109-72-8

Basic information

• Product Name: n-Butyllithium
• Synonyms: butyl-lithiu;Lithiumn-butyl;LITHIUM-1-BUTANIDE;LITHIUMBUTYL;BUTYLLITHIUM;N-BULI;N-BUTYLLITHIUM;Butyllithium solution
• CAS NO: 109-72-8
• Molecular Formula: C₄H₉Li
• Molecular Weight: 64.06
• EINECS: 203-698-7
• Product Categories: Metal Compounds;Organometallics;Alkyl Metals;Classes of Metal Compounds;Grignard Reagents & Alkyl Metals;Li (Lithium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;metal alkyl;Alkyl;Chemical Synthesis;Organic Bases;Organolithium;Organometallic Reagents;Synthetic Reagents
• Mol File: 109-72-8.mol

Chemical Properties

• Melting Point: -95 °C
• Boiling Point: 80 °C
• Flash Point: 10 °F
• Appearance: yellow/liquid
• Density: 0.68 g/mL at 20 °C
• Storage Temp.: 2-8°C
• Solubility: Miscible with diethyl ether and cyclohexane.
• Water Solubility: vigorous reaction
• Sensitive: Air & Moisture Sensitive
• BRN: 1209227
• CAS DataBase Reference: n-Butyllithium(CAS DataBase Reference)
• NIST Chemistry Reference: n-Butyllithium(109-72-8)
• EPA Substance Registry System: n-Butyllithium(109-72-8)

Safety Data

• Hazard Codes: F,C,N
• Statements: 14/15-17-34-48/20-51/53-62-65-67-63-35-11-15-50/53-66
• Safety Statements: 6-9-16-26-36/37/39-45-61-62-6A-46-43B-43-60-33-29-5
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 3
• F: 3-10
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: I
• Hazardous Substances Data: 109-72-8(Hazardous Substances Data)

Usage

Chemical Description

n-butyllithium is an organolithium compound, and indene is an organic compound with a bicyclic structure.

Uses

Used in Pharmaceutical Industry:
n-Butyllithium is used as a pharmaceutical intermediate for the synthesis of anionic polymerization initiators, liquid crystal monomers, and as a catalyst in pesticide production.
Used in Rubber Industry:
n-Butyllithium is used as a polymerization initiator in the production of elastomers like polybutadiene and styrene-butadiene-styrene, which are versatile diene rubbers.
Used in Organic Syntheses:
n-Butyllithium is widely used in organic syntheses, especially for growing carbon chains. It is a staple laboratory product in reactions such as metallization, direct metallization, nucleophilic addition and substitution, and halogen-metal replacement.
Used in Fragrance and Liquid Crystal Materials Industries:
n-Butyllithium is utilized in the production of fragrances and liquid crystal materials due to its properties as a chemical product intermediate and catalyst.
Used in Laboratory Research:
n-Butyllithium is a common reagent in laboratory research for its strong nucleophilic properties and its ability to initiate various chemical reactions.

Identifying Procedures

N-Butyllithium must be calibrated through single titration as follows: 1) Titration solution: 1mol/L SEC butanol/dimethylbenzene solution (butanol and dimethylbenzene must be dried with an activated 5A molecular sieve) 2) Indicator: 2,2’-dipyridine 3) Solvent: dimethylbenzene (must be dried with an activated 5A molecular sieve). 4) Operation method: Under the protection of argon, add magneton, 20ml dimethylbenzene and a small amount of indicator into a 100ml 3-lipped bottle with a tipping plug. Then use a precisely marked 2ml injector to swiftly transfer 2ml N-Butyllithium into the bottle (the air in the injector must be replaced with argon, which must then be expelled when collecting the N-Butyllithium; fill and drain the injector in the N-Butyllithium multiple times to prevent any water or air from remaining in the injector). The system should turn a purplish red. Then, wash, dry, and rinse the same injector with titration solution 2-3 times (to prevent any change in the amount added) and titrate the solution until the system turns yellow, and cease titration. 5) Repeat titration once; if the percent error between the two times is within 2%, the result can be regarded as correct. 6) Titration result: titration solution (ml)/2 to obtain N-Butyllithium concentration.

