36437-19-1

Basic information

• Product Name: 2-CHLOROMALONALDEHYDE
• Synonyms: 2-CHLOROMALONALDEHYDE;chloromalonaldehyde;2-CHLOROMALONALDEHYDE 95%;2-Chloromalonaldehyde,95%;2-Chloromalonaldehyde ,94%;2-Chloro-1,3-propanedial;Chloromalondialdehyde;Chloromalonic dialdehyde
• CAS NO: 36437-19-1
• Molecular Formula: C₃H₃ClO₂
• Molecular Weight: 106.51
• Mol File: 36437-19-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 140-145 °C
• Boiling Point: 111℃
• Flash Point: 32℃
• Appearance: Brown/Crystalline Powder
• Density: 1.261
• Vapor Pressure: 22.8mmHg at 25°C
• Refractive Index: 1.4100 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly, Heated), Methanol (Slightly)
• PKA: 1.48±0.10(Predicted)
• CAS DataBase Reference: 2-CHLOROMALONALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROMALONALDEHYDE(36437-19-1)
• EPA Substance Registry System: 2-CHLOROMALONALDEHYDE(36437-19-1)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26
• RIDADR: 1759
• Hazardous Substances Data: 36437-19-1(Hazardous Substances Data)

Usage

Chemical Properties

BROWN CRYSTALLINE POWDER

Uses

2-Chloromalonaldehyde is used in the synthesis of novel heterocyclic acetyl coenzyme-A carboxylase inhibitors. Also used in the production of aldose reductase inhibitors used in the treatment of diabetes mellitus.

InChI:InChI=1/C3H3ClO2/c4-3(1-5)2-6/h1-3H

Synthetic route

malondialdehyde bis(diethyl acetal) (122-31-6) → 2-chloromalonaldehyde (36437-19-1)

Conditions	Yield
With phosphorus pentachloride anschliessend Behandeln mit Sulfurylchlorid unter Zusatz von Dibenzoylperoxid und Schuetteln mit wss.Natriumcarbonat-Loesung;

1,2,3,3-tetrachloro-1-propene (20589-85-9) → 2-chloromalonaldehyde (36437-19-1)

Conditions	Yield
With sulfuric acid
With sulfuric acid at 30 - 40℃;

5-tert-butoxy-6-chloro-2,3-dihydro-5H-[1,4]dioxepine (65041-41-0) → 2-chloromalonaldehyde (36437-19-1)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane Ambient temperature;

7,7-dichloro-2,5-dioxybicyclo <4.1.0> heptane (53923-47-0) → 2-chloromalonaldehyde (36437-19-1)

Conditions	Yield
With acetic acid Heating;

1,2,3,3-tetrachloro-1-propene (20589-85-9) + sulfuric acid (7664-93-9) → 2-chloromalonaldehyde (36437-19-1)

Conditions	Yield
at 30 - 40℃;

trimethylene glycol diacetate → 2-chloromalonaldehyde (36437-19-1)

Conditions	Yield
With chlorine Irradiation.durch UV bei Raumtemperatur und 4-stdg. Erwaermen des Chlorierungsprodukts mit Aethanol oder laengeres Behandeln mit konz. H2SO4, zuletzt bei 40grad;

3-anilino-2-chloro-acrylaldehyde (131139-84-9) + acid → 2-chloromalonaldehyde (36437-19-1) + aniline (62-53-3)

3-anilino-2-chloro-acrylaldehyde (131139-84-9) + alkali → 2-chloromalonaldehyde (36437-19-1) + aniline (62-53-3)

3-benzoyloxy-2-chloro-acrylaldehyde + alcoholic potash → 2-chloromalonaldehyde (36437-19-1) + benzoic acid (65-85-0)

C10H15NO2S (951330-88-4) + 2-chloromalonaldehyde (36437-19-1) → C13H15NO3S

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 50℃; for 14h;	94%

2-chloromalonaldehyde (36437-19-1) → 3-amino-2-chloroacrolein

Conditions	Yield
With ammonium hydroxide	93%

2-chloromalonaldehyde (36437-19-1) + 4-chlorothiobenzamide (2521-24-6) → 2-(4-chloro-phenyl)-thiazole-5-carbaldehyde (721920-84-9)

Conditions	Yield
With basic magnesium carbonate In water at 60℃; for 3h;	92%
With magnesium carbonate hexahydrate In 1,2-dimethoxyethane at 60℃; for 3h; Inert atmosphere;

(3-amino-1H-1,2,4-triazol-5-yl)methanol (27277-03-8) + 2-chloromalonaldehyde (36437-19-1) → (6-chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-yl)methanol (749929-28-0)

Conditions	Yield
In acetic acid at 80℃; for 4h;	92%

2-chloromalonaldehyde (36437-19-1) + 5-(2-fluoro-5-nitrophenyl)-4H-1,2,4-triazol-3-amine → C11H5ClFN5O2

