aminothiophenol (3 mmol) and CdSnanosphere (5 mg) was taken in a 100 ml double walled quartz beaker flaskhaving water inlet and outlet to maintain the temperature of the reactionvessel at room temperature in methanol (20 ml). The beaker was exposed tovisible light under stirring condition for the required time period (Table 3).After completion of the reaction (monitored by TLC and GC), methanol wasevaporated by rotary and the product was dissolved in dichloromethane. Thecatalyst was separated from the reaction mixture by centrifugation.Dichloromethane was then evaporated to dryness and the product waspurified by column chromatography using silica gel G60.
91%	With lithium bromide In ethanol at 25 - 30℃; for 0.25 h; Sonication	General procedure: Aromatic aldehydes (1.0 mmol), o-aminothiophenol (1.0 mmol), and lithiumbromide (20 mol percent) in ethanol (5 mL) were added into a 50-mL round-bottomedflask. The reaction flask was placed in the ultrasonic cleaner bath with the surface ofreactants slightly lower than the water level and irradiated at 25–30 C for theperiod of time indicated in Table 4. The progress of the reaction was monitored byTLC, using petroleum ether/ethyl acetate (8:2) as a solvent system. Aftercompletion of the reaction, the reaction mixture was poured into ice-cold water.The precipitate was filtered off and washed with water, dried, and purified bycrystallization from ethanol as solvent to afford pure product.
89.2%	at 25 - 30℃; for 1.4 h; Sonication	General procedure: Aromatic aldehydes (2, 1.0 mmol), o-aminothiophenol (1, 1.0 mmol), FeCl₃/Montmorillonite K-10 (160 mg, 0.1 mmol, based on FeCl₃) and absolute methanol (5 mL) were added into a 25 mL conical flask. The reaction flask was placed in the ultrasonic cleaner bath, where the surface of reactants was slightly lower than the water level and irradiated at 25–30 °C for the period of time (sonication was continued until aromatic aldehydes disappeared as indicated by TLC) as indicated in Tables 1–4 . After completion of the reaction, the reaction mixture was dissolved in ethyl acetate and FeCl₃/Montmorillonite K-10 was filtered off. The filtrate was concentrated and purified by silica-gel column chromatography (200–300 mesh) using petroleum ether or the mixture of petroleum ether and ethyl acetate as eluent to give a light yellow crystalline solid. All of the products described herein were previously reported in the literatures [16–35]. The authenticity of the products was established by spectroscopic data and by comparing their melting points with literature values. brown crystals, IR (KBr, cm^-1): 3099, 3004, 2934, 1616, 1604, 1584, 1559, 1529, 1478, 1462, 1427, 1387, 1364, 1315, 1279, 1256, 1194, 1124, 1033, 1011, 894, 872, 776, 756, 727; ¹H NMR: δ_H 9.85 (s, 1H, OH), 8.06 (d, J = 8.2 Hz, 1H, ArH), 7.89 (d, J = 7.9 Hz, 1H, ArH), 7.75 (d, J = 1.8 Hz, 1H, ArH), 7.56 (dd, 1H, J₁ = 8.2 Hz, J₂ = 1.9 Hz, ArH), 7.48-7.51 (m, 1H, ArH), 7.37-7.39 (m, 1H, ArH), 7.03 (d, J = 8.2 Hz, 1H, ArH), 4.00 (s, 3H, CH₃); ¹³C NMR: δ_C 168.2, 154.0, 148.6, 147.0, 134.8, 126.3, 126.2, 124.9, 122.7, 122.0, 121.5, 114.8, 109.3, 56.2; m/z (ESI): 258 [M+H]⁺.

