246869-08-9

Basic information

• Product Name: 2-(cyclopropylmethoxy)acetic acid
• Synonyms: 2-(cyclopropylmethoxy)acetic acid;(CyclopropylMethoxy)acetic Acid
• CAS NO: 246869-08-9
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130
• Product Categories: Miscellaneous Reagents
• Mol File: 246869-08-9.mol

Chemical Properties

• Boiling Point: 267.1±13.0 °C(Predicted)
• Appearance: /
• Density: 1.201±0.06 g/cm3(Predicted)
• Solubility: Acetone, Dichloromethane, Methanol
• PKA: 3.51±0.10(Predicted)
• CAS DataBase Reference: 2-(cyclopropylmethoxy)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(cyclopropylmethoxy)acetic acid(246869-08-9)
• EPA Substance Registry System: 2-(cyclopropylmethoxy)acetic acid(246869-08-9)

Safety Data

• Hazardous Substances Data: 246869-08-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(Cyclopropylmethoxy)acetic acid is used as a synthetic building block for the creation of more complex organic molecules. Its cyclopropylmethoxy group provides a unique structural feature that can be further modified or functionalized to synthesize a wide range of compounds with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(cyclopropylmethoxy)acetic acid is used as an intermediate in the development of new drugs. Its unique chemical structure allows for the design and synthesis of novel therapeutic agents with potential applications in various medical fields.
Used in Chemical Research:
2-(Cyclopropylmethoxy)acetic acid is also employed in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methodologies. Its reactivity and structural features make it an ideal candidate for exploring new chemical transformations and understanding the underlying principles of organic chemistry.
Used in Material Science:
In the field of material science, 2-(cyclopropylmethoxy)acetic acid can be used as a precursor to develop new materials with specific properties. Its unique structure can be incorporated into polymers, coatings, or other materials to impart desired characteristics such as improved stability, enhanced reactivity, or tailored physical properties.
Overall, 2-(cyclopropylmethoxy)acetic acid is a versatile compound with a wide range of applications across various industries, including organic synthesis, pharmaceuticals, chemical research, and material science. Its unique chemical properties and structural features make it a valuable asset in the development of new compounds, materials, and therapeutic agents.

Synthetic route

Cyclopropylmethanol (2516-33-8) + bromoacetic acid (79-08-3) → 2-(cyclopropylmethoxy)acetic acid (246869-08-9)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -5 - 5℃; for 18h; Temperature; Solvent;	90%

Cyclopropylmethanol (2516-33-8) + sodium monochloroacetic acid (3926-62-3) → 2-(cyclopropylmethoxy)acetic acid (246869-08-9)

Conditions	Yield
With sodium hydride In tetrahydrofuran
Stage #1: Cyclopropylmethanol With sodium hydride In tetrahydrofuran for 3h; Reflux; Stage #2: sodium monochloroacetic acid In tetrahydrofuran for 8.5h;	1.59 g
Stage #1: Cyclopropylmethanol With potassium tert-butylate In tetrahydrofuran at 50℃; for 1h; Inert atmosphere; Stage #2: sodium monochloroacetic acid In tetrahydrofuran at 20 - 40℃; for 40.5h;	8.08 g
Williamson Ether Synthesis;

2-bromo-2-methyl-1-(4-(methylsulfonyl)phenyl-[13C6])propan-1-one + 2-(cyclopropylmethoxy)acetic acid (246869-08-9) → 2-methyl-1-(4-(methylsulfonyl)phenyl-[13C6])-1-oxopropan-2-yl 2-(cyclopropylmethoxy)acetate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol for 14h; Heating;	97%

2-(cyclopropylmethoxy)acetic acid (246869-08-9) + 2-bromo-2-methyl-1-[4-(methylsulfonyl)phenyl]propan-1-one (189955-79-1) → 2-cyclopropylmethoxyacetic acid [1,1-dimethyl-2-(4-methanesulfonylphenyl)-2-oxoethyl]ester (246869-15-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at -10 - 20℃;	83%
With N-ethyl-N,N-diisopropylamine In methanol at 0℃; for 7h; Reflux;	52%

2-(cyclopropylmethoxy)acetic acid (246869-08-9) + 2-hydroxy-2-methyl-1-(4-(methylsulfonyl)-phenyl)propan-1-one (180048-73-1) → 2-cyclopropylmethoxyacetic acid [1,1-dimethyl-2-(4-methanesulfonylphenyl)-2-oxoethyl]ester (246869-15-8)

Conditions	Yield
With dmap In dichloromethane
Stage #1: 2-(cyclopropylmethoxy)acetic acid With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 6h; Stage #2: 2-hydroxy-2-methyl-1-(4-(methylsulfonyl)-phenyl)propan-1-one With dmap; triethylamine In dichloromethane at 20℃; for 8h;	6.1 g

2-(cyclopropylmethoxy)acetic acid (246869-08-9) → 3-(Cyclopropylmethoxy)-5.5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1: CMC, DMAP / CH2Cl2 2: DBU / acetonitrile View Scheme
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 10 - 35 °C 2: triethylamine / dichloromethane / 0 - 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene; isopropyl Trifluoroacetate / toluene / 100 °C 4: copper(l) iodide; (2S,4R)-N-(2,6-dimethylphenyl)-4-hydroxypyrrolidine-2-carboxamide; potassium phosphate / dimethyl sulfoxide / 24 h / 90 °C / Inert atmosphere View Scheme

2-(cyclopropylmethoxy)acetic acid (246869-08-9) → 2-(cyclopropylmethoxy)acetyl chloride

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 10 - 35℃;

2-(cyclopropylmethoxy)acetic acid (246869-08-9) → C16H19BrO4

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 10 - 35 °C 2: triethylamine / dichloromethane / 0 - 20 °C View Scheme

2-(cyclopropylmethoxy)acetic acid (246869-08-9) → 4-(4-bromophenyl)-3-(cyclopropylmethoxy)-5,5-dimethylfuran-2(5H)-one

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 10 - 35 °C 2: triethylamine / dichloromethane / 0 - 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene; isopropyl Trifluoroacetate / toluene / 100 °C View Scheme

Upstream product

• 2516-33-8 Cyclopropylmethanol 
• 3926-62-3 sodium monochloroacetic acid 
• 79-08-3 bromoacetic acid 

Downstream Products

• 246869-15-8 2-cyclopropylmethoxyacetic acid [1,1-dimethyl-2-(4-methanesulfonylphenyl)-2-oxoethyl]ester 
• 189954-96-9 3-(Cyclopropylmethoxy)-5.5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one 

Relevant articles and documents

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