Conditions	Yield
With acetic acid at 120℃; for 3h;	87.7%

2-chloromalonaldehyde (36437-19-1) → Chloromalondialdehyd-kaliumsalz

Conditions	Yield
With potassium hydroxide In water ice-cooled, pH 9;	85%

2-chloromalonaldehyde (36437-19-1) + (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (304853-90-5) → 6-(4-chloro-1H-pyrazol-1-yl)-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one (1248589-27-6)

Conditions	Yield
Stage #1: (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid With di-tert-butyl-diazodicarboxylate; copper(II) acetate monohydrate In methanol at 65℃; for 1h; Stage #2: 2-chloromalonaldehyde With hydrogenchloride In 1,4-dioxane; methanol at 20 - 80℃;	78%

2-chloromalonaldehyde (36437-19-1) + bromopentafluorobenzene (344-04-7) → 4-chloro-1-(perfluorophenyl)-1H-pyrazole (1152719-80-6)

Conditions	Yield
Stage #1: bromopentafluorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	75%

2-chloromalonaldehyde (36437-19-1) + p-trifluoromethylphenyl bromide (402-43-7) → 4-chloro-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole (1152719-79-3)

Conditions	Yield
Stage #1: p-trifluoromethylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	75%

2-chloromalonaldehyde (36437-19-1) + 2-methylphenyl bromide (95-46-5) → 4-chloro-1-(o-tolyl)-1H-pyrazole (1152719-75-9)

Conditions	Yield
Stage #1: 2-methylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	73%

5-bromo-2-chloropyridine (53939-30-3) + 2-chloromalonaldehyde (36437-19-1) → 2-chloro-5-(4-chloro-1H-pyrazol-1-yl)pyridine (1152719-84-0)

Conditions	Yield
Stage #1: 5-bromo-2-chloropyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	67%

2-chloromalonaldehyde (36437-19-1) → Dichloromalondialdehyd (77084-28-7)

Conditions	Yield
With chlorine In dichloromethane at 5℃; 1.) 5 deg C, 2.) r.t., 1 h;	64%

2-bromo-6-methylpyridine (5315-25-3) + 2-chloromalonaldehyde (36437-19-1) → 2-(4-chloro-1H-pyrazol-1-yl)-6-methylpyridine (1152719-82-8)

Conditions	Yield
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	64%

2-chloromalonaldehyde (36437-19-1) + 4-fluoro-1-iodobenzene (352-34-1) → 4-chloro-1-(4-fluorophenyl)-1H-pyrazole (1152719-73-7)

Conditions	Yield
Stage #1: 4-fluoro-1-iodobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	64%

2-chloromalonaldehyde (36437-19-1) + tert-butyl (S)-(1-amino-1-thioxopropan-2-yl)carbamate (141041-86-3, 96929-01-0, 140903-30-6) → tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamate (1332873-08-1)

Conditions	Yield
With magnesium carbonate In 1,4-dioxane at 60℃; for 3h;	64%

2-chloromalonaldehyde (36437-19-1) + C12H13BrF2O2 (1152719-91-9) → 1-(3-bromo-5-(5,5-dimethyl-1,3-dioxan-2-yl)-2,6-difluorophenyl)-4-chloro-1H-pyrazole (1152719-86-2)

Conditions	Yield
Stage #1: C12H13BrF2O2 With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 100℃; for 0.0833333h;	61%

2-chloromalonaldehyde (36437-19-1) + C18H24BrF2NO3 (1152719-89-5) → (2R,6R)-4-(4-(4-chloro-1H-pyrazol-1-yl)-6-(5,5-dimethyl-1,3-dioxan-2-yl)-2,3-difluorophenyl)-2,6-dimethylmorpholine (1152719-72-6)

Conditions	Yield
Stage #1: C18H24BrF2NO3 With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 20℃; for 0.583333h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; hexane; water at 100℃; for 0.0833333h;	60%

3-methoxyphenyl bromide (2398-37-0) + 2-chloromalonaldehyde (36437-19-1) → 4-chloro-1-(3-methoxyphenyl)-1H-pyrazole (1152719-76-0)

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	60%

5-bromo-2-fluoropyridine (766-11-0) + 2-chloromalonaldehyde (36437-19-1) → 5-(4-chloro-1H-pyrazol-1-yl)-2-fluoropyridine (1152719-83-9)

Conditions	Yield
Stage #1: 5-bromo-2-fluoropyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	58%

3-amino-4-bromo-1H-pyrazole (16461-94-2) + 2-chloromalonaldehyde (36437-19-1) → 3-bromo-6-chloropyrazolo[1,5-a]pyrimidine (1314893-92-9)

Conditions	Yield
With acetic acid In methanol at 70℃; for 2h;	57%

2-chloromalonaldehyde (36437-19-1) + 1-iodo-2,3-difluorobenzene (64248-57-3) → 4-chloro-1-(2,3-difluorophenyl)-1H-pyrazole (1152719-78-2)

Conditions	Yield
Stage #1: 1-iodo-2,3-difluorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	55%