85%	Stage #1: With sodium hydrogen sulfate In ethanol Stage #2: Reflux	General procedure: Equimolar mixture of NaHSO3 (1.25 g, 0.012 mol) and corresponding aldehyde, viz. anisaldehyde (1.63 g, 0.012 mol) for mpb, vanillin (1.82 g, 0.012 mol) for mhpb, and salicylaldehyde (1.47 g, 0.012 mol) for hpbH, were refluxed in ethanol (15 mL) for 15–20 min. To the mixture o-aminothiophenol (1.25 g, 0.01 mol) was added and continued to reflux for 4–5 h. On slow cooling, colorless crystalline compound formed in each case was filtered, washed with water, recrystallized from ethanol, and dried over fused CaCl2. The solids were recrystallised from hot ethanol (scheme 1).
73.4%	With sodium metabisulfite In N,N-dimethyl-formamideReflux	General procedure: Sodium metabisulfite (0.49 g, 2.5 mmol) was added to a DMF solution of 2-aminothiophenol (2.50 g, 20 mmol) and 4-hydroxybenzaldehyde (2.46 g, 20.2 mmol ). The reaction mixture was stirred and heated to reflux for 2–2.5 h. The progress of reaction was monitored periodically by TLC for completion. Then the mixture was poured into crushed ice, the formed precipitate was separated by filtration and washing to obtain 4-(benzothiazol-2-yl)phenol 4a. Other benzothiazole intermediates 4-(benzothiazol-2-yl)-2-methoxyphenol 4b and 3-(benzothiazol-2-yl)phenol 4c were prepared using a similar synthetic method.21 (see Supplementary file.)
55.6%	at 20℃; for 22 h; Inert atmosphere	General procedure: To a stirred solution or suspension of substituted benzaldehydes (1.33 mmol, 1a-1l) in MeOH (3-7 mL), 2-aminothiophenol (1.60 mmol) was added and the reaction mixture was stirred at room temperature for 5-96 h. Work-up was conducted by one of the following three methods (Methods A-C). Method A: After evaporation of methanol, the resulting solid was filtered and the filter cake was washed with hexane, methylene chloride, ethyl acetate, and/or cold methanol. Method B: After evaporation of methanol, the resultant residue was dissolved in a small amount of methylene chloride, ethyl acetate, and/or cold methanol, followed by the addition of hexane. After cooling, the resulting precipitate was filtered and washed with hexane, methylene chloride, ethyl acetate, and/or cold methanol. Method C: After evaporation of half the volume of methanol, the reaction mixture was kept in a refrigerator, or water (20 ml) was added to the reaction mixture before refrigerator storage. The resulting precipitate was filtered and the filter cake was washed with hexane, methylene chloride, ethyl acetate, and/or cold methanol. In the cases of compounds, 2b and 2k, flash column chromatography (hexane/methylene chloride = 4/1 to 2/1 for 2b; methylene chloride/MeOH = 90/1 and then methylene chloride only for 2k) was conducted for further purification. The title products (2a-2l) were generated in yields ranging from 15.2percent to 82.6percent.
47.1%	With montmorillonite K-10; air In ethanol at 20℃; for 40 h;	General procedure: Aldehyde (2, 1.0 mmol) and o-aminothiophenol (1, 1.0 mmol) were mixed inabsolute ethanol (10 mL) in a 50-mL three-necked flask equipped with a watercooledcondenser and a gas inlet, as reported elsewhere [45]. The solution wasstirred at room temperature, then montmorillonite K-10 (25 mg) was added. Air wasbubbled continuously through the reaction system, at a speed of 60 bubbles perminute on average, by means of a small air pump. After completion of the reaction(monitored by TLC) the catalyst was recovered by filtration and washed with EtOH.The filtrate was concentrated and purified by short column chromatography on silicagel, with petroleum ether or a mixture of petroleum ether and ethyl acetate aseluent, to give the pure product. The products (3a–r) are all known compounds andwere identified by 1H NMR spectroscopy, by comparison of their melting pointswith those reported in the literature, and by comparison of their TLC Rf values withthose of standards.
20.23%	for 24 h; Reflux	General procedure: A mixture of 2-aminothiophenol (0.32 ml, 3 mmol), 0.30 ml(3 mmol) of benzaldehyde and 5 ml of pyridine in a 50 mlround-bottomed flask was refluxed for 24 hrs. Workup includedcooling the reaction mixture and transferred into 50ml of HCl 0.5 N solution. Precipitates formed were filteredand washed with water and dried at 60-70°C to dryness togive brown needle.

