148185-66-4|4,7-Dibromo-1H-benzo[d]imidazole| Ambeed

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Quality Control of [ 148185-66-4 ] Purity: 98% SDS Specification

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Product Details of [ 148185-66-4 ]

CAS No. :	148185-66-4
Formula :	C₇H₄Br₂N₂
M.W :	275.93
SMILES Code :	BrC1=C(NC=N2)C2=C(Br)C=C1
MDL No. :	MFCD16872346
InChI Key :	ZGLGYSCEKIFGMB-UHFFFAOYSA-N
Pubchem ID :	21504698

Safety of [ 148185-66-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 148185-66-4 ]

* 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 [ 148185-66-4 ]

[ 148185-66-4 ] Synthesis Path-Downstream 1~35

1
[ 148185-66-4 ]
[ 74-88-4 ]
[ 1235442-60-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; for 1h;Reflux;	4,7-dibromo- lH-benzo[d]imidazole ( lc) (300 mg, 1.08 mmol) was dissolved in dry ethanol ( 10 ml) under stirring. K2CO3 (414 mg, 3.24 mmol) was added to the resulting solution. The reaction mixture was heated at reflux to which iodomethane (0. 13 ml, 2.17 mmol) was added dropwise and the mixture was maintained at reflux for 1 hour. The reaction mixture was cooled at room temperature to which water (20 ml) was added. From the said mixture ethanol was evaporated and the so formed precipitate was collected by filtration. The resulting solid cake was washed with water, hexane/ diethyl ether ( 1 / 1), and dried to afford (250 mg, 79% yield) 4,7- dibromo- l-methyl- lH-benzo[d]imidazole (2a) as a solid. MS (EI) m/z: 290.9 (M+l). Ή NMR (400 MHz, DMSG-d6): 8 8.32 (s, 1H), 7.34 (s, 2H), 4.05 (s, 3H).

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 9262 - 9264.
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 4982 - 4986.
Angew. Chem.,2017,vol. 129,p. 5064 - 5068.
[3]Patent: WO2013/5157,2013,A1 .Location in patent: Page/Page column 26.
[4]Inorganic Chemistry,2021,vol. 60,p. 2112 - 2116.

2
[ 69272-50-0 ]
[ 122-51-0 ]
[ 148185-66-4 ]

Yield	Reaction Conditions	Operation in experiment
	With aminosulfonic acid; In methanol;	Diamine ( lb) (1 g, 3.76 mmol) was dissolved in methanol (20 ml) under stirring. To the resulting solution triethyl orthoformate (0.748 ml, 4.5 mmol) and sulfamic acid ( 18 mg, 0.18 mmol) was added. The resulting reaction mixture was stirred overnight. Solvent was evaporated from the reaction mass to obtain the residue which was rinsed with ether, dried under air to afford (950 mg, 50% yield for 2 steps) 4,7-dibromo- lH-benzo[d]imidazole ( lc) as a yellow solid. MS (EI) m/z: 276.9 (M+l). NMR (400 MHz, DMSO-d6): 5 13.2 (bs, 1H), 8.36 (s, 1H), 7.35 (s, 2H).

References: [1]New Journal of Chemistry,2013,vol. 37,p. 3084 - 3091.
[2]RSC Advances,2019,vol. 9,p. 21671 - 21678.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 4982 - 4986.
Angew. Chem.,2017,vol. 129,p. 5064 - 5068.
[4]Journal of the American Chemical Society,2010,vol. 132,p. 9262 - 9264.
[5]Patent: WO2013/5157,2013,A1 .Location in patent: Page/Page column 24.

3
[ 696-63-9 ]
[ 148185-66-4 ]
[ 1417568-64-9 ]

Yield	Reaction Conditions	Operation in experiment
23%	With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 18h;Inert atmosphere; Reflux;	4,7-dibromo- lH-benzo[d]imidazole ( lc) (150 mg, 0.54 mmol) was dissolved in dry 1 ,4-dioxane (5 ml) under stirring to which diisopropylethyl amine (281 mg, 1.63 mmol) was added. The reaction mixture was evacuated and backfilled with nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (24.88 mg, 0.027 mmol), xantphos (31.41 mg, 0.054 mmol) and 4-methoxybenzenethiol (0.2 ml, 1.63 mmol) were added and the reaction mixture was again degassed twice more. The reaction mixture was heated to reflux for 18 hour. After the completion of reaction, the reaction mixture allowed to reach ambient temperature, filtered and concentrated. The crude product so obtained was purified by flash column chromatography to afford 4,7-bis((4-methox rphenyl)thio)- lH-benzo[d]imidazole ( Id) (50 mg, 23% ) as an oil. MS (EI) m/z: 395. 1 (M+l ). iH NMR (400 MHz, DMSO-d6): 8 12.85 (s, 1H), 8.24 (s, 1H), 7.49 (d, J = 8.8 Hz, 2H), 7.24 (d, J = 8.8 Hz, 2H), 7.03-7.09 (m, 4H), 6.89 (d, J = 8.8 Hz, 1H), 6.46 (d, J = 8.8 Hz, 1H), 3.79 (s, 3H), 3.70 (s, 3H).

References: [1]Patent: WO2013/5157,2013,A1 .Location in patent: Page/Page column 24; 25.

4
[ 15155-41-6 ]
[ 148185-66-4 ]

References: [1]Patent: WO2013/5157,2013,A1 .
[2]New Journal of Chemistry,2013,vol. 37,p. 3084 - 3091.
[3]Heteroatom Chemistry,2015,vol. 26,p. 236 - 248.
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 4982 - 4986.
Angew. Chem.,2017,vol. 129,p. 5064 - 5068.
[5]RSC Advances,2019,vol. 9,p. 21671 - 21678.

5
[ 148185-66-4 ]
[ 1417568-60-5 ]

References: [1]Patent: WO2013/5157,2013,A1 .

6
[ 148185-66-4 ]
[ 100-39-0 ]
[ 1467575-61-6 ]

References: [1]New Journal of Chemistry,2013,vol. 37,p. 3084 - 3091.

7
[ 110-87-2 ]
[ 148185-66-4 ]
[ 1467575-64-9 ]

References: [1]New Journal of Chemistry,2013,vol. 37,p. 3084 - 3091.

8
[ 22706-22-5 ]
[ 148185-66-4 ]

References: [1]New Journal of Chemistry,2013,vol. 37,p. 3084 - 3091.
[2]Heteroatom Chemistry,2015,vol. 26,p. 236 - 248.
[3]Chemical Communications,2015,vol. 51,p. 10864 - 10867.
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 4982 - 4986.
Angew. Chem.,2017,vol. 129,p. 5064 - 5068.

9
[ 5324-30-1 ]
[ 148185-66-4 ]
diethyl (2-(4,7-dibromo-1H-benzimidazol-1-yl)ethyl)phosphonate [ No CAS ]