Warnings and precautions

1) N-Butyllithium is extremely combustible when in contact with air; when measuring, the needle of the injector will eject sparks. 2) The entire process must be protected by argon for safety precaution. 3) If N-Butyllithium catches fire, it must be extinguished with sand, which must be placed within arm’s reach at all times. When preparing and using N-Butyllithium, do not operate alone in case of emergency

Explosivity characteristics

May explode in combination with phenylethylene

Flammability characertistics

Combusts in air at a concentration abover 20%; combusts upon contact with water and carbon dioxide; flammable when in contact with heat and open flame.

Storage

Store in ventilated, cool and dry spaces; must be waterproof and carbon dioxide-proof.

Extinguisher

Dry powder

Preparation

Industrially, n-butyllithium is produced by the reaction of n-butyl chloride with lithium metal dispersion in various hydrocarbon solvents. Hexane is the most commonly used solvent. Up to one-half of the lithium is replaced with sodium in order to lower the cost of the butyllithium and increase the reactivity of the dispersion. The reaction is carried out below the boiling point of the solvent.The laboratory procedure is essentially the same except that pentane and diethyl ether are two of the more popular solvents. The preparation runs smoothly in ether at lower temperatures but the product must either be used immediately or kept refrigerated due to the rapid cleavage of ether by n-butyllithium.

Flammability and Explosibility

The risk of fire or explosion on exposure of butyllithium solutions to the atmosphere depends on the identity of the organolithium compound, the nature of the solvent, the concentration of the solution, and the humidity. t-Butyllithium solutions are the most pyrophoric and may ignite spontaneously on exposure to air. Dilute solutions (1.6 M, 15% or less) of n-butyllithium in hydrocarbon solvents, although highly flammable, have a low degree of pyrophoricity and do not spontaneously ignite. Under normal laboratory conditions (25 °C, relative humidity of 70% or less), solutions of -20% concentration will usually not ignite spontaneously on exposure to air. More concentrated solutions of n-butyllithium (50 to 80%) are most dangerous and will immediately ignite on exposure to air. Contact with water or moist materials can lead to fires and explosions, and the butyllithiums also react violently with oxygen.

storage

In particular, butyllithium should be stored and handled in areas free of ignition sources, and containers of butyllithium should be stored under an inert atmosphere. Work with butyllithium should be conducted in a fume hood under an inert gas such as nitrogen or argon. Safety glasses, impermeable gloves, and a fire-retardant laboratory coat are required.

Incompatibilities

The butyllithiums are extremely reactive organometallic compounds. Violent explosions occur on contact with water with ignition of the solvent and of the butane produced. t-Butyllithium will ignite spontaneously in air. The butyllithiums ignite on contact with water, carbon dioxide, and halogenated hydrocarbons. The butyllithiums are incompatible with acids, halogenated hydrocarbons, alcohols, and many other classes of organic compounds.

Waste Disposal

Excess butyllithium solution can be destroyed by dilution with hydrocarbon solvent to a concentration of approximately 5 wt %, followed by gradual addition to water with vigorous stirring under an inert atmosphere. Alternatively, the butyllithium solution can be slowly poured (transfer by cannula for s- or tbutyllithium) into a plastic tub or other container of powdered dry ice. The residues from the above procedures and excess butyllithium should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.

InChI:InChI=1/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/rC4H9Li/c1-2-3-4-5/h2-4H2,1H3

Synthetic route

n-butyllithium (109-72-8) + C5H4FeC5H3(CH(CH3)CH2CH(C5H5))(C(H)C12H8) → C5H4FeC5H3(CH(CH3)CH2CH(C5H4))(CC12H8)(2-)*2Li(1+)=C5H4FeC5H3(CHCH3CH2CHC5H4Li)(CLiC12H8)

