[ CAS No. 80-48-8 ] {[proInfo.proName]}

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Quality Control of [ 80-48-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 80-48-8 ]

SDS Specification

Alternatived Products of [ 80-48-8 ]

Product Citations

Achieving Smart Photochromics Using Water-Processable, High-Contrast, Oxygen-Sensing, and Photoactuating Thiazolothiazole-Embedded Polymer Films

Tyler J. Adams ; Naz F. Tumpa ; Maithili Acharya , et al. ACS Appl. Opt. Mater.,2024,2(5):704-713. DOI: 10.1021/acsaom.4c00014

Abstract: Water-soluble dipyridinium thiazolo[5,4-d]thiazole (TTz) compounds are incorporated into inexpensive poly(vinyl alcohol) (PVA)/borax films and exhibit fast (<1 s), high-contrast photochromism, photofluorochromism, and oxygen sensing. Under illumination, the films change from clear/yellow TTz2+ to purple TTz?+ and then blue TTz0. The contrast and speed of the photochromism are dependent on the polymer matrix redox properties and the concentration of TTz2+. The photoreduced films exhibit strong, near-infrared light (1000–1500 nm) absorbances in addition to visible color changes. Spectroscopic ellipsometry was used to establish the complex dielectric function for the TTz2+ and TTz0 states. Incorporating non-photochromic dyes yields yellow-to-green and pink-to-purple photochromism. Additionally, when illuminated, reversible photoactuation occurs, causing mechanical contraction in the TTz-embedded films. The blue film returns to its colorless state via exposure to O2, making the films able to sense oxygen and leak direction for smart packaging. These films show potential for use in self-tinting smart windows, eyeglasses, displays, erasable memory devices, fiber optic communication, and oxygen sensing.

Keywords: photochromic ; photofluorochromic ; photoactuator ; thiazolothiazole ; oxygen sensor ; sensing ; green chemistry

Purchased from AmBeed: 872-85-5 ; 80-48-8 ; 79-40-3 ; 3779-42-8

Product Details of [ 80-48-8 ]

CAS No. :	80-48-8	MDL No. :	MFCD00008417
Formula :	C₈H₁₀O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VUQUOGPMUUJORT-UHFFFAOYSA-N
M.W :	186.23	Pubchem ID :	6645
Synonyms :

Calculated chemistry of [ 80-48-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.59
TPSA :	51.75 ?2

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) :	-6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.9
Log Po/w (XLOGP3) :	1.54
Log Po/w (WLOGP) :	2.41
Log Po/w (MLOGP) :	1.78
Log Po/w (SILICOS-IT) :	1.11
Consensus Log Po/w :	1.75

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.2
Solubility :	1.17 mg/ml ; 0.00627 mol/l
Class :	Soluble
Log S (Ali) :	-2.24
Solubility :	1.08 mg/ml ; 0.00581 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.84
Solubility :	0.27 mg/ml ; 0.00145 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.02

Safety of [ 80-48-8 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P270-P272-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P333+P313-P362+P364-P405-P501	UN#:	3265
Hazard Statements:	H302-H314-H317-H401	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 80-48-8 ]

* 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.

Upstream synthesis route of [ 80-48-8 ]
Downstream synthetic route of [ 80-48-8 ]

[ 80-48-8 ] Synthesis Path-Upstream 1~1

1
[ 80-48-8 ]
[ 400827-68-1 ]
[ 400827-64-7 ]

Yield	Reaction Conditions	Operation in experiment
74.3%	Stage #1: for 12 h; Reflux Stage #2: With pyridine; phosphorus pentachloride In dichloromethane at -10 - -5℃; for 2 h; Stage #3: With hydrogenchloride In dichloromethane; 2-methyl-propan-1-ol; acetone at 25 - 30℃;	A glass round bottom flask was charged with 35g (51,7 mmol) of 5-Thia-1-azabicyclo[4.2.0]oct- 2-ene-2-carboxylic acid, 8-oxo-7-[(2-phenylacetyl)amino]-3-[[4-(4-pyridinyl)-2-thiazolyl]thio]-, diphenylmethyl ester, (6R,7R) and 75 mE of dichloromethane, at 25°C. To the obtained solution were added 48 mE (258,5 mmol) of methyl paratoluenesulphonate and the mixture was heated to reflux and maintained for 12 hours under reflux, then cooled to room temperature. In glass lined reactor were charged 32,3 g (155,1 mmol) of phosphorous pentachloride and 75 mE of dichloromethane. The obtained suspension was cooled to -5÷0°C and 12.3 g (155,1 mmol)of pyridine were added dropwise by maintaining the temperature at -5÷0°C, then the mixture was maintained under stifling for 15 minutes at the same temperature. To the mixture, cooled to -1 0÷-5°C, was carefully added the solution prepared in the round bottom flask, keeping the temperature between -1 0÷-5°C; the mixture thus obtained was maintained under stifling for 2 hours at the same temperature. 105 mE of isobutanol were carefully added, in about 30 minutes, by maintaining the temperature at -5°C0°C; the obtained mixture was heated at 28÷30°C and left to react at the same temperature for 3.5 hours. The mixture was concentrated under vacuum to 1/3 of its volume, diluted with 200 mE of acetone and maintained under stifling for 1 hour at 25÷30°C. 70 mE of 32percent hydrochloric acid were added, keeping the temperature in the range of 25÷30°C, and themixture was maintained under stirring overnight. The obtained suspension was filtered, the cake was washed with acetone (2 x 35 ml). The wet solid was dried under vacuum at 40°C overnight yielding 18.4 g (38,4 mmol) of 4-[2- [[(6R,7R)-7-amino-2-carboxy-8-oxo-5-thia- 1- azabicyclo [4.2.01 oct-2-en-3-yl]thio] -4-thiazolyl] -1 -methyl pyridinium, chloride, hydrochloride (1:1:1) as a crystalline solid. Yield 74,3percent.

