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246611 Aldrich

Lithium diisopropylamide

97%

Synonym: LDA

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Properties

Related Categories Acids & Bases, Bases, Chemical Synthesis, Organic Bases, Synthetic Reagents More...
vapor density   >1 (vs air)
assay   97%
density   0.864 g/mL at 25 °C(lit.)

Description

Packaging

25, 100 g in glass bottle

Application

Hindered non-nucleophilic strong base widely used for the generation of carbanions,1 including the initiation of anionic polymerization.2

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.



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Lithium diisopropylamide

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Lithium diisopropylamide solution

1.0 M in THF/hexanes

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
F,C
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36/37/39-43-45
RIDADR 
UN 3393 4.2(4.3)
WGK Germany 
3
Flash Point(F) 
12.2 °F
Flash Point(C) 
-11 °C

Protocols & Articles

Articles

Acids and Bases

Acids and bases have been used by chemists for centuries, and are among the most fundamental reagents employed in synthetic organic chemistry. This Aldrich product line ranges from Brønsted and Lewis...
Chemfiles Volume 1 Article 3

Related Content

Molarity Calculator and Normality Calculator for Acids and Bases

The molarity calculator tool provides lab-ready directions describing how to prepare an acid or base solution of specified Molarity (M) or Normality (N) from a concentrated acid or base solution.  To...

Peer-Reviewed Papers

References

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1. Aldrichimica Acta 17, 80, (1984)

2. J. Polym. Sci. A Polym. Chem. 32, 2425, (1994)

Diisopropylammonium chloride: a ferroelectric organic salt with a high phase transition temperature and practical utilization level of spontaneous polarization. Fu DW, Zhang W, Cai HL, et al. Adv. Mater. 23(47), 5658-62, (2011)

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Lithium diisopropylamide-mediated ortholithiations: lithium chloride catalysis. Gupta L, Hoepker AC, Singh KJ, et al. J. Org. Chem. 74(5), 2231-3, (2009)

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Mechanisms of drug resistance reversal in Dox-resistant MCF-7 cells by pH-responsive amphiphilic polyphosphazene containing diisopropylamino side groups. Qiu L, Zheng C, and Zhao Q Mol. Pharm. 9(5), 1109-17, (2012)

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Lithium diisopropylamide: solution kinetics and implications for organic synthesis. Collum DB, McNeil AJ, and Ramirez A Angew. Chem. Int. Ed. Engl. 46(17), 3002-17, (2007)

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Metal enolates of alpha-CF3 ketones: theoretical guideline, direct generation, and synthetic use. Mikami K and Itoh Y Chem. Rec. 6(1), 1-11, (2006)

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Regioselective lithium diisopropylamide-mediated ortholithiation of 1-chloro-3-(trifluoromethyl)benzene: role of autocatalysis, lithium chloride catalysis, and reversibility. Hoepker AC, Gupta L, Ma Y, et al. J. Am. Chem. Soc. 133(18), 7135-51, (2011)

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Diisopropylamide and TMP turbo-Grignard reagents: a structural rationale for their contrasting reactivities. Armstrong DR, García-Alvarez P, Kennedy AR, et al. Angew. Chem. Int. Ed. Engl. 49(18), 3185-8, (2010)

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1,4-addition of lithium diisopropylamide to unsaturated esters: role of rate-limiting deaggregation, autocatalysis, lithium chloride catalysis, and other mixed aggregation effects. Ma Y, Hoepker AC, Gupta L, et al. J. Am. Chem. Soc. 132(44), 15610-23, (2010)

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Decoupling deprotonation from metalation: Thia-Fries rearrangement. Dyke AM, Gill DM, Harvey JN, et al. Angew. Chem. Int. Ed. Engl. 47(27), 5067-70, (2008)

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Lithium diisopropylamide-mediated enolization: catalysis by hemilabile ligands. Ramirez A, Sun X, and Collum DB J. Am. Chem. Soc. 128(31), 10326-36, (2006)

