[ CAS No. 943-08-8 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 943-08-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 943-08-8 ]

SDS Specification

Alternatived Products of [ 943-08-8 ]

Product Details of [ 943-08-8 ]

CAS No. :	943-08-8	MDL No. :	MFCD00518584
Formula :	C₈H₅F₂NS₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XYUPZERKMMCICQ-UHFFFAOYSA-N
M.W :	217.26	Pubchem ID :	1522327
Synonyms :

Safety of [ 943-08-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 943-08-8 ]

* 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 [ 943-08-8 ]

[ 943-08-8 ] Synthesis Path-Downstream 1~17

Yield	Reaction Conditions	Operation in experiment
61%	With tert.-butylhydroperoxide; trifluoroacetic acid; In dichloromethane; water; for 16h;	General procedure: Difluoromethylation of Heterocycles Standard Procedures: Procedure B: To a solution of heterocycle (0.25 mmol, 1.0 equiv) and zinc difluoromethanesulfinate (DFMS) (173 mg, 0.50 mmol, 2.0 equiv ‘calculated as anhydrous’) in dichloromethane (1.0 mL) and water (0.4 rnL) at room temperature was added trifluoroacetic acid (20 μL, 0.25 rnmol, 1.0 equiv) followed by slow addition of tert-butyl hydroperoxide (70% solution in water, 0.1 mL, 0.75 mmol, 3.0 equiv) with vigorous stirring. The reaction was monitored by thin layer chromatography until completion. For substrates which do not go to completion in 24 hours, a second addition of DFMS (2.0 equiv) and tert-butyl hydroperoxide (3.0 equiv) may be added to drive the reaction further. Upon consumption of starting material, the reaction was partitioned between dichioromethane (2.0 mL) and saturated sodium bicarbonate (2.0 mL) . The organic layer was separated, and the aqueous layer was extracted with dichioromethane (3 X 2.0 mL) . The organic layers were dried with sodium sulfate, concentrated and purified by column chromatography on silica gel. If substrates are less reactive, α,α,-trifluorotoluene can be substituted for DCM, as it causes improved reactivity for some cases. For water-soluble starting materials, a purely aqueous reaction (1.0 mL of water) can be run and in some cases, it was also found to display improved reactivity. In lieu of a workup, these reactions can be concentrated and the product purified directly. If the addition of tert-butyl hydroperoxide is performed too rapidly, the resulting exotherm can result in reduced yield and selectivity. This is especially important on larger scales (see gram scale procedure: substrate 2), where a syringe pump can be used to meter in tert-butyl hydroperoxide.It is noted that trifluoroacetic acid (TFA) is not required in either of the above procedures. It was also found that TFA showed improved rate and conversion for selected nitrogen heteroarene substrates, but was not essential to achieve the desired reactivity for most cases. When present, TFA is typically used at about 0.25 to about 2 equivalents per equivalent of nitrogen heteroarene, and more preferably at about 0.5 to about 1.5 equivalents relative to the nitrogen heteroarene.

2
[ 75-45-6 ]
[ 149-30-4 ]
[ 943-08-8 ]
3-(difluoromethyl)benzo[d]thiazole-2(3H-)-thione [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2001,vol. 108,p. 211 - 214

3
[ 1097192-99-8 ]
[ 149-30-4 ]
[ 943-08-8 ]
3-(difluoromethyl)benzo[d]thiazole-2(3H-)-thione [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 2109 - 2112

4
[ 943-08-8 ]
[ 186204-66-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide; In ethanol; at 20℃; for 42h;	A mixture of 7.18 g (33.05 mmol) of 2-[(difluoromethyl)sulfanyl]-1,3-benzothiazole, 2.04 g (1.65 mmol) of ammonium molybdate (NH4)6Mo7O24 x 4 H2O, 33.0 mL of ethanol, and 12.8 mL (132 mmol) of 30% H2O2 was stirred for 24 h at room temperature. An additional 3.5 mL of 30% H2O2 was added, the mixture was stirred for 18 h and diluted with 300 mL of water, and the precipitate was filtered off, washed with 500 mL of water, and dried at 120-130C. Yield 6.80 g (83%), white needles, mp 155-158C (from EtOAc); published data: mp 133-135C [11], 149C [12]. 1H NMR spectrum (CDCl3), δ, ppm: 6.60 t (1H, JHF = 53.1 Hz), 7.66 m (1H), 7.72 m (1H), 8.08 m (1H), 8.33 m (1H). 13C NMR spectrum (CDCl3), δC, ppm: 114.50 t (JCF = 288.1 Hz), 122.38, 126.25, 128.26, 129.07, 137.85, 153.01, 158.90. 19F NMR spectrum (CDCl3): δF -121.41 ppm.
	With sodium periodate; rhodium(III) chloride hydrate; In tetrachloromethane; water; acetonitrile; at 20℃; for 48h;	in a round bottom flask, add B in order.Acetonitrile,Carbon tetrachloride,Water and hydrated barium chloride.Place it on a stirrer and stir it vigorously.Then add 2.5 equivalents of sodium periodate to it,Finally let it continue to react at room temperature for 48 h.After treatment: saturated sodium bicarbonate solution and the reaction solution,filter,The filter residue was washed with ethyl acetate,The filtrate was extracted three times with ethyl acetate.After the organic phases are combined, they are dried over anhydrous magnesium sulfate.Spin-dry the solvent to give the desired product as a white solid.
	With sodium periodate; ruthenium(III) chloride trihydrate; In tetrachloromethane; water; acetonitrile; at 25℃; for 0.5h;Inert atmosphere;	Step 2: To a solution of 2-((difluoromethyl)thio)benzo[rfjthiazole (11.1 g, 51 mmol) in a mixture of ACN / CC / water (v : v : v :::: 1 : 1 : 2, 222 mL) were added sodium periodate (34.2 g , 160 mmol) and ruthenium(III) chloride trihydrate (33 mg, 0.13 mmol) portion wise. The resulting solution was stirred at room temperature for 3 h. The mixture was diluted with water (800 ml) and extracted with DCM (1500 mL). The organic phase w?as washed with brine (800 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica (0-20% ethyl acetate/DCM) to give 2-((difluoromethyl)suifonyl)benzo[

