Name: 3H-Imidazo[4,5-b]pyridine, 5,7-dichloro-
SKU: 24485-01-6

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Basic Information

Molecular Structure:
CAS No.:	24485-01-6
Name:	3H-Imidazo[4,5-b]pyridine, 5,7-dichloro-
Article Data:	9

Formula:	C₆H₃Cl₂N₃
Molecular Weight:	188.016
Synonyms:	1H-Imidazo[4,5-b]pyridine,5,7-dichloro- (8CI,9CI);5,7-Dichloro-1H-imidazo[4,5-b]pyridine;5,7-Dichloroimidazo[4,5-b]pyridine;NSC 264046;
Density:	1.675 g/cm³
Melting Point:	273-274 °C
Boiling Point:	416.867 °C at 760 mmHg
Flash Point:	238.425 °C
PSA:	41.57000
LogP:	2.26470

Synthetic route

: 14432-11-2
7-nitro-1H-imidazo[4,5-b]pyridine 4-oxide

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

Conditions

Conditions	Yield
With trichlorophosphate In N,N-dimethyl-formamide at 0 - 120℃; for 3h;	90%
With trichlorophosphate at 100℃; for 2.5h;	86%
Multi-step reaction with 2 steps 1: 51 percent / H2 / 5percent Pd on charcoal / ethanol / 5 h / 2280 Torr / Ambient temperature 2: phosphoryl chloride View Scheme

: 14432-11-2
7-nitroimidazo<4,5-b>pyridine 4-oxide

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

Conditions

Conditions	Yield
With trichlorophosphate In N,N-dimethyl-formamide for 2h; Heating;	80%
With trichlorophosphate In N,N-dimethyl-formamide at 115℃; for 0.166667h;	50%
With trichlorophosphate In N,N-dimethyl-formamide
With trichlorophosphate In N,N-dimethyl-formamide

: 77712-93-7
7-Amino-3H-imidazo<4,5-b>pyridine 4-N-Oxide

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

Conditions

Conditions	Yield
With trichlorophosphate

: 6863-46-3
3H-Imidazo<4,5-b>pyridine 4-N-oxide

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / trifluoroacetic acid; HNO3 / 3 h / 90 °C 2: 80 percent / POCl3 / dimethylformamide / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: trifluoroacetic acid; nitric acid / 4 h / 90 °C 2: trichlorophosphate / N,N-dimethyl-formamide / 0.17 h / 115 °C View Scheme

: 273-21-2
3H-imidazo[4,5-b]pyridine

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / aq. H2O2; acetic acid / 19 h / 60 - 70 °C 2: 67 percent / trifluoroacetic acid; HNO3 / 3 h / 90 °C 3: 80 percent / POCl3 / dimethylformamide / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid / 72 h / 20 °C 2: trifluoroacetic acid; nitric acid / 4 h / 90 °C 3: trichlorophosphate / N,N-dimethyl-formamide / 0.17 h / 115 °C View Scheme

: 7-chloro-3H-imidazo[4,5-b]pyridine-4-oxide

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

Conditions

Conditions	Yield
With trichlorophosphate In water

: 273-21-2
1H-Imidazo[4,5-b]pyridine

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dihydrogen peroxide / acetic acid / 50 - 70 °C 2: nitric acid / trifluoroacetic acid / 3.5 h / 0 - 90 °C 3: trichlorophosphate / N,N-dimethyl-formamide / 3 h / 0 - 120 °C View Scheme

: 6863-46-3
Imidazo<4,5-b>pyridine 4-Oxide

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / trifluoroacetic acid / 3.5 h / 0 - 90 °C 2: trichlorophosphate / N,N-dimethyl-formamide / 3 h / 0 - 120 °C View Scheme

: 452-58-4
2,3-Diaminopyridine

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: orthoformic acid triethyl ester / 3 h / 145 °C 1.2: 2 h / 110 °C 1.3: activated charcoal / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / 72 h / 20 °C 3.1: trifluoroacetic acid; nitric acid / 4 h / 90 °C 4.1: trichlorophosphate / N,N-dimethyl-formamide / 0.17 h / 115 °C View Scheme

: 24485-01-6
5,7-dichloro-3H-imidazo<4,5-b>pyrimidine

: 13035-61-5
1,2,3,5-tetraacetylribose

: 57521-46-7
1-(5,7-dichloro-imidazo[4,5-b]pyridin-3-yl)-O2,O3-isopropylidene-β-D-1-deoxy-ribofuranose

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile at 20℃;	82%
With tin(IV) chloride
Stage #1: 5,7-dichloro-3H-imidazo<4,5-b>pyrimidine With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 85℃; for 1h; Stage #2: 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 85℃; for 4h;

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Specification

The IUPAC name of 5,7-Dichloro-1H-imidazo[4,5-beta]pyridine is 5,7-Dichloro-1H-imidazo[4,5-b]pyridine. With the CAS registry number 24485-01-6, it is also named as 3H-Imidazo[4,5-b]pyridine,5,7-dichloro-. The product's category is chiral chemicals. In addition, its molecular formula is C₆H₃Cl₂N₃ and its molecular weight is 188.01.

The other characteristics of 5,7-Dichloro-1H-imidazo[4,5-beta]pyridine can be summarized as: (1)ACD/LogP: 1.63; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.59; (4)ACD/LogD (pH 7.4): 0.72; (5)ACD/BCF (pH 5.5): 9.35; (6)ACD/BCF (pH 7.4): 1.26; (7)ACD/KOC (pH 5.5): 167.83; (8)ACD/KOC (pH 7.4): 22.59; (9)H bond acceptors: 3; (10)H bond donors: 1; (11)Freely Rotating Bonds: 0; (12)Polar Surface Area: 30.71 Å²; (13)Index of Refraction: 1.723; (14)Molar Refractivity: 44.5 cm³; (15)Molar Volume: 112.2 cm³; (16)Polarizability: 17.64×10^-24cm3; (17)Surface Tension: 75.4 dyne/cm; (18)Density: 1.675 g/cm³; (19)Flash Point: 238.4 °C; (20)Enthalpy of Vaporization: 64.42 kJ/mol; (21)Boiling Point: 416.9 °C at 760 mmHg; (22)Vapour Pressure: 8.95E-07 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES:Clc1c2c(nc(Cl)c1)ncn2
(2)InChI:InChI=1/C6H3Cl2N3/c7-3-1-4(8)11-6-5(3)9-2-10-6/h1-2H,(H,9,10,11)
(3)InChIKey:IKJFWUNKUZVHGU-UHFFFAOYAX
(4)Std. InChI:InChI=1S/C6H3Cl2N3/c7-3-1-4(8)11-6-5(3)9-2-10-6/h1-2H,(H,9,10,11)
(5)Std. InChIKey:IKJFWUNKUZVHGU-UHFFFAOYSA-N