5,7-Dichloro-1H-imidazo[4,5-b]pyridine supplier

Name
3H-Imidazo[4,5-b]pyridine, 5,7-dichloro-
EINECS
CAS No. 24485-01-6
Article Data9
CAS DataBase
Density 1.675 g/cm³
Solubility
Melting Point 273-274 °C
Formula C₆H₃Cl₂N₃
Boiling Point 416.867 °C at 760 mmHg
Molecular Weight 188.016
Flash Point 238.425 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
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;

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

: 90580-88-4
(2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate

: 3-(2-O-acetyl-5-O-benzoyl-3-deoxy-D-ribofuranosyl)-5,7-dichloro-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 160℃;	81%

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

: 90580-88-4
(2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate

: 232277-31-5
3-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-5,7-dichloro-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile Substitution;	69%
With tin(IV) chloride In acetonitrile	69%

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

: 90580-88-4
(2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate

A: 232277-32-6
5,7-dichloro-3-deoxy-3-deoxy-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine

B: 232277-35-9
5,7-dichloro-3-(3-deoxy-α-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Stage #1: 5,7-dichloro-3H-imidazo<4,5-b>pyrimidine; (2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate With toluene-4-sulfonic acid Stage #2: With ammonia In methanol	A 56% B 29%

...Expand

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

: 90580-88-4
(2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate

A: 232277-31-5
3-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-5,7-dichloro-3H-imidazo[4,5-b]pyridine

B: 3-(2-O-acetyl-5-O-benzoyl-3-deoxy-α-D-ribofuranosyl)-5,7-dichloro-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
toluene-4-sulfonic acid at 160℃; for 0.166667h; Glycosylation;	A 52% B 29%
With toluene-4-sulfonic acid at 160℃; for 0.166667h; Substitution; Title compound not separated from byproducts;
With toluene-4-sulfonic acid Heating;

...Expand

: 261952-16-3
1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene

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

: 1445877-12-2
5,7-dichloro-3-(2-methyl-3-(trifluoromethyl)benzyl)-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Stage #1: 5,7-dichloro-3H-imidazo<4,5-b>pyrimidine With potassium carbonate In N,N-dimethyl-formamide for 0.416667h; Stage #2: 1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene In N,N-dimethyl-formamide at 20℃;	47.6%

: 100-44-7
benzyl chloride

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

: 500896-84-4
2,6-dichloro-9-benzyl-1-deazapurine

Conditions

Conditions	Yield
Stage #1: 5,7-dichloro-3H-imidazo<4,5-b>pyrimidine With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 20℃; for 16h;	42%

: 110-87-2
3,4-dihydro-2H-pyran

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

: 5 ,7-dichloro-3-(tetrahydro-2H-pyran-2-yl)-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran at 70℃; for 16h;	35.53%

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

: 3163-27-7
2-(bromomethyl)naphthalene

: 1445877-14-4
5,7-dichloro-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Stage #1: 5,7-dichloro-3H-imidazo<4,5-b>pyrimidine With potassium carbonate In N,N-dimethyl-formamide for 25h; Stage #2: 2-(bromomethyl)naphthalene at 20℃;	26.2%

: 3601-89-6, 4330-21-6, 52304-86-6, 3056-12-0, 141846-57-3
Hoffer's chlorosugar

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

A: 5,7-dichloro-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-imidazo<4,5-b>pyridine

B: 5,7-dichloro-3-(2-deoxy-α-D-erythro-pentofuranosyl)-3H-imidazo<4,5-b>pyridine

C: 159944-82-8
5,7-dichloro-3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
With ammonia; sodium hydride 1.) CH3CN, 0 deg C, 3 h, 2.) MeOH, RT, 36 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 3601-89-6, 4330-21-6, 52304-86-6, 3056-12-0, 141846-57-3
Hoffer's chlorosugar

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

A: 5,7-dichloro-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3H-imidazo<4,5-b>pyridine

B: 5,7-dichloro-3-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)-3H-imidazo<4,5-b>pyridine

Conditions

Conditions	Yield
With sodium hydride at 0℃; for 3h;

...Expand

: 131487-19-9
2,3-dideoxy-5-O-<(1,1-dimethylethyl)dimethylsilyl>-α/β-D-glycero-pentofuranosyl chloride

