69506-85-0|1,3-Di(1H-imidazol-1-yl)propane| Ambeed

CAS No. :	69506-85-0
Formula :	C₉H₁₂N₄
M.W :	176.22
SMILES Code :	N1(CCCN2C=CN=C2)C=CN=C1
MDL No. :	MFCD11110663
InChI Key :	ISXPITWIJWSEKJ-UHFFFAOYSA-N
Pubchem ID :	15028898

Safety of [ 69506-85-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 69506-85-0 ]

* 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 [ 69506-85-0 ]

[ 69506-85-0 ] Synthesis Path-Downstream 1~55

1
[ 288-32-4 ]
[ 109-64-8 ]
[ 69506-85-0 ]

Yield	Reaction Conditions	Operation in experiment
63%		General procedure: The general procedure for the Nalkylation of heterocycles was as follows.22 Heterocycle (1 mmol) wasdissolved in 5 ml anhydrous DMF. Then complex(0.05 mmol) and K2CO3 was added to the solution atroom temperature. Shortly afterwards (20 min),1,3-dibromopropane (1 mmol) was added in portions to the reaction mixture. The reaction was stirred at room temperature. The inorganic salt was removed byfiltration and rinsed twice with dichloromethane. The solution was poured into water and extracted withdichloromethane (2 x 25 ml). The combined organiclayers were washed with brine, dried over anhydroussodium sulphate, filtered, and concentrated in vacuoresulting in the formation of the product in 92 % yieldwith coupling ratio 1:1 and product yield 78 % withcoupling ratio 2:1. Nalkylation of heterocycles with1,3-dibromopropane having 1:1 coupling proportion(Scheme-2) is easier than 2:1 coupling proportion(Scheme-3).
52%		1,3-Di(imidazolyl-1)propane: Imidazole (13.6 g,0.2 mol) was dissolved in 50 mL of acetonitrile, and22.4 g (0.2 mol) of potassium tert-butoxide was addedportionwise (the reaction is exothermic) with stirringon a magnetic stirrer. The resulting mixture was stirredfor 1 h, and the solvent was then distilled off in vacuum(to remove tert-butanol). Acetonitrile (70 mL) wasadded to the dry residue, and 20.4 g (0.1 mol) of1,3-dibromopropane dissolved in 20 mL of acetonitrilewas added dropwise over 1 h under stirring. Theprecipitate of KBr was filtered off the next day, the filtratewas evaporated in vacuum, and the residue wasdistilled in vacuum. The product was distilled at 198-200C/<1 mmHg as a pale-yellow viscous liquid thatcrystallizes later, m.p. 45C. The yield was 9.1 g (52%).

References: [1]Organometallics,2021,vol. 40,p. 3775 - 3784.
[2]Heterocycles,2003,vol. 60,p. 779 - 784.
[3]Angewandte Chemie - International Edition,2007,vol. 46,p. 6525 - 6528.
[4]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3350 - 3355.
[5]Journal of Chemical Sciences,2020,vol. 132.
[6]Russian Journal of Physical Chemistry,2015,vol. 89,p. 2204 - 2209.
Zh. Fiz. Khim.,2015,vol. 89,p. 1858 - 1863,6.

2
[ 3022-16-0 ]
[ 69506-85-0 ]
C₄₂H₅₆N₈⁽⁴⁺⁾*4Cl^(1-) [ No CAS ]

References: [1]Heterocycles,2003,vol. 60,p. 779 - 784.

3
[ 5036-48-6 ]
[ 50-00-0 ]
[ 131543-46-9 ]
[ 69506-85-0 ]

References: [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 4201 - 4208.

4
[ 627-31-6 ]
[ 69506-85-0 ]
C₂₁H₃₀N₈⁽²⁺⁾*2I^(1-) [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 4201 - 4208.

5
[ 91-13-4 ]
[ 69506-85-0 ]
C₆H₄(CH₂N₂C₃H₃CH₂)2CH₂⁽²⁺⁾*2Br^(1-)=C₆H₄(CH₂N₂C₃H₃CH₂)2CH₂Br₂ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 5966 - 5970.

6
[ 627-31-6 ]
[ 69506-85-0 ]
1,1':3,3'-bis(trimethylene)bis(imidazolium) diiodide [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 5178 - 5183.