Conditions	Yield
In toluene; pentane (Ar); 1.6 M n-BuLi in pentane was added at 0°C to soln. of ferrocene in toluene, stirred for 6 h at room temp.; filtered, washed with pentane, dried in vac., elem. anal.;	93%

n-butyllithium (109-72-8) + (CH3)2Ge(C5(CH3)4H)(C5H5) (384378-22-7) → 2Li(1+)*(CH3)2Ge(C5(CH3)4)(C5H4)(2-)=Li2[(CH3)2Ge(C5(CH3)4)(C5H4)]

Conditions	Yield
In diethyl ether under N2, Schlenk technique; mixing at -78°C (BuLi in hexane), mixt. was warmed to room temp. and stirred for 15 h; solvent was removed, ppt. was washed with hexane, dried under vac.; elem. anal.;	92%

n-butyllithium (109-72-8) + dimethyl sulfide borane (13292-87-0) → lithium borohydride + lithium [butyl(trihydrido)borate] (82111-98-6) + LiHB(s-Bu)3 (67335-72-2)

Conditions	Yield
In tetrahydrofuran; hexane; dichloromethane under dry N2, hexane soln. of BuLi cooled to -20°C, H3B-SMe2 added to vigorously stirred soln. within 60 min, 2 hours later all volatiles removed in vac.; material suspended in hexane, THF added to form soln., solvents removed, oily material dissolved in CH2Cl2, pentane added to separate LiBH4, repetition of procedure gave slightly purer product;	A n/a B 91% C n/a

n-butyllithium (109-72-8) + bis(tetramethylcyclopentadienyl)dimethylgermanium (134939-44-9) → 2Li(1+)*(CH3)2Ge(C5(CH3)4)2(2-)=Li2[(CH3)2Ge(C5(CH3)4)2]

Conditions	Yield
In diethyl ether under N2, Schlenk technique; mixing at -78°C (BuLi in hexane), mixt. was warmed to room temp. and stirred for 15 h; solvent was removed, ppt. was washed with hexane, dried under vac.; elem. anal.;	91%

n-butyllithium (109-72-8) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + trimethylamine borane (1231953-83-5) → lithium borohydride + Li(tetramethylethylenediamine)BH3(benzyl)

Conditions	Yield
In hexane; toluene byproducts: (CH3)3N; under dry N2, hexane soln. of n-BuLi added to soln. of TMEDA in toluene, after 30 min added H3B-NMe3, heated for 1 h to reflux, soln. kept for 3 d at -25°C; elem. anal.;	A 10% B 90%

n-butyllithium (109-72-8) + (CH3)2Ge(C5(CH3)4H)(C5H4CH3) (478038-85-6) → 2Li(1+)*(CH3)2Ge(C5(CH3)4)(C5H3CH3)(2-)=Li2[(CH3)2Ge(C5(CH3)4)(C5H3CH3)]

Conditions	Yield
In diethyl ether under N2, Schlenk technique; mixing at -78°C (BuLi in hexane), mixt. was warmed to room temp. and stirred for 15 h; solvent was removed, ppt. was washed with hexane, dried under vac.; elem. anal.;	90%

aluminium trichloride (7446-70-0) + n-butyllithium (109-72-8) + N-(2,6-bis(isopropyl)phenyl)-5-tert-butylpyrrolylaldimine (443890-22-0) → [N-(2,6-bis(isopropyl)phenyl)-5-tert-butylpyrrolylaldiminato]aluminium(III) dichloride (443890-21-9)

Conditions	Yield
In toluene under N2, Schlenk techques; n-BuLi was added to the soln. of ligand at -35°C, mixt. was warmed to room temp., stirred for 2 h, soln. was cooled to -35°C again and added to suspn. of AlCl3 with stirring,mixt. stirred at room temp. for 36 h; mixt. was filtered, washed with toluene, filtrate was concd., cooled to -35°C; elem. anal.;	88%

n-butyllithium (109-72-8) + dimethyl sulfide borane (13292-87-0) → lithium borohydride + lithium [butyl(trihydrido)borate] (82111-98-6) + n-butylborane-dimethyl sulfide + Li{B(n-C4H9)4} (15243-31-9)

