Production Method 1

95548-93-9

84367-31-7

Reaction Conditions

1.1 Solvents: Methanol

Reference

Short and practical syntheses of (R)-(-)-carnitine and (R)-(-)-γ-amino-β-hydroxybutyric acid (GABOB)

Kolb, Hartmuth C.; et al, Tetrahedron: Asymmetry, 1993, 4(1), 133-41

Production Method 2

84367-31-7

Reaction Conditions

1.1 Reagents: Hydrogen-halide-lyase, halohydrin

Reference

A new enzymic synthesis of (R)-γ-chloro-β-hydroxybutyronitrile

Nakamura, Tetsuji; et al, Tetrahedron, 1994, 50(41), 11821-26

Production Method 3

51594-55-9

84367-31-7

Reaction Conditions

1.1 Solvents: Water ;  30 min; 12 h

Reference

pH-controlled regioselective nucleophilic ring-opening of epoxide: an improved process for the preparation of (R)-(-)- or (S)-(+)-3-hydroxytetrahydrofuran

Chakraborty, Ankita; et al, Organic & Biomolecular Chemistry, 2022, 20(34), 6863-6868

Production Method 4

95548-93-9

84367-31-7

Reaction Conditions

1.1 Solvents: Methanol ;  6 h, rt

Reference

Practical and efficient utilization of (R)-3-chloro-1,2-propanediol in synthesis of L-carnitine

Yang, Yunxu; et al, Journal of Chemical Research, 2011, 35(6), 371-372

Production Method 5

146864-18-8

84367-31-7

Reaction Conditions

1.1 4 h, 45 °C
1.2 Reagents: Sulfuric acid Solvents: Water

Reference

Asymmetric synthesis of L-carnitine from (R)-3-chloro-1,2-propanediol

Li, Xu Qin; et al, Chinese Chemical Letters, 2011, 22(7), 765-767

Production Method 6

84367-31-7

Reaction Conditions

1.1 Reagents: Hydrogen-halide-lyase, halohydrin

Reference

A new enzymic synthesis of (R)-γ-chloro-β-hydroxybutyronitrile

Nakamura, Tetsuji; et al, Tetrahedron, 1994, 50(41), 11821-26

(R)-(+)-4-Chloro-3-hydroxybutyronitrile Raw materials

• (2R)-2-(chloromethyl)oxirane
• 2-Propanol, 1-bromo-3-chloro-, 2-acetate, (2S)-
• 1,3,2-Dioxathiolane, 4-(chloromethyl)-, 2-oxide, (4R)-

(R)-(+)-4-Chloro-3-hydroxybutyronitrile Preparation Products

• (R)-(+)-4-Chloro-3-hydroxybutyronitrile (84367-31-7)

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• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Halohydrins Chlorohydrins
• Solvents and Organic Chemicals Organic Compounds cyanides/Cyanides

(R)-(+)-4-Chloro-3-hydroxybutyronitrile and Its Significance in Modern Chemical Biology

The compound with the CAS number 84367-31-7, identified as (R)-(+)-4-Chloro-3-hydroxybutyronitrile, represents a fascinating molecule with a unique structural framework that has garnered considerable attention in the field of chemical biology. This enantiomerically pure compound, characterized by its chiral center, plays a pivotal role in synthetic chemistry and has been explored for its potential applications in pharmaceuticals, agrochemicals, and material science. The presence of both a chloro and a hydroxyl group on a nitrile-substituted butyric acid backbone imparts distinct reactivity, making it a valuable intermediate in the synthesis of more complex molecules.

In recent years, the study of chiral compounds has seen significant advancements, particularly in understanding their role in biological systems. The enantiomeric purity of (R)-(+)-4-Chloro-3-hydroxybutyronitrile is crucial for its applications, as even minor impurities can drastically alter the biological activity of the final product. This compound has been utilized in the synthesis of various pharmacologically active agents, where stereochemistry dictates efficacy and safety. The ability to produce enantiomerically pure forms of such compounds has been made possible through advancements in asymmetric synthesis techniques, which are essential for producing drugs with high specificity and minimal side effects.

One of the most compelling aspects of (R)-(+)-4-Chloro-3-hydroxybutyronitrile is its versatility as a building block in organic synthesis. The nitrile group can be readily converted into other functional groups such as carboxylic acids, amides, and esters, while the hydroxyl and chloro substituents provide opportunities for further derivatization. This flexibility has made it a preferred choice for chemists working on complex natural product syntheses and drug discovery programs. For instance, recent studies have demonstrated its utility in constructing peptidomimetics, which are designed to mimic the bioactivity of natural peptides but with improved stability and pharmacokinetic properties.

The pharmaceutical industry has shown particular interest in this compound due to its potential as a precursor for bioactive molecules. Researchers have explored its use in developing treatments for neurological disorders, where precise stereochemical control is essential. The chiral nature of (R)-(+)-4-Chloro-3-hydroxybutyronitrile allows for the creation of enantiomerically pure drugs that can interact selectively with biological targets. This selectivity is critical for minimizing off-target effects and improving therapeutic outcomes. Moreover, the compound's compatibility with various synthetic methodologies makes it an attractive candidate for large-scale production processes.

In addition to its pharmaceutical applications, (R)-(+)-4-Chloro-3-hydroxybutyronitrile has found utility in agrochemical research. The demand for environmentally friendly pesticides and herbicides has spurred interest in developing new compounds that are both effective and sustainable. The structural features of this molecule make it a promising candidate for designing novel agrochemicals that can target specific pests while minimizing ecological impact. Recent studies have highlighted its role in synthesizing bioactive compounds that exhibit herbicidal properties, contributing to more efficient crop protection strategies.

The material science sector has also benefited from the unique properties of (R)-(+)-4-Chloro-3-hydroxybutyronitrile. Its ability to undergo polymerization reactions has led to the development of novel polymers with tailored properties. These polymers can be engineered to exhibit specific mechanical strength, thermal stability, or biodegradability, making them suitable for a wide range of applications from packaging materials to biodegradable implants. The chiral nature of the compound can also be exploited to create polymers with hierarchical structures that mimic natural materials, opening up new possibilities in nanotechnology and smart materials.

The synthesis of (R)-(+)-4-Chloro-3-hydroxybutyronitrile itself is an area of active research. Advances in catalytic methods have enabled more efficient and sustainable production processes. For example, asymmetric hydrogenation techniques have been employed to achieve high yields of the desired enantiomer with minimal waste generation. These green chemistry approaches align with global efforts to reduce the environmental footprint of chemical manufacturing while maintaining high standards of purity and efficiency.

In conclusion, (R)-(+)-4-Chloro-3-hydroxybutyronitrile (CAS no: 84367-31-7) is a versatile and highly valuable compound with significant implications across multiple sectors. Its unique structural features and reactivity make it indispensable in pharmaceuticals, agrochemicals, and material science. As research continues to uncover new applications and synthetic methodologies, this compound is poised to remain at the forefront of chemical innovation.

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