butyllithium

• ChemBase ID: 128505
• Molecular Formular: C4H9Li
• Molecular Mass: 64.05526
• Monoisotopic Mass: 64.08642984
• SMILES: CCCC[Li]
• Canonical SMILES: [Li]CCCC
• InChI: InChI=1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3
• InChIKey: MZRVEZGGRBJDDB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: butyllithium
• IUPAC Traditional name: butyllithium
• Synonyms: n-BuLi; Butyl lithium; Butyllithium solution; Lithium-1-butanide; n-Butyllithium solution; n-Butyllithium, 1.6M in hexane; Secondary Butyllithium; sec-Butyllithium; NBL; BuLi; 1-lithiobutane; N-Butyllithium; U - Chromosorb® W; sec-Butyllithium, 1.3M in cyclohexane; n-Butyllithium, 2.2M in hexane; n-Butyllithium, 2.5M in hexane; 1-丁基锂; 正丁基锂, 1.6M 己烷溶液, 可重封的瓶盖包装; 正丁基锂, 2.2M正己烷溶液; 仲丁基锂; Chromosorb® W; 仲丁基锂, 1.3M环己烷溶液, 氩气下可重封的ChemSeal™瓶包装; 正丁基锂, 2.2M 己烷溶液, 氩气下可重封的ChemSeal™瓶包装; 正丁基锂, 2.5M 己烷溶液 (非可重封的瓶盖)

Database IDs

• CAS Number: 68855-54-9; 598-30-1; 109-72-8
• EC Number: 209-927-7; 203-698-7
• MDL Number: MFCD00009323; MFCD00009414
• Beilstein Number: 3587206; 1209227
• PubChem SID: 24851205; 162222812; 24858234; 24853832; 24858232; 24853833; 24852017; 24852012
• PubChem CID: 61028
• CHEBI ID: 51469
• Chemspider ID: 10254339
• Wikipedia Title: N-Butyllithium

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.4875
• LogD (pH = 7.4): 1.4875
• Log P: 1.4875
• Molar Refractivity: 19.3179 cm^3
• Polarizability: 9.328749 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Diethyl ether, cyclohexane; Reaction in water
• Apperance: colorless liquid; unstable; usually obtained; as solution; Liquid; orange-red liquid; yellow liquid
• Melting Point: -76 °C (<273 K)
• Boiling Point: 80 °C; decomposes
• Flash Point: -.4 °F; 10.4 °F; -12 °C; -14.8 °F; -17°C(1°F); -18 °C; -18°C(-0.4°F); 21 °F; -21°C(-5°F); -21°C(-7°F); -22 °C; -22°C(-8°F); -26 °C; 39.2 °F; 4 °C; -49 °C; -56.2 °F; -6 °C; -7.6 °F
• Density: 0.658 g/mL at 25 °C; 0.68 g/cm3, solvent defined; 0.68 g/mL at 25 °C; 0.680; 0.693; 0.693 g/mL at 25 °C; 0.71 g/mL at 20 °C; 0.750; 0.761 g/mL at 25 °C; 0.775 g/mL at 25 °C; 0.83 g/mL at 20 °C; 0.849 g/mL at 25 °C
• pKa: 50

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); Highly flammable (F+); Nature polluting (N); X
• UN Number: 3394; 3399; UN3394
• German water hazard class: 2
• Hazard Class: 4.2; 4.3
• Packing Group: 1; I
• Risk Statements: 11-14/15-17-34-48/20-51/53-62-65-67; 11-14/15-17-34-48/20-62-51/53-65-67; 11-14/15-17-34-48/20-63-65-67; 11-14/15-17-34-50/53-65-67; 11-14/15-17-34-51/53-65-67; 11-14/15-34-48/20-51/53-62-65-67; 11-14/15-34-48/20-62-51/53-65-67; 11-14/15-34-50/53-65-67; 12-14/15-17-34-48/20-62-51/53-65-67; 14/15-17-34-48/20-62-51/53; 14/15-17-34-50/53-65-67; 63-11-14/15-17-34-48/20-65-67
• Safety Statements: 16-23-26-36/37/39-43-45-57; 16-26-36/37/39-43-45-62; 26-36/37/39-43.11-45-62; 26-36/37/39-43-45-61-62; 7/8-16-20-23-26-30-33-36/37/39-43-45-57-60; 7/8-16-26-36/37/39-43-45-61; 9-16-23-26-36/37/39-43-45-57; 9-16-26-36/37/39-43-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• Main Hazard: pyrophoric (inflames in air),; decomposes to corrosive LiOH
• NFPA704:
  