Conditions	Yield
In tetrahydrofuran; hexane under dry N2, hexane soln. of n-BuLi cooled to -20°C, H3B-SMe2 added to vigorously stirred soln. within 4 h, resulting suspn. stirred overnight; filtered, detected by NMR;	A 13% B 87% C n/a D n/a
In hexane; dichloromethane; pentane under dry N2, hexane soln. of BuLi cooled to -20°C, H3B*SMe2 added to vigorously stirred soln. within 4 h, stirred overnight, solid filtered, solvent from filtrate removed; residue treated with 1:1 mixt. of CH2Cl2 and pentane, not isolated, detected in CH2Cl2-rich phase by NMR;

n-butyllithium (109-72-8) + buta-1,3-dien-2-yltin trichloride (519005-12-0, 439099-43-1) → buta-1,3-dien-2-yl-tributylstannane (2244-38-4)

Conditions	Yield
In not given	86%

n-butyllithium (109-72-8) + 1-phenyl-1,2-closo-C2B10H11 (16390-61-7) + formic acid ethyl ester (109-94-4) → 1-(CH(o-CB10H10CC6H5)OH)-2-(C6H5)-1.2-C2B10H10 (16450-20-7)

Conditions	Yield
With hydrogenchloride In diethyl ether; benzene nitrogen atmosphere; ether soln. of formate addn. at 50 to 60°C to benzene soln. of Li-salt of carborane (obtained from carborane and BuLi), stirring (1 h), treating with aq. HCl, extracting with ether; extract drying over MgSO4 and evapn., residue recrystn. (hexane);	85%

n-butyllithium (109-72-8) + diethyl ether (60-29-7) + N-(2,6-bis(isopropyl)phenyl)-5-tert-butylpyrrolylaldimine (443890-22-0) + hafnium tetrachloride (13499-05-3) → [Hf(5-tert-butyl-2-[(2,6-diisopropylphenyl)aldimino]pyrrolyl)Cl2(μ-Cl)2Li(OEt2)2] (610270-20-7)

Conditions	Yield
In diethyl ether under N2, Schlenk techques; n-BuLi was added to the soln. of ligand at -35°C, mixt. was warmed to room temp., stirred for 2 h, soln. was cooled to -35°C again and added to suspn. of HfCl4 with stirring,mixt. stirred at room temp. for 20 h; mixt. was filtered, washed with Et2O, ether filtrate was concd., cooled to -35°C; elem. anal.;	85%

n-butyllithium (109-72-8) + (R)-(-)-benzyl-α-d chloride (4181-91-3) + tri-n-butyl-tin hydride (688-73-3) + diisopropylamine (108-18-9) → (S)-(-)-(.alfa.-deuteriobenzyl)tributyltin (84369-11-9)

Conditions	Yield
In tetrahydrofuran; hexane to THF soln. of (i-Pr)2NH at 0°C added hexane soln. of BuLi, stirred at 0°C for 30 min, Bu3SnH added, stirred at 0°C for 30 min, soln. added to THF soln. of (R)-PhCHDCl at 0°C over 30 min, mixt. kept at 0°C for 5 h; added water, mixt. extd. with ether, sepd., washed with water and brine, extract dried with MgSO4, concd., chromd.;	84%

n-butyllithium (109-72-8) + trimethylamine borane (1231953-83-5) → lithium borohydride + lithium [butyl(trihydrido)borate] (82111-98-6) + lithium [(dimethylamino)methyl]trihydroborate (84280-42-2) + lithium benzyltrihydroborate (84280-43-3)

Conditions	Yield
In hexane; toluene under dry N2, refluxing for 30 min;	A 4% B 80% C 4% D 2%
In hexane; toluene under dry N2, refluxing for 2 d;	A 15% B 64% C 15% D 6%

n-butyllithium (109-72-8) + borane tetrahydrofuran → lithium borohydride + lithium di-n-butylborohydride (84280-32-0) + LiHB(s-Bu)3 (67335-72-2) + Li{B(n-C4H9)4} (15243-31-9)

