4462-55-9

Basic information

• Product Name: 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride
• Synonyms: 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolecarbonylchlorid;3-(2,6-DICHLOROPHENYL)-5-METHYLISOXAZOLE-4-CARBONYL CHLORIDE;3-(2,6-Dichlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl chloride;3-(2,6-DICHLOROPHENYL)-5-METHYL-4-CHLOROCARBONYL ISOXAZOLE;3-(2,6-DICHLOROPHENYL)-5-METHYL-4-ISOXAZOLE-CARBONYL CHLORIDE;3-(2,6-Dichlorophenyl)-5-methyl-3-phenyl-4-chlorocarbonylisoxazole;DICHLOROPHENYL-5-METHYLISOXAZOLE-4-CARBONYLCHLORIDE;3-(2,6-Dichlorophenyl)-5-Methyl-4-Carbonylisoxazolechloride
• CAS NO: 4462-55-9
• Molecular Formula: C₁₁H₆Cl₃NO₂
• Molecular Weight: 290.53
• EINECS: 224-723-8
• Product Categories: Oxazole&Isoxazole;Aromatics;Heterocycles
• Mol File: 4462-55-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 92 °C
• Boiling Point: 390.9 °C at 760 mmHg
• Flash Point: 190.2 °C
• Appearance: Yellow to brown powder
• Density: 1.472 g/cm³
• Vapor Pressure: 2.57E-06mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -6.62±0.50(Predicted)
• Water Solubility: 22.98mg/L at 25℃
• CAS DataBase Reference: 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride(4462-55-9)
• EPA Substance Registry System: 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride(4462-55-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-36/37/39/45
• RIDADR: 3261
• Hazardous Substances Data: 4462-55-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to brown powde

Uses

3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride is used for preparing isoxazolyl penicillin derivatives.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C11H6Cl3NO2/c1-5-8(11(14)16)10(15-17-5)9-6(12)3-2-4-7(9)13/h2-4H,1H3

Synthetic route

3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid (3919-76-4) → 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide at 60℃;	94%
With phosphorus pentachloride at 45℃; for 1h;	84%
With thionyl chloride

2,6-dichlorobenzaldehyde (83-38-5) → 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) NH2OH, (ii) Cl2, CHCl3, (iii) /BRN= 506727/, MeOH 2: aq. KOH / ethanol 3: SOCl2 View Scheme
Multi-step reaction with 5 steps 1.1: hydroxylamine sulfate / methanol / 0.5 h 1.2: 0.5 h / pH 8 - 9 / Reflux 2.1: chlorine / methanol / 0 - 5 °C 3.1: sodium hydroxide / methanol / 0.5 h / 0 - 5 °C / pH 10 3.2: 2 h / 0 - 20 °C / pH 9 4.1: water; sodium hydroxide / methanol / 1 h / pH 11 - 13 / Reflux 5.1: phosphorus pentachloride / 1 h / 45 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydroxylamine sulfate / methanol / 1 h / 20 - 40 °C 1.2: 24 h / 0 - 20 °C / pH ~ 9.5 / Inert atmosphere 1.3: pH ~ 7 - 7.5 2.1: phosphorus pentachloride / toluene View Scheme
Multi-step reaction with 5 steps 1: hydroxylamine hydrochloride; sodium hydroxide / water; ethanol / 0 - 90 °C 2: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 20 °C 3: triethylamine / dichloromethane / 0 - 20 °C 4: lithium hydroxide monohydrate; water / ethanol / 50 °C 5: thionyl chloride; N,N-dimethyl-formamide / 60 °C View Scheme

SPB 06193 → 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. KOH / ethanol 2: SOCl2 View Scheme
Multi-step reaction with 2 steps 1: water; sodium hydroxide / methanol / 1 h / pH 11 - 13 / Reflux 2: phosphorus pentachloride / 1 h / 45 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / water; methanol / 3 h 2: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 40 °C View Scheme

2,6-dichlorobenzohydroximoyl chloride (6579-27-7) → 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / methanol / 0.5 h / 0 - 5 °C / pH 10 1.2: 2 h / 0 - 20 °C / pH 9 2.1: water; sodium hydroxide / methanol / 1 h / pH 11 - 13 / Reflux 3.1: phosphorus pentachloride / 1 h / 45 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: lithium hydroxide monohydrate; water / ethanol / 50 °C 3: thionyl chloride; N,N-dimethyl-formamide / 60 °C View Scheme

