4,6-Dichloro-1H-imidazo[4,5-c]pyridine supplier

Name
4,6-DICHLOROIMIDAZO[4,5-C]PYRIDINE
EINECS
CAS No. 2589-12-0
Article Data7
CAS DataBase
Density 1.675 g/cm³
Solubility
Melting Point 253-254°C
Formula C₆H₃Cl₂N₃
Boiling Point 482.902 °C at 760 mmHg
Molecular Weight 188.016
Flash Point 277.938 °C
Transport Information
Appearance Beige solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1H-Imidazo[4,5-c]pyridine,4,6-dichloro- (7CI,9CI);2,6-Dichloro-3-deazapurine;4,6-Dichloroimidazo[4,5-c]pyridine;NSC 264047;
PSA 41.57000
LogP 2.26470

Synthetic route

: 101079-63-4
3,4-diamino-2,6-dichloropyridine

: 122-51-0
orthoformic acid triethyl ester

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
With acetic anhydride for 4.5h; Heating;	96%
Stage #1: 3,4-diamino-2,6-dichloropyridine; orthoformic acid triethyl ester With acetic anhydride for 4.5h; Reflux; Stage #2: With sodium hydroxide In water at 50℃; for 0.666667h;
Stage #1: 3,4-diamino-2,6-dichloropyridine; orthoformic acid triethyl ester With acetic anhydride at 90℃; for 4.5h; Stage #2: With sodium hydroxide In water at 85 - 90℃; for 0.75h;	3.4 g

: 3,4-diamino-2,6-dichloropyridine dihydrochloride

: 122-51-0
orthoformic acid triethyl ester

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
With acetic anhydride at 145℃; for 0.5h;	90%

: 668268-66-4
3-amino-4-acetamido-2,6-dichloropyridine

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / Heating 2: 96 percent / Ac2O / 4.5 h / Heating View Scheme

: 2402-78-0
2,6-dichloropyridine

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: CF3COOH; aq. H2O2 / 6.5 h / Heating 2: HNO3; H2SO4 / 160 °C 3: AcOH; Fe / Heating 4: HNO3; H2SO4 / 20 °C 5: H2SO4 / 100 °C 6: 51 percent / Fe / 2 h / Heating 7: aq. NaOH / Heating 8: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 7 steps 1: CF3COOH; aq. H2O2 / 6.5 h / Heating 2: HNO3; H2SO4 / 160 °C 3: AcOH; Fe / Heating 4: HNO3; H2SO4 / 20 °C 5: H2SO4 / 100 °C 6: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 7: 96 percent / Ac2O / 4.5 h / Heating View Scheme

: 2587-02-2
2,6-dichloro-[4]pyridylamine

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: HNO3; H2SO4 / 20 °C 2: H2SO4 / 100 °C 3: 51 percent / Fe / 2 h / Heating 4: aq. NaOH / Heating 5: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: HNO3; H2SO4 / 20 °C 2: H2SO4 / 100 °C 3: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 4: 96 percent / Ac2O / 4.5 h / Heating View Scheme

: 2587-00-0
2,6-dichloropyridine N-oxide

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 51 percent / Fe / 2 h / Heating 6: aq. NaOH / Heating 7: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 6 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 6: 96 percent / Ac2O / 4.5 h / Heating View Scheme

: 2587-03-3
2,6-dichloro-N-nitro-4-pyridinamine

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: H2SO4 / 100 °C 2: 51 percent / Fe / 2 h / Heating 3: aq. NaOH / Heating 4: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: H2SO4 / 100 °C 2: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 3: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / 1 h / 100 °C 2.1: hydrogen / methanol / 4 h 3.1: acetic anhydride / 4.5 h / 90 °C 3.2: 0.75 h / 85 - 90 °C View Scheme

: 2897-43-0
2,6-dichloro-3-nitropyridin-4-amine

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 51 percent / Fe / 2 h / Heating 2: aq. NaOH / Heating 3: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 2: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: iron; hydrogenchloride / water; ethanol / 16 h / Reflux 2: 5 h / 145 °C 3: formic acid / 5 h / 110 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen / methanol / 4 h 2.1: acetic anhydride / 4.5 h / 90 °C 2.2: 0.75 h / 85 - 90 °C View Scheme

