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Cas Database

1188286-70-5

1188286-70-5

Identification

  • Product Name:C21H24N2O*ClH

  • CAS Number: 1188286-70-5

  • EINECS:

  • Molecular Weight:356.895

  • Molecular Formula: C21H25N2O*Cl

  • HS Code:

  • Mol File:1188286-70-5.mol

Synonyms:C21H24N2O*ClH

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Relevant articles and documentsAll total 2 Articles be found

Facile derivatization of a chemo-active NHC incorporating an enolate backbone and relevant tuning of its electronic properties

Benhamou, Laure,Vujkovic, Nadia,Cesar, Vincent,Gornitzka, Heinz,Lugan, Noel,Lavigne, Guy

experimental part, p. 2616 - 2630 (2010/08/04)

The present report discloses a modular synthetic route to a new type of anionic N-heterocyclic carbene ligand incorporating an enolate group as a reactive backbone component of its heterocyclic framework. The presence of such a reactive unit facilitates further tailoring of the ligand, even after its complexation to transition metals, with concomitant tuning of the electronic donor properties of the carbene center. Simple acylation of the formamidine Ar-NH-CH=NAr (1a,b) (a: Ar = mesityl (Mes); b: Ar = 2,6-diisopropylphenyl (DIPP)) by chloroacetyl chloride gives an acylated formamidine (2a,b), which undergoes a thermally induced cyclization to afford the 4-hydroxyimidazolium salt 3a,b. Single deprotonation by NEt3 gives the zwitterionic imidazolium-4-olate 4, whereas double deprotonation by 2 equiv of LiHMDS gives the imidazolin-2-ylidene-4-olate ligand 5-, which reacts with 0.5 equiv of [RhCl(1,5-COD)]2 to give, after acidification with HCl, the complex [(5H)RhCl(COD)] (7), in which the acidified carbene ligand noted 5H adopts the keto form. By contrast, treatment of 4 with electrophilic reagents E-X (E1 = tBuCO; E2 = Me; E3 = Tf) results in the O-functionalized imidazolium derivatives [4E1-3]+X-, which can be subsequently complexed under the form of the carbene 5E1-3 to give [(5E1-3)RhCl(COD)] (7E1-3). Alternatively, the carbene ligand 5 can be post-functionalized from its complex [(5H)RhCl(COD)] (7) by a simple sequence involving (i) base-induced deprotonation and (ii) addition of E-X, exemplified by the generation of [(5E4-5)RhCl(COD)] (7E4-5) (with E4 = Ph2PO; E5 = tBuSiMe2 (TBDMS)). In parallel, C-functionalization of the metal-bound ligand can be achieved from 7 by deprotonation with LiHMDS, leading to [(5-)RhCl(COD)]Li(thf)n+ followed by a classical aldolization/elimination sequence leading to [(5CH2) RhCl(COD)] (8), in which the C5 carbon of the NHC bears a methylene group. Parallel direct transformations can be achieved after ligand complexation to copper, as exemplified by the generation of [(5H)CuCl] (9) or [(5E5)CuCl] (9E5) (E5 = TBDMS). The donor properties of all the above NHC ligands were evaluated from the standard complexes (NHC)RhCl(CO)2 against the classical IR ν(CO) scale. The resulting order of nucleophilicities for the modulated carbenes is 5 CH2 H ? 5E4 E1 E2 E5 ? 5-. The X-ray structures analyses of 7E2 and 7E4 are reported.

Imidazol-2-ylidene-4-olate: An anionic N-heterocyclic carbene pre-programmed for further derivatization

Benhamou, Laure,Cesar, Vincent,Gornitzka, Heinz,Lugan, Noel,Lavigne, Guy

supporting information; experimental part, p. 4720 - 4722 (2010/01/15)

The 4-hydroxyimidazolium salt, readily prepared in two steps by acylation of a formamidine and quaternization of the second nitrogen, affords, after deprotonation, the anionic imidazol-2-ylidene-4-olate, which can be complexed to a transition metal and st