Reference： [1] Patent: WO2016/128580, 2016, A1, . Location in patent: Page/Page column 21

[ 80-48-8 ] Synthesis Path-Downstream 1~11

1
[ 2346-00-1 ]
[ 120879-63-2 ]
[ 80-48-8 ]
(3-methyl-4,5-dihydro-thiazol-2-yl)-(1-methyl-[2]pyridyl)-methinium ; iodide [ No CAS ]

Reference： [1]Patent: US2095855,1933,
[2]Patent: US2202827,1934,

2
[ 2346-00-1 ]
1-methyl-2-[2]naphthylsulfanyl-pyridinium; iodide [ No CAS ]
[ 80-48-8 ]
(3-methyl-4,5-dihydro-thiazol-2-yl)-(1-methyl-[2]pyridyl)-methinium ; iodide [ No CAS ]

Reference： [1]Patent: US2095855,1933,
[2]Patent: US2202827,1934,

3
[ 2346-00-1 ]
[ 80-48-8 ]
(3-methyl-thiazolidin-2-ylidene)-dithioacetic acid [ No CAS ]

Reference： [1]Patent: US2334711,1942,

4
[ 2346-00-1 ]
[ 80-48-8 ]
[ 61173-21-5 ]

Reference： [1]Patent: US2094580,1933,
[2]Patent: DE698814,1933,
DRP/DRBP Org.Chem.,

5
[ 2346-00-1 ]
[ 80-48-8 ]
1-(3-methyl-benzothiazol-2-yl)-3-(3-methyl-4,5-dihydro-thiazol-2-yl)-trimethinium ; iodide [ No CAS ]

Reference： [1]Journal of the Chemical Society,1948,p. 687,690

6
[ 20485-41-0 ]
[ 80-48-8 ]
5-carboxy-3,4-dimethyl-thiazolium; toluene-4-sulfonate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1971,vol. 93,p. 7045 - 7049

7
[ 80-48-8 ]
[ 13406-29-6 ]
[ 120360-41-0 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 2580 - 2586

8
[ 120277-39-6 ]
[ 80-48-8 ]
3-(3-hydroxy-1-propenyl)-1-methylpyridinium p-toluenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	In 30 ml of acetone 710 mg of 3-(3-pyridyl)-2-propen-1-ol and 980 mg of methyl p-toluenesulfonate were heated under reflux for 22 hours. The reaction mixture was subjected by decantation to remove the solvent and then washed with acetone and ether. The residue was dried under reduced pressure to give 1.3 g of the desired compound as an orange-colored oil. 1 H NMR (CD3 OD) delta: 2.34 (s, 3H), 4.28 (d, 2H), 4.34 (s, 3H), 6.7-6.8 (m, 2H), 7.1-8.9 (m, 8H). IR (neat) cm-1: 3350, 3050, 1700, 1500, 1440, 1360, 1290, 1210, 1180, 1115, 1030, 1000, 960, 815, 670.

Reference： [1]Patent: US4962096,1990,A

9
[ 20845-34-5 ]
[ 80-48-8 ]
1,1-Dimethyl-2-hydroxymethylpiperidinium p-toluenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		REFERENCE EXAMPLE 4 1,1-Dimethyl-2-hydroxymethylpiperidinium p-toluenesulfonate The procedures of Reference Example 3 were repeated using 2.58 g of 1-methyl-2-piperidinemethanol and 3.72 g of methyl p-toluenesulfonate to give 4.95 g of the desired compound. 1 H NMR (CDCl3) delta: 1.3-1.9 (m, 6H), 2.32 (s, 3H), 3.04 (s, 3H), 3.1-3.6 (m, 2H), 3.36 (s, 3H), 3.7-4.0 (m, 2H), 5.34 (t, 1H), 7.0-7.8 (m, 4H). IR (KBr) cm-1: 3325, 2925, 1490, 1470, 1445, 1190, 1125, 1040, 1000, 810, 680, 560.

