5428-02-4

Basic information

• Product Name: 2-NITRO-2-PHENYLPROPANE-1,3-DIOL
• Synonyms: 2-NITRO-2-PHENYL-1,3-PROPANEDIOL;2-NITRO-2-PHENYLPROPANE-1,3-DIOL;AURORA KA-563;Nitodiol
• CAS NO: 5428-02-4
• Molecular Formula: C₉H₁₁NO₄
• Molecular Weight: 197.19
• EINECS: 410-360-4
• Product Categories: Propanes/propenes
• Mol File: 5428-02-4.mol

Chemical Properties

• Melting Point: 100-102°C
• Boiling Point: 396 °C at 760 mmHg
• Flash Point: 175.7 °C
• Appearance: /
• Density: 1.337 g/cm³
• Vapor Pressure: 5.56E-07mmHg at 25°C
• Refractive Index: 1.58
• PKA: 12.53±0.10(Predicted)
• CAS DataBase Reference: 2-NITRO-2-PHENYLPROPANE-1,3-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITRO-2-PHENYLPROPANE-1,3-DIOL(5428-02-4)
• EPA Substance Registry System: 2-NITRO-2-PHENYLPROPANE-1,3-DIOL(5428-02-4)

Safety Data

• Hazard Codes: T,N
• Statements: 21/22-39-41-43-51/53-48/25
• Safety Statements: 45-53-61
• RIDADR: 3077
• HazardClass: IRRITANT
• Hazardous Substances Data: 5428-02-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-NITRO-2-PHENYLPROPANE-1,3-DIOL is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex organic molecules. Its unique chemical properties, including the reactivity of the nitro group, make it a valuable component in the development of new drugs.
Used in Organic Compound Synthesis:
In the field of organic chemistry, 2-NITRO-2-PHENYLPROPANE-1,3-DIOL serves as a starting material for the synthesis of a range of organic compounds. Its structural features allow for further chemical reactions and modifications, facilitating the creation of diverse chemical entities.
Used in Medicinal Chemistry and Drug Development:
2-NITRO-2-PHENYLPROPANE-1,3-DIOL is utilized in medicinal chemistry for its potential to be incorporated into drug candidates. Its unique properties can be leveraged to enhance the efficacy, selectivity, or pharmacokinetics of new therapeutic agents.

InChI:InChI=1/C9H11NO4/c11-6-9(7-12,10(13)14)8-4-2-1-3-5-8/h1-5,11-12H,6-7H2

Upstream product

• 622-42-4 1-nitro-1-phenylmethane 
• 50-00-0 formaldehyd 
• 121-44-8 triethylamine 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 5428-03-5 2-amino-2-phenyl-propane-1,3-diol 
• 90918-76-6 5-nitro-5-phenyl-[1,3]oxazinane 
• 97260-34-9 5-nitro-2,5-diphenyl-[1,3,2]dioxaborinane 
• 873975-55-4 1,3-dimethyl-5-nitro-5-phenyl-hexahydro-pyrimidine 
• 37561-37-8 2,2-dimethyl-5-nitro-5-phenyl[1,3]dioxane 
• 861198-44-9 2,2-dimethyl-5-nitrone-N-(2-methyl-1-propene)-5-phenyl[1,3]dioxane 
• 861198-45-0 2,2-dimethyl-5-nitroxide-N-(2-methyl-1-phenylpropyl)-5-phenyl[1,3]dioxane 
• 861198-46-1 N-(2,2-dimethyl-5-phenyl[1,3]dioxan-5-yl)-N-(2-methyl-1-phenylpropyl)-O-(1-phenylethyl)hydroxylamine 
• 92959-70-1 3-acetyl-5-nitro-5-phenyl-[1,3]oxazinane 
• 93332-71-9 5-nitro-3-(4-nitro-benzoyl)-5-phenyl-[1,3]oxazinane 
• 1570-95-2 2-phenylpropane-1, 3-diol 
• 37561-42-5 2,2-dimethyl-5-phenyl-1,3-dioxan-5-amine 

Relevant articles and documents

Broadening antifungal spectrum and improving metabolic stablity based on a scaffold strategy: Design, synthesis, and evaluation of novel 4-phenyl-4,5-dihydrooxazole derivatives as potent fungistatic and fungicidal reagents

5-phenylthiophene derivatives exhibited excellent antifungal activity against Candida albicans, Candida tropicalis and Cryptococcus neoformans. However, optimal compound 7 was inactive against Aspergillus fumigatus and unstable in human liver microsomes in vitro with a half-life of 18.6 min. To discover antifungal agents with a broad spectrum and improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of 4-phenyl-4,5-dihydrooxazole derivatives were designed and synthesized. It was especially encouraging that compound 22a displayed significant antifungal activities against eight susceptible strains and seven FLC-resistant strains. Furthermore, the potent compound 22a could prevent the formation of fungalbiofilms and displayed satisfactory fungicidal activity. In addition, the metabolic stability of compound 22a was improved significantly, with the half-life of 70.5 min. Compound 22a was almost nontoxic to mammalian A549, MCF-7, HepG2, and 293T cells. Moreover, pharmacokinetic studies in SD rats showed that compound 22a exhibited pharmacokinetic properties with a bioavailability of 15.22% and a half-life of 4.44 h, indicating that compound 22a is worthy of further study.

