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33016-47-6

Basic Information
CAS No.: 33016-47-6
Name: 1-Tritylimidazole-4-carboxaldehyde
Article Data: 59
Molecular Structure:
Molecular Structure of 33016-47-6 (1-Tritylimidazole-4-carboxaldehyde)
Formula: C23H18N2O
Molecular Weight: 338.409
Synonyms: Imidazole-4-carboxaldehyde,1-trityl- (8CI);(1-Triphenylmethyl-1H-imidazol-4-yl)carboxaldehyde;1-Triphenylmethylimidazole-4-carboxaldehyde;1-Trityl-1H-imidazol-4-ylcarboxaldehyde;1-Trityl-4-formyl-1H-imidazole;1-Trityl-4-imidazole-4-carboxaldehyde;4-(N-Triphenylmethyl)imidazolecarboxaldehyde;N-(Triphenylmethyl)-4-imidazolecarboxaldehyde;
EINECS: 620-447-0
Density: 1.1 g/cm3
Melting Point: 180-190 °C
Boiling Point: 502.8 °C at 760 mmHg
Flash Point: 257.9 °C
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37/39
PSA: 34.89000
LogP: 4.53580
Synthetic route
76-83-5

trityl chloride

3034-50-2

4(5)formylimidazole

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;100%
With triethylamine In N,N-dimethyl-formamide at 20℃;99%
3034-50-2

5-imidazolecarboxaldehyde

76-83-5

trityl chloride

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃;98%
With triethylamine In acetonitrile at 20℃;94%
With triethylamine In acetonitrile at 20℃; for 20.3333h;94%
33769-07-2

4-(hydroxymethyl)-1-(triphenylmethyl)imidazole

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With manganese(IV) oxide In 1,4-dioxane for 5h; Heating;95%
With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -70℃; for 0.333333h;82%
With Mn2O In 1,4-dioxane at 85℃; for 6h;80%
96797-15-8

N-trityl-4(5)-iodoimidazole

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

96797-16-9

1-tritylimidazole-2,4-dicarboxaldehyde

B

67478-50-6

1-(triphenylmethyl)-1H-imidazole-2-carboxaldehyde

C

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane Product distribution; cooling in a dry ice acetone bath, excess n-BuLi;A 8 mg
B 11%
C 83%
With n-butyllithium 1.) THF, hexane, 5 s, cooling in a dry ice acetone bath; Yield given. Multistep reaction. Yields of byproduct given;
96797-15-8

N-trityl-4(5)-iodoimidazole

68-12-2, 33513-42-7

N,N-dimethyl-formamide

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
Stage #1: N-trityl-4(5)-iodoimidazole With ethylmagnesium bromide In diethyl ether; dichloromethane at 20℃; for 0.5h;
Stage #2: N,N-dimethyl-formamide In diethyl ether; dichloromethane at 20℃; for 0.5h;
82%
Stage #1: N-trityl-4(5)-iodoimidazole With ethylmagnesium bromide In dichloromethane
Stage #2: N,N-dimethyl-formamide In dichloromethane at 20℃;
82%
Stage #1: N-trityl-4(5)-iodoimidazole With isopropylmagnesium chloride In dichloromethane at 10 - 20℃;
Stage #2: N,N-dimethyl-formamide In dichloromethane at -5 - 20℃; for 10.5h;
Stage #3: With water; ammonium chloride In dichloromethane at 20℃;
73.2%
96797-15-8

N-trityl-4(5)-iodoimidazole

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

15469-97-3

N-tritylimidazole

B

4-iodo-2-formyl-1-tritylimidazole

C

67478-50-6

1-(triphenylmethyl)-1H-imidazole-2-carboxaldehyde

D

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane Product distribution; cooling in a dry ice acetone bath, stoichiometric n-BuLi;A 19%
B 16%
C 7%
D 51%
With n-butyllithium 1.) THF, hexane, 5 s, cooling in a dry ice acetone bath; Yield given. Multistep reaction. Yields of byproduct given;
2591-86-8

N-Formylpiperidine

96797-15-8

N-trityl-4(5)-iodoimidazole

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With ethylmagnesium bromide 1.) THF, Et2O, room temp., 30 min., 2.) 1 h; Yield given. Multistep reaction;
76-83-5

trityl chloride

amalgamated silver

amalgamated silver

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / TEA / dimethylformamide
View Scheme
76-83-5

trityl chloride

Me-X

Me-X

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: imidazole / dimethylformamide
2: MnO2 / dioxane
View Scheme
76-83-5

trityl chloride

DL-lysine methyl ester dihydrochloride

DL-lysine methyl ester dihydrochloride

33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / Et3N / dimethylformamide / 18 h
2: 80 percent / Mn2O / dioxane / 6 h / 85 °C
View Scheme
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    Product Name: 1-Tritylimidazole-4-carboxaldehyde CARBOXALDEHYDE CAS: 33016-47-6 MF: C23H18N2O MW: 338.4 EINECS: 620-447-0 Mol File: 33016-47-6.mol 1-Tritylimidazole-4-carboxaldehyde Structure 1-Tritylimidazole-4-carboxaldehyde Chem

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Chemistry

IUPAC Name: 1-Tritylimidazole-4-carbaldehyde 
Following is the structure of 1H-Imidazole-4-carboxaldehyde,1-(triphenylmethyl)- (CAS NO.33016-47-6):
                           
Empirical Formula: C23H18N2O
Molecular Weight: 338.4018 g/mol
Molar Refractivity: 106.74 cm3
Molar Volume: 306.8 cm3
Density: 1.1 g/cm3
Flash Point: 257.9 °C
Melting point: 180-190 °C
Index of Refraction: 1.612
Surface Tension: 45.6 dyne/cm
Enthalpy of Vaporization: 77.2 kJ/mol
Boiling Point: 502.8 °C at 760 mmHg
Vapour Pressure: 3.06E-10 mmHg at 25 °C
Product Categories of 1H-Imidazole-4-carboxaldehyde,1-(triphenylmethyl)- (CAS NO.33016-47-6): Aldehydes; blocks; Imidazoles; Heterocyclic Building Blocks
Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)N4C=C(N=C4)C=O
InChI: InChI=1S/C23H18N2O/c26-17-22-16-25(18-24-22)23(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-18H
InChIKey: YQYLLBSWWRWWAY-UHFFFAOYSA-N

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
Hazard Note: Irritant

Specification

 1H-Imidazole-4-carboxaldehyde,1-(triphenylmethyl)- , its cas register number is 33016-47-6. It also can be called 1-Trityl-1H-imidazole-4-carbaldehyde ; 1-Trityl-4-formylimidazole ; and 1-Tritylimidazole-4-carboxaldehyde .