Reference： [1]Organic Letters,2010,vol. 12,p. 1444 - 1447
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
    Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5
[3]Russian Journal of Organic Chemistry,2017,vol. 53,p. 539 - 546
    Zh. Org. Khim.,2017,vol. 53,p. 533 - 540
[4]Angewandte Chemie - International Edition,2011,vol. 50,p. 2559 - 2563
[5]Organic Letters,2018,vol. 20,p. 6901 - 6905
[6]Angewandte Chemie - International Edition,2019,vol. 58,p. 13149 - 13154
    Angew. Chem.,2019,vol. 131,p. 13283 - 13288,6
[7]European Journal of Organic Chemistry,2015,vol. 2015,p. 871 - 875
[8]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2471 - 2480
[9]Patent: CN107556261,2018,A .Location in patent: Paragraph 0127-0128; 0131-0132
[10]Patent: WO2020/33288,2020,A1 .Location in patent: Page/Page column 78-79

5
[ 75-45-6 ]
[ 149-30-4 ]
[ 943-08-8 ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium hydroxide; In 1,4-dioxane; water; for 1h;	Chloro(difluoro)methane was bubbled over a period of 1 h at a rate of 15-18 mL/min through a mixture of 3.34 g (20 mmol) of 1,3-benzothiazole-2-thiol, 20 mL of dioxane, 13.17 g (200 mmol) of 85% KOH, and 40 mL of water under stirring. The mixture was diluted with 40 mL of water and extracted with methylene chloride (3 x 25 mL), the organic phase was dried over MgSO4, and the solvent was removed under reduced pressure. Yield 2.55 g (59%), yellow liquid. 1H NMR spectrum (CDCl3), δ, ppm: 7.42 t.d (1H, J = 7.7, 1.2 Hz), 7.50 t.d (1H, J = 7.7, 1.2 Hz), 7.65 t (1H, CHF2, J = 56.0 Hz), 7.84 d (1H, J = 8.1 Hz), 8.01 d (1H, J = 8.1 Hz). 13C NMR spectrum (CDCl3), δC, ppm: 120.24 t (CH, JCF = 276.6 Hz), 121.16 (CH), 122.84 (CH), 125.64 (CH), 126.60 (CH), 135.96, 152.90, 157.00 t (JCF = 4.2 Hz). 19F NMR spectrum (CDCl3): δF -93.18 ppm [8].
13.25 g		Under N2 atmosphere,Add 1.1 equivalents of 3.2g NaH to the pre-dried N2 pumping three timesShould be in the bottle,Then inject 15mL anhydrous DMF into it.Then the DMF solution of A was added dropwise to the reaction flask.Then after stirring for about half an hour at room temperature, the reaction system was bubbled inChlorodifluoromethane gas about 2h,Finally, the reaction flask was placed in a 60-degree oil bath and stirred for 12 h.After treatment: quench with water,Ether extraction,After the organic phase is washed with 5% potassium hydroxide,Dry with anhydrous magnesium sulfateSpin dry and vacuum distillation13.25 g of the target product B was obtained as a pale yellow oily liquid.
	With potassium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 13h;Sealed tube;	Step 1 : To a solution of benzo[i/]thiazole-2-thiol (50 g, 300 mmol) in 1,4-dioxane (125 mL) and water (125 mL) was added potassium hydroxide (30 g, 540 mmol) at 0 C. Excess chlorodifluorometliane vras bubbled through the resulting mixture over 5h. The reactor was sealed, and the mixture was stirred at room temperature for 8 h before being concentrated under reduced pressure. The residue was purified by column chromatography on silica (neutralized with triethylamine) (0-30% ethyl acetate/hexanes) to give 2-((difluoromethyl)thio)benzo[ jthiazole. MS: 218 (M+l). -NM11 (300 MHz, Chloroform-tf) d 8.05 - 8.02 (m, 1H), 7.89 - 7.86 (m, 1H), 7.67 - 7.41 (m, 3H). 1SF-NMR (282 MHz, Chloroform- d) d -93 20 (s, CF2H).