7
[ 69506-85-0 ]
(CH₂C₃H₃N₂CH₂)4(CH₂)4⁽⁴⁺⁾*4I^(1-)=((CH₂C₃H₃N₂CH₂)4(CH₂)4)I₄ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 4201 - 4208.

8
[ 627-31-6 ]
[ 69506-85-0 ]
(CH₂C₃H₃N₂CH₂)4(CH₂)4⁽⁴⁺⁾*4I^(1-)=((CH₂C₃H₃N₂CH₂)4(CH₂)4)I₄ [ No CAS ]
1,1':3,3'-bis(trimethylene)bis(imidazolium) diiodide [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 6525 - 6528.

9
[ 69506-85-0 ]
[ 74-88-4 ]
1,1’-dimethyl-3,3’-propylene-diimidazolium diiodide [ No CAS ]

References: [1]Synthesis,2010,p. 2609 - 2615.

10
copper(II) acetate dihydrate [ No CAS ]
[ 46331-50-4 ]
potassium hydroxide [ No CAS ]
[ 69506-85-0 ]
[Cu₅(.mu3.-OH)2(1,3-bis(imidazol)propane)2(5-methoxyisophthalate)4]n [ No CAS ]

References: [1]Dalton Transactions,2012,vol. 41,p. 2078 - 2083.

11
α-K6[P2W18O62]*12H2O [ No CAS ]
[ 6046-93-1 ]
[ 69506-85-0 ]
[Cu((1,1'-(1,3-propanediyl)bis(imimdazole)H)]4[P₂W₁₈O₆₂]2 [ No CAS ]

References: [1]Journal of Molecular Structure,2010,vol. 968,p. 19 - 23.

12
[ 2359-09-3 ]
[ 5743-04-4 ]
[ 69506-85-0 ]
[Cd2(5-tert-butyl isophthalato)2(1,3-bis(imidazole-1-yl)propane)2]·4H2O}n [ No CAS ]

References: [1]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2013,vol. 43,p. 682 - 686.

13
dodecamolybdophosphoric acid * 13 H₂O [ No CAS ]
[ 69506-85-0 ]
[(PMo₁₂O₄₀)(1,1'-(1,3-propanediyl)bis(imidazole)(+2H))(1,1'-(1,3-propanediyl)bis(imidazole)(+H))] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With hydrogenchloride; In water; at 25 - 160℃; for 96h;pH 4.0;Autoclave;	A mixture of H3PMo12O40·13H2O (0.6178g, 0.3mmol), bpi (0.035g, 0.2mmol) and H2O (10ml) was stirred for 30min in air until it was homogeneous. When the pH value of the mixture was adjusted to 4 with 1M HCl, the solution was transferred and sealed in a 30-ml Teflon-lined stainless steel autoclave, which was heated at 160C under autogenous pressure for 4days. The dark blue block crystals were isolated and collected by filtration, washed thoroughly with distilled water, and dried at room temperature (60% yield based on Mo). Anal. Calc. C18H27N8O40PMo12 (4295.10): C, 4.99 (Calc. 5.03); H, 0.69 (0.63); N, 2.69 (2.61); P, 0.74(0.72); Mo, 26.79 (26.82) wt.%

References: [1]Inorganica Chimica Acta,2013,vol. 400,p. 59 - 66.

14
[ 69506-86-1 ]
dodecamolybdophosphoric acid * 13 H₂O [ No CAS ]
[ 69506-85-0 ]
[(PMo₁₂O₄₀)(1,1 '-(1,4-butanediyl)bis(imidazole)(+2H))0.5(1,1'-(1,3-propanediyl)bis(imidazole)(+H))] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With hydrogenchloride; In water; at 25 - 170℃; for 96h;pH 4.0;Autoclave;	A mixture of H3PMo12O40·13H2O (0.6178g, 0.3mmol), bpi (0.0175g, 0.1mmol), bbi (0.019g, 0.1mmol) and H2O (10ml) was stirred for 30min in air until it was homogeneous. When the pH value of the mixture was adjusted to 4 with 1M HCl, the solution was transferred and sealed in a 30-ml Teflon-lined stainless steel autoclave, which was heated at 170C under autogenous pressure for 4days. The light blue sheet crystals were isolated and collected by filtration, washed thoroughly with distilled water, and dried at room temperature (63% yield based on Mo). Anal. Calc. C14H21N6O40PMo12 (2095.62): C, 7.99 (Calc. 8.02); H, 0.99 (1.00); N, 3.99 (4.01); P, 1.44 (1.48); Mo, 54.61 (54.97) wt.%.