Reference： [1]Patent: US4962096,1990,A

10
[ 6086-21-1 ]
[ 80-48-8 ]
[ 89315-67-3 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 5316 - 5318

11
[ 1253790-58-7 ]
[ 80-48-8 ]
[ 880468-89-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrabutylammomium bromide; potassium hydroxide; In toluene; at -1 - 2℃;	Toluene (820 mL), Intermediate III (50 g), methyl p-toluenesulfonate (63.5 g),Tetrabutylammonium bromide (5.4 g) was added and the mixture was cooled with stirring to -1 to 2 ° C. Potassium hydroxide aqueous solution (40 g / 34 mL) was added at -1 to 2 ° C, and the addition was completed in about 5 minutes. The addition was complete, continue to control the temperature at -1 ~ 2 reaction 4 ~ 4.5 hours (TLC detection or HPLC control) to stop the reaction. After completion of the reaction, water (400 mL) was added to separate the layers. Organic layer followed by 5percent phosphoric acid, saturated sodium bicarbonate, water each200mL wash. Decompression 40 ~ 45 ° C The solvent was evaporated to give an oil, the reaction was used directly for the next step. HPLC purity 95percent, chiral Purity 99.1percent.
60.97g	With tetrabutylammomium bromide; potassium hydroxide; In water; toluene; at 20℃; for 3h;	Toluene (330 mL) was added sequentially to the 1 L reaction flask,The compound of formula II (20.00 g, 68 mmol)P-toluenesulfonic acid methyl ester (63.50 g, 340 mmol),Tetrabutylammonium bromide (2.63 g, 8.16 mmol),Stir evenly,An aqueous solution of potassium hydroxide (16.00 g of potassium hydroxide + 16 mL of water) was added at room temperature,Plus complete, room temperature reaction 3 hours.Reaction completed, adding water (160mL), stirring 5min, standing stratification, liquid separation,Organic layer followed by 5percent phosphoric acid(80 mL), water (160 mL x 2), and the organic layer was concentrated at 55 ° C under reduced pressure. The solvent was evaporated to give 60.97 g of an oil.The product of this example was the same as in Example 1 by isolation and identification.
38.5 g	With tetrabutylammomium bromide; sodium hydroxide; In water; at 20℃; for 3h;	To a 1L reaction flask were sequentially added toluene (330 mL), Compound II (20.00 g, 68 mmol), methyl p-toluenesulfonate (38.10 g, 204 mmol), tetrabutylammonium bromide (2.63 g, 8.16 mmol), Stir well, add aqueous sodium hydroxide solution (16.00g of sodium hydroxide + 16mL of water) at room temperature, complete the addition, and react at room temperature for 3 hours. After the reaction is complete, add water (160 mL), stir for 5 min, stand for layering, separate the liquid, and use 5percent phosphoric acid in order for the organic layer.(80 mL) and water (160 mL×2) were washed. The organic layer was concentrated under reduced pressure at 55° C., and the solvent was evaporated to give 38.5 g of an oil.

38.5 g

With tetrabutylammomium bromide; sodium hydroxide; In water; toluene; at 20℃; for 3h;

Toluene (330 mL) was added sequentially to a 1L reaction flask,Compound II (20.00 g, 68 mmol),Methyl p-toluenesulfonate (38.10 g, 204 mmol),Tetrabutylammonium bromide (2.63 g, 8.16 mmol),Stir well,An aqueous solution of sodium hydroxide (16.00 g of sodium hydroxide + 16 mL of water) was added at room temperature.After the addition, the reaction was carried out at room temperature for 3 hours.After the reaction is complete, add water (160 mL) and stir for 5 min.Static stratification, liquid separation,The organic layer was successively washed with 5percent phosphoric acid (80 mL) and water (160 mL×2), and the organic layer was concentrated under reduced pressure at 55° C.After the solvent was distilled off, 38.5 g of an oil was obtained.

Reference： [1]Patent: CN106699605,2017,A .Location in patent: Paragraph 0043; 0044; 0046; 0048; 0049
[2]Patent: CN104892460,2017,B .Location in patent: Paragraph 0045; 0081; 0082; 0083; 0084; 0085-0092
[3]Patent: CN104892461,2017,B .Location in patent: Paragraph 0085; 0086; 0087
[4]Patent: CN105037209,2017,B .Location in patent: Sheet 0083; 0084; 0085

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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. 80-48-8 ] {[proInfo.proName]}

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[ 80-48-8 ] Synthesis Path-Upstream 1~1

[ 80-48-8 ] Synthesis Path-Downstream 1~11

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Aryls

Sulfonates

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[ 80-48-8 ]