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5
[2]Organic Letters,2018,vol. 20,p. 6901 - 6905
[3]Organic Letters,2010,vol. 12,p. 1444 - 1447
[4]Russian Journal of Organic Chemistry,2017,vol. 53,p. 539 - 546
Zh. Org. Khim.,2017,vol. 53,p. 533 - 540
[5]European Journal of Organic Chemistry,2015,vol. 2015,p. 871 - 875
[6]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2471 - 2480
[7]Patent: CN107556261,2018,A .Location in patent: Paragraph 0127-0130
[8]Patent: WO2020/33288,2020,A1 .Location in patent: Page/Page column 78

6
[ 943-08-8 ]
[ 1286740-21-3 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 2559 - 2563

7
[ 75-45-6 ]
[ 2492-26-4 ]
[ 943-08-8 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 2559 - 2563

8
bis(((difluoromethyl)sulfinyl)oxy)zinc [ No CAS ]
[ 149-30-4 ]
[ 943-08-8 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 1494 - 1497

9
[ 1895-39-2 ]
[ 149-30-4 ]
[ 943-08-8 ]
3-(difluoromethyl)benzo[d]thiazole-2(3H-)-thione [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5036 - 5039

10
[ 149-30-4 ]
2,2‐difluoro‐2‐(triphenylphosphonio)acetate [ No CAS ]
[ 943-08-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	In tetrahydrofuran; at 60℃; for 8h;Sealed tube;	In a 5 mL sealed tube,Triphenyl difluoromethylidene phosphonium salt inner salt (0.57 g, 1.6 mmol)And 2-mercaptobenzothiazole (0.13 g, 0.8 mmol) were dissolved in tetrahydrofuran,At 60 , the tube closure reaction 8h.Then the heating was stopped. After the reaction was cooled, the system was directly separated by column chromatography (petroleum ether: dichloromethane = 4: 1) to give the product (0.15 g). Yield: 87%.

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 15261 - 15266
[2]Patent: CN103965242,2017,B .Location in patent: Paragraph 0245-0248

11
[ 115262-01-6 ]
[ 149-30-4 ]
[ 943-08-8 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 12390 - 12394
Angew. Chem.,2013,vol. 125,p. 12616 - 12620,5

12
[ 943-08-8 ]
2-((difluoromethyl)sulfinyl)benzo[d]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid; In acetone; at -5℃;Inert atmosphere;	General procedure: Underthe N2 atmosphere at -15 oC (for Het-SCH3, and-5 oC for Het-SCF2H and Het-SCFH2),the acetone solution of 3-chloroperoxybenzoic acid (mCPBA, 1.05 equiv) wasslowly added (within 1 hour) to the stirring acetone solution of the sulfide ether. The reaction was maintained at thesame temperature and monitored by TLC, 1H NMR, or 19F NMR (forfluorinated sulfoxide) to avoid over oxidation of sulfoxide to sulfone. Aftercompletion, the resulting mixture was quenched with excess NaHCO3(aq)and then extracted with ether (Et2O, 350 mL). The combined organic layer was washed withsaturated NaHCO3(aq) and NaCl(aq), and then dried with Na2SO4.Solvent was evaporated, the sulfoxide was obtained after flash chromatographypurification.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4180 - 4183

13
[ 136-95-8 ]
(1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-yl)(difluoromethylthio)silver [ No CAS ]
[ 943-08-8 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7648 - 7652
Angew. Chem.,2015,vol. 127,p. 7758 - 7762,5

14
[ 943-08-8 ]
bis(2,4-difluorophenanthridin-6-yl)difluoromethane [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
    Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
    Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5
[3]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
    Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5

15
[ 943-08-8 ]
2-((1,1-difluoroethyl)sulfonyl)benzo[d]thiazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5

16
[ 943-08-8 ]
2-((chlorodifluoromethyl)sulfonyl)benzo[d]thiazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5

17
[ 943-08-8 ]
2-((bromodifluoromethyl)sulfonyl)benzo[d]thiazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 2743 - 2747
Angew. Chem.,2016,vol. 128,p. 2793 - 2797,5

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P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
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. 943-08-8 ] {[proInfo.proName]}

Quality Control of [ 943-08-8 ]

Related Doc. of [ 943-08-8 ]

Product Details of [ 943-08-8 ]

Safety of [ 943-08-8 ]

Application In Synthesis of [ 943-08-8 ]

[ 943-08-8 ] Synthesis Path-Downstream 1~17

Technical Information

Related Functional Groups of [ 943-08-8 ]

Fluorinated Building Blocks

Sulfides

Related Parent Nucleus of [ 943-08-8 ]

Benzothiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 943-08-8 ]

Related Parent Nucleus of
[ 943-08-8 ]