5-Pyrimidinecarboxaldehyde,2,4-dichloro- supplier

Name
5-Pyrimidinecarboxaldehyde, 2,4-dichloro-
EINECS
CAS No. 871254-61-4
Article Data9
CAS DataBase
Density 1.588 g/cm³
Solubility
Melting Point
Formula C₅H₂Cl₂N₂O
Boiling Point 294 °C at 760 mmHg
Molecular Weight 176.99
Flash Point 131.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5-Pyrimidinecarboxaldehyde, 2,4-dichloro-;2,4-DichloropyriMidine-5-...;2,4-Dichloro-5-pyriMidinecarboxaldehyde;2,4-Dichloropyrimidine-5-Carboxaldehyde
PSA 42.85000
LogP 1.59590

Synthetic route

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 58-96-8
uridine

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With boric acid; trichlorophosphate at 5℃; for 0.5h; Stage #2: uridine at 5℃; for 2h; Reagent/catalyst; Temperature;	96.6%

: 4394-85-8
4-morpholinecarboxaldehyde

: 36082-50-5
2,4-dichloro-5-bromopyrimidine

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

Conditions

Conditions	Yield
Stage #1: 2,4-dichloro-5-bromopyrimidine With TurboGrignard In tetrahydrofuran at -78 - -42℃; for 1.25h; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at -78 - -42℃; for 3.91667h;	87%
Stage #1: 2,4-dichloro-5-bromopyrimidine With TurboGrignard In tetrahydrofuran at 78℃; for 1h; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at -78 - -35℃; for 1.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at -35℃;	71%

: 1195-08-0
2,4-dihydroxypyrimidine-5-carbaldehyde

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

Conditions

Conditions	Yield
With triethylamine; trichlorophosphate at 30 - 35℃; for 3.5h;	69%
With trichlorophosphate at 80℃; for 0.5h;	8.1 g

: 36082-50-5
2,4-dichloro-5-bromopyrimidine

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

Conditions

Conditions	Yield
Stage #1: 2,4-dichloro-5-bromopyrimidine With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - -35℃; for 4h;	31%
Stage #1: 2,4-dichloro-5-bromopyrimidine With hydrogenchloride In tetrahydrofuran at -78 - 35℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 2h;	28%

: 107-31-3
Methyl formate

: 13544-44-0
2,4-dichloro-5-iodopyrimidine

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

Conditions

Conditions	Yield
Stage #1: 2,4-dichloro-5-iodopyrimidine With n-butyllithium In diethyl ether; hexane at -78℃; for 0.333333h; Inert atmosphere; Stage #2: Methyl formate In diethyl ether; hexane at -78℃; for 0.166667h; Inert atmosphere;

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 66-22-8
uracil

A: 3934-20-1
2,6-Dichloropyrimidine

B: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at -5 - 5℃; for 0.5h; Stage #2: uracil at 5℃; for 2h; Temperature;

...Expand

: 4433-40-3
5-hydroxymethyl uracil

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dipotassium peroxodisulfate; silver nitrate / water 2: trichlorophosphate; triethylamine / 3.5 h / 30 - 35 °C View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 75-16-1
methylmagnesium bromide

: 130825-17-1
1-(2,4-dichloropyrimidin-5-yl)ethanol

Conditions

Conditions	Yield
Stage #1: 2,4-dichloro-5-pyrimidinecarboxaldehyde; methylmagnesium bromide In tetrahydrofuran; diethyl ether at -78℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water	97%

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 20342-65-8
2-hydroxypropanedinitrile

: 2-(2,4-dichloropyrimidin-5-yl)-2-hydroxyacetamide

Conditions

Conditions	Yield
With dmap; ammonium chloride In acetonitrile at 10℃; for 1.33333h;	85%

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 89479-61-8
N-cyclopentylglycine ethyl ester

ethyl 2-((2-chloro-5-formylpyrimidin-4-yl)(cyclopentylamino))acetate: ethyl 2-((2-chloro-5-formylpyrimidin-4-yl)(cyclopentylamino))acetate

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 20℃;	84%

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 23002-51-9
6-chloro-1H-pyrazolo[3,4-d]pyrimidine

