[ CAS No. 27231-36-3 ]

Name: 27231-36-3|2-Mercapto-5-methylbenzimidazole|98%
Brand: Ambeed
SKU: A190566
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Quality Control of [ 27231-36-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 27231-36-3 ]

CAS No. :	27231-36-3	MDL No. :	MFCD00010617
Formula :	C₈H₈N₂S	Boiling Point :	282.5°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	164.23 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 27231-36-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 27231-36-3 ]

Downstream synthetic route of [ 27231-36-3 ]

[ 27231-36-3 ] Synthesis Path-Downstream 1~26

1
[ 39267-05-5 ]
[ 27231-36-3 ]
3,10-dimethyl-benzo[4',5']imidazo[2',1':2,3]thiazolo[4,5-b]quinoxaline [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1970,vol. 47,p. 415 - 418

2
[ 2379-60-4 ]
[ 27231-36-3 ]
10-methyl-2-nitro-benzo[4',5']imidazo[2',1':2,3]thiazolo[4,5-b]quinoxaline [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1970,vol. 47,p. 415 - 418

3
[ 2958-87-4 ]
[ 27231-36-3 ]
3-chloro-10-methyl-benzo[4',5']imidazo[2',1':2,3]thiazolo[4,5-b]quinoxaline [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1970,vol. 47,p. 415 - 418

4
[ 75-03-6 ]
[ 27231-36-3 ]
[ 106039-67-2 ]

Yield	Reaction Conditions	Operation in experiment
	With DBN In N,N-dimethyl-formamide at 45 - 55℃; for 14h;

Reference： [1]Lazer; Matteo; Possanza [Journal of Medicinal Chemistry, 1987, vol. 30, # 4, p. 726 - 729]

5
[ 140-89-6 ]
[ 496-72-0 ]
[ 27231-36-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol; water monomer for 8h; Heating;
81%	With water monomer In ethanol at 80℃; for 16h; Sealed tube;	2.3.1 Preparation of 5-methyl-2-thiobenzimidazole (3) To a 10 mL microwave vial was added 5-methyl-1,2-diaminobenzene (181 mg, 1.5 mmol) and potassium ethyl xanthogenate (285 mg, 1.8 mmol, 1.2 equiv).2 mL ethanol was added, followed by 1 mL water and the mixture was sonicated for 10 min until only a fine powder remained. The vial was capped and crimped and the reaction was then placed in an 80 °C bath and heated for 16 h. The vial was then allowed to cool to room temperature and water (15 mL) was added. A white solid precipitated. The pH of the solution was adjusted to ca.5 (some solid dissolved) and the solution was filtered and the residue was washed with water (2 x 30 mL). The residue was then dried under airflow to afford a white solid.198 mg, 81%.1H NMR (300 MHz, DMSO-d6) δ 12.78 - 11.90 (br s, 2H), 7.08 - 6.99 (m, 1H), 6.94 (d, J = 8.1 Hz, 2H), 2.34 (s, 3H). Spectral data are in agreement with the literature. Mavrova et al., 2015.
81%	With water monomer In ethanol at 80℃; for 16h; Sealed tube;	2.3.1 Preparation of 5-methyl-2-thiobenzimidazole (3) To a 10 mL microwave vial was added 5-methyl-1,2-diaminobenzene (181 mg, 1.5 mmol) and potassium ethyl xanthogenate (285 mg, 1.8 mmol, 1.2 equiv).2 mL ethanol was added, followed by 1 mL water and the mixture was sonicated for 10 min until only a fine powder remained. The vial was capped and crimped and the reaction was then placed in an 80 °C bath and heated for 16 h. The vial was then allowed to cool to room temperature and water (15 mL) was added. A white solid precipitated. The pH of the solution was adjusted to ca.5 (some solid dissolved) and the solution was filtered and the residue was washed with water (2 x 30 mL). The residue was then dried under airflow to afford a white solid.198 mg, 81%.1H NMR (300 MHz, DMSO-d6) δ 12.78 - 11.90 (br s, 2H), 7.08 - 6.99 (m, 1H), 6.94 (d, J = 8.1 Hz, 2H), 2.34 (s, 3H). Spectral data are in agreement with the literature. Mavrova et al., 2015.

