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

Uses

Methylzinc chloride can be used in: Ni-catalyzed one-pot Negishi coupling with amino-heteroaryl chlorides.Cross-coupling with aryl fluorides in the presence of a nickel catalyst.

Upstream product

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

Downstream Products

• 98-83-9 isopropenylbenzene 
• 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 
• 2528-02-1 methyl 3-bromo-2-methylfuran-5-carboxylate 
• 211751-33-6 Diethyl-carbamic acid 4-methoxy-3-methyl-phenyl ester 
• 529-19-1 2-Methylbenzonitrile 
• 604-53-5 1,1'-bisnaphthalene 

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).