2,6-dichlorobenzaldoxime (25185-95-9) → 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: chlorine / methanol / 0 - 5 °C 2.1: sodium hydroxide / methanol / 0.5 h / 0 - 5 °C / pH 10 2.2: 2 h / 0 - 20 °C / pH 9 3.1: water; sodium hydroxide / methanol / 1 h / pH 11 - 13 / Reflux 4.1: phosphorus pentachloride / 1 h / 45 °C View Scheme
Multi-step reaction with 4 steps 1: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 20 °C 2: triethylamine / dichloromethane / 0 - 20 °C 3: lithium hydroxide monohydrate; water / ethanol / 50 °C 4: thionyl chloride; N,N-dimethyl-formamide / 60 °C View Scheme

ethyl 3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carboxylate (24248-21-3) → 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hydroxide monohydrate; water / ethanol / 50 °C 2: thionyl chloride; N,N-dimethyl-formamide / 60 °C View Scheme

6-Aminopenicillanic Acid (551-16-6) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → sodium dicloxacillin (343-55-5)

Conditions	Yield
Stage #1: 6-Aminopenicillanic Acid With sodium hydroxide In water at 0 - 5℃; for 0.333333h; Stage #2: 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride In acetone at 5℃; for 1h; pH=7; Stage #3: With sodium 2-ethylhexanoic acid In isopropyl alcohol at 30℃; for 0.5h; Temperature; Solvent;	80.21%
With ammonium hydroxide In ethyl acetate pH=2 - 8;

propargyl alcohol (107-19-7) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → prop-2-ynyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate (661452-05-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	79%

3,4-dihydro-6-t-butyl-2H-1,4-benzoxazine (937681-62-4) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → C23H22Cl2N2O3

Conditions	Yield
With potassium carbonate In toluene at 40℃; for 0.416667h; Microwave irradiation;	70%

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) + 3,4-dihydro-7-methyl-2H-1,4-benzoxazine (71472-58-7) → C20H16Cl2N2O3

Conditions	Yield
With potassium carbonate In toluene at 40℃; for 0.416667h; Microwave irradiation;	60%

6-bromo-3, 4-dihydro-2H-benzo[β][1, 4]oxazine (105655-01-4) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → C19H13BrCl2N2O3

Conditions	Yield
With potassium carbonate In toluene at 40℃; for 0.416667h; Microwave irradiation;	55%

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) + 6-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine (70558-11-1) → C19H13Cl3N2O3

Conditions	Yield
With potassium carbonate In toluene at 40℃; for 0.416667h; Microwave irradiation;	54%

1,4-benzoxazine (5735-53-5) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → C19H14Cl2N2O3

Conditions	Yield
With potassium carbonate In toluene at 40℃; for 0.416667h; Microwave irradiation;	53%

2-amino-6-ethylbenzo[d]thiazole (21224-16-8) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichlorophenyl)-N-(6-ethylbenzo[d]thiazol-2-yl)-5-methylisoxazole-4-carboxamide

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 60℃; for 18.5h; Inert atmosphere;	51%

anthranilic acid allyl ester (7493-63-2) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 2-{[3-(2,6-Dichloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-benzoic acid allyl ester (848187-10-0)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃;	49%
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) + (1R,3S,5S)-tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (143557-91-9) → tert-butyl (1R,3R,5S)-3-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyloxy]-8-azabicyclo[3,2.1]octane-8-carboxylate

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 30℃;	41%

2-amino-6-(methylsulfonyl)benzothiazole (17557-67-4) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichlorophenyl)-N-(6-methanesulfonylbenzo[d]thiazol-2-yl)-5-methylisoxazole-4-carboxamide

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 40 - 45℃; for 24h; Inert atmosphere;	37%

PVS (5535-48-8) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → C19H15Cl2NO4S

Conditions	Yield
With crithmene; potassium ethyl xanthogenate; sodium phosphate In dichloromethane at 60℃; for 24h; Giese Free Radical Synthesis; Irradiation;	35%

9b-amino-4b-hydroxy-7-isopropyl-4b,9b-dihydro-10H-indeno[1,2-b]benzofuran-10-one (1416231-32-7) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichlorophenyl)-N-(4b-hydroxy-7-isopropyl-10-oxo-9b,10-dihydro-4bH-benzo[d]indeno[1,2-b]furan-9b-yl)-5-methylisooxazole-4-carboxamide (1416233-43-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	19%

3-methyl-6-nitro-1H-indazole (6494-19-5) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 1-[3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-3-methyl-6-nitro-1H-indazole (62235-36-3)

Conditions	Yield
With triethylamine In benzene

aniline (62-53-3) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid anilide (4402-85-1)

Conditions	Yield
In acetone

chlorhydrate de (β-aminoethyl)-4 benzenesulfonamide (6325-22-0) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 4-sulfamoyl-phenethylamide (24477-34-7)

