Lithium bis(trimethylsilyl)amide (LHMDS) - 1.5 M in THF , CAS No.4039-32-1

CAS: 4039-32-1 Cat. No.: L432695 Molecular Weight: 167.32 Beilstein Registry Number: 3567910 EC Number: 223-725-6

GRADE & PURITY 1.5 M in THF

Synonyms

EINECS 223-725-6 | A825085 | Lithiobis(trimethylsilyl)amide; Lithiohexamethyldisilazane; Lithium bis(trimethylsilyl)amide; Lithium bis(trimethylsilyl)amide(1-) | lithium bis (trimethylsilyl)amide | lithium bis trimethylsilyl amide | BCP21718 | Lithium hex

Storage

Room temperature,Argon charged

Shipped In

Normal

Overview

Lithium bis(trimethylsilyl)amide is commonly used in organic synthesis as a non-nucleophilic strong Bronsted base. It is soluble in most nonpolar solvents such as aromatic hydrocarbons, hexanes, and THF.
Application
Lithium bis(trimethylsilyl)amide can be used as a reagent:     
In the deprotonation and nucleophilic difluoromethylation reactions.
3-methoxy substituted dihydropyrrole derivatives by reacting with aldehydes and lithiated methoxyallene via in situ formations of N-trimethylsilylated imines.  
In Darzens condensation and directed aldol condensation reactions.      
To synthesize poly(N-octyl-p-benzamide)s by chain-growth polycondensation of 4-octylaminobenzoic acid methyl ester.

Specifications

Synonyms

EINECS 223-725-6 | A825085 | Lithiobis(trimethylsilyl)amide; Lithiohexamethyldisilazane; Lithium bis(trimethylsilyl)amide; Lithium bis(trimethylsilyl)amide(1-) | lithium bis (trimethylsilyl)amide | lithium bis trimethylsilyl amide | BCP21718 | Lithium hex

Specifications & Purity

1.5 M in THF

Storage

Room temperature, Argon charged

Shipped In

Normal

Names and Identifiers

• Canonical Smiles: [Li+].C[Si](C)(C)[N-][Si](C)(C)C
• IUPAC Name: lithium;bis(trimethylsilyl)azanide
• InChIKey: YNESATAKKCNGOF-UHFFFAOYSA-N
• INCHI: 1S/C6H18NSi2.Li/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
• Isomeric SMILES: [Li+].C[Si](C)(C)[N-][Si](C)(C)C
• WGK Germany: 3
• Molecular Weight: 167.32
• Beilstein: 3567910
• Reaxy-Rn: 8136861
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8136861&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organometallic compounds
    • Class Organometalloid compounds
      • Subclass Organosilicon compounds
        • Level5 Organoheterosilanes
          • Level6 Trialkylheterosilanes

• Kingdom: Organic compounds
• Superclass: Organometallic compounds
• Class: Organometalloid compounds
• Subclass: Organosilicon compounds
• Intermediate Tree Nodes: Organoheterosilanes
• Direct Parent: Trialkylheterosilanes
• Alternative Parents: Organic metalloid salts Organic lithium salts N-silyl compounds Organic nitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Trialkylheterosilane - N-silyl compound - Organic lithium salt - Organic alkali metal salt - Organic metalloid salt - Organic nitrogen compound - Hydrocarbon derivative - Organic salt - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as trialkylheterosilanes. These are organoheterosilanes, bearing a silicon atom linked to three alkyl groups and one heteroatom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Air sensitive；Moisture sensitive
• Flash Point(°F): 1.4℉
• Flash Point(°C): -17℃
• Molecular Weight: 167.400 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 167.114 Da
• Monoisotopic Mass: 167.114 Da
• Topological Polar Surface Area: 1.000 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 80.900
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

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