7144-49-2

Basic information

• Product Name: 2-(METHYLSULFONYL)BENZOTHIAZOLE, 97
• Synonyms: 2-(METHYLSULFONYL)BENZOTHIAZOLE, 97;2-(methylsulfonyl)benzothiazole;Benzothiazole, 2-(methylsulfonyl)- (6CI,8CI,9CI);Methyl 2-benzothiazolyl sulfone;NSC 51671;2-(Methylsulfonyl)benzo[d]thiazole
• CAS NO: 7144-49-2
• Molecular Formula: C₈H₇NO₂S₂
• Molecular Weight: 213.27668
• Product Categories: BENZOTHIAZOLE
• Mol File: 7144-49-2.mol
• Article Data: 32

Chemical Properties

• Melting Point: 86-89 °C(lit.)
• Boiling Point: 370.3°C at 760 mmHg
• Flash Point: 177.7°C
• Appearance: /
• Density: 1.440
• Vapor Pressure: 2.38E-05mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: 2-8°C
• PKA: -2.43±0.10(Predicted)
• CAS DataBase Reference: 2-(METHYLSULFONYL)BENZOTHIAZOLE, 97(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(METHYLSULFONYL)BENZOTHIAZOLE, 97(7144-49-2)
• EPA Substance Registry System: 2-(METHYLSULFONYL)BENZOTHIAZOLE, 97(7144-49-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 7144-49-2(Hazardous Substances Data)

Usage

General Description

2-(Methylsulfonyl)benzothiazole, 97 is a chemical compound with the molecular formula C8H7NO2S2. It is commonly used as an accelerator in rubber and latex production, as well as in the manufacturing of industrial products such as adhesives, sealants, and coatings. 2-(METHYLSULFONYL)BENZOTHIAZOLE, 97 is known for its high purity (97%) and is often used in various industrial and commercial applications. It is a white to light yellow powder that is soluble in organic solvents and has a characteristic sulfurous odor. 2-(Methylsulfonyl)benzothiazole, 97 is considered to be a versatile and important chemical in the production of various rubber and plastic products.

InChI:InChI=1/C8H7NO2S2/c1-13(10,11)8-9-6-4-2-3-5-7(6)12-8/h2-5H,1H3

Synthetic route

2-(benzothiazol-2-ylsulfonyl)acetic acid → 2-methanesulfonylbenzothiazole (7144-49-2)

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 1.1h;	100%

2-methylmercaptobenzothiazole (615-22-5) → 2-methanesulfonylbenzothiazole (7144-49-2)

Conditions	Yield
With sodium hypochlorite; isocyanuric acid In water; toluene at 20℃; for 2.5h;	99.7%
With sodium hypochlorite; water; isocyanuric acid In toluene at 20℃; for 2.5h; Inert atmosphere;	99%
With chromium(VI) oxide; periodic acid In ethyl acetate; acetonitrile at 0℃; for 1.75h;	94%

2-methylmercaptobenzothiazole (615-22-5) → 2-(methylsulfinyl)benzothiazole (3507-54-8) + 2-methanesulfonylbenzothiazole (7144-49-2)

Conditions	Yield
Stage #1: 2-methylmercaptobenzothiazole With sodium tungstate (VI) dihydrate In ethanol at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: With dihydrogen peroxide In ethanol; water at 0 - 20℃; for 10.5h; Inert atmosphere;	A n/a B 84%
With dihydrogen peroxide; phosphotungstate-non-cross-linked amphiphilic polymer compl at 50℃; for 7h;	A 17% B 78%
With phosphotungstic acid; poly(acrylamide) based ammonium salt; dihydrogen peroxide at 50℃; for 7h;	A 17% B 78%

2-(difluoromethanesulfonyl)-1,3-benzothiazole (186204-66-0) + 3,5-difluoro-2-isocyano-1,1’-biphenyl + methyl iodide (74-88-4) → 2-methanesulfonylbenzothiazole (7144-49-2) + 6-(difluoromethyl)-2,4-difluorophenanthridine (1610500-99-6)

