4778-96-5

Basic information

• Product Name: (5alpha,6alpha)-17-(2-phenylethyl)-4,5-epoxymorphinan-3,6,14-triol
• CAS NO: 4778-96-5
• Molecular Formula: C₂₄H₂₇NO₄
• Molecular Weight: 393.4755
• Mol File: 4778-96-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 604.9°C at 760 mmHg
• Flash Point: 319.6°C
• Density: 1.42g/cm³
• Vapor Pressure: 1.75E-15mmHg at 25°C
• Refractive Index: 1.718
• CAS DataBase Reference: (5alpha,6alpha)-17-(2-phenylethyl)-4,5-epoxymorphinan-3,6,14-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (5alpha,6alpha)-17-(2-phenylethyl)-4,5-epoxymorphinan-3,6,14-triol(4778-96-5)
• EPA Substance Registry System: (5alpha,6alpha)-17-(2-phenylethyl)-4,5-epoxymorphinan-3,6,14-triol(4778-96-5)

Safety Data

• Hazardous Substances Data: 4778-96-5(Hazardous Substances Data)

Usage

General Description

"(5alpha,6alpha)-17-(2-phenylethyl)-4,5-epoxymorphinan-3,6,14-triol" is a chemical compound classified under the morphinan class of opioids. Morphines are known for their strong analgesic properties. While the exact properties of this specific compound are not widely known, it is likely to share the core attributes of morphinan compounds. These typically include the potential for pain relief, sedation, and euphoria, alongside risks such as tolerance, addiction, and physical dependence. Further research is needed to fully understand the precise activities, applications and impacts of this particular morphinan compound.

Synthetic route

4,5α-epoxy-3-methoxy-17-phenethyl-morphinane-6α,14-diol (6474-98-2) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
With boron tribromide In chloroform at 0 - 5℃; for 1h;	63%

beta-Noroxycodol (116499-16-2) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 2: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

1-phenyl-2-bromoethane (103-63-9) + sodium salt of 4H-benz<1,4>oxazin-3-one → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 2: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

C22H24N2O6 (116388-83-1) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 10percent aq. HCl / 16 h / Heating 2: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 3: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

C24H27NO8 (142641-92-7) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl gas / CH2Cl2 / 1 h 2: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 3: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

6α,14β-diacetoxy-4,5percenta-epoxy-3-methoxy-17-methyl-morphinan (67210-64-4) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / CHCl3 / 16 h / Heating 2: 10percent aq. HCl / 16 h / Heating 3: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 4: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme
Multi-step reaction with 4 steps 1: 70 percent / NaHCO3 / 1,2-dichloro-ethane 2: HCl gas / CH2Cl2 / 1 h 3: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 4: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

Upstream product

• 6474-98-2 4,5α-epoxy-3-methoxy-17-phenethyl-morphinane-6α,14-diol 
• 67210-64-4 6α,14β-diacetoxy-4,5percenta-epoxy-3-methoxy-17-methyl-morphinan 
• 142641-92-7 C₂₄H₂₇NO₈ 
• 116388-83-1 C₂₂H₂₄N₂O₆ 
• 103-63-9 1-phenyl-2-bromoethane 
• 116499-16-2 beta-Noroxycodol 

Relevant articles and documents

Morphine Alkaloids, Part 114 A. Stereohomogeneous Synthesis of N-Demethyl-N-Substituted-14-Hydroxydihydromorphines

A new route for the stereohomogeneous synthesis of N-demethyl-N-substituted-14-hydroxydihydromorphines 2a-f has been elaborated, involving O-demethylation of the novel dihydrocodeine derivatives 6a-f, obtained upon alkylation of the hitherto unknown N-demethyl-14-hydroxydihydrocodeine (5). Keywords. 6α,14β-Diacetoxy-4,5α-epoxy-3-methoxy-17-methyl-morphinan, N-demethylation of; 3,6α,14β-Triacetoxy-17-alkyl-4,5α-epoxymorphinan, N-demethylation of; 17-Alkyl-4,5α-epoxy-6α,14β-dihydroxy-3-methoxymorphinan, O-demethylation of; 4,5α-Epoxy-6α,14β-dihydroxy-3-methoxymorphinan, N-alkylation of.