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Sigma-Aldrich

Phenyllithium solution

Phenyllithium solution
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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
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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.[1]
  • 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.[2]
  • 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.[2]

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6042
STBL3897
SHBR6041
SHBQ8897
SHBQ2207

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The first synthesis of 2-amino-1, 4-dihydroquinolines.
Viault G, et al.
Tetrahedron, 65(49), 10149-10154 (2009)
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)
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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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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