  4

  3

  3

  W
• GHS Hazard statements: H224-H250-H260-H252-H304-H314-H318-H400-H410-H336; H224-H250-H260-H252-H314-H318-H361-H373-H411-H401; H225-H250-H260-H252-H304-H361-H373-H314-H336-H411; H225-H250-H260-H304-H314-H336-H361f-H373-H411; H225-H250-H260-H304-H314-H336-H411; H225-H250-H261-H304-H314-H336-H361d-H373; H225-H250-H261-H304-H314-H336-H361f-H373-H411; H225-H250-H261-H304-H314-H336-H410; H250-H260-H304-H314-H318-H400-H410-H336; H250-H260-H304-H361-H373-H314-H336-H411-H401; H250-H261-H304-H314-H336-H410
• GHS Precautionary statements: P210-P222-P223-P231 + P232-P370 + P378-P422; P210-P222-P231 + P232-P261-P273-P422; P210-P222-P231 + P232-P261-P280-P422; P210-P222-P231+P232-P303+P361+P353-P305+P351+P338-P501A; P210-P222-P301+P310-P303+P361+P353-P305+P351+P338-P501A; P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P422A-P501A; P222-P231 + P232-P261-P273-P280-P422; P280-P273-P305+P351+P338-P309+P311-P370+P378I-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3394 4.2/PG 1; UN 3399 4.3/PG 1
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: 12% (ca 1.4M) in cyclohexane/hexane, packed in resealable septum seal bottle
• Concentration: ~1.6 M in hexanes; 1.3M in cyclohexane; 1.4 M in toluene; 1.6 M in hexanes; 1.6M in hexane; 10.0 M in hexanes; 2.0 M in cyclohexane; 2.0 M in pentane; 2.2M in hexane; 2.5 M in hexanes; 2.5 M in toluene; 2.5M in hexane; 2.7 M in heptane
• Grade: technical grade
• Packaging: packaged in resealable septum cap bottle; packaged under Argon in resealable ChemSeal? bottles
• Shelf Life: (limited shelf life)
• Linear Formula: CH3(CH2)3Li

DETAILS

Sigma Aldrich - 20159

Caution
a precipitate of lithium hydride can form on longer storage
Packaging
100, 500 mL in Sure/Seal™

Sigma Aldrich - 710776

Packaging
100, 800 mL in Sure/Seal™

Sigma Aldrich - 186171

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Other Notes
May contain trace amounts of LiCl.
Packaging
1 L in Sure/Seal™
View returnable container options.
4×25, 50, 100, 800 mL in Sure/Seal™
8, 18 L in Kilo-Lab™

Sigma Aldrich - 302104

Packaging
1 L in Sure/Seal™
100, 800 mL in Sure/Seal™

Sigma Aldrich - 20164

Caution
a precipitate of lithium hydride can form on longer storage
Packaging
100, 500 mL in Sure/Seal™

Sigma Aldrich - 230715

Packaging
4×25, 100, 800 mL in Sure/Seal™

Sigma Aldrich - 230707

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Packaging
4×25, 100, 800 mL in Sure/Seal™
8, 18 L in Kilo-Lab™
View returnable container options.

Sigma Aldrich - 302120

Packaging
4×25, 100, 800 mL in Sure/Seal™

Sigma Aldrich - 20159

Caution
a precipitate of lithium hydride can form on longer storage
Packaging
100, 500 mL in Sure/Seal™

Sigma Aldrich - 20160

Caution
a precipitate of lithium hydride can form on longer storage

REFERENCES

• There are also many examples throughout this catalog. For a useful monograph with many practical procedures, see: B. J. Wakefield, Organolithium Methods, Academic Press, N.Y. (1988).
• Numerous examples of the use of n-BuLi are to be found in Org. Synth. Coll., 7 (1990), 8, (1993), 9 (1998) and in subsequent annual volumes.
• See also N,N,N',N'-Tetramethylethylenediamine, A12536.
• Widely used base for directed metallation reactions. For use in combination with TMEDA for ortho-lithiation of an N,N-dialkyl benzamide, and of 1-Boc-indoline at the 7-position, see: Org. Synth. Coll., 8, 124, 559 (1998).
• With KO-t-Bu forms a "superbasic" reagent (Schlosser's Base): Angew. Chem. Int. Ed., 12, 508 (1973). For use in the conversion of ɑ?-unsaturated acetals to alkoxy dienes, see: J. Org. Chem., 59, 3494, 5458 (1994).
• Limited shelf life. During storage white precipitate of LiH may form.
• Supplied in septum cap bottle.