References: [1]Inorganica Chimica Acta,2013,vol. 400,p. 59 - 66.

15
[ 499-49-0 ]
[ 5743-04-4 ]
[ 69506-85-0 ]
[ 1470065-49-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium hydroxide; In water; at 139.84℃; for 72h;Autoclave;	The reaction condition is similar to those described in 1 except that 1,2-bie was replaced by 1,3-bip (17.6mg, 0.1mmol). Colorless block crystals of 2 were obtained. Yield: 19.6mg, 42percent (Based on Cd). Anal. Calc. for C18H18CdN4O4: C, 46.32; H, 3.89; N, 12.00. Found: C, 46.28; H, 3.93; N, 11.96percent. IR (cm?1): 3484 m, 3118 m, 1615 m, 1546 s, 1370 s, 1090 s, 780 s, 730 s, 659 s.

References: [1]Inorganica Chimica Acta,2013,vol. 407,p. 153 - 159.

16
[ 69506-85-0 ]
C₃₂H₃₄Ag₂N₁₀⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

References: [1]New Journal of Chemistry,2013,vol. 37,p. 4176 - 4184.

17
[ 69506-85-0 ]
C₃₂H₃₄Au₂N₁₀⁽³⁺⁾*2F₆P^(1-) [ No CAS ]

References: [1]New Journal of Chemistry,2013,vol. 37,p. 4176 - 4184.

18
[ 69506-85-0 ]
C₃₂H₃₄Ag₂N₁₀⁽²⁺⁾*2Br^(1-) [ No CAS ]

References: [1]New Journal of Chemistry,2013,vol. 37,p. 4176 - 4184.

19
[ 69506-85-0 ]
C₃₂H₃₄Au₂N₁₀⁽³⁺⁾*2Br^(1-) [ No CAS ]

References: [1]New Journal of Chemistry,2013,vol. 37,p. 4176 - 4184.

20
[ 7703-74-4 ]
[ 69506-85-0 ]
C₁₆H₁₉N₅⁽²⁺⁾*2Br^(1-) [ No CAS ]

References: [1]New Journal of Chemistry,2013,vol. 37,p. 4176 - 4184.
[2]Organometallics,2014,vol. 33,p. 2182 - 2188.

21
[ 69506-85-0 ]
C₁₆H₁₇Br₂N₅Pd [ No CAS ]

References: [1]Organometallics,2014,vol. 33,p. 2182 - 2188.

22
[ 69506-85-0 ]
C₁₆H₁₇Br₃N₅Pt⁽¹⁺⁾*Br^(1-) [ No CAS ]

References: [1]Organometallics,2014,vol. 33,p. 2182 - 2188.

23
[ 69506-85-0 ]
C₁₆H₁₇Br₂N₅Pt [ No CAS ]

References: [1]Organometallics,2014,vol. 33,p. 2182 - 2188.

24
2,3′,5,5′-biphenyltetracarboxylic acid [ No CAS ]
[ 5743-04-4 ]
[ 69506-85-0 ]
[Cd₂(2,3′,5,5′-biphenyltetracarboxylic acid)₂(H₂O)₂]*(1,3-bis(imidazole)propane) [ No CAS ]

References: [1]CrystEngComm,2014,vol. 16,p. 6417 - 6424.

25
(3-carboxyl-phenyl)-(4-(2'-carboxyl-phenyl)-benzyl)ether [ No CAS ]
[ 6156-78-1 ]
[ 69506-85-0 ]
[Mn((3-carboxyl-phenyl)-(4-(2'-carboxyl-phenyl)-benzyl)ether(-2H))(1,3-bis(imidazol-1'-yl)propane)] [ No CAS ]

References: [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2014,vol. 640,p. 2217 - 2225.

26
9,9-dimethylfluorene-2,7-dicarboxylic acid [ No CAS ]
[ 7732-18-5 ]
[ 5970-45-6 ]
[ 69506-85-0 ]
2Zn⁽²⁺⁾*2C₁₇H₁₂O₄^(2-)*H₂O*C₉H₁₂N₄ [ No CAS ]

References: [1]CrystEngComm,2014,vol. 16,p. 7459 - 7468.