Reference： [1] Chemistry Letters, 2004, vol. 33, # 3, p. 274 - 275
[2] Tetrahedron Letters, 2013, vol. 54, # 9, p. 1090 - 1096
[3] Heterocycles, 2007, vol. 71, # 8, p. 1837 - 1842
[4] Research on Chemical Intermediates, 2015, vol. 41, # 10, p. 7509 - 7516
[5] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 1, p. 91 - 95
[6] Ultrasonics Sonochemistry, 2013, vol. 20, # 2, p. 627 - 632
[7] Journal of Coordination Chemistry, 2015, vol. 68, # 13, p. 2253 - 2270
[8] Chinese Chemical Letters, 2010, vol. 21, # 7, p. 790 - 793
[9] Research on Chemical Intermediates, 2013, vol. 39, # 5, p. 2077 - 2086
[10] RSC Advances, 2014, vol. 4, # 74, p. 39606 - 39611
[11] Arkivoc, 2018, vol. 2018, # 7, p. 86 - 99
[12] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2445 - 2449
[13] Research on Chemical Intermediates, 2015, vol. 41, # 8, p. 5159 - 5166
[14] Medicinal Chemistry, 2011, vol. 7, # 2, p. 127 - 134
[15] New Journal of Chemistry, 2015, vol. 39, # 7, p. 5116 - 5120
[16] Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5129 - 5132
[17] Journal of Molecular Structure, 2017, vol. 1148, p. 282 - 292

2
[ 95-16-9 ]
[ 121-33-5 ]
[ 36341-25-0 ]

Yield	Reaction Conditions	Operation in experiment
46%	With silver(I) 4-methylbenzenesulfonate In water at 100℃; for 12 h; Sealed tube; Inert atmosphere; Green chemistry	General procedure: A sealed pressure vessel was charged with benzothiazole (68 mg, 0.5 mmol), AgOTs (280 mg, 1 mmol),aldehyde (0.6 mmol) and 2.0 mL of H2O. The resulting solution was stirred at 100 C for 12 h under N2.Upon completion of the reaction, H2O (8.0 mL) was added, then extracted with EtOAc (5 mL × 3), driedover Na2SO4, and concentrated under reduced pressure. The residue was further purified with flashcolumn chromatography.

Reference： [1] Green Chemistry, 2012, vol. 14, # 6, p. 1577 - 1580
[2] Heterocycles, 2018, vol. 96, # 7, p. 1226 - 1237

3
[ 1173707-00-0 ]
[ 36341-25-0 ]

Reference： [1] Angewandte Chemie, International Edition, 2009, vol. 48, # 23, p. 4222 - 4225

4
[ 121-33-5 ]
[ 1141-88-4 ]
[ 36341-25-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	at 190℃; for 0.333333 h; Microwave irradiation; Green chemistry	General procedure: 2,2-Disulfanediyldianiline (1a) or 5,5-dichloro-2,2-dithiobisaniline (1b) (0.50 mmol), the corresponding aldehydes(2a-p) (1.1 mmol), NaSH (0.3 mmol) and PEG-300 (2 mL) wereput into a round-bottomed ask, and the reaction mixture wasirradiated for 20 min at 25 W. After completion of the reactionmonitored by TLC with a mixture of petroleum ether and ethylacetate as eluent, the mixture was allowed to cool to roomtemperature. Distilled water (25 mL) was added into the ask,and then the solid was precipitated from the aqueous phaseafter stirring by magnetic stirrers in 5 min. The solid precipitatewas isolated by fltration, washed twice by distilled water (5 mL)and dried for 3 h. The pure targetproducts3a-3o were obtaineddirectly. The pure products 3p and 3q were obtained by columnchromatography(PE/EtOAc as eluent).Complete characterization of the products (all known) is found in the SupplementalMaterials (Figures S 1–S 34).