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Enantioselective modular synthesis of 2,4-disubstituted cyclopentenones by iridium-catalyzed allylic alkylation. Schelwies M, Dübon P, and Helmchen G Angew. Chem. Int. Ed. Engl. 45(15), 2466-9, (2006)

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Lithium diisopropylamide-mediated ortholithiation and anionic fries rearrangement of aryl carbamates: role of aggregates and mixed aggregates. Singh KJ and Collum DB J. Am. Chem. Soc. 128(42), 13753-60, (2006)

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Computational studies of lithium diisopropylamide deaggregation. Hoepker AC and Collum DB J. Org. Chem. 76(19), 7985-93, (2011)

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Lithium diisopropylamide-mediated lithiations of imines: insights into highly structure-dependent rates and selectivities. Liao S and Collum DB J. Am. Chem. Soc. 125(49), 15114-27, (2003)

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Interactions of diorganolead(IV) with 3-(2-thienyl)-2-sulfanylpropenoic acid and/or thiamine: chemical and in vitro and in vivo toxicological results. Casas JS, Castaño MV, Sánchez A, et al. Inorg. Chem. 49(5), 2173-81, (2010)

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Characterizing the Memory Effect on the amylose tris(3,5-dimethylphenyl) carbamate stationary phase. Putnam J and Guiochon G J. Chromatogr. A 1216(48), 8488-95, (2009)

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Autocatalysis in lithium diisopropylamide-mediated ortholithiations. Singh KJ, Hoepker AC, and Collum DB J. Am. Chem. Soc. 130(52), 18008-17, (2008)

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Lithium diisopropylamide solvated by hexamethylphosphoramide: substrate-dependent mechanisms for dehydrobrominations. Ma Y, Ramirez A, Singh KJ, et al. J. Am. Chem. Soc. 128(48), 15399-404, (2006)

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Mechanism of lithium diisopropylamide-mediated substitution of 2,6-difluoropyridine. Viciu MS, Gupta L, and Collum DB J. Am. Chem. Soc. 132(18), 6361-5, (2010)

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A novel hexanuclear silver(I) cluster containing a regular Ag6 ring with short Ag-Ag distances and an argentophilic interaction. Barreiro E, Casas JS, Couce MD, et al. Dalton Trans. 42(16), 5916-23, (2013)

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Synthesis of a four-coordinate titanium(IV) oxoanion via deprotonation and decarbonylation of complexed formate. Mendiratta A, Figueroa JS, and Cummins CC Chem. Commun. (Camb.) (27), 3403-5, (2005)

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A new mechanism for nucleophilic substitution at a thiophosphoryl centre revealed by the reaction of diisopropylamine with PSCl3. Harger MJ Chem. Commun. (Camb.) (22), 2863-5, (2005)

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Design, synthesis, and sustained-release property of 1,3-cyclic propanyl phosphate ester of 18β-glycyrrhetinic acid. Sun W, Peng W, Li G, et al. Chem. Biol. Drug Des. 77(3), 206-11, (2011)

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Application of colorimetric indicators and thermo-hand method to determine base permeation through chemical protective gloves. Vo E J. Occup. Environ. Hyg. 1(12), 799-805, (2004)

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α-Lithiation and electrophilic substitution of 1,4,4-trimethyl-3,4-dihydroquinolin-2-one. Sébastien B, Jérôme G, and Marie-Claude VM Molecules 15(11), 7742-9, (2010)

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Use of a directional spray system design to control respirable dust and face gas concentrations around a continuous mining machine. Goodman GV and Pollock DE J. Occup. Environ. Hyg. 1(12), 806-15, (2004)

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Merck 14,3196

Fieser 1,611 / Fieser 2,249 / Fieser 3,184 / Fieser 4,298 / Fieser 5,400 / Fieser 6,334 / Fieser 7,204 / Fieser 8,292 / Fieser 9,280 / Fieser 10,241 / Fieser 11,296 / Fieser 12,277 / Fieser 13,163 / Fieser 15,188 / Fieser 16,196 / Fieser 17,165

Corp MSDS 1 (1), 2154:C / Corp MSDS 1 (1), 2154:D / RegBook 1 (2), 3061:H / Structure Index 1, 485:C:6

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