27
9,9-dimethylfluorene-2,7-dicarboxylic acid [ No CAS ]
[ 7732-18-5 ]
[ 6147-53-1 ]
[ 69506-85-0 ]
2Co⁽²⁺⁾*2C₁₇H₁₂O₄^(2-)*4H₂O*C₉H₁₂N₄ [ No CAS ]

References: [1]CrystEngComm,2014,vol. 16,p. 7459 - 7468.

28
[ 100-21-0 ]
[ 5743-04-4 ]
[ 69506-85-0 ]
[Cd(1,3-bis(imidazole)propane)(terephthalic acid)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydroxide; In water; at 110℃; for 72h;	A mixture of Cd(OAc)2.2H2O (0.2 mmol, 60 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.20 mmol, 35.2 mg), NaOH (0.2 mmol, 8 mg) and 1.4-bdc (0.20 mmol, 38.0 mg) in distilled water (4 mL) was placed in a vial, heated to 110C for 3 d, and then cooled to room temperature over 24 h. Colorless block crystals of 1 were collected. Yield: 82% based on cadmium. Elemental analysis (%): calcd for C17H16N4O4Cd (Mr = 452.75): C 45.06, H 3.53, N 12.37; found: C 45.36, H 4.12, N12.81. IR (cm-1): 3417 (w), 3120 (m), 2945 (m), 2884 (w), 1610(s), 1565 (s), 1513 (s), 1379 (s), 1279 (m), 1027 (m), and 833 (m).

References: [1]Journal of Molecular Structure,2015,vol. 1081,p. 79 - 84.

29
[ 100-21-0 ]
[ 5970-45-6 ]
[ 69506-85-0 ]
[Zn(1,3-bis(imidazole)propane)(terephthalic acid)]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydroxide; In water; at 110℃; for 72h;	General procedure: A mixture of Cd(OAc)2.2H2O (0.2 mmol, 60 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.20 mmol, 35.2 mg), NaOH (0.2 mmol, 8 mg) and 1.4-bdc (0.20 mmol, 38.0 mg) in distilled water (4 mL) was placed in a vial, heated to 110C for 3 d, and then cooled to room temperature over 24 h. Colorless block crystals of 1 were collected. Yield: 82% based on cadmium. Elemental analysis (%): calcd for C17H16N4O4Cd (Mr = 452.75): C 45.06, H 3.53, N 12.37; found: C 45.36, H 4.12, N12.81. IR (cm-1): 3417 (w), 3120 (m), 2945 (m), 2884 (w), 1610(s), 1565 (s), 1513 (s), 1379 (s), 1279 (m), 1027 (m), and 833 (m).

References: [1]Journal of Molecular Structure,2015,vol. 1081,p. 79 - 84.

30
[ 121-91-5 ]
[ 7732-18-5 ]
[ 5743-04-4 ]
[ 69506-85-0 ]
[Cd(1,3-bis(imidazole)propane)(isophthalic acid)]*H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydroxide; at 110℃; for 72h;	A mixture of Cd(OAc)2.2H2O (0.2 mmol, 60 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.20 mmol, 35.2 mg), NaOH (0.2 mmol, 8 mg) and 1.3-bdc (0.20 mmol, 38.0 mg) in distilled water (4 mL) was placed in a vial, heated to 110C for 3 d, and then cooled to room temperature over 24 h. Colorless block crystals of 3 were obtained. Yield: 76% based on cadmium. Elemental analysis (%): calcd for C17H18CdN4O5 (Mr = 470.75): C 43.33, H 3.82, N 11.89; found: C 43.28, H 3.77, N11.96. IR (cm-1): 3414 (bs), 3122 (w), 1601 (s), 1551 (s), 1435(w), 1232 (m), 1096 (m), 932 (w), 749 (s), and 622 (w).

References: [1]Journal of Molecular Structure,2015,vol. 1081,p. 79 - 84.

31
[ 121-91-5 ]
[ 7732-18-5 ]
[ 5970-45-6 ]
[ 69506-85-0 ]
[Zn(1,3-bis(imidazole)propane)(isophthalic acid)]*2H₂O}_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium hydroxide; at 110℃; for 72h;	General procedure: A mixture of Cd(OAc)2.2H2O (0.2 mmol, 60 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.20 mmol, 35.2 mg), NaOH (0.2 mmol, 8 mg) and 1.3-bdc (0.20 mmol, 38.0 mg) in distilled water (4 mL) was placed in a vial, heated to 110C for 3 d, and then cooled to room temperature over 24 h. Colorless block crystals of 3 were obtained. Yield: 76% based on cadmium. Elemental analysis (%): calcd for C17H18CdN4O5 (Mr = 470.75): C 43.33, H 3.82, N 11.89; found: C 43.28, H 3.77, N11.96. IR (cm-1): 3414 (bs), 3122 (w), 1601 (s), 1551 (s), 1435(w), 1232 (m), 1096 (m), 932 (w), 749 (s), and 622 (w).

