5158-46-3

Basic information

• Product Name: METHYLZINC CHLORIDE
• Synonyms: METHYLZINC CHLORIDE;methylzinc chloride solution;METHYLZINC CHLORIDE, 2M SOLUTION IN TETR AHYDROFURAN;METHYLZINC CHLORIDE SOLUTION, ~2 M IN TH F;Methylzinc chloride solution 2.0 in THF;Methylzinc chloride, 2M solution in THF, AcroSeal;Methylzinc(II) chloride;Methylzinc chloride solution 2.0 M in THF
• CAS NO: 5158-46-3
• Molecular Formula: CH₃*Cl*Zn
• Molecular Weight: 115.88
• Product Categories: Alkyl;Organozinc Halides;Reike and Organozinc Reagents;Chemical Synthesis;Organometallic Reagents;Organozinc Halides;Rieke and Organozinc Reagents
• Mol File: 5158-46-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 67 °C
• Flash Point: −18 °F
• Appearance: Colorless to light yellow/Turbid Solution
• Density: 1.033 g/mL at 25 °C
• BRN: 969141
• CAS DataBase Reference: METHYLZINC CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLZINC CHLORIDE(5158-46-3)
• EPA Substance Registry System: METHYLZINC CHLORIDE(5158-46-3)

Safety Data

• Hazard Codes: F,Xi,C
• Statements: 11-19-36/37/38-40-37-34
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 1
• F: 10-21
• Hazardous Substances Data: 5158-46-3(Hazardous Substances Data)

Usage

Description

Methylzinc chloride is an organometallic compound that consists of a zinc atom bonded to a methyl group. It is known for its reactivity and is commonly used in various chemical reactions and processes.

Uses

Used in Pharmaceutical Industry:
Methylzinc chloride is used as a reagent for the synthesis of various pharmaceutical compounds. Its ability to participate in cross-coupling reactions with aryl fluorides and amino-heteroaryl chlorides makes it a valuable tool in the development of new drugs and medications.
Used in Chemical Synthesis:
Methylzinc chloride is used as a catalyst in Ni-catalyzed one-pot Negishi coupling reactions. This application allows for the efficient formation of carbon-carbon bonds, which are essential in the synthesis of complex organic molecules and materials.
Used in Material Science:
In the field of material science, methylzinc chloride can be utilized in the development of new materials with specific properties. Its involvement in cross-coupling reactions can lead to the creation of novel polymers, coatings, and other materials with potential applications in various industries.

Upstream product

• 42536-20-9 WCl(CO)2(NO)(P(C₆H₅)3)2 
• 544-97-8 dimethyl zinc(II) 

Downstream Products

• 1005-64-7 trans-1-phenyl-1-butene 
• 934-10-1 3-phenylbut-1-ene 
• 73275-02-2 10-Methyl-1,8-diphenyl-anthracene 
• 7042-34-4 ethyl c-α–methylcinnamate 
• 103240-63-7 (5-methylhexa-3,4-dienyl)benzene 
• 100516-58-3 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 84253-63-4 trans-5-methyl-1-phenyl-1,3,4-hexatriene 
• 21777-85-5 cyclopropylphenylethyne 
• 18712-30-6 [2‐(1‐methylcyclopropyl)ethynyl]benzene 
• 51384-73-7 (Z)-4-Phenyl-3-penten-2-one 
• 827-69-0 (E)-4-phenyl-3-penten-2-one 
• 503624-63-3 (1SR,2SR)-2-methyl-1,2-dihydronaphthalen-1-ol 
• 18699-87-1 2-methyl-3-nitropyridine 
• 896722-51-3 1-benzenesulfonyl-6-methyl-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

Synthesis and reactivity of a neutral tungsten(0) alkyl complex. Insertion of CO2 into the W-CH3 bond of trans,trans-W(CH3)(CO)2(NO)(PPh3)2 and the structural characterization of trans-W(η2-O2CCH3)(CO)(NO)(PPh 3)2

Reaction of trans,trans-WCl(CO)2(NO) (PPh3)2 (1) with CH3Li or (CH3)2Zn affords trans,trans-W-(CH3)(CO)2(NO)(PPH3)2 (2) in good yields. Treatment of 2 with DCl gives 1 and CH3D quantitatively. Reaction of 2 with carbon monoxide (2 atm, 80°C) results in a reversible substitution of CO for PPh3 to give mer-W(CH3)(CO)3(NO)(PPh3) (3). Carbon dioxide undergoes a 1,2-insertion reaction with 2 to give the monodentate acetate complex trans,trans-W[η1-OC(O)CH3](CO) 2(NO)(PPh3)2 (4), which reversibly loses CO on heating to yield the bidentate acetate derivative trans-W(η2-O2CCH3)(CO)(NO)(PPh 3)2 (5). Monoclinie prisms of 5 were grown from a dichloromethane/benzene solution and crystallized in space group P21L/a with Z = 4, a = 20.864 (5) A?, b = 9.729 (2) A?, c = 17.504 (4) A?, and β = 103.21 (1)°. An X-ray diffraction study at -91 ± 3°C showed that the acetate ligand is bound in an asymmetric fashion to the tungsten center and that the nitrosyl and carbonyl ligands are not substantially disordered. Salient metrical parameters of the structure include the following: W(1)-O(4) = 2.249 (5) A?, W(1)-O(5) = 2.217 (5) A?, O(4)-C(6) = 1.270 (10) A?, O(5)-C(6) = 1.302 (10) A?, W(1)-C(8) = 1.914 (8) A?, C(8)-O(9) = 1.171 (9) A?, W(1)-N(10) = 1.836 (7) A?, N(10)-O(11) = 1.203 (9) A?, and W(1)-N(10)-O(11) = 178.3 (6)°. The least-squares refinement converged to R(F) = 0.036 and RW(F) = 0.036 for 3518 unique data with F > 3σ(F).