: 25194-01-8
2,6-dichloro-4-nitro-pyridine

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: AcOH; Fe / Heating 2: HNO3; H2SO4 / 20 °C 3: H2SO4 / 100 °C 4: 51 percent / Fe / 2 h / Heating 5: aq. NaOH / Heating 6: 96 percent / Ac2O / 4.5 h / Heating View Scheme
Multi-step reaction with 5 steps 1: AcOH; Fe / Heating 2: HNO3; H2SO4 / 20 °C 3: H2SO4 / 100 °C 4: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 5: 96 percent / Ac2O / 4.5 h / Heating View Scheme

: 101079-63-4
3,4-diamino-2,6-dichloropyridine

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 h / 145 °C 2: formic acid / 5 h / 110 °C View Scheme

: C8H9Cl2N3O

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
With formic acid at 110℃; for 5h;	390 mg

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

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: 4,6-dichloro-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 3h;	91%
With toluene-4-sulfonic acid In tetrahydrofuran Reflux;	55%

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

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

: 63423-94-9
2,6-dichloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3-deazapurine

Conditions

Conditions	Yield
Heating;	90%
With toluene-4-sulfonic acid at 160℃; for 0.166667h; stereoselective reaction;	76%

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

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

: benzoic acid 4-acetoxy-5-(4,6-dichloro-imidazo[4,5-c]pyridin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid Heating;	90%

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: 100-51-6
benzyl alcohol

: 52559-19-0
2-benzyloxy-7-chloropyrido[4,5-c]imidazole

Conditions

Conditions	Yield
With sodium at 120℃;	85%

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: (2R,3R,4R,5R)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-2,3,4-triyl tribenzoate

: 1254180-69-2
C33H25Cl2N3O7

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃; for 3h;	70%

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

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

A: 220249-14-9
1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine

B: 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-α-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine

C: 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-α-D-arabinofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 160℃; under 25 Torr; for 0.166667h;	A 52% B 24% C 14%
With toluene-4-sulfonic acid at 160℃; for 0.166667h; Substitution;

...Expand

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

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

A: 220249-17-2
4,6-dichloro-1-(3-deoxy-β-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine

B: 220249-18-3
4,6-dichloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine

C: 4,6-dichloro-1-(3-deoxy-α-D-arabinofuranosyl)-1H-imidazo<4,5-c>pyridine

D: (2R,3S,5S)-2-(4,6-Dichloro-imidazo[4,5-c]pyridin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol

Conditions

Conditions	Yield
Stage #1: 4,6-dichloro-1H-imidazo<4,5-c>pyridine; (2S,3R,5S)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate With toluene-4-sulfonic acid Heating; Stage #2: With ammonia In methanol	A 51% B 23% C 13% D 3%

...Expand

: 915694-38-1
(3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: 1-((3aR,3bR,4aS,5R,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-yl)-4,6-dichloro-1H-imidazo[4,5-c]pyridine

Conditions

Conditions	Yield
Stage #1: 4,6-dichloro-1H-imidazo<4,5-c>pyridine With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.333333h; Stage #2: (3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol In tetrahydrofuran at 20℃;	50%
Stage #1: 4,6-dichloro-1H-imidazo<4,5-c>pyridine With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.333333h; Stage #2: (3aR,3bR,4aS,5S,5aS)-3b-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-ol In tetrahydrofuran at 20℃;	50%

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: 52559-17-8
2-chloro-3-deazaadenine

Conditions

Conditions	Yield
With ammonia In methanol at 160℃; for 90h;	49%
With ammonia In methanol at 160℃; for 90h;

: 52554-29-7
2,3,5-tri-O-benzyl-α- and β-D-arabinofuranosyl chlorides

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

A: 3-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,6-dichloro-3H-imidazo[4,5-c]pyridine

B: 80161-98-4
4,6-dichloro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazo<4,5-c>pyridine

C: 80161-98-4
4,6-dichloro-1-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
With 4 A molecular sieve In 1,2-dichloro-ethane Heating; Yield given;	A n/a B 37% C n/a
With 4 A molecular sieve In 1,2-dichloro-ethane Heating; Yields of byproduct given;	A n/a B 37% C n/a

