(S)-3-Dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
[CAS# 850222-40-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: (S)-3-Dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
• Synonyms: (2S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one
• Molecular Formula: C₁₃H₁₉NO₂
• Molecular Weight: 221.30
• Protein Sequence: X
• CAS Registry Number: 850222-40-1
• EC Number: 617-655-9
• SMILES: C[C@@H](CN(C)C)C(=O)C1=CC(=CC=C1)OC

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*, 1.012
• Index of Refraction: 1.508, Calc.^*
• Boiling Point: 315.8±22.0 °C (760 mmHg), Calc.^*
• Flash Point: 144.8±22.3 °C, Calc.^*

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS09 Danger
• Risk Statements: H225-H302-H315-H317-H319-H411
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P272-P273-P280-P301+P317-P302+P352-P303+P361+P353-P305+P351+P338-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P370+P378-P391-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Flammable liquids	Flam. Liq.	2	H225
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovery and Applications

(S)-3-Dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone, often referred to as a chiral ketone, is a significant compound in the realm of organic chemistry, particularly in the synthesis of pharmaceutical agents and other bioactive molecules. This compound is characterized by its unique structural configuration, which includes a dimethylamino group and a methoxyphenyl substituent, contributing to its distinct reactivity and biological activity.

The discovery of (S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone can be traced back to research focused on the development of chiral intermediates for asymmetric synthesis. Asymmetric synthesis plays a crucial role in pharmaceuticals, where the chirality of a molecule can significantly affect its therapeutic efficacy and safety. Researchers have increasingly sought methods to produce chiral compounds efficiently and with high enantiomeric purity. This compound emerged as a valuable intermediate for the synthesis of various pharmaceuticals due to its ability to undergo further transformations while maintaining its chiral integrity.

One of the primary applications of (S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone is in the synthesis of novel therapeutic agents. For example, it serves as a building block in the development of drugs targeting central nervous system disorders, where modifications of the amine and ketone functional groups can lead to compounds with enhanced pharmacological profiles. The ability to fine-tune the structure of the compound facilitates the design of more effective and selective drugs.

Additionally, this compound finds applications in the field of agrochemicals. The unique chemical properties of (S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone allow it to be used in the synthesis of herbicides and pesticides, contributing to agricultural productivity and pest management. Its effectiveness in these applications is attributed to its ability to interact with specific biological targets in plants and pests, thus enhancing its utility in the agricultural sector.

Moreover, (S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone is valuable in academic research. Its chiral nature and reactivity make it a suitable candidate for studying reaction mechanisms and developing new synthetic methodologies. Researchers often use it as a model compound to explore new catalytic systems or reaction pathways that involve chiral centers, thereby contributing to the advancement of organic synthesis techniques.

Despite its numerous applications, safety considerations surrounding the handling and use of (S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone are crucial. Proper safety protocols must be established during its synthesis and application to mitigate any potential risks associated with exposure or environmental impact.

In conclusion, (S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone is a significant compound in organic chemistry, particularly in the synthesis of pharmaceuticals and agrochemicals. Its discovery has enabled researchers to develop more effective drugs and agricultural products, making it a valuable component in various scientific and industrial applications. Continued research on this compound will likely lead to further advancements in synthetic methodologies and the development of novel therapeutic agents.

References

2010. Tapentadol. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0218