Conditions	Yield
In pyridine

2,4-dichlorobenzamidoxime (22179-80-2) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → C18H11Cl4N3O3

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃; for 24h; Acylation;

(2R,3R)-3-amino-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine-2-sulfonic acid tetrabutylammonium salt (180468-20-6) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → (2R,3R)-3-{[3-(2,6-dichlorophenyl)-5-methyl-isoxazole-4-carbonyl]amino}-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine-2-sulfonic acid

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2.16667h; Condensation;

(2R,3S)-3-amino-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine2-sulfonic acid (180468-23-9) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → (2R,3S)-3-{[3-(2,6-dichlorophenyl)-5-methyl-isoxazole-4-carbonyl]amino}-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine-2-sulfonic acid

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2.16667h; Condensation;

dimethyl amine (124-40-3) + 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-Dichlorophenyl)-N,N,5-trimethylisoxazole-4-carboxamide (349131-41-5)

Conditions	Yield
In tetrahydrofuran at 20℃;

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 2-{[3-(2,6-Dichloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino }-benzoic acid (848187-11-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / NaHCO3 / tetrahydrofuran / 20 °C 2: 100 percent / Pd(PPh3)4; morpholine / CH2Cl2 / 20 °C View Scheme

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid (2-diethylcarbamoyl-phenyl)-amide

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / NaHCO3 / tetrahydrofuran / 20 °C 2: 100 percent / Pd(PPh3)4; morpholine / CH2Cl2 / 20 °C 3: TBTU; DIPEA / dimethylformamide / 20 °C View Scheme

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid (2-benzylcarbamoyl-phenyl)-amide

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / NaHCO3 / tetrahydrofuran / 20 °C 2: 100 percent / Pd(PPh3)4; morpholine / CH2Cl2 / 20 °C 3: TBTU; DIPEA / dimethylformamide / 20 °C View Scheme

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid [2-(piperidine-1-carbonyl)-phenyl]-amide

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / NaHCO3 / tetrahydrofuran / 20 °C 2: 100 percent / Pd(PPh3)4; morpholine / CH2Cl2 / 20 °C 3: TBTU; DIPEA / dimethylformamide / 20 °C View Scheme

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid [2-(azepane-1-carbonyl)-phenyl]-amide

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / NaHCO3 / tetrahydrofuran / 20 °C 2: 100 percent / Pd(PPh3)4; morpholine / CH2Cl2 / 20 °C 3: TBTU; DIPEA / dimethylformamide / 20 °C View Scheme

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → N-(2-{[(1,3-benzodioxol-5-ylmethyl)amino]carbonyl}phenyl)-3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / NaHCO3 / tetrahydrofuran / 20 °C 2: 100 percent / Pd(PPh3)4; morpholine / CH2Cl2 / 20 °C 3: TBTU; DIPEA / dimethylformamide / 20 °C View Scheme

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → (4-{2-[3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carbonylamino]-ethyl}-benzenesulfonyl)-carbamic acid methyl ester (52320-56-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: 1,2-dimethoxy-ethane View Scheme

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride (4462-55-9) → 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 4-(azepan-1-ylcarbamoyl-sulfamoyl)-phenethylamide (52320-40-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine 2: 1,2-dimethoxy-ethane 3: 1,2-dimethoxy-ethane View Scheme

Upstream product

• 3919-76-4 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 4402-83-9 SPB 06193 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 24248-21-3 ethyl 3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-carboxylate 
• 25185-95-9 2,6-dichlorobenzaldoxime 
• 6579-27-7 2,6-dichlorobenzohydroximoyl chloride 

Downstream Products

• 24477-34-7 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 4-sulfamoyl-phenethylamide 
• 848187-10-0 2-{[3-(2,6-Dichloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-benzoic acid allyl ester 
• 661452-05-7 prop-2-ynyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate 
• 1391026-14-4 (1-(2-morpholino-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-caroboxylate 
• 1391026-15-5 (1-benzyl-1H-1,2,3-triazol-4-yl)methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate 
• 1391026-16-6 (1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-1H-1,2,3-triazol-4-yl)methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate 
• 1391026-17-7 (1-butyl-1H-1,2,3-triazol-4yl)methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate 
• 1391026-18-8 (1-allyl-1H-1,2,3-triazol-4-yl)methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4 carboxylate 
• 4402-85-1 3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid anilide 
• 62235-36-3 1-[3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-3-methyl-6-nitro-1H-indazole 
• 263255-98-7 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carbohydrazide 

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