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244187-81-3

Basic Information
CAS No.: 244187-81-3
Name: 1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE
Article Data: 40
Molecular Structure:
Molecular Structure of 244187-81-3 (1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE)
Formula: C27H36N2
Molecular Weight: 388.596
Synonyms: 1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene;1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene;1,3-Bis(2,6-diisopropylphenyl)imidazolylidene;1,3-Bis-(2,6-di-isopropylphenyl)-4,5-dihydroimidazol-2-ylidene;N,N'-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene;
Melting Point: 213-217 °C
Boiling Point: 464.8 °C at 760 mmHg
Flash Point: 204.1 °C
Risk Codes: 10
Safety: 16
PSA: 6.48000
LogP: 7.81790
Synthetic route

1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazole trafluoroborate

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 6h;97%
With potassium tert-butylate In tetrahydrofuran at 20℃; for 4h;96.5%
With potassium tert-butylate; sodium hydride In tetrahydrofuran for 12h; Schlenk technique; Inert atmosphere;78%
250285-32-6

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
With [Fe(η5-cyclopentadienyl)(η-benzene)]; oxygen In tetrahydrofuran-d8 at 20℃; for 0.0166667h;95%
With potassium tert-butylate In tetrahydrofuran at 20℃; for 3.5h; Inert atmosphere;93%
With potassium tert-butylate In tetrahydrofuran for 4h; Glovebox;90%

1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
With potassium tert-butylate90%
With potassium tert-butylate In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; Schlenk technique;
1201311-20-7

N,N-bis(2,6-diisopropylphenyl)-2,4-diphenylimidazol-5-ylidene-1-ium

1228185-08-7

1,3-bis(2,6-diisopropylphenyl)-2-benzoylimidazolium chloride

A

1228185-25-8

C46H49N2O(1+)*Cl(1-)

B

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;A 73%
B n/a

N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
With potassium tert-butylate; sodium hydride In tetrahydrofuran for 16h;68%
With potassium tert-butylate Schlenk technique; Inert atmosphere;
24544-04-5

2,6-diisopropylbenzenamine

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 77.5 percent / formic acid / ethanol; H2O / 48 h
2.1: toluene / 100 °C
2.2: 47 percent / HCl / toluene; dioxane / 5 h / 70 °C
3.1: 79 percent / KOt-Bu / tetrahydrofuran / 4 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 90 percent / propan-1-ol; H2O / 1 h / 70 °C
2: 47 percent / water / tetrahydrofuran / 16 h / 40 °C
3: 80 percent / KO-t-Bu / tetrahydrofuran / 0.33 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid / water; methanol / 50 °C
2: chloro-trimethyl-silane / ethyl acetate / 70 °C
3: potassium tert-butylate / tetrahydrofuran / 3.5 h / 23 °C / Inert atmosphere
View Scheme
74663-75-5

(1E,2E)-N1,N2-bis(2,6-diisopropylphenyl)-ethane-1,2-diimine

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene / 100 °C
1.2: 47 percent / HCl / toluene; dioxane / 5 h / 70 °C
2.1: 79 percent / KOt-Bu / tetrahydrofuran / 4 h / 20 °C
View Scheme
74663-75-5

1,2-bis(2,6-diisopropylphenylimino)ethane

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 47 percent / water / tetrahydrofuran / 16 h / 40 °C
2: 80 percent / KO-t-Bu / tetrahydrofuran / 0.33 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: chloro-trimethyl-silane / ethyl acetate / 70 °C
2: potassium tert-butylate / tetrahydrofuran / 3.5 h / 23 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: chloro-trimethyl-silane / ethyl acetate / 2.75 h / 70 °C
2: potassium tert-butylate / tetrahydrofuran / 3.5 h / 23 °C / Inert atmosphere; Glovebox
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 0 - 20 °C / Inert atmosphere; Schlenk technique
2: potassium tert-butylate / tetrahydrofuran / 0.5 h / Glovebox; Schlenk technique
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / ethyl acetate; 1,4-dioxane
2: potassium tert-butylate / tetrahydrofuran / 4 h / Glovebox
View Scheme

N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene tetrafluoroborate

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
With potassium tert-butylate; sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere;

C27H36N3O

A

1060651-05-9

1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-one

B

10102-43-9

nitrogen(II) oxide

C

10024-97-2

dinitrogen monoxide

D

244187-81-3

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

Conditions
ConditionsYield
at 120℃; for 0.5h; Sealed tube;A 48 %Chromat.
B n/a
C n/a
D 52 %Chromat.
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Specification

The 2H-Imidazol-2-ylidene,1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro- is an organic compound with the formula C27H36N2. The systematic name of this chemical is 1,3-bis(2,6-diisopropylphenyl)imidazole. With the CAS registry number 244187-81-3, it is also named as 1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene.

Physical properties about 2H-Imidazol-2-ylidene,1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro- are: (1)ACD/LogP: 7.78; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.78; (4)ACD/LogD (pH 7.4): 7.78; (5)ACD/BCF (pH 5.5): 484615.88; (6)ACD/BCF (pH 7.4): 484627.03; (7)ACD/KOC (pH 5.5): 408485.34; (8)ACD/KOC (pH 7.4): 408494.78; (9)#H bond acceptors: 2; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 6.48 Å2; (12)Flash Point: 204.1 °C; (13)Enthalpy of Vaporization: 72.63 kJ/mol; (14)Boiling Point: 464.8 °C at 760 mmHg; (15)Vapour Pressure: 8.11E-09 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)c1cccc(c1N2C=CN([C]2)c3c(cccc3C(C)C)C(C)C)C(C)C
(2)InChI: InChI=1/C27H36N2/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8/h9-16,18-21H,1-8H3
(3)InChIKey: VYCIHDBIKGRENI-UHFFFAOYAR
(4)Std. InChI: InChI=1S/C27H36N2/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8/h9-16,18-21H,1-8H3
(5)Std. InChIKey: VYCIHDBIKGRENI-UHFFFAOYSA-N