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

: 3-[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5,7-dichloro-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Yield given;

: 133635-44-6
methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside

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

A: 5,7-dichloro-3-(2,3-dideoxy-5-O-p-toluoyl-α-D-glycero-pentofuranosyl)-3H-imidazo<4,5-b>pyridine

B: 165126-97-6
5,7-dichloro-3-(2,3-dideoxy-5-O-p-toluoyl-β-D-glycero-pentofuranosyl)-3H-imidazo<4,5-b>pyridine

...Expand

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

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: K2CO3 / dimethylformamide / 0.5 h 1.2: 42 percent / dimethylformamide / 16 h / 20 °C 2.1: 91 percent / K2CO3 / Pd(PPh3)4 / toluene / 0.5 h / 150 °C / microwave irradiation 3.1: 41 percent / ammonium formate / Pd(OH)2/C / ethanol / 0.33 h / 140 - 150 °C / microwave irradiation View Scheme

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

: 929533-19-7
3-benzyl-5,7-diphenyl-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: K2CO3 / dimethylformamide / 0.5 h 1.2: 42 percent / dimethylformamide / 16 h / 20 °C 2.1: 91 percent / K2CO3 / Pd(PPh3)4 / toluene / 0.5 h / 150 °C / microwave irradiation View Scheme

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

: (3R,5S)-2-(5,7-Dichloro-imidazo[4,5-b]pyridin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / TsOH / 160 °C 2: 85 percent / NH3 / methanol / 20 °C View Scheme

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

: 5-chloro-7-benzylsulfanyl-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: SnCl4 2: 85 percent / triethylamine / dimethylformamide / 18 h / 20 °C 3: 65 percent / ammonia / methanol / 18 h / 0 °C View Scheme

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

: 5-chloro-7-(4-nitrobenzylsulfanyl)-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: SnCl4 2: 75 percent / triethylamine / dimethylformamide / 18 h / 20 °C 3: 88 percent / ammonia / methanol / 18 h / 0 °C View Scheme

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

: 566194-66-9
5-chloro-7-(benzylsulfanyl)-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: SnCl4 2: 85 percent / triethylamine / dimethylformamide / 18 h / 20 °C View Scheme

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

: 566194-68-1
5-chloro-7-(4-nitrobenzylsulfanyl)-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: SnCl4 2: 75 percent / triethylamine / dimethylformamide / 18 h / 20 °C View Scheme

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

: 7-amino-3-(3-deoxy-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 69 percent / SnCl4 / acetonitrile 2: NH3 / methanol 3: NH3 / 130 °C 4: H2 / Pd-C View Scheme
Multi-step reaction with 4 steps 1: TsOH / Heating 2: NH3 / methanol 3: NH3 / 130 °C 4: H2 / Pd-C View Scheme
Multi-step reaction with 3 steps 1.1: p-toluenesulfonic acid 1.2: 56 percent / NH3 / methanol 2.1: NH3 / 130 °C 3.1: H2 / Pd-C View Scheme

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

: 232277-32-6
5,7-dichloro-3-deoxy-3-deoxy-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / SnCl4 / acetonitrile 2: NH3 / methanol View Scheme
Multi-step reaction with 2 steps 1: TsOH / Heating 2: NH3 / methanol View Scheme
Multi-step reaction with 2 steps 1: 69 percent / SnCl4 / acetonitrile 2: 85 percent / NH3 / methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: p-TsOH / 0.17 h / 160 °C 2: 85 percent / NH3 / methanol / 20 °C View Scheme

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

: 232277-33-7
7-amino-5-chloro-3-(3-deoxy-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / SnCl4 / acetonitrile 2: NH3 / methanol 3: NH3 / 130 °C View Scheme
Multi-step reaction with 3 steps 1: TsOH / Heating 2: NH3 / methanol 3: NH3 / 130 °C View Scheme
Multi-step reaction with 2 steps 1.1: p-toluenesulfonic acid 1.2: 56 percent / NH3 / methanol 2.1: NH3 / 130 °C View Scheme

5,7-Dichloro-1H-imidazo[4,5-b]pyridine 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

Product Name

3H-Imidazo[4,5-b]pyridine, 5,7-dichloro-

Synthetic route

5,7-Dichloro-1H-imidazo[4,5-b]pyridine Specification

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