...Expand

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

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

: 220249-14-9
1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
With tin(IV) chloride In acetonitrile	27%

: 4330-21-6
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: 91713-45-0
4,6-dichloro-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
With sodium hydride 1.) acetonitrile, r.t., 30 min; 2.) 50 deg C, 2 h; Yield given. Multistep reaction;

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

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

A: 220249-17-2
4,6-dichloro-1-(3-deoxy-β-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine

B: 220249-18-3
4,6-dichloro-1-(3-deoxy-α-D-ribofuranosyl)-1H-imidazo<4,5-c>pyridine

C: 4,6-dichloro-1-(3-deoxy-α-D-arabinofuranosyl)-1H-imidazo<4,5-c>pyridine

Conditions

Conditions	Yield
With ammonia; toluene-4-sulfonic acid 1.) neat, 160 deg C, 25 Torr, 5-10 min, 2.) MeOH, rt, 24 h; Yield given; Multistep reaction. Yields of byproduct given;

...Expand

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

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

A: 220249-14-9
1-(2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine

B: 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-α-D-ribofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine

C: 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-α-D-arabinofuranosyl)-4,6-dichloro-1H-imidazo<4,5-c>pyridine

D: Benzoic acid (2S,4S,5R)-4-acetoxy-5-(4,6-dichloro-imidazo[4,5-c]pyridin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid Heating;

...Expand

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: 8-chloro-3-deazaadenine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 3: 31 percent / t-butyl hypochlorite / dimethylsulfoxide / 144 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 3: HCl; mCPBA / N,N-dimethyl-acetamide / 0.42 h / 20 °C View Scheme

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: 3-chloro-3-deazaadenine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 3: 6.2 percent / HCl; mCPBA / N,N-dimethyl-acetamide / 0.42 h / 20 °C View Scheme

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: 2,8-dichloro-3-deazaadenine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 38 percent / HCl; mCPBA / N,N-dimethyl-acetamide / 20 °C View Scheme

: 2589-12-0
4,6-dichloro-1H-imidazo<4,5-c>pyridine

: 6811-77-4
3-deazaadenine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / ammonia / methanol / 90 h / 160 °C 2: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr View Scheme

4,6-Dichloro-1H-imidazo[4,5-c]pyridine Specification

The 4,6-Dichloro-1H-imidazo[4,5-c]pyridine, with the CAS registry number 2589-12-0, is also known as ZINC13283647. This chemical's molecular formula is C₆H₃Cl₂N₃ and molecular weight is 188.01. Its IUPAC name is called 4,6-dichloro-1H-imidazo[4,5-c]pyridine.

Physical properties of 4,6-Dichloro-1H-imidazo[4,5-c]pyridine: (1)ACD/LogP: 1.54; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.54; (4)ACD/LogD (pH 7.4): 1.5; (5)ACD/BCF (pH 5.5): 8.66; (6)ACD/BCF (pH 7.4): 7.97; (7)ACD/KOC (pH 5.5): 163.01; (8)ACD/KOC (pH 7.4): 150.02; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.723; (13)Molar Refractivity: 44.5 cm³; (14)Molar Volume: 112.2 cm³; (15)Surface Tension: 75.4 dyne/cm; (16)Density: 1.675 g/cm³; (17)Flash Point: 277.9 °C; (18)Enthalpy of Vaporization: 71.94 kJ/mol; (19)Boiling Point: 482.9 °C at 760 mmHg; (20)Vapour Pressure: 5.15E-09 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=C2C(=C(N=C1Cl)Cl)N=CN2
(2)InChI: InChI=1S/C6H3Cl2N3/c7-4-1-3-5(6(8)11-4)10-2-9-3/h1-2H,(H,9,10)
(3)InChIKey: FDXNZTUWNBRZDX-UHFFFAOYSA-N

Product Name

4,6-DICHLOROIMIDAZO[4,5-C]PYRIDINE

Synthetic route

4,6-Dichloro-1H-imidazo[4,5-c]pyridine Specification

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