Conditions	Yield
Stage #1: 2-(difluoromethanesulfonyl)-1,3-benzothiazole; 3,5-difluoro-2-isocyano-1,1’-biphenyl With tris(bipyridine)ruthenium(II) dichloride hexahydrate; sodium carbonate In dimethyl sulfoxide at 20℃; for 4h; Inert atmosphere; Schlenk technique; Irradiation; Stage #2: methyl iodide In dimethyl sulfoxide at 20℃; for 5h; Inert atmosphere; Schlenk technique; Darkness;	A 69% B 84%

2-methylthiobenzothiazole hydroiodide (117883-09-7) → 2-methanesulfonylbenzothiazole (7144-49-2)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 17h; Ambient temperature;	72.4%

2-(methylsulfinyl)benzothiazole (3507-54-8) → 2-methanesulfonylbenzothiazole (7144-49-2) + (S)-2-(methylsulfinyl)benzothiazole + C8H7NOS2

Conditions	Yield
With manganese(II) triflate; 1-Adamantanecarboxylic acid; C32H38N4O2; dihydrogen peroxide In water; acetonitrile at -30 - 20℃; for 0.5h; Inert atmosphere; Resolution of racemate; stereoselective reaction;	A 71% B n/a C n/a

2-bromo-1,3-benzothiazole (2516-40-7) + sodium methansulfinate (20277-69-4) → 2(3H)-Benzothiazolone (934-34-9) + 2-methanesulfonylbenzothiazole (7144-49-2)

Conditions	Yield
In dimethyl sulfoxide at 110℃; for 10h; Overall yield = 47.5 mg;	A n/a B 55%

2-Mercaptobenzothiazole (149-30-4) → 2-methanesulfonylbenzothiazole (7144-49-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, a) 0 deg C, 20 min, b) RT, 30 min, 2.) DMF, RT, 1 h 2: aq. KMnO4, AcOH / 2 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: 48.7 percent / acetone / 0.75 h 2: 72.4 percent / 3-chloroperbenzoic acid / CH2Cl2 / 17 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: NaH 2: aq. KMnO4 View Scheme

2-methanesulfonylbenzothiazole (7144-49-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate (910803-59-7)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; di-tert-butyl dicarbonate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	98%
Stage #1: 2-methanesulfonylbenzothiazole; di-tert-butyl dicarbonate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	94%

2-methanesulfonylbenzothiazole (7144-49-2) + methyl chloroformate (79-22-1) → methyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate (24045-01-0)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; methyl chloroformate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	98%
Stage #1: 2-methanesulfonylbenzothiazole; methyl chloroformate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	89%

2-methanesulfonylbenzothiazole (7144-49-2) + Benzoyl bromide (618-32-6) → 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-one (331984-42-0)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; Benzoyl bromide With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	97%

2-methanesulfonylbenzothiazole (7144-49-2) + benzoyl chloride (98-88-4) → 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-one (331984-42-0)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; benzoyl chloride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	97%

2-methanesulfonylbenzothiazole (7144-49-2) → C7H4(2)HNO2S2

Conditions	Yield
With hydrogen chloride; lithium hexamethyldisilazane In tetrahydrofuran; deuteromethanol at -78℃; for 0.00833333h;	97%

2-methanesulfonylbenzothiazole (7144-49-2) + benzoyl chloride (98-88-4) → 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-one (331984-42-0) + 2-<(benzothiazol-2-ylmethyl)sulfonyl>benzothiazole (134792-21-5)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; benzoyl chloride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	A 96% B 5%

2-methanesulfonylbenzothiazole (7144-49-2) + Allyl chloroformate (2937-50-0) → allyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate (1271301-01-9)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; Allyl chloroformate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	95%
Stage #1: 2-methanesulfonylbenzothiazole; Allyl chloroformate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	95%

2-methanesulfonylbenzothiazole (7144-49-2) + C15H20N2O4S (1187788-81-3) → C22H23N3O4S2 (1382089-57-7)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.333333h; pH=7.4; aq. phosphate buffer;	95%