Conditions	Yield
In tetrahydrofuran; hexane under dry N2, soln. of BH3 in THF cooled to -78°C, hexane soln. of n-BuLi added with stirring, mixt. allowed to warm to -30°C within 1 h; not isolated, detected by NMR;	A 77% B 3% C 13% D 7%

n-butyllithium (109-72-8) + dimethyl sulfide borane (13292-87-0) → lithium borohydride + lithium [butyl(trihydrido)borate] (82111-98-6) + Li{B(n-C4H9)4} (15243-31-9)

Conditions	Yield
In hexane under dry N2, hexane soln. of n-BuLi cooled to -10°C, H3B-SMe2 added with stirring for few minutes, after 20 min all volatile material stripped in vac.; residue dissolved in THF, not isolated, detected by NMR;	A 18% B 77% C 5%
In hexane under dry N2, hexane soln. of n-BuLi added over period of 10 min to H3B-SMe2 with stirring; residue dissolved in minimum THF, not isolated, detected by NMR;	A 44% B 41% C 15%

n-butyllithium (109-72-8) + (2S, 5R, 7S, 8R, 2E, 4E)-tricarbonyliron[(η4-2-5)-8-(tert-butoxycarbonylamino)-7-methoxynona-2,4-dienal] + pentyltriphenylphosphonium bromide (21406-61-1) → (2R, 3S, 5R, 8S, 5E, 7E, 9Z)-tricarbonyliron[(η4-5-8)-2-(tert-butoxycarbonylamino)-3-methoxytetradodeca-5,7,9-triene]

Conditions	Yield
In hexane; toluene (N2 atmosphere); addn. of BuLi to susp. of C5H11PPh3Br (stirring, 0°C), addn. of soln. of Fe complex (after 5 min, -78°C), stirring (-78°C, 30 min, 0°C, 30 min), addn. of H2O (0°C),extraction (EtOAc), drying (MgSO4); evapn. (in vacuo), chromatography (SiO2 hexane/EtOAc);	73%

n-butyllithium (109-72-8) + C20H8N4(BCl)2(C6H4CH3)4*(n)C6H5CH3 n:0.5-1; → anti-C20H8N4(BC4H9)2(C6H4CH3)4

Conditions	Yield
In hexane byproducts: LiCl, toluene; C4H9Li soln. added to suspn. of C20H8N4(BCl)2(C6H5CH3)4*(n)C6H5CH3 in hexane (-78 °C), warmed up to room temp., stirred (16 h); ppt. filtered, washed with hexane, extd. with CH2Cl2; detd. by MAS, UV, (1)H NMR, (11)B NMR;	71%

iron(II) chloride tetrahydrate + n-butyllithium (109-72-8) + benzyl chloride (100-44-7) + 1,2-benzenedithiole (17534-15-5) → 2-(Benzylthio)thiophenol (116089-38-4)

Conditions

Yield

With hydrogenchloride; carbon monoxide In tetrahydrofuran under N2; reaction of dithiol and BuLi at -78 °C; addn. of Fe-salt at room temp.; CO introduced for 2h; benzyl chloride added; stirring for 1h at room temp.; evapn.; excess of benzyl chloride removed by hexane; HCl and THF added; refluxed for 2h;; evapn.; treatment with H2O/CCl4; organic layer dried (Na2SO4), filtered and evapd.; distn. (180-220 °C, vacuum); elem. anal.;;

70%

n-butyllithium (109-72-8) + chloro(trifluoromethyl)disulfane (53268-50-1) → 1-Trifluoromethyldisulfanyl-butane

Conditions	Yield
	68%
	68%

n-butyllithium (109-72-8) + 1-trimethylsiloxy-3,7,10-trimethylgermatrane (131498-79-8) → tetrabutylgermanium (1067-42-1)

Conditions	Yield
In tetrahydrofuran byproducts: LiOSi(CH3)3; a suspn. of germatrane in THF was treated with an excess of n-BuLi in n-hexane at room temp. for 4 h; evap., filtered;	65%

N,N-dimethylaminomethylferrocene (1271-86-9) + n-butyllithium (109-72-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-(N,N-dimethylaminomethyl)ferrocenecarboxaldehyde (162762-18-7, 212901-69-4, 174225-69-5)