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

Improving the metabolic stability of antifungal compounds based on a scaffold hopping strategy: Design, synthesis, and structure-activity relationship studies of dihydrooxazole derivatives

L-amino alcohol derivatives exhibited high antifungal activity, but the metabolic stability of human liver microsomes in vitro was poor, and the half-life of optimal compound 5 was less than 5 min. To improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of antifungal compounds with a dihydrooxazole scaffold was designed and synthesized. Compounds A33-A38 substituted with 4-phenyl group on dihydrooxazole ring exhibited excellent antifungal activities against C. albicans, C. tropicalis and C. krusei, with MIC values in the range of 0.03–0.25 μg/mL. In addition, the metabolic stability of compounds A33 and A34 in human liver microsomes in vitro was improved significantly, with the half-life greater than 145 min and the half-life of 59.1 min, respectively. Moreover, pharmacokinetic studies in SD rats showed that A33 exhibited favourable pharmacokinetic properties, with a bioavailability of 77.69%, and half-life (intravenous administration) of 9.35 h, indicating that A33 is worthy of further study.

Preparation method of 2-nitro-2-substituted phenylpropane-1,3-diol

The invention discloses a preparation method of 2-nitro-2-substituted phenylpropane-1,3-diol. According to the technical scheme, the preparation method is characterized by comprising the steps of S1,conducting a mixing reaction, specifically, sequentially adding benzyl chloride, an organic solvent, a base catalyst, nitrite and a formaldehyde solution into a reaction kettle, controlling the temperature to be 30-60 DEG C, and carrying out heat preservation reaction for 8-15 hours; S2, conducting extraction, specifically, transferring the mixed liquid obtained after the mixing reaction in the step S1 into a reaction bottle, adding ice water, immediately adding an extraction agent for extraction, repeatedly extracting for three times, and combining organic phases; and S3, washing with water,specifically, repeatedly washing with clean water for three times, and then dehydrating and drying with anhydrous sodium sulfate; The method has the advantages that the reaction steps are shortened, the complicated operation process is avoided, potential safety hazards are avoided, less waste water is generated, the energy-saving and environment-friendly requirements are met, the yield is increased, the cost is low, the method is suitable for large-scale industrial production, and greater economic benefits are achieved.

2, 4, 4-trisubstituted dihydrooxazole derivative and application thereof

The invention belongs to the technical field of drug synthesis, and relates to 2, 4, 4-trisubstituted dihydrooxazole derivatives, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, preparation methods of the 2, 4, 4-trisubstituted dihydrooxazole derivatives and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and an application of the 2, 4, 4-trisubstituted dihydrooxazole derivatives and the prodrugs thereof as drugs for treating various diseases caused by fungal infection. The general formula of the 2, 4, 4-trisubstituted dihydrooxazole derivative and the stereoisomer or the pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof is shown as (I), wherein MBG, X, Y, M and R1 are shown in the claims and the specification. .

Enantioselective formation of tert-alkylamines by desymmetrization of 2-substituted serinols

Novel enantioselective desymmetrization of 2-substituted 2-amino-1,3-propanediols has been established to generate asymmetric quaternary carbon centers comprising an amino group. Enantioselective as well as chemical conversion proved to be greatly dependent on the protecting group of the amino group in the substrate, desymmetrizing reagent, base, solvent, and naturally, catalyst. The highly effective desymmetrization has been implemented by using N-benzoylated substrates with benzoyl Chloride and triethylamine in the presence of tetraphenylbisoxazoline (24)-CuCl2 complex in THF at ambient temperature. An extensive survey of catalysts revealed that dimethylmalonate- bridged bisoxazoline-CuCl2 complexes were superior. Among them, the tetraphenylbisoxazoline (24)-CuCl2 complex turned out to work most efficiently with a wide array of the substrates. All the examined substrates, with the exception of 2-phenylserinol 36, were desymmetrized in the presence of 24-CuCl2 complex to give high enantioselectivities ranging from 85 to 95% ee. Complementary use of the diisopropylbisoxazoline (22)-CuCl2 complex has remedied the mediocre desymmetrization of 36 to give a significantly improved enantioselectivity from 63 to 83% ee.

Synthesis of 2-phenyl-1,3-propanediol

A novel method of preparing 2-phenyl substituted-1, 3-propanediols, useful intermediates in the synthesis of pharmaceutical preparations is disclosed.

Preparation of 2-phenyl-1, 3-propane diol and its dicarbamate

A method for the preparation of 2-phenyl-1, 3-propanediol dicarbamate which comprises: a) reacting benzaldehyde with a compound selected from hydroxylamine sulphate and hydroxyalmine hydro-chloride to form benzaldehyde oxime; b) oxidizing the benzaldehyde oxime of step (a) to obtain nitromethylbenzene; c) reacting the nitromethylbenzene obtained in step (b) with formaldehyde to form 2-nitro-2-phenyl-1,3--propanediol; d) reducing 2-nitro-2-phenyl-1, 3-propanediol with hydrogen to form 2-phenyl-1, 3-propanediol; e) converting 2-phenyl-1, 3-propanediol to the desired dicarbamate.

Synthesis of 2-phenyl-1,3-propanediol

A novel method for preparing 2-phenyl-1, 3-propanediol and its dicarbamate is disclosed which readily lends itself to commercial production.