2-methanesulfonylbenzothiazole (7144-49-2) + (R)-2-acetylamino-N-benzyl-3-mercaptopropionamide (215598-85-9) → C19H19N3O2S2 (1382089-51-1)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.333333h; pH=7.4; aq. phosphate buffer;	95%
In tetrahydrofuran; aq. phosphate buffer at 20℃; for 1h; pH=7.4; Inert atmosphere;

2-methanesulfonylbenzothiazole (7144-49-2) + Ac-Cys-OMe (7652-46-2) → C13H14N2O3S2 (1382089-54-4)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.333333h; pH=7.4; aq. phosphate buffer;	95%

2-methanesulfonylbenzothiazole (7144-49-2) + N-benzyloxycarbonyl-L-alanyl-L-cysteine methyl ester (34804-98-3) → C22H23N3O5S2 (1382089-60-2)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.333333h; pH=7.4; aq. phosphate buffer;	95%

2-methanesulfonylbenzothiazole (7144-49-2) + Ethyl chlorothioformate (2941-64-2) → S-ethyl 2-(benzo[d]thiazol-2-ylsulfonyl)ethanethioate (1357556-60-5) + 2-<(benzothiazol-2-ylmethyl)sulfonyl>benzothiazole (134792-21-5)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; Ethyl chlorothioformate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	A 94% B 11%

2-methanesulfonylbenzothiazole (7144-49-2) + benzoyl fluoride (455-32-3) → 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-one (331984-42-0)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; benzoyl fluoride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	93%

1-benzoylimidazole (10364-94-0) + 2-methanesulfonylbenzothiazole (7144-49-2) → 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-one (331984-42-0)

Conditions	Yield
Stage #1: 1-benzoylimidazole; 2-methanesulfonylbenzothiazole With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	92%
Stage #1: 1-benzoylimidazole; 2-methanesulfonylbenzothiazole With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	92%

2-methanesulfonylbenzothiazole (7144-49-2) + acetic anhydride (108-24-7) → 1-(benzo[d]thiazol-2-ylsulfonyl)propan-2-one (105445-57-6)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; acetic anhydride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	92%
Stage #1: 2-methanesulfonylbenzothiazole; acetic anhydride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	92%

2-methanesulfonylbenzothiazole (7144-49-2) + benzoic acid anhydride (93-97-0) → 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-one (331984-42-0)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; benzoic acid anhydride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	92%
Stage #1: 2-methanesulfonylbenzothiazole; benzoic acid anhydride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	92%

benzoyl cyanide (613-90-1) + 2-methanesulfonylbenzothiazole (7144-49-2) → 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-one (331984-42-0)

Conditions	Yield
Stage #1: benzoyl cyanide; 2-methanesulfonylbenzothiazole With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	92%

tetrahydrofuran (109-99-9) + 2-methanesulfonylbenzothiazole (7144-49-2) → (±)-2-(oxolan-2-yl)-1,3-benzothiazole (1226555-45-8)

Conditions	Yield
With 4-Benzoylpyridine In acetone at 20℃; for 6h; Irradiation; Inert atmosphere;	92%

2-methanesulfonylbenzothiazole (7144-49-2) + propynoic acid methyl ester (922-67-8) → methyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate (24045-01-0)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; propynoic acid methyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	91%

1-phenylmethylpiperazine (2759-28-6) + 2-methanesulfonylbenzothiazole (7144-49-2) → 2-(4-benzyl-piperazin-1-yl)-benzothiazole (35463-75-3)

Conditions	Yield
With sodium hydrogencarbonate at 60 - 80℃; for 0.5h;	90%

2-methanesulfonylbenzothiazole (7144-49-2) + acetyl chloride (75-36-5) → 1-(benzo[d]thiazol-2-ylsulfonyl)propan-2-one (105445-57-6)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; acetyl chloride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	90%
Stage #1: 2-methanesulfonylbenzothiazole; acetyl chloride With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	90%

