110035-28-4

Basic information

• Product Name: Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime
• Synonyms: Pyrazole-1,3-dimethyl-5-phenoxy-4-oxime;1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde oxime;Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime;1，3-dimethyl-5-phenoxy-oxim-1H-pyrazole-4-carboxaldehyde;1,3-DiMethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxiMe;(E)-1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime
• CAS NO: 110035-28-4
• Molecular Formula: C₁₂H₁₃N₃O₂
• Molecular Weight: 231.25
• EINECS: 1312995-182-4
• Mol File: 110035-28-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 133-134 °C
• Boiling Point: 359.4 °C at 760 mmHg
• Flash Point: 171.2 °C
• Appearance: /
• Density: 1.21
• Storage Temp.: 2-8°C
• PKA: 10.45±0.10(Predicted)
• CAS DataBase Reference: Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime(110035-28-4)
• EPA Substance Registry System: Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime(110035-28-4)

Safety Data

• Hazardous Substances Data: 110035-28-4(Hazardous Substances Data)

Usage

General Description

Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime is a chemical compound that is commonly used as a building block in organic synthesis. It contains a pyrazole ring with a dimethyl substituent at the 1 and 3 positions, a phenoxy group at the 5 position, and a carboxaldehyde oxime at the 4 position. Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime has the potential for various applications in medicinal chemistry, such as in the development of pharmaceuticals or agrochemicals. Additionally, it can be utilized in the synthesis of various heterocyclic compounds and organic intermediates due to its versatile reactivity. Overall, Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime is a valuable chemical compound with diverse potential uses in the field of organic chemistry.

Synthetic route

5-chloro-4-formyl-1,3-dimethylpyrazole (27006-76-4) → 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 40 - 110 °C 2: potassium hydroxide; hydroxylamine hydrochloride / methanol View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / Reflux 1.2: 105 °C 2.1: hydroxylamine hydrochloride; potassium hydroxide / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide / 2 h / 45 °C 1.2: 110 °C 2.1: potassium hydroxide; hydroxylamine hydrochloride / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 6 h / 40 °C 1.2: 100 °C 2.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 0.5 h / 20 - 30 °C View Scheme

phenol (108-95-2) → 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 40 - 110 °C 2: potassium hydroxide; hydroxylamine hydrochloride / methanol View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / Reflux 1.2: 105 °C 2.1: hydroxylamine hydrochloride; potassium hydroxide / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide / 2 h / 45 °C 1.2: 110 °C 2.1: potassium hydroxide; hydroxylamine hydrochloride / Reflux View Scheme

1,3-dimethyl-5-phenoxypyrazole-4-carbaldehyde (109925-10-2) → 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4)

Conditions	Yield
With hydroxylamine hydrochloride; potassium hydroxide In methanol
With hydroxylamine hydrochloride; potassium hydroxide Reflux;
With hydroxylamine hydrochloride; potassium hydroxide Reflux;
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 20 - 30℃; for 0.5h;

1,3-dimethyl-5-pyrazolone (2749-59-9) → 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 10.5 h / 0 °C / Heating 2.1: potassium hydroxide / N,N-dimethyl-formamide / 6 h / 40 °C 2.2: 100 °C 3.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 0.5 h / 20 - 30 °C View Scheme

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + allyl phenyl ether (1746-13-0) → 3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-5-(phenoxymethyl)-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Solvent; Reflux;	85%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + allyl naphthyl ether (20009-25-0) → 3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-5-[(naphthalen-1-yloxy)methyl]-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	79%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + allyl o-tolyl ether (936-72-1) → 3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-5-[(o-tolyloxy)methyl]-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	78%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + C10H11NO3 → 3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-5-[(2-methyl-4-nitrophenoxy)methyl]-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	76%

2-(chloromethyl)-5-ethoxy-1,3,4-thiadiazole (4153-74-6) + 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) → C17H19N5O3S

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Reflux;	75.2%
With potassium carbonate In acetonitrile Reflux;

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + C13H16O → 3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-5-(((1,4,4a,8a-tetrahydronaphthalen-1-yl)oxy)methyl)-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	75%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 4-(2-propenyloxy)benzaldehyde (40663-68-1) → 4-{[3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-4,5-dihydroisoxazol-5-yl]methoxy}benzaldehyde

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	75%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + allyl (4-methoxyphenyl) ether (13391-35-0) → 3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-5-[(4-methoxyphenoxy)methyl]-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	75%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 4-allyloxy-benzonitrile (33148-47-9) → 4-{[3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-4,5-dihydroisoxazol-5-yl]methoxy}benzonitrile

