5463-71-8

Basic information

• Product Name: Bromosaffrole
• Synonyms: Bromosaffrole;5-(2-BroMopropyl)benzo[d][1,3]dioxole
• CAS NO: 5463-71-8
• Molecular Formula: C₁₀H₁₁BrO₂
• Molecular Weight: 243.09714
• Mol File: 5463-71-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 286.5°C at 760 mmHg
• Flash Point: 124.3°C
• Appearance: /
• Density: 1.486g/cm³
• Vapor Pressure: 0.00452mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: Bromosaffrole(CAS DataBase Reference)
• NIST Chemistry Reference: Bromosaffrole(5463-71-8)
• EPA Substance Registry System: Bromosaffrole(5463-71-8)

Safety Data

• Hazardous Substances Data: 5463-71-8(Hazardous Substances Data)

Usage

General Description

Bromosaffrole is a chemical compound that belongs to the safrole family and is a derivative of the natural compound safrole. It is a colorless to yellow liquid with a strong, sweet, aromatic odor. Bromosaffrole is commonly used as a precursor in the synthesis of various pharmaceuticals, particularly in the production of amphetamines and other psychoactive substances. However, it is also known to be toxic and potentially carcinogenic, with exposure to high levels of the compound posing a risk to human health. Due to its use in the illegal drug trade and its potential health hazards, bromosaffrole is a controlled substance in many countries.

InChI:InChI=1/C10H11BrO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6H2,1H3

Synthetic route

diethyl 4-(1-(benzo[d][1,3]dioxol-5-yl)propan-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate → 3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8)

Conditions	Yield
With dipotassium peroxodisulfate; tris(2,2′-bipyridyl)dichlororuthenium(II) hexahydrate; sodium bromide In water; acetonitrile at 20℃; for 24h; Sealed tube; Inert atmosphere; Irradiation; regioselective reaction;	94%

1-allyl-3,4-methylenedioxybenzene (94-59-7) → 3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8)

Conditions	Yield
With water; hydrogen bromide

1-allyl-3,4-methylenedioxybenzene (94-59-7) → 3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8) + 3-<3,4-(methylenedioxy)phenyl>-1-bromopropane (28437-31-2)

Conditions	Yield
With borane; bromine 1.) 0 deg C, 1 h, THF, 2.) 0 deg C, 30 min, THF, H2O; Yield given. Multistep reaction. Yields of byproduct given;

3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8) → 1-(1,3-benzodioxol-5-yl)-2-propanone (4676-39-5)

Conditions	Yield
With potassium hydroxide; 2-nitropropane

3-<3,4-(methylenedioxy)-phenyl>-2-bromopropane (5463-71-8) + (3,4,5-trimethoxyphenyl)acetone (16603-18-2) → erythro-2,3-dimethyl-4-(3,4-methylenedioxyphenyl)-1-(3,4,5-trimethoxyphenyl)-2-butanol + threo-2,3-dimethyl-4-(3,4-methylenedioxyphenyl)-1-(3,4,5-trimethoxyphenyl)-2-butanol

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide 1.) THF, HMPA, 5 min, 2.) THF, HMPA, 25 deg C, 40 min;
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide 1.) THF, HMPA, 5 min, 2.) THF, HMPA, 25 deg C, 40 min; Yield given. Yields of byproduct given;

Upstream product

• 94-59-7 1-allyl-3,4-methylenedioxybenzene 

Downstream Products

• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 

Relevant articles and documents

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Facile Conversion of Alkenes into Alkyl Bromides via Reaction of Organoboranes with Bromine or Bromine Chloride

Organoboranes react with either bromine or bromine chloride in aqueous media to yield the corresponding alkyl bromides under surprisingly mild conditions.The reaction is ideal for the synthesis of functionally substituted organic bromides.Sodium bromide may be utilized as the bromine source via its in situ conversion to bromine chloride by using mild oxidizing agents.