Conditions

Conditions	Yield
With hydrazine In tetrahydrofuran at 20℃; for 0.5h;	82%
With hydrazine hydrate; triethylamine In tetrahydrofuran at 20℃; for 1h;	68%
With hydrazine hydrate In tetrahydrofuran at 0 - 20℃; for 0.5h;	57%
With hydrazine hydrate In tetrahydrofuran at 0 - 20℃; for 1.25h;	50%
With hydrazine In tetrahydrofuran at 20℃; for 1h;	34%

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 2-(cyclopentylamino)-N,N-dimethylacetamide

: 2-((2-chloro-5-formylpyrimidin-4-yl)(cyclopentylamino))-N,N-dimethylacetamide

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 20℃;	82%

: 67-56-1
methanol

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 20342-65-8
2-hydroxypropanedinitrile

: 2,4-dichloro-(α-hydroxy)-5-pyrimidineacetic acid methyl ester

Conditions

Conditions	Yield
With dmap; acetic acid at 50℃; for 0.666667h;	80%

...Expand

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 64-17-5
ethanol

: 20342-65-8
2-hydroxypropanedinitrile

: ethyl 2,4-dichloro-(α-hydroxy)-5-pyrimidineacetate

Conditions

Conditions	Yield
With dmap; acetic acid at 10℃; for 0.666667h;	77%

...Expand

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 67-63-0
isopropyl alcohol

: 20342-65-8
2-hydroxypropanedinitrile

: isopropyl 2,4-dichloro-(α-hydroxy)-5-pyrimidineacetate

Conditions

Conditions	Yield
With dmap; acetic acid at 10℃; for 0.666667h;	77%

...Expand

: 67-56-1
methanol

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 149-73-5
trimethyl orthoformate

: 2,4-dichloro-5-(dimethoxymethyl)pyrimidine

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate at 65℃; for 14h;	75%

...Expand

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 3-nitrobenzylhydrazine dihydrochloride

: 1428444-27-2
6-chloro-1-(3-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions

Conditions	Yield
Stage #1: 2,4-dichloro-5-pyrimidinecarboxaldehyde In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 3-nitrobenzylhydrazine dihydrochloride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	62%

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 4-nitrobenzylhydrazine dihydrochloride

: 6-chloro-1-(4-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions

Conditions	Yield
Stage #1: 2,4-dichloro-5-pyrimidinecarboxaldehyde In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 4-nitrobenzylhydrazine dihydrochloride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	56%

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 1356483-58-3
N1‐cyclopropyl‐4,5‐difluorobenzene‐1,2‐diamine

: 1-cyclopropyl-2-(2,4-dichloropyrimidin-5-yl)-5,6-difluoro-1H-benzo[d]imidazole

Conditions

Conditions	Yield
With Oxone In water; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	38%

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 2365-48-2
Methyl thioglycolate

: methyl 2-((2-methoxy-2-oxoethyl)thio)thieno[2,3-d]pyrimidine-6-carboxylate

Conditions

Conditions	Yield
Stage #1: 2,4-dichloro-5-pyrimidinecarboxaldehyde; Methyl thioglycolate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 120℃; for 1.5h;	32%

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 1356483-73-2
4-amino-3-(cyclopropylamino)benzonitrile

: 1-cyclopropyl-2-(2,4-dichloropyrimidin-5-yl)-1H-benzo[d]imidazole-6-carbonitrile

Conditions

Conditions	Yield
With Oxone In water; N,N-dimethyl-formamide at 20℃; for 5h; Time;	31%

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 1H-pyrazolo[3,4-d]pyrimidin-6-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine / tetrahydrofuran / 1 h / 20 °C 2: ammonium formate / palladium 10% on activated carbon / methanol / 4 h / Reflux View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: tert-butyl (trans-4-((6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexyl)methylcarbamate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine / tetrahydrofuran / 1 h / 20 °C 2: ammonium formate / palladium 10% on activated carbon / methanol / 4 h / Reflux 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 16 h / 20 °C View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 106-95-6
allyl bromide

: 1-(2,4-dichloropyrimidin-5-yl)but-3-en-1-ol

Conditions

Conditions	Yield
With indium; sodium iodide In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;	120 mg

