lithiobis(propan-2-yl)amine

• ChemBase ID: 136732
• Molecular Formular: C6H14LiN
• Molecular Mass: 107.12306
• Monoisotopic Mass: 107.128629
• SMILES: [Li]N(C(C)C)C(C)C
• Canonical SMILES: CC(N(C(C)C)[Li])C
• InChI: InChI=1S/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1
• InChIKey: ZCSHNCUQKCANBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: lithiobis(propan-2-yl)amine
• IUPAC Traditional name: diisopropyl(lithio)amine
• Synonyms: LDA; Lithium diisopropylamide; Lithium diisopropylamide solution; 二异丙基氨基锂; 二异丙基氨基锂 溶液

Database IDs

• CAS Number: 4111-54-0
• EC Number: 223-893-0
• MDL Number: MFCD00064449
• Beilstein Number: 3655042
• PubChem SID: 24854817; 24872914; 24862259; 24857890; 162231002; 24882230; 24870688
• PubChem CID: 2724682

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.6576294
• LogD (pH = 7.4): 1.2812551
• Log P: 1.2994
• Molar Refractivity: 32.2282 cm^3
• Polarizability: 14.515772 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: brown liquid
• Boiling Point: 65 °C
• Flash Point: 10 °F; 10.4 °F; -12 °C; 2 °C; -23 °C; 33 °C; 35.6 °F; -9.4 °F; 91.4 °F
• Density: 0.81 g/mL at 20 °C; 0.812 g/mL at 25 °C; 0.836 g/mL at 25 °C; 0.864 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)

Safety Information

• European Hazard Symbols: Corrosive (C); Flammable (F); Nature polluting (N)
• UN Number: 2924; 3393; 3399
• German water hazard class: 3
• Hazard Class: 3; 4.2; 4.3
• Packing Group: 1; 2; 3
• Risk Statements: 11-14/15-34-50/53-65-67; 63-10-14/15-17-34-62; 63-11-14/15-17-19-34-37-50/53-62-65-67; 63-11-14/15-34-62; 63-14/15-17-62
• Safety Statements: 16-26-36/37/39-43-45; 26-36/37/39-43.11-45-60-61-62; 26-36/37/39-43-45; 26-36/37/39-43-45-61-62
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H250-H261-H304-H314-H335-H336-H361-H400-H411; H225-H250-H261-H304-H314-H335-H336-H361-H410; H225-H314-H361; H226-H314-H361; H250-H261-H314-H361
• GHS Precautionary statements: P210-P222-P231 + P232-P261-P273-P422; P210-P280-P305 + P351 + P338-P310; P222-P231 + P232-P280-P305 + P351 + P338-P310-P422; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 2924 3/PG 2; UN 2924 3/PG 3; UN 3393 4.2/PG 1; UN 3399 4.3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (NT); 97%
• Concentration: ~2 M in THF/heptane/ethylbenzene; 1.8 M in THF/heptane/ethylbenzene; 10 wt. % suspension in hexanes; 2.0 M in THF/heptane/ethylbenzene; 30 wt. % suspension in mineral oil
• Grade: technical
• Impurities: 3 wt. % diisopropylamine
• Linear Formula: [(CH3)2CH]2NLi

DETAILS

Sigma Aldrich - 470848

Packaging
75 g in Sure/Seal™

Sigma Aldrich - 361798

Application
Titanium-ate enolates prepared from ketones by Ti(OiPr)4 and LDA underwent efficient radical trifluoromethylation providing trifluoromethyl ketones in good yield.1 Used in directed ortho-lithiation of arylsulfonyloxazolidinones to prepare N-substituted saccharin analogs.2
Packaging
4×25, 100, 800 mL in Sure/Seal™

Sigma Aldrich - 296961

Packaging
75, 500 g in glass bottle

Sigma Aldrich - 246611

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

Sigma Aldrich - 494585

Application
Titanium-ate enolates prepared from ketones by Ti(OiPr)4 and LDA underwent efficient radical trifluoromethylation providing trifluoromethyl ketones in good yield.1 Also used in directed ortholithiation of arylsulfonyloxazolidinones to prepare N-substituted saccharin analogs.2
Packaging
1 L in Sure/Seal™
100 mL in Sure/Seal™

Sigma Aldrich - 62491

Caution
may contain precipitate