References: [1]Journal of Molecular Structure,2015,vol. 1081,p. 79 - 84.

32
[ 499-81-0 ]
zinc(II) nitrate hexahydrate [ No CAS ]
[ 7732-18-5 ]
[ 69506-85-0 ]
[Zn(1,3-bis(imidazolyl)propane)(pyridine-3,5-dicarboxylate)]·2H2O}n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	at 120℃; for 72h;High pressure; Autoclave;	A mixture of 3,5-pdc (0.10 mmol,16.7 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.10 mmol, 17.6 mg) and Zn(NO3)2.6H2O (0.10 mmol, 30.8 mg) in distilled water (15 mL) was placed in a Teflon-lined stainless steel vessel, heated to 120 C for 3 days, and then cooled to room temperature over 24 h. Colourless block crystals of 1 were obtained. Yield 51%. Anal calcd for C16H19N5O6Zn (Mr = 442.72): C, 43.38; H, 4.29; N, 15.81; found: C, 43.24; H, 3.96; N, 15.90%. IR(cm-1): 3455 (s), 3125 (m),2934 (w), 1668 (s), 1627 (s), 1530 (m), 1353(s),1247 (w), 1103 (s), 946 (w), 835 (w).

References: [1]Journal of Chemical Research,2014,vol. 38,p. 726 - 730.

33
[ 121-91-5 ]
[ 7732-18-5 ]
copper(II) nitrate [ No CAS ]
[ 69506-85-0 ]
[Cu(1,3-bis(imidazolyl)propane)(isophthalate)]·H2O}n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	at 120℃; for 72h;Autoclave; High pressure;	A mixture of 1,3-bdc (0.10 mmol,16.7 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.10 mmol, 17.6 mg) and Cu(NO3)2 (0.10 mmol,24.1 mg) in distilled water (15 mL) was placed in a Teflon-lined stainless steel vessel, heated to 120 C for 3 d, and then cooled to room temperature over 24 h. Blue block crystals of the title compound were collected. Yield 71%. Anal calcd for C17H18CuN4O5 (Mr = 421.88):C, 48.35; H, 4.26; N, 13.27; found: C, 48.61; H, 4.04; N, 13.40%. IR (cm-1): 3433 (s),3120 (s),2928 (m),1612 (s),1557 (m),1396(m),1352 (s),1235 (w), 1096 (m), 733 (m).

References: [1]Journal of Chemical Research,2014,vol. 38,p. 726 - 730.

34
[ 2417-69-8 ]
[ 69506-85-0 ]
C₃₉H₅₈N₄O₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In acetonitrile; at 75℃;Schlenk technique; Inert atmosphere;	General procedure: A mixture of the properly functionalised benzyl bromide (1 mmol) and <strong>[69506-85-0]1,3-di(1H-imidazol-1-yl)propane</strong> (0.5 mmol) in acetonitrile (15 mL) was left under stirring at 75 C for 16 h. Addition of diethyl ether (20 mL) to the reaction mixture affords the precipitation of the product. The obtained white solid was isolated, washed with diethyl ether (2 x 5 mL) and dried under vacuum. 1·2HBr: White solid, yield 62%. Anal Calcd for C39H58Br2N4O25H2O: C, 54.17; H, 7.93; N, 6.48%. Found: C, 54.44; H, 7.68; N, 6.60%. 1H NMR (CDCl3): δ=0.88 (m, 6H, CH3), 1.10-1.50 (m, 20H, CH2), 1.77 (m, 4H, OCH2CH2), 2.88 (m, 2H, CH2 propylene), 3.94 (m, 4H, OCH2), 4.72 (m, 4H, NCH2 propylene), 5.31 (s, 4H, NCH2Ar), 6.91 (d, 3J=8.5Hz, 4H, Ar-H), 6.96 (s, 2H, CH), 7.35 (d, 3J=8.5Hz, 4H, Ar-H), 8.05 (s, 2H, CH), 10.21 (s, 2H, NCHN).