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Quality Control of 5-Azabenzimidazole Purity: 98% SDS Specification

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Product Details of 5-Azabenzimidazole

CAS No. :	272-97-9
Formula :	C₆H₅N₃
M.W :	119.12
SMILES Code :	C1(NC=N2)=C2C=CN=C1
MDL No. :	MFCD00051808
InChI Key :	UBOOKRVGOBKDMM-UHFFFAOYSA-N
Pubchem ID :	9227

Safety of 5-Azabenzimidazole

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 5-Azabenzimidazole

* 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 [ 272-97-9 ]

[ 272-97-9 ] Synthesis Path-Downstream 1~35

1
[ 54-96-6 ]
[ 50-00-0 ]
[ 272-97-9 ]

References: [1]Chemische Berichte,1938,vol. 71,p. 2347,2358.

2
[ 54-96-6 ]
[ 64-18-6 ]
[ 272-97-9 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 9532 - 9533.
[2]Journal of Natural Products,2013,vol. 76,p. 1637 - 1646.
[3]Journal of the Chemical Society,1956,p. 4683.
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5023 - 5026.

3
[ 2770-01-6 ]
[ 272-97-9 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1949,vol. 68,p. 1013,1024.

4
[ 18997-19-8 ]
[ 272-97-9 ]
[ 105952-97-4 ]
[ 105952-96-3 ]

References: [1]Tetrahedron,1986,vol. 42,p. 1511 - 1528.

5
[ 272-97-9 ]
[ 76513-69-4 ]
[ 148720-59-6 ]
[ 148720-52-9 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 1885 - 1888.

6
[ 272-97-9 ]
[ 36016-40-7 ]
[ 105952-93-0 ]

References: [1]Tetrahedron,1986,vol. 42,p. 1511 - 1528.

7
[ 272-97-9 ]
[ 127167-47-9 ]
[ 142535-74-8 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3402 - 3413.

8
[ 272-97-9 ]
[ 151965-56-9 ]
7-(2-phosphonomethoxyethyl)-3-deazapurine [ No CAS ]
9-(2-phosphonomethoxyethyl)-3-deazapurine [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1419 - 1429.

9
[ 272-97-9 ]
[ 23788-74-1 ]
7-(S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl-3-deazapurine [ No CAS ]
9-(S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl-3-deazapurine [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 629 - 648.

10
[ 272-97-9 ]
[ 7239-81-8 ]

References: [1]Chemistry of Heterocyclic Compounds,1988,p. 653 - 658.
Khimiya Geterotsiklicheskikh Soedinenii,1988,vol. 24,p. 799 - 804.

11
[ 105952-94-1 ]
[ 272-97-9 ]
[ 105952-95-2 ]

References: [1]Tetrahedron,1986,vol. 42,p. 1511 - 1528.

12
[ 951-78-0 ]
[ 272-97-9 ]
[ 98858-23-2 ]

References: [1]Collection of Czechoslovak Chemical Communications,1994,vol. 59,p. 2303 - 2330.

13
[ 272-97-9 ]
1H-Imidazo[4,5-c]pyridine; compound with bromine [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1994,vol. 30,p. 928 - 933.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1076 - 1081.

Yield	Reaction Conditions	Operation in experiment
74.5%		EXAMPLE 16 Imidazo[4,5-c]pyridine(3-deazapurine) To 5.0 of 3,4-diaminopyridine (Aldrich, 45.82 mmol) suspended in 45 ml of 2-methoxyethanol was added 6.4 g of formamidine acetate (Aldrich, 61.5 mmol) and the mixture heated at reflux (it becomes a solution) for 16 hrs. The solution was then evaporated in vacuo to a solid residue which was recrystallized from 50 ml of acetonitrile. This afforded 4.06 g of imidazo[4,5-c]pyridine (74.5%) m.p. 166-168 C. [lit 162-163 C., Y. Mizuno, et al. Chem. Phar. Bull., 12, 866-872 (1964)]. 200 MHz NMR (D2 O, delta from TSP): 7.6 (1H, d, J=6 Hz) 8.23 (1H, d, J=6 Hz) 8.30 (1H,s) 8.84 (1H,s).
		To a solution of 2-methyl-1H-imidazo[4,5-c]pyridine in 50 ml of dimethylformamide was added 1.43 g of 50% sodium hydride in oil followed, after 20 minutes, by 1.86 ml of methyl iodide. After stirring at room temperature overnight, the solvent was concentrated in vacuo and the residue treated with chloroform and filtered. Removal of the chloroform gave a brown solid which was chromatographed on 150 g of silica gel using 5% methanol in chloroform as the eluent giving 774 mg of a less polar isomer and 356 mg of the desired 1H-imidazo[4,5-c]pyridine isomer.
		(B) 1-[4-(1-Cyclohexyl-1H-tetrazol-5-yl)butyl]-1H-imidazo[4,5-b]pyridine Utilizing the procedure described in Example 1(a) employing 5-(4-chlorobutyl)-1-cyclohexyl-1H-tetrazole in lieu of ethyl 4-bromomethylbenzoate and imidazo[4,5-b]pyridine in lieu of imidazo[4,5-c]pyridine yielded an impure mixture of isomers.