Reference： [1]Uchida; Morita; Chihiro; Kanbe; Yamasaki; Yabuuchi; Nakagawa [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 6, p. 1517 - 1523]
[2]Current Patent Assignee: THE JOHNS HOPKINS UNIVERSITY; COMMONWEALTH SYSTEM OF HIGHER EDUCATION - WO2022/61140, 2022, A1 Location in patent: Page/Page column 79; 81
[3]Current Patent Assignee: THE JOHNS HOPKINS UNIVERSITY; COMMONWEALTH SYSTEM OF HIGHER EDUCATION - WO2022/61140, 2022, A1 Location in patent: Page/Page column 79; 81

6
[ 79-11-8 ]
[ 27231-36-3 ]
[ 27231-37-4 ]

Yield	Reaction Conditions	Operation in experiment
54.1%	With potassium hydroxide In ethanol; water for 6h; Heating;
	With sodium hydroxide In ethanol Heating;
	With sodium hydroxide In ethanol Heating;

With sodium hydroxide Reflux;

Reference： [1]Tanaka; Ino; Murakami [Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 7, p. 1876 - 1886]
[2]Mavrova, Anelia Ts.; Anichina, Kamelya K.; Vuchev, Dimitar I.; Tsenov, Jordan A.; Kondeva, Magdalena S.; Micheva, Mitka K. [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 19, p. 5550 - 5559]
[3]Mavrova, Anelia Ts.; Anichina, Kamelya K.; Vuchev, Dimitar I.; Tsenov, Jordan A.; Denkova, Pavletta S.; Kondeva, Magdalena S.; Micheva, Mitka K. [European Journal of Medicinal Chemistry, 2006, vol. 41, # 12, p. 1412 - 1420]
[4]Anichina, Kameliya; Mavrova, Anelia; Yancheva, Denitsa; Tsenov, Jordan; Dimitrov, Rasho [Journal of Molecular Structure, 2017, vol. 1150, p. 179 - 187]

7
[ 125163-08-8 ]
[ 27231-36-3 ]
[ 104658-76-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium hydroxide In methanol; water for 1h; Heating;

Reference： [1]Uchida; Morita; Chihiro; Kanbe; Yamasaki; Yabuuchi; Nakagawa [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 6, p. 1517 - 1523]

8
[ 353-83-3 ]
[ 27231-36-3 ]
[ 105771-14-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	With DBN In N,N-dimethyl-formamide at 45 - 55℃; for 14h;

Reference： [1]Lazer; Matteo; Possanza [Journal of Medicinal Chemistry, 1987, vol. 30, # 4, p. 726 - 729]

9
1-(2-chloroethyl)-2-methyl-5-nitro-1H-imidazole hydrochloride [ No CAS ]
[ 27231-36-3 ]
5-Methyl-2-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethylsulfanyl]-1H-benzoimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In acetone for 20h; Heating;

Reference： [1]Demirayak; Kiraz [Il Farmaco, 1993, vol. 48, # 3, p. 443 - 446]

10
[ 114060-09-2 ]
[ 27231-36-3 ]
[ 106746-94-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	In ethanol for 2h;

Reference： [1]Adelstein, Gilbert W.; Yen, Chung H.; Haack, Richard A.; Yu, Stella; Gullikson, Gary; et al. [Journal of Medicinal Chemistry, 1988, vol. 31, # 6, p. 1215 - 1220]

11
[ 27231-36-3 ]
potassium 5-methylbenzimidazole-2-sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With KO₂ In pyridine at 60℃; for 6h;

Reference： [1]Crank, George; Makin, Mohammad I. H. [Australian Journal of Chemistry, 1984, vol. 37, # 11, p. 2331 - 2337]

12
[ 67-56-1 ]
[ 27231-36-3 ]
[ 614-97-1 ]
5-methyl-2-methoxybenzimidazole [ No CAS ]