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

A: (Z)-methyl 5-(2,4-dichloropyrimidin-5-yl)-5-hydroxypent-2-enoate

B: (E)-methyl 5-(2,4-dichloropyrimidin-5-yl)-5-hydroxypent-2-enoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: indium; sodium iodide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 50 °C / Inert atmosphere View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: methyl 2-((2-methoxy-2-oxoethyl)sulfonyl)thieno[2,3-d]pyrimidine-6-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 1.2: 1.5 h / 120 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 25 °C View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: methyl 2-aminothieno[2,3-d]pyrimidine-6-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 1.2: 1.5 h / 120 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 25 °C 3.1: ammonium hydroxide / tetrahydrofuran / 5 h / 0 - 10 °C View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 2-aminothieno[2,3-d]pyrimidine-6-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 1.2: 1.5 h / 120 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 25 °C 3.1: ammonium hydroxide / tetrahydrofuran / 5 h / 0 - 10 °C 4.1: water; sodium hydroxide / ethanol / 1 h / 80 °C 4.2: pH 1 View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 1614233-64-5
6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 20 °C View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 1614233-65-6
6-(3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane / 1.5 h / 110 °C / Microwave irradiation View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 1614233-66-7
6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane / 1.5 h / 110 °C / Microwave irradiation 4: sulfuryl dichloride / dichloromethane / 4 h / 0 - 20 °C View Scheme

: 871254-61-4
2,4-dichloro-5-pyrimidinecarboxaldehyde

: 1614233-67-8
6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane / 1.5 h / 110 °C / Microwave irradiation 4: sulfuryl dichloride / dichloromethane / 4 h / 0 - 20 °C 5: N-iodo-succinimide / N,N-dimethyl-formamide / 80 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C
2: toluene-4-sulfonic acid / dichloromethane / 20 °C
3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane / 1.5 h / 110 °C / Microwave irradiation
4: sulfuryl dichloride / dichloromethane / 4 h / 0 - 20 °C
5: N-iodo-succinimide / N,N-dimethyl-formamide / 80 °C
View Scheme

5-Pyrimidinecarboxaldehyde,2,4-dichloro- Specification

The 5-Pyrimidinecarboxaldehyde,2,4-dichloro- is an organic compound with the formula C₅H₂Cl₂N₂O. The systematic name of this chemical is 2,4-dichloropyrimidine-5-carbaldehyde. With the CAS registry number 871254-61-4, it is also named as 2,4-dichloro-5-formylpyrimidine.

Physical properties about 5-Pyrimidinecarboxaldehyde,2,4-dichloro- are: (1)ACD/LogP: 1.21; (2)ACD/LogD (pH 5.5): 1.21; (3)ACD/LogD (pH 7.4): 1.21; (4)ACD/BCF (pH 5.5): 4.91; (5)ACD/BCF (pH 7.4): 4.91; (6)ACD/KOC (pH 5.5): 108.69; (7)ACD/KOC (pH 7.4): 108.69; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 42.85 Å²; (11)Index of Refraction: 1.616; (12)Molar Refractivity: 38.97 cm³; (13)Molar Volume: 111.4 cm³; (14)Polarizability: 15.45×10^-24cm³; (15)Surface Tension: 61.7 dyne/cm; (16)Density: 1.588 g/cm³; (17)Flash Point: 131.6 °C; (18)Enthalpy of Vaporization: 53.36 kJ/mol; (19)Boiling Point: 294 °C at 760 mmHg; (20)Vapour Pressure: 0.00167 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1nc(Cl)ncc1C=O
(2)InChI: InChI=1/C5H2Cl2N2O/c6-4-3(2-10)1-8-5(7)9-4/h1-2H
(3)InChIKey: MTIXQNKVUJSOQH-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C5H2Cl2N2O/c6-4-3(2-10)1-8-5(7)9-4/h1-2H
(5)Std. InChIKey: MTIXQNKVUJSOQH-UHFFFAOYSA-N

Product Name

5-Pyrimidinecarboxaldehyde, 2,4-dichloro-

Synthetic route

5-Pyrimidinecarboxaldehyde,2,4-dichloro- Specification

Related Products

Hot Products