16
[ 272-97-9 ]
[ 91184-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; at 0 - 20℃; for 22h;	Compound 2 (2.5 g, 20.83 mmol) was dissolved in a mixture of 60 mL DCM + 30 mL of MeOH and 10.3 g of m-CPBA (41.67?mmol) dissolved in methanol was added dropwise at 0?C. The reaction was stirred at room temperature for 22?h, after which the mixture was concentrated in vacuum. Methanol (30?mL) was added to the residue which was adsorbed on silica. The title compound 3 was isolated via silica gel chromatography using EA/MeOH (65:35) in 80% yield. 1H NMR (300?MHz, DMSO-d6) delta 8.68 (d, J?=?1.5?Hz, 1H), 8.39 (s, 1H), 8.07 (dd, J?=?6.9, 1.8?Hz, 1H), 7.64 (d, J?=?6.9?Hz, 1H). 13C NMR (75?MHz, DMSO) delta 147.96, 137.85, 136.67, 133.51, 128.35, 111.77. HRMS (ESI): m/z calcd. for C6H6N3O [M+H]+: 136.0505; found, 136.0510.

References: [1]ChemMedChem,2013,vol. 8,p. 985 - 993.
[2]Synlett,2001,p. 73 - 74.
[3]Journal of the American Chemical Society,2004,vol. 126,p. 9532 - 9533.
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5023 - 5026.
[5]European Journal of Medicinal Chemistry,2018,vol. 148,p. 384 - 396.

17
[ 64-18-6 ]
[ 272-97-9 ]
[ 88-89-1 ]
picric acid; compound with 1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carbaldehyde [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2002,vol. 38,p. 419 - 423.

18
[ 29632-74-4 ]
[ 272-97-9 ]
[ 774218-68-7 ]
[ 774218-69-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5263 - 5267.

19
[ 777076-50-3 ]
[ 272-97-9 ]
[ 777076-54-7 ]

References: [1]Tetrahedron,2004,vol. 60,p. 8397 - 8404.

20
[ 777076-51-4 ]
[ 272-97-9 ]
[ 777076-54-7 ]

References: [1]Tetrahedron,2004,vol. 60,p. 8397 - 8404.

21
[ 6974-32-9 ]
[ 272-97-9 ]
[ 26884-45-7 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179.

22
2-methanesulfinyl-7-methyl-4-(1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid tert-butyl ester [ No CAS ]
[ 272-97-9 ]
2-imidazo[4,5-c]pyridin-1-yl-7-methyl-4-(1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid tert-butyl ester [ No CAS ]
[ 930300-69-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1250 - 1253.

23
[ 272-97-9 ]
[ 7465-42-1 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 173 - 179.

24
[ 272-97-9 ]
[ 848393-26-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5263 - 5267.

25
[ 272-97-9 ]
[ 848393-25-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5263 - 5267.

26
[ 272-97-9 ]
2-(3-carbamimidoyl-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (2-fluoro-4-imidazo[4,5-c]pyridin-1-yl-phenyl)-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5263 - 5267.

27
[ 272-97-9 ]
2-(3-carbamimidoyl-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (2-fluoro-4-imidazo[4,5-c]pyridin-3-yl-phenyl)-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5263 - 5267.

28
[ 272-97-9 ]
[ 82722-74-5 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 9532 - 9533.

29
[ 272-97-9 ]
[ 3243-24-1 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 9532 - 9533.

30
[ 272-97-9 ]
[ 201416-36-6 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 9532 - 9533.

31
[ 272-97-9 ]
4-chloro-3-[2'-deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl]-7-nitro-3H-imidazo[4,5-c]pyridine [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 9532 - 9533.

32
[ 272-97-9 ]
4-chloro-1-[2'-deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl]-7-nitro-1H-imidazo[4,5-c]pyridine [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 9532 - 9533.

33
[ 272-97-9 ]
[ 62002-31-7 ]

References: [1]Russian Journal of Organic Chemistry,2002,vol. 38,p. 419 - 423.

34
[ 272-97-9 ]
7-(S)-(2,3-dihydroxypropyl)-3-deazapurine [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 629 - 648.

35
[ 272-97-9 ]
9-(S)-(2,3-dihydroxypropyl)-3-deazapurine [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 629 - 648.

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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CAS No.: 272-97-9

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CAS No.: 272-97-9

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Product Details of 5-Azabenzimidazole

Safety of 5-Azabenzimidazole

Application In Synthesis of 5-Azabenzimidazole

[ 272-97-9 ] Synthesis Path-Downstream 1~35

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