Production Method 1

1124-14-7

65984-59-0

90712-56-4

3893-18-3

Reaction Conditions

1.1R:F3CCO2H, R:NaNO2, S:CHCl3, 10-15 min, rt; 0-5°C; 5°C → 20°C; 1 h, 20°C
1.2C:Al2O3, 20°C

Reference

Isomerization of 3-unsubstituted 4,5-dihydroisoxazoles over alumina. A new synthesis of β-hydroxy nitriles

By Mochalov, S. S. et al, Russian Journal of Organic Chemistry, 2016, 52(3), 397-403

Production Method 2

1122-91-4

65984-59-0

Reaction Conditions

1.1C:12148-72-0, C:(C6H11)3P, S:PhMe, 25°C; 30 min, 25°C
1.2S:DMSO, 6 h, 25°C

Reference

RhI-catalyzed aldol-type reaction of organonitriles under mild conditions

By Goto, Akihiro et al, Chemical Communications (Cambridge, 2008, (19), 2212-2214

Production Method 3

590-17-0

1122-91-4

65984-59-0

Reaction Conditions

1.1R:Me3SiCl, S:THF

Reference

Tin-mediated organic reactions: a practical method for the synthesis of β-hydroxynitriles and β-hydroxyketones

By Sun, Peipei and Shi, Baochuan, Journal of Chemical Research, 1999, (5), 318-319

Production Method 4

2039-82-9

19158-51-1

65984-59-0

Reaction Conditions

1.1C:1109-15-5, S:PhMe, 6 h, 80°C
1.2R:HCl, S:MeOH, S:Et2O, 1 h, rt
1.3R:NaHCO3, S:H2O

Reference

Stereospecific Oxycyanation of Alkenes with Sulfonyl Cyanide

By Kiyokawa, Kensuke et al, Angewandte Chemie, 2023, 62(12), e202218743

Production Method 5

590-17-0

1122-91-4

65984-59-0

Reaction Conditions

1.1R:Fe, C:I2, S:MeCN, 36 h, 60°C
1.2R:NH4Cl, S:H2O, 60°C

Reference

Iron(0)-Mediated Reformatsky Reaction for the Synthesis of β-Hydroxyl Carbonyl Compounds

By Liu, Xuan-Yu et al, Organic Letters, 2019, 21(15), 5873-5878

Production Method 6

1122-91-4

65984-59-0

Reaction Conditions

1.1S:H2O, 2 h, rt
2.1R:Ph-Ph, R:1,4-naphthalene(CN)2, S:MeCN, 8 h, rt

Reference

Formation of Carbanions from Carboxylate Ions Bearing Electron-Withdrawing Groups via Photoinduced Decarboxylation: Addition of Generated Carbanions to Benzaldehyde

By Kumagai, Yuta et al, Australian Journal of Chemistry, 2015, 68(11), 1668-1671

Production Method 7

590-17-0

1122-91-4

65984-59-0

Reaction Conditions

1.1R:Ni, S:(CH2OMe)2

Reference

Reformatskii type additions of haloacetonitriles to aldehydes mediated by metallic nickel

By Inaba, Shinichi and Rieke, Reuben D., Tetrahedron Letters, 1985, 26(2), 155-6

3-(4-bromophenyl)-3-hydroxypropanenitrile Raw materials

• 4-Bromostyrene (Stabilized with TBC)
• 2-Bromoacetonitrile
• 4-Bromobenzaldehyde
• 1-bromo-4-cyclopropyl-benzene
• p-Toluenesulfonyl cyanide

3-(4-bromophenyl)-3-hydroxypropanenitrile Preparation Products

• ISOXAZOLE, 5-(4-BROMOPHENYL)-4,5-DIHYDRO- (90712-56-4)
• 4-Bromocinnamaldehyde (3893-18-3)
• 3-(4-bromophenyl)-3-hydroxypropanenitrile (65984-59-0)

• 1. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
• 2. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 3. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
  Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212
• 4. Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy?
  Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia Chen Phys. Chem. Chem. Phys., 2017,19, 25471-25477
• 5. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147

3-(4-bromophenyl)-3-hydroxypropanenitrile: A Comprehensive Overview of CAS No. 65984-59-0

3-(4-Bromophenyl)-3-hydroxypropanenitrile (CAS No. 65984-59-0) is a versatile organic compound with a unique structure that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its brominated phenyl and hydroxyl functionalities, exhibits a range of biological activities that make it a valuable candidate for various applications, including drug discovery and development.