2-chloromalonaldehyde (36437-19-1) + 2-iodochlorobenzene (615-41-8) → 4-chloro-1-(2-chlorophenyl)-1H-pyrazole (1152719-77-1)

Conditions	Yield
Stage #1: 2-iodochlorobenzene With n-butyllithium; di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78℃; for 0.133333h; Inert atmosphere; Stage #2: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at -78 - 80℃;	54%

2-chloromalonaldehyde (36437-19-1) + 4-Bromophenylboronic acid (5467-74-3) → 1-(4-bromophenyl)-4-chloro-1H-pyrazole (1248589-16-3)

Conditions	Yield
Stage #1: 4-Bromophenylboronic acid With di-tert-butyl-diazodicarboxylate; copper(II) acetate monohydrate In methanol at 65℃; for 1h; Stage #2: 2-chloromalonaldehyde With hydrogenchloride In 1,4-dioxane; methanol at 20 - 80℃;	53%

2-chloromalonaldehyde (36437-19-1) + 4-bromo-1-(4-fluorophenyl)-1H-pyrazole (957062-56-5) → 4-(4-chloro-1H-pyrazol-1-yl)-1-(4-fluorophenyl)-1H-pyrazole (1152719-88-4)

Conditions	Yield
Stage #1: 4-bromo-1-(4-fluorophenyl)-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	50%

2-chloromalonaldehyde (36437-19-1) + 3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (398491-59-3) → 6-chloro-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester (1444116-15-7)

Conditions	Yield
With acetic acid at 20℃; for 18h;	47%
With acetic acid at 20℃; for 18h;	47%
With acetic acid at 20℃; for 18h;	47%
With acetic acid at 20℃; for 18h;	47%

2-chloromalonaldehyde (36437-19-1) + C28H43F2N3O7 (1152719-90-8) → (2R,6R)-4-(4-(4-chloro-1H-pyrazol-1-yl)-6-(5,5-dimethyl-1,3-dioxan-2-yl)-2,3-difluorophenyl)-2,6-dimethylmorpholine (1152719-72-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane Heating;	45%

2-chloromalonaldehyde (36437-19-1) + (4-methyl-3-nitrophenyl)boronic acid (80500-27-2) → 4-chloro-1-(4-methyl-3-nitrophenyl)-1H-pyrazole (1248589-25-4)

Conditions	Yield
Stage #1: (4-methyl-3-nitrophenyl)boronic acid With di-tert-butyl-diazodicarboxylate; copper(II) acetate monohydrate In methanol at 65℃; for 1h; Stage #2: 2-chloromalonaldehyde With hydrogenchloride In 1,4-dioxane; methanol at 20 - 80℃;	45%

2-chloromalonaldehyde (36437-19-1) + 2,4,6-trimethylphenyl bromide (576-83-0) → 4-chloro-1-mesityl-1H-pyrazole (1152719-81-7)

Conditions	Yield
Stage #1: 2,4,6-trimethylphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane at -78 - 23℃; for 0.5h; Stage #3: 2-chloromalonaldehyde With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; hexane at 80℃; for 0.166667h;	43%

2-chloromalonaldehyde (36437-19-1) + 5-amino-1H-pyrazole-4-carboxylic acid (41680-34-6) → 6-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid (1204926-24-8)

Conditions	Yield
With acetic acid In ethanol at 80℃; for 1h; Inert atmosphere;	40%
With acetic acid In ethanol at 60℃; for 2h;

Upstream product

• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 131139-84-9 3-anilino-2-chloro-acrylaldehyde 
• 20589-85-9 1,2,3,3-tetrachloro-1-propene 
• 7664-93-9 sulfuric acid 
• 53923-47-0 7,7-dichloro-2,5-dioxybicyclo <4.1.0> heptane 
• 65041-41-0 5-tert-butoxy-6-chloro-2,3-dihydro-5H-[1,4]dioxepine 

Downstream Products

• 110181-27-6 6-(5-chloro-pyrimidin-2-ylamino)-hexanoic acid ; hydrogen sulfate 
• 131139-84-9 3-anilino-2-chloro-acrylaldehyde 
• 34771-50-1 5-chloro-2-phenylpyrimidine 
• 42588-71-6 N'-phenyl-glyoxylohydrazonoyl chloride 
• 5428-89-7 5-chloropyrimidin-2-amine 
• 6831-92-1 4-Chloro-1-phenyl-1H-pyrazole 
• 77139-57-2 5-chloro-2-m-nitrophenylpyrimidine 
• 877385-86-9 2-cyclopropylthiazole-5-carbaldehyde 
• 1003-60-7 2-methylthiazole-4-carboxyaldehyde 
• 171515-67-6 2-n-butyl-1-{[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl}-1H-imidazole-5-carbaldehyde 
• 1190235-00-7 2-[3-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde 
• 7631-86-9 SiO₂ 
• 936074-36-1 ethyl 6-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 1204926-24-8 6-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid 

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