2-methanesulfonylbenzothiazole (7144-49-2) + propan-2-yl carbonohalodate → iso-propyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate (24045-03-2)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 3h; Sealed tube;	90%

2-methanesulfonylbenzothiazole (7144-49-2) + N,N-dimethyl acetamide (127-19-5) → N-(benzo[d]thiazol-2-ylmethyl)-N-methylacetamide

Conditions	Yield
With di-tert-butoxydiazene; potassium hydrogencarbonate In chlorobenzene at 50℃; for 24h; Solvent;	90%

N-Acetylimidazole (2466-76-4) + 2-methanesulfonylbenzothiazole (7144-49-2) → 1-(benzo[d]thiazol-2-ylsulfonyl)propan-2-one (105445-57-6)

Conditions	Yield
Stage #1: N-Acetylimidazole; 2-methanesulfonylbenzothiazole With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	89%
Stage #1: N-Acetylimidazole; 2-methanesulfonylbenzothiazole With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	89%

2-methanesulfonylbenzothiazole (7144-49-2) + methyl 1-imidazolecarboxylate (61985-23-7) → methyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate (24045-01-0)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; methyl 1-imidazolecarboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	89%
Stage #1: 2-methanesulfonylbenzothiazole; methyl 1-imidazolecarboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	89%

2-methanesulfonylbenzothiazole (7144-49-2) + tert-butyl 1H-imidazole-1-carboxylate (49761-82-2) → tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate (910803-59-7)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; tert-butyl 1H-imidazole-1-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;	89%
Stage #1: 2-methanesulfonylbenzothiazole; tert-butyl 1H-imidazole-1-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	89%

2-methanesulfonylbenzothiazole (7144-49-2) + (4S,4aR,5R,6R,8aR)-5-azido-4-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-6-hydroxy-6-methyloctahydronaphthalen-1(2H)-one (1354928-41-8) → (1R,2R,4aS,8S,8aS)-1-azido-8-((2R,5S)-5-chloro-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)-2-methyl-5-methylenedecahydronaphthalen-2-ol (1354928-46-3)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 3h;	88%

2-methanesulfonylbenzothiazole (7144-49-2) + tetramethylurea (632-22-4) → 1-(benzo[d]thiazol-2-ylmethyl)-1,3,3-trimethylurea

Conditions	Yield
With di-tert-butoxydiazene; potassium hydrogencarbonate at 50℃; for 24h;	87%

Upstream product

• 615-22-5 2-methylmercaptobenzothiazole 
• 3507-54-8 2-(methylsulfinyl)benzothiazole 
• 2516-40-7 2-bromo-1,3-benzothiazole 
• 20277-69-4 sodium methansulfinate 
• 186204-66-0 2-(difluoromethanesulfonyl)-1,3-benzothiazole 
• 74-88-4 methyl iodide 
• 149-30-4 2-Mercaptobenzothiazole 
• 117883-09-7 2-methylthiobenzothiazole hydroiodide 

Downstream Products

• 13294-73-0 1-tert-butyl-4-methylenecyclohexane 
• 2039-80-7 N,N-dimethy-4-vinylaniline 
• 1712-69-2 1-isopropenyl-4-methoxybenzene 
• 95-16-9 1,3-Benzothiazole 
• 20277-69-4 sodium methansulfinate 
• 37015-97-7 2-<4-(diphenylmethyl)piperazin-1-yl>benzothiazole 
• 1382089-57-7 C₂₂H₂₃N₃O₄S₂ 
• 1382089-51-1 C₁₉H₁₉N₃O₂S₂ 
• 1394256-54-2 C₂₂H₂₃N₃O₄S₂ 
• 1382089-54-4 C₁₃H₁₄N₂O₃S₂ 
• 1382089-60-2 C₂₂H₂₃N₃O₅S₂ 
• 960156-22-3 C₃₅H₃₃O₆S₂N 
• 898803-42-4 2-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylidenemethanesulfonyl)-benzothiazole 
• 134001-24-4 (3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-bis(phenoxymethyl)dihydrofuran-2(3H)-one 

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