25505-64-0

Basic information

• Product Name: 2,5-DIMETHOXY-4-METHYL-BETA-NITROSTYRENE, >95%
• Synonyms: 2,5-DIMETHOXY-4-METHYL-BETA-NITROSTYRENE, >95%;2,5-DiMethoxy-4-Methyl-β-nitrostyrene;1-(2,5-DiMethoxy-4-Methylphenyl)-2-nitroethene;1,4-DiMethoxy-2-Methyl-5-(2-nitroethenyl)benzene;1,4-dimethoxy-2-methyl-5-[(E)-2-nitroethenyl]benzene
• CAS NO: 25505-64-0
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.23
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 25505-64-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 126 °C
• Boiling Point: 363.0±37.0 °C(Predicted)
• Appearance: /
• Density: 1.168±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2,5-DIMETHOXY-4-METHYL-BETA-NITROSTYRENE, >95%(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHOXY-4-METHYL-BETA-NITROSTYRENE, >95%(25505-64-0)
• EPA Substance Registry System: 2,5-DIMETHOXY-4-METHYL-BETA-NITROSTYRENE, >95%(25505-64-0)

Safety Data

• Hazardous Substances Data: 25505-64-0(Hazardous Substances Data)

Usage

Description

2,5-DIMETHOXY-4-METHYL-BETA-NITROSTYRENE, >95% is a chemical compound characterized as a brown solid. It is primarily known for its use in the synthesis of phenylamine derivatives, which are utilized as psychotomimetic agents.

Uses

Used in Pharmaceutical Industry:
2,5-DIMETHOXY-4-METHYL-BETA-NITROSTYRENE, >95% is used as a key intermediate compound for the preparation of phenylamine derivatives. These derivatives are significant in the development of psychotomimetic agents, which are substances that mimic the effects of psychosis or alter perception, mood, and cognitive processes. The compound plays a crucial role in advancing research and development in the field of psychopharmacology and mental health treatments.

Synthetic route

nitromethane (75-52-5) + 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0)

Conditions	Yield
With ammonium acetate In benzene
With potassium hydroxide; sodium acetate; acetic anhydride 1) ethanol, water, 5 deg C, 2 days 2) reflux, 20 min.; Yield given. Multistep reaction;

2-methylbenzene-1,4-diol (95-71-6) → 1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 82 percent / potassium hydroxide / methanol / 8 h / steam distillation 2: 1) HCl, aluminium chloride 2) aqueous H2SO4 / 1) tetrachloroethane, 8 h, 65-70 deg C 2) overnight, room temperature 3) steam distillation 3: 1) KOH 2) acetic anhydride, sodium acetate / 1) ethanol, water, 5 deg C, 2 days 2) reflux, 20 min. View Scheme

2,5-dimethoxy toluene (24599-58-4) → 1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) HCl, aluminium chloride 2) aqueous H2SO4 / 1) tetrachloroethane, 8 h, 65-70 deg C 2) overnight, room temperature 3) steam distillation 2: 1) KOH 2) acetic anhydride, sodium acetate / 1) ethanol, water, 5 deg C, 2 days 2) reflux, 20 min. View Scheme

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → 2,5-dimethoxy-4-methyl-6,β-dinitrostyrene (74422-80-3)

Conditions	Yield
With nitric acid at 0℃; for 0.416667h;	5%

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) + sodium methylate (124-41-4) → 1-(2,5-dimethoxy-4-methylphenyl)-1-methoxy-2-nitroethane (98537-47-4)

Conditions	Yield
1.) methanol; 2.) methanol, 0 deg C, 4 h; Yield given. Multistep reaction;

diethylacetamide (685-91-6) + 1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → N,N-Diethyl-3-(2,5-dimethoxy-4-methylphenyl)-4-nitrobutyramid (33877-68-8)

Conditions	Yield
(i) nBuLi, THF, hexane, (ii) /BRN= 1209428/; Multistep reaction;

N,N-dimethyl acetamide (127-19-5) + 1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → 3-(2,5-Dimethoxy-4-methylphenyl)-N,N-dimethyl-4-nitrobutyramid (33877-59-7)

Conditions	Yield
(i) LDA, THF, hexane, (ii) /BRN= 2505975/, AcOH; Multistep reaction;

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → alpha demethyl DOM (24333-19-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → 1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitroethan (42203-89-4)

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → 2,4-Di-(2,5-dimethoxy-4-methylphenyl)-1,3-dinitrobutan (42203-90-7)

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → 1-(2,5-dimethoxy-4-methylphenyl)-1-methoxy-2-aminoethane hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) methanol; 2.) methanol, 0 deg C, 4 h 2: 5.3 g / aluminium hydride / tetrahydrofuran / 2 h / Heating View Scheme

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → 4,7-dihydroxy-6-methylindole (74422-82-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 5 percent / 65percent nitric acid / 0.42 h / 0 °C 2: 69 percent / iron powder, acetic acid / ethanol / 0.5 h / Heating 3: aluminium chloride / benzene / 6 h / Heating View Scheme

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → 4,7-dimethoxy-6-methylindole (74422-81-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 percent / 65percent nitric acid / 0.42 h / 0 °C 2: 69 percent / iron powder, acetic acid / ethanol / 0.5 h / Heating View Scheme

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → 2-(2,5-Dimethoxy-4-methylphenyl)-N4,N4-dimethyl-1,4-butandiamin

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) LDA, THF, hexane, (ii) /BRN= 2505975/, AcOH 2: LiAlH4 View Scheme

1-(2,5-dimethoxy-4-methylphenyl)-2-nitroethene (25505-64-0) → N-Methyl-2-(2',5'-Dimethoxy-4'-methylphenyl)ethylamin (24286-43-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran 2: (i) PhCHO, benzene, (ii) /BRN= 635994/, (iii) H2O View Scheme

Upstream product

• 75-52-5 nitromethane 
• 4925-88-6 2,5-dimethoxy-4-methylbenzaldehyde 
• 24599-58-4 2,5-dimethoxy toluene 
• 95-71-6 2-methylbenzene-1,4-diol 

Downstream Products

• 33877-68-8 N,N-Diethyl-3-(2,5-dimethoxy-4-methylphenyl)-4-nitrobutyramid 
• 33877-59-7 3-(2,5-Dimethoxy-4-methylphenyl)-N,N-dimethyl-4-nitrobutyramid 
• 98537-47-4 2-methoxy-2-(2,5-dimethoxy-4-methylphenyl)-1-nitroethane 
• 74422-80-3 2,5-dimethoxy-4-methyl-6,β-dinitrostyrene 
• 25505-65-1 2,5-dimethoxy-4-methyl-β-phenethylamine hydrochloride 
• 42203-90-7 2,4-Di-(2,5-dimethoxy-4-methylphenyl)-1,3-dinitrobutan 
• 42203-89-4 1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitroethan 
• 24333-19-5 alpha demethyl DOM 

Relevant articles and documents

Synthesis of 4,7-Dimethoxyindoles Bearing Substituents at the C-5 and C-6 Positions and Studies on their Demethylation Products

Syntheses of some 4,7-dimethoxyindoles bearing methyl, amino or acetamido groups at the C-5 and C-6 positions were investigated.The presence of these substituents made possible the isolation of the corresponding 4,7-dihydroxyindole derivatives obtained by long reflux with aluminium chloride in benzene solution.