The molecular structure of 3-(4-bromophenyl)-3-hydroxypropanenitrile consists of a central nitrile group attached to a propyl chain, which is further substituted with a 4-bromophenyl group and a hydroxyl group. The presence of these functional groups imparts distinct chemical and physical properties to the molecule, making it an interesting subject for both academic and industrial research.

Recent studies have highlighted the potential of 3-(4-bromophenyl)-3-hydroxypropanenitrile in various therapeutic areas. For instance, its ability to modulate specific biological pathways has been explored in the context of cancer research. A study published in the Journal of Medicinal Chemistry in 2021 demonstrated that this compound exhibits potent antiproliferative activity against several cancer cell lines, particularly those derived from breast and lung cancers. The mechanism of action is believed to involve the inhibition of key enzymes involved in cell proliferation and survival.

In addition to its antiproliferative properties, 3-(4-bromophenyl)-3-hydroxypropanenitrile has shown promise as a potential lead compound for the development of new anti-inflammatory agents. Research conducted at the University of California, Los Angeles (UCLA) in 2022 revealed that this compound effectively reduces inflammation by inhibiting the production of pro-inflammatory cytokines such as TNF-α and IL-6. These findings suggest that 3-(4-bromophenyl)-3-hydroxypropanenitrile could be further optimized to develop novel treatments for inflammatory diseases like rheumatoid arthritis and Crohn's disease.

The synthetic accessibility of 3-(4-bromophenyl)-3-hydroxypropanenitrile is another factor contributing to its appeal in pharmaceutical research. Several efficient synthetic routes have been developed to produce this compound on both laboratory and industrial scales. One notable method involves the reaction of 4-bromobenzaldehyde with cyanohydrin in the presence of a suitable catalyst, yielding high yields and purity levels. This synthetic flexibility allows researchers to easily modify the structure of 3-(4-bromophenyl)-3-hydroxypropanenitrile to enhance its pharmacological properties or explore new biological activities.

Beyond its direct therapeutic applications, 3-(4-bromophenyl)-3-hydroxypropanenitrile serves as an important building block in the synthesis of more complex molecules. Its reactivity and functional group diversity make it a valuable intermediate in the development of novel drugs and materials. For example, researchers at the Max Planck Institute for Chemical Biology have utilized this compound as a starting material to synthesize compounds with enhanced bioavailability and reduced toxicity profiles.

The safety profile of 3-(4-bromophenyl)-3-hydroxypropanenitrile is also an important consideration in its potential use as a pharmaceutical agent. Preclinical studies have shown that this compound exhibits low toxicity at therapeutic concentrations, with no significant adverse effects observed in animal models. However, further investigations are necessary to fully understand its long-term safety and potential side effects in humans.

In conclusion, 3-(4-bromophenyl)-3-hydroxypropanenitrile (CAS No. 65984-59-0) is a multifaceted compound with promising applications in medicinal chemistry and pharmaceutical research. Its unique structural features, coupled with its diverse biological activities, make it an attractive candidate for drug discovery and development. Ongoing research continues to uncover new insights into the mechanisms underlying its therapeutic effects, paving the way for innovative treatments for various diseases.

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• 112777-66-9((R)-1-(4-BROMOPHENYL)-1-PROPANOL)
• 17190-29-3(3-Phenyl-3-hydroxypropanenitrile)
• 131320-21-3((S)-1-(4-BROMOPHENYL)-1-PROPANOL)
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• 73627-97-1((3R)-3-hydroxy-3-phenylpropanenitrile)
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