Reference： [1] RSC Advances, 2015, vol. 5, # 89, p. 72745 - 72754
[2] European Journal of Organic Chemistry, 2010, # 15, p. 2849 - 2851
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2017, vol. 192, # 4, p. 464 - 468

5
[ 121-33-5 ]
[ 88-73-3 ]
[ 36341-25-0 ]

Reference： [1] Green Chemistry, 2017, vol. 19, # 18, p. 4289 - 4293

6
[ 3292-42-0 ]
[ 121-33-5 ]
[ 36341-25-0 ]

Reference： [1] Journal of the American Chemical Society, 1925, vol. 47, p. 3078[2] Journal of the Chemical Society, 1926, vol. 48, p. 250
[3] Chemische Berichte, 1916, vol. 49, p. 1145

7
[ 121-34-6 ]
[ 137-07-5 ]
[ 36341-25-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 5, p. 984 - 1000

8
[ 98370-54-8 ]
[ 121-33-5 ]
[ 36341-25-0 ]

Reference： [1] Journal of the American Chemical Society, 1925, vol. 47, p. 3078[2] Journal of the Chemical Society, 1926, vol. 48, p. 250

[ 36341-25-0 ] Synthesis Path-Downstream 1~1

1
[ 36341-25-0 ]
[ 10199-89-0 ]
4-(4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy)-7-nitrobenzo[c][1,2,5]oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.6%	With triethylamine In acetonitrile at 20℃; for 9h;	Synthesis of Probe BMNO BTMP-OH (200 mg, 0.77 mmol), 4-Chloro-7-nitrobenzofurazan (155.1 mg, 0.77 mmol) and triethylamine (0.92 mmol) were successively added to the CH3CN (20 mL) solution. The mixture was stirred for 9 h at room temperature. The yellow precipitate was collected after filtration, which was purified by column chromatography (dichloromethane/ethyl acetate, v/v = 50/1) to afford a pure yellow solid (224.3 mg, 68.6%). m.p.177.9-178.2 °C. 1H NMR (Fig. S6) (600 MHz, DMSO-d6) δ (ppm) 8.62 (d, J = 8.4 Hz,1H), 8.20 (d, J = 7.9 Hz, 1H), 8.12 (d, J = 8.1 Hz, 1H), 7.98(d, J = 1.8 Hz, 1H), 7.83 (dd, J = 8.2, 1.9 Hz, 1H), 7.63 (d,J = 8.3 Hz, 1H), 7.59 (t, J = 7.6 Hz, 1H), 7.51 (t, J = 7.6 Hz,1H), 6.76 (d, J = 8.4 Hz, 1H), 3.94 (s, 3H). 13C NMR (Fig.S7) (151 MHz, DMSO-d6) δ (ppm) 166.61, 153.95, 152.67,151.75, 145.34, 144.79, 143.48, 135.78, 135.24, 133.23,131.02, 127.32, 126.28, 123.87, 123.52, 122.94, 121.47, 112.19, 109.66, 56.80. HRMS: m/z (TOF MS ES-) (Fig.S8): Calcd. for C20H12N4O5S: 443.0426 [BMNO + Na+]+,found: 443.0424.

Reference： [1]Liu, Ting-Ting; Li, Shi-Jie; Zhang, Xiao-Song; Wang, Jing; Deng, Yun-Xiu; Sun, Xue-Jiao; Xing, Zhi-Yong; Wu, Ruo-Fei [Journal of Fluorescence, 2022, vol. 32, # 1, p. 175 - 188]

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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

[ CAS No. 36341-25-0 ] {[proInfo.proName]}

Quality Control of [ 36341-25-0 ]

Related Doc. of [ 36341-25-0 ]

Product Details of [ 36341-25-0 ]

Calculated chemistry of [ 36341-25-0 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 36341-25-0 ]

Application In Synthesis of [ 36341-25-0 ]

[ 36341-25-0 ] Synthesis Path-Upstream 1~8

[ 36341-25-0 ] Synthesis Path-Downstream 1~1

Precautionary Statements-General

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Physical hazards

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