16466-97-0

Basic information

• Product Name: 1-PROPYNYLMAGNESIUM BROMIDE
• Synonyms: 1-PROPYNYLMAGNESIUM BROMIDE;1-propynylmagnesium bromide solution;1-PROPYNYLMAGNESIUM BROMIDE SOLUTION, ~0 .5 M IN THF;1-PROPYNYLMAGNESIUM BROMIDE, 0.5M SOLUTI ON IN TETRAHYDROFURAN;(1-Propynyl)bromomagnesium;1-Propynylbromomagnesium;Bromo(1-propynyl) magnesium;1-Propynylmagnesium bromide,0.5M solution inTHF
• CAS NO: 16466-97-0
• Molecular Formula: C₃H₃BrMg
• Molecular Weight: 143.26
• Product Categories: Alkynyl;Grignard Reagents;Organometallic Reagents;Chemical Synthesis;Grignard Reagents;Organometallic Reagents;Grignard Reagent
• Mol File: 16466-97-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 53.5 °C(Solv: methanol (67-56-1))
• Boiling Point: 65-67 °C
• Flash Point: <−30 °F
• Appearance: /
• Density: 0.941 g/mL at 25 °C
• Storage Temp.: 2-8°C
• Solubility: THF
• Stability: Moisture Sensitive, Pyrophoric
• BRN: 3929146
• CAS DataBase Reference: 1-PROPYNYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PROPYNYLMAGNESIUM BROMIDE(16466-97-0)
• EPA Substance Registry System: 1-PROPYNYLMAGNESIUM BROMIDE(16466-97-0)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14/15-34-40-37-19
• Safety Statements: 16-26-36/37/39-43-45
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 1
• F: 1-10
• Hazardous Substances Data: 16466-97-0(Hazardous Substances Data)

Usage

Description

1-PROPYNYLMAGNESIUM BROMIDE is an organomagnesium compound that consists of a magnesium atom bonded to a propynyl group and a bromide ion. It is a highly reactive reagent used in various chemical reactions and organic synthesis processes.

Uses

Used in Chemical Synthesis:
1-PROPYNYLMAGNESIUM BROMIDE is used as a reagent for the preparation of hydroxy enynes, which can undergo gold(I)-catalyzed benzannulation to form tetrahydronaphthalenes. This process is important in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Organic Transformations:
1-Propynylmagnesium Bromide Solution is a useful research reagent for chemical and organic transformations. It is particularly employed in the synthesis of lasonolides, a novel class of polyketides with significant biological activity. These compounds have demonstrated in vitro effectiveness against a variety of cancer cell lines, making them potential candidates for the development of new anticancer drugs.

InChI:InChI=1/C3H2Br.Mg/c1-2-3-4;/h3H2;/q;+1/rC3H2BrMg/c4-2-1-3-5/h2H2/q+1

Upstream product

• 74-99-7 prop-1-yne 
• 74-96-4 ethyl bromide 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 184577-40-0 (+/-)-1-phenylhex-4-yn-3-ol 
• 764-01-2 methyl propargyl alcohol 
• 10420-91-4 hexadiyne-1,4 
• 84443-10-7 3-hydroxy-2,2-dimethyl-5-phenyl-3-(1-propynyl)-2,3-dihydrofuran 
• 590-93-2 2-Butynoic acid 
• 905717-16-0 (S)-tert-butyl 4-oxo-1-phenylhept-5-yn-2-ylcarbamate 
• 636598-32-8 4-hydroxy-3-phenylhept-5-ynaldehyde dimethyl acetal 
• 92956-83-7 Methyl α-Phenyl-α-(1-propynyl)glycolate 
• 1214914-44-9 (7aS,11S,13R)-11-(propyn-1-yl)-13-phenyl-7a,8,10,11-tetrahydro-9H,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine 

Relevant articles and documents

Palladium(II)-catalyzed dicarboxymethylation of chiral allylic alcohols: Chirality transfer affording optically active diesters containing three contiguous chiral centers

This manuscript describes the extension of Stille's palladium-catalyzed olefin dicarbonylation reaction to chiral allylic alcohols with chirality transfer to afford the corresponding chiral alcohol functionalized with bis-carbomethoxy esters, containing three contiguous chiral centers, in good to excellent diastereoselectivities (78-98%).

Poly(dimethylsilmethylene) methylacetylene compound and a method for the preparation thereof

The invention provides a novel organosilicon compound poly(dimethylsilmethylene) methylacetylene compound of the formula MeC C--SiMe2 --CH2 --SiMe2)n Me, in which Me is a methyl group and n is a positive integer of 1 to 25. The compound is synthesized by reacting a propynylmagnesium halide of the formula MeC CMgX, in which X is a halogen atom, or (propynyl dimethylsilyl)methylmagnesium chloride of the formula MeC C--SiMe2 --CH2 MgCl with chloromethyl dimethyl chlorosilane in the presence of metallic magnesium and hydrolyzing the reaction product. Specifically, 1-propynyl-1,1,3,3,3-pentamethyl disilmethylene, i.e. the inventive compound with n=1, is synthesized by reacting (propynyl dimethylsilyl)methylmagnesium chloride with trimethyl chlorosilane.