Process route upstream and downstream products

Process route

1-(1-oxo-2-chloreth-1-yl)-1,3-dimesitylformamidine
1188286-69-2

1-(1-oxo-2-chloreth-1-yl)-1,3-dimesitylformamidine

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride
1188286-70-5

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride

Conditions
Conditions Yield
In N,N-dimethyl-formamide; at 100 ℃; for 1h; Inert atmosphere;
75%
1-(1-oxo-2-chloreth-1-yl)-1,3-dimesitylformamidine
1188286-69-2

1-(1-oxo-2-chloreth-1-yl)-1,3-dimesitylformamidine

C<sub>21</sub>H<sub>24</sub>N<sub>2</sub>O*ClH
1188286-70-5

C21H24N2O*ClH

Conditions
Conditions Yield
In N,N-dimethyl-formamide; at 100 ℃; for 1h; Inert atmosphere;
75%
5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride
1188286-70-5

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride

1,3-bis(2,4,6-trimethylphenyl)imidazolium-4-olate
1188286-71-6

1,3-bis(2,4,6-trimethylphenyl)imidazolium-4-olate

Conditions
Conditions Yield
With triethylamine; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;
92%
5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride
1188286-70-5

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride

1,3-dimesitylimidazolin-2-thione-4-one
1188286-72-7

1,3-dimesitylimidazolin-2-thione-4-one

Conditions
Conditions Yield
5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; Inert atmosphere;
With sulfur; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
68%
C<sub>21</sub>H<sub>24</sub>N<sub>2</sub>O*ClH
1188286-70-5

C21H24N2O*ClH

1,3-bis(2,4,6-trimethylphenyl)imidazolium-4-olate
1188286-71-6

1,3-bis(2,4,6-trimethylphenyl)imidazolium-4-olate

Conditions
Conditions Yield
With triethylamine; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;
92%
5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride
1188286-70-5

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride

1,3-dimesityl-4-oxoimidazole-2-selenone

1,3-dimesityl-4-oxoimidazole-2-selenone

Conditions
Conditions Yield
With selenium; sodium hexamethyldisilazane; In tetrahydrofuran; at 0 - 20 ℃; for 3.33333h;
45%
5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride
1188286-70-5

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride

C<sub>14</sub>H<sub>19</sub>NO<sub>6</sub>S

C14H19NO6S

C<sub>34</sub>H<sub>40</sub>N<sub>3</sub>O<sub>4</sub><sup>(1+)</sup>*Cl<sup>(1-)</sup>

C34H40N3O4(1+)*Cl(1-)

Conditions
Conditions Yield
With potassium carbonate; potassium iodide; In acetone; at 60 ℃;
74%
5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride
1188286-70-5

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride

2,5,8,11-tetraoxatridecan-13-ol tosylate
62921-76-0,58320-73-3

2,5,8,11-tetraoxatridecan-13-ol tosylate

C<sub>30</sub>H<sub>43</sub>N<sub>2</sub>O<sub>5</sub><sup>(1+)</sup>*C<sub>7</sub>H<sub>7</sub>O<sub>3</sub>S<sup>(1-)</sup>

C30H43N2O5(1+)*C7H7O3S(1-)

Conditions
Conditions Yield
With potassium carbonate; In acetonitrile; at 82 ℃;
45%
5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride
1188286-70-5

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride

C<sub>40</sub>H<sub>74</sub>O<sub>19</sub>S

C40H74O19S

C<sub>54</sub>H<sub>91</sub>N<sub>2</sub>O<sub>17</sub><sup>(1+)</sup>*C<sub>7</sub>H<sub>7</sub>O<sub>3</sub>S<sup>(1-)</sup>

C54H91N2O17(1+)*C7H7O3S(1-)

Conditions
Conditions Yield
With potassium carbonate; In acetonitrile; at 82 ℃;
45%
1-bromomethylpyrene
2595-90-6

1-bromomethylpyrene

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride
1188286-70-5

5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride

C<sub>38</sub>H<sub>35</sub>N<sub>2</sub>O<sup>(1+)</sup>*Br<sup>(1-)</sup>

C38H35N2O(1+)*Br(1-)

Conditions
Conditions Yield
5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride; With potassium carbonate; potassium bromide; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere;
1-bromomethylpyrene; In acetonitrile; at 60 ℃; for 18h; Inert atmosphere;
71%

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