17680-04-5

Basic information

• Product Name: 3,4-(METHYLENEDIOXY)PHENYLMAGNESIUM BROMIDE
• Synonyms: 3,4-(METHYLENEDIOXY)PHENYLMAGNESIUM BROMIDE;3,4-Methylenedioxyphenylmagnesium;3,4-(METHYLENEDIOXY)PHENYLMAGNESIUM BROM , 1.0M SOLUTION IN TOLUENE/THF (50:50);3,4-(methylenedioxy)phenylmagnesium bromide solution;3,4-(Methylenedioxy)phenylMagnesiuM broMide, 0.8M solution in toluene/THF (50:50), AcroSeal;3,4-(Methylenedioxy)phenylMagnesiuM broMide, 1.0M solution in THF/toluene (1/1), J&KSeal;3,4-(Methylenedioxy)phenylmagnesium bromide solution 1.0 M in THF: toluene (1:1);3,4-(Methylenedioxy)phenylmagnesium bromide, 0.5M THF
• CAS NO: 17680-04-5
• Molecular Formula: C₇H₅BrMgO₂
• Molecular Weight: 225.32
• Product Categories: Aryl;Grignard Reagents;Organometallic Reagents
• Mol File: 17680-04-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 173°C at 760 mmHg
• Flash Point: 14 °F
• Appearance: Colorless to yellow/Liquid
• Density: 1.04 g/mL at 25 °C
• Vapor Pressure: 1.73mmHg at 25°C
• Water Solubility: It reacts with water.
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: 3,4-(METHYLENEDIOXY)PHENYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-(METHYLENEDIOXY)PHENYLMAGNESIUM BROMIDE(17680-04-5)
• EPA Substance Registry System: 3,4-(METHYLENEDIOXY)PHENYLMAGNESIUM BROMIDE(17680-04-5)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34-48/20-63-65-67-40-37-19-14
• Safety Statements: 26-36/37/39-45-62-16
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 2
• HazardClass: 3
• Hazardous Substances Data: 17680-04-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to amber liquid

Uses

3,4-(Methylenedioxy)phenylmagnesium bromide is used as an organic chemical synthesis intermediate.

InChI:InChI=1/C7H5O2.BrH.Mg/c1-2-4-7-6(3-1)8-5-9-7;;/h1,3-4H,5H2;1H;/q-1;;+2/p-1

Upstream product

• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 7439-95-4 magnesium 

Downstream Products

• 240122-42-3 4-benzo[1,3]dioxol-5-yl-2,3-bis-benzyloxymethyl-4-hydroxy-N,N-dimethyl-butyramide 
• 120040-58-6 Benzo[1,3]dioxol-5-yl-((R)-5-benzyloxy-2,5-dihydro-furan-3-yl)-methanol 
• 120040-58-6 Benzo[1,3]dioxol-5-yl-((S)-5-benzyloxy-2,5-dihydro-furan-3-yl)-methanol 
• 139025-50-6 (3R*,4aR*,11S*,11aR*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-Δ¹⁽²⁾-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 139039-77-3 (2S*,3R*,4aR*,11S*,11aR*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-2-hydroxy-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 139025-51-7 (2R*,3R*,4aR*,11S*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-2-chloro-Δ^1(11a)-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 139025-47-1 (3R*,4aR*,11S*,11aR*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-2-oxo-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 144609-87-0 (3R*,4aR*,11S*,11aR*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-1-chloro-Δ¹⁽²⁾-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 139025-46-0 (2S*,3R*,4aR*,11S*,11aR*)-5,11a-cis-11,11a-syn-2,3-O-benzylidene-2,3-dihydroxy-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 139025-48-2 (3R*,4aR*,11aR*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-2-oxo-8,9-(methylenedioxy)-Δ^1(11a)-5,11-methanomorphanthridine 
• 144609-85-8 (3R*,4aR*,11R*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-2,2-dimethoxy-Δ^1(11a)-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 144609-84-7 (2S*,3R*,4aR*,11S*,11aR*)-5,11a-cis-11,11a-syn-3-acetoxy-2-(benzyloxy)-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 144609-83-6 (2S*,3R*,4aR*,11S*,11aR*)-5,11a-cis-11,11a-syn-2-acetoxy-3-(benzyloxy)-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 139039-79-5 (2S*,3R*,4aR*,11S*,11aR*)-5,11a-cis-11,11a-syn-3-(benzyloxy)-2-(mesyloxy)-8,9-(methylenedioxy)-5,11-methanomorphanthridine 

Relevant articles and documents

Chromium(II)-Catalyzed Diastereoselective and Chemoselective Csp2-Csp3 Cross-Couplings Using Organomagnesium Reagents

A simple protocol for performing chromium-catalyzed highly diastereoselective alkylations of arylmagnesium halides with cyclohexyl iodides at ambient temperature has been developed. Furthermore, this ligand-free CrCl2 enables efficient electrophilic alkenylations of primary, secondary, and tetiary alkylmagnesium halides with readily available alkenyl acetates. Moreover, this chemoselective C-C coupling reaction with stereodefined alkenyl acetates proceeds in a stereoretentive fashion. A wide range of functional groups on alkyl iodides and alkenyl acetates are well tolerated, thus furnishing functionalized Csp2-Csp3 coupling products in good yields and high diastereoselectivity. Detailed mechanistic studies suggest that the in situ generated low-valent chromium(I) species might be the active catalyst for these Csp2-Csp3 cross-couplings.

Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates

Nickel-catalyzed enantioselective cross-couplings between symmetric cyclic sulfates and aromatic Grignard reagents are described. These reactions are effective with a broad range of substituted cyclic sulfates and deliver products with asymmetric tertiary carbon centers. Mechanistic experiments point to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate.

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