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593230

Sigma-Aldrich

Phenyllithium solution

1.9 M in dibutyl ether

Synonym(s):

PhLi

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About This Item

Empirical Formula (Hill Notation):
C6H5Li
CAS Number:
591-51-5
Molecular Weight:
84.04
Beilstein:
506502
MDL number:
MFCD00014254
UNSPSC Code:
12352103
PubChem Substance ID:
24881428
NACRES:
NA.22

Quality Level

100

concentration

1.9 M in dibutyl ether

density

0.835 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[Li]c1ccccc1

InChI

1S/C6H5.Li/c1-2-4-6-5-3-1;/h1-5H;

InChI key

NHKJPPKXDNZFBJ-UHFFFAOYSA-N

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Application

Phenyllithium solution can be used to synthesize:
  • 1-Acetyl-1′-diphenylphosphinoferrocene from ferrocenophane.
  • Ethyl 2-acetylimino-1-benzyl-6-bromo-4-phenyl-1,4-dihydroquinoline-3-carboxylate from ethyl 1-benzyl-6-bromo-2-imino-1,2-dihydroquinoline-3-carboxylate.
  • Ethyl 2-amino-1-benzoyl-6-bromo-4-phenyl-1,4-dihydroquinoline-3-carboxylate from (E)-ethyl 2-(acetylimino)-1-benzoyl-6-bromo-1,2-dihydroquinoline-3-carboxylate.

Signal Word

Danger

Hazard Statements

H226,H314,H335,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

77.0 °F - closed cup

Flash Point(C)

25 °C - closed cup

Certificates of Analysis (COA)

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The synthesis of ?-N, N-dimethyl-1?-diphenylphosphinoferrocenylethylamine and related ligands.
Butler I R, et al.
Canadian Journal of Chemistry, 61(1), 147-153 (1983)
The first synthesis of 2-amino-1, 4-dihydroquinolines.
Viault G, et al.
Tetrahedron, 65(49), 10149-10154 (2009)
Luka A Wright et al.
Dalton transactions (Cambridge, England : 2003), 44(16), 7230-7241 (2015-03-20)
The 2-(2′-aniline)-6-imine-pyridines, 2-(C6H4-2′-NH2)-6-(CMe=NAr)C5H3N (Ar = 4-i-PrC6H4 (HL1a), 2,6-i-Pr2C6H3 (HL1b)), have been synthesised via sequential Stille cross-coupling, deprotection and condensation steps from 6-tributylstannyl-2-(2-methyl-1,3-dioxolan-2-yl)pyridine and 2-bromonitrobenzene. The palladium(II) acetate N,N,N-pincer complexes, [{2-(C6H4-2′-NH)-6-(CMe=NAr)C5H3N}Pd(OAc)] (Ar = 4-i-PrC6H4 (1a), 2,6-i-Pr2C6H3 (1b)), can be prepared by

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