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	74%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + C11H10N2O → 3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-5-[(quinoxalin-2-yloxy)methyl]-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	73%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + C11H9ClN2O → 5-{[(6-chloroquinoxalin-2-yl)oxy]methyl}-3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	72%

2-allyloxy-6-nitrotoluene + 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) → 3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-5-[(2-methyl-3-nitrophenoxy)methyl]-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	72%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 1-(allyloxy)-3-bromobenzene (41388-50-5) → 5-[(3-bromophenoxy)methyl]-3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	70%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 1-allyloxy-4-chlorobenzene (13997-70-1) → 5-[(4-chlorophenoxy)methyl]-3-(1,3-dimethyl-5-phenoxy-1Hpyrazol-4-yl)-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	70%

8-(allyloxy)-5-chloroquinoline + 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) → 5-{[(5-chloroquinolin-8-yl)oxy]methyl}-3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	70%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + methyl 4-allyloxybenzoate (35750-24-4) → methyl 4-{[3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-4,5-dihydroisoxazol-5-yl]methoxy}benzoate

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	70%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 1-(allyloxy)-2-naphthaldehyde (135522-20-2) → 1-{[3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-4,5-dihydroisoxazol-5-yl]methoxy}-2-naphthaldehyde

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	70%

1-allyloxy-1H-benzo[d][1,2,3]triazole (77204-11-6) + 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) → 5-{[(1H-benzo[d][1,2,3]triazol-1-yl)oxy]methyl}-3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	68%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 2-allyloxy-1,4-dimethylbenzene (3727-20-6) → 3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-5-[(2,5-dimethylphenoxy)methyl]-4,5-dihydroisoxazole

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	68%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + allyl 3-cyanophenyl ether (91880-75-0) → 3-{[3-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)-4,5-dihydroisoxazol-5-yl]methoxy}benzonitrile

Conditions	Yield
With N-chloro-4-methylbenzenesulfonamide In N,N-dimethyl-formamide Reflux;	65%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 2-[4-(chloromethyl)phenoxy]-5-(trifluoromethyl)pyridine → 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde-O-[4-(5-trifluoromethylpyridin-2-yloxy)phenylmethyl]oxime

Conditions	Yield
With caesium carbonate In acetonitrile Reflux;	56%
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 10h;	43.8%

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 4-(2-ethoxy-1,3,4-thiadiazole-5-ylmethoxy)benzyl chloride → C24H25N5O4S

Conditions	Yield
With potassium carbonate; caesium carbonate In acetonitrile for 20h; Reflux;	45.1%

1-bromo-2-fluoro-6,6-dimethylhept-2-ene-4-yne + 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) → 1,3-dimethyl-5-phenoxypyrazol-4-carboaldoxime O-2-fluoro-6,6-dimethylhept-2-ene-4-ynyl ether (129306-40-7)

Conditions	Yield
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + (E)-6,6-dimethyl-2-hepten-4-ynyl bromide (78629-21-7) → 1,3-dimethyl-5-phenoxypyrazol-4-carboaldoxime O-6,6-dimethylhept-2-ene-4-ynyl ether (126763-66-4)

Conditions	Yield
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 4-((2-chlorothiazol-5-yl)methoxy)benzyl chloride (1234623-97-2) → C23H21ClN4O3S (1620883-58-0)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;

2-(chloromethyl)-5-methoxy-1,3,4-thiadiazole (3914-44-1) + 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) → C16H17N5O3S

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;

1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime (110035-28-4) + 4-(1H-pyrazol-1-yl)phenylmethyl chloride (143426-52-2) → C22H21N5O2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 18h;

Upstream product

• 2749-59-9 1,3-dimethyl-5-pyrazolone 
• 109925-10-2 1,3-dimethyl-5-phenoxypyrazole-4-carbaldehyde 
• 108-95-2 phenol 
• 27006-76-4 5-chloro-4-formyl-1,3-dimethylpyrazole 

Downstream Products

• 1620883-58-0 C₂₃H₂₁ClN₄O₃S 

Relevant articles and documents

Design of a simple and efficient synthesis for bioactive novel pyrazolyl-isoxazoline hybrids

A simple and new methodology has been developed for the synthesis of novel bioactive pyrazolyl-isoxazoline hybrids from a pyrazolyl-substituted oxime and various substituted allyloxybenzenes, which are easily available, inexpensive starting materials. All the novel synthesized target hybrids were characterized by NMR, IR, and mass spectroscopic techniques. We have employed some of the hybrid materials in anti-bacterial and anti-fungal activity studies. The hybrid materials 6m and 6p exhibited the best anti-bacterial and anti-fungal activities.

Synthesis and biological activities of novel 1,3,4-thiadiazole-containing pyrazole oxime derivatives

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