Conditions	Yield
In not given addn. of LiBu (1 equiv., room temp.), stirring (24 h), addn. of DMF (-78°C), stirring (4 h, room temp.), hydrolysis; extn. (Et2O), chromy. (alumina, Et2O/pentane 1:2); elem. anal.;	62%

n-butyllithium (109-72-8) + 1-bromogermatrane (70559-35-2) → tetrabutylgermanium (1067-42-1)

Conditions	Yield
In tetrahydrofuran a suspn. of germatrane in THF was treated with an excess of n-BuLi in n-hexane at room temp. for 4 h;	61%

n-butyllithium (109-72-8) + trimethylamine borane (1231953-83-5) → lithium borohydride

Conditions	Yield
In hexane under dry N2, refluxing for 20 h;	60%

tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0) (26743-81-7) + n-butyllithium (109-72-8) + methylmercury(II) chloride (115-09-3) → Mo(CO)4((C6H5)2PCH(HgCH3)P(C6H5)2)

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Mo-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

tetracarbonyl-bis(diphenylphosphino)methane-chromium(0) (16743-46-7) + n-butyllithium (109-72-8) + methylmercury(II) chloride (115-09-3) → Cr(CO)4((C6H5)2PCH(HgCH3)P(C6H5)2)

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Cr-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

n-butyllithium (109-72-8) + tetracarbonyl-bis(diphenylphosphino)methane-tungsten(0) (41830-14-2) + methylmercury(II) chloride (115-09-3) → W(CO)4((C6H5)2PCH(HgCH3)P(C6H5)2)

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of W-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0) (26743-81-7) + n-butyllithium (109-72-8) + ethylmercury(II) chloride (107-27-7) → Mo(CO)4((C6H5)2PCH(HgCH2CH3)P(C6H5)2)

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Mo-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

tetracarbonyl-bis(diphenylphosphino)methane-chromium(0) (16743-46-7) + n-butyllithium (109-72-8) + ethylmercury(II) chloride (107-27-7) → Cr(CO)4((C6H5)2PCH(HgCH2CH3)P(C6H5)2)

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Cr-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

n-butyllithium (109-72-8) + tetracarbonyl-bis(diphenylphosphino)methane-tungsten(0) (41830-14-2) + ethylmercury(II) chloride (107-27-7) → W(CO)4((C6H5)2PCH(HgCH2CH3)P(C6H5)2)

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of W-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0) (26743-81-7) + n-butyllithium (109-72-8) + phenylmercury(II) chloride (100-56-1) → Mo(CO)4((C6H5)2PCH(HgC6H5)P(C6H5)2)

Conditions	Yield
In tetrahydrofuran addn. of LiBu (hexane soln.) to soln. of Mo-complex (0°C), stirring (2 h), addn. of Hg-compd., warming (room temp.), stirring (2 h); THF removal (reduced pressure), recrystn. (CH2Cl2-methanol);	60%

Upstream product

• 109-69-3 n-Butyl chloride 
• 629-35-6 dibutylmercury 
• 109-65-9 1-bromo-butane 
• 71-43-2 benzene 
• 60-29-7 diethyl ether 
• 7439-93-2 lithium 
• 27484-93-1 (C₄H₉)2BSB(C₄H₉)2 
• 1643-19-2 tetrabutylammomium bromide 
• 5432-85-9 4-isopropyl-cyclohexanone 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 917-64-6 methyl magnesium iodide 
• 62735-89-1 α-chloro-nitroso-2,2,6,6-tetramethylcyclohexane 
• 2744-08-3 decahydroisoquinoline 
• 681-84-5 tetramethylorthosilicate 

Downstream Products

• 109-79-5 n-butanethiol 
• 1613-46-3 butyl propyl sulfide 
• 867129-71-3 1-butylsulfanyl-3-propylsulfanyl-propane 
• 217-59-4 triphenylene 
• 477-75-8 triptycene 
• 1657-60-9 2,2-dimethyl-1,1-diphenyl-propan-1-ol 
• 110-83-8 cyclohexene 
• 1578-33-2 2-furyltrimethylsilane 
• 2786-07-4 2-thienyl lithium 
• 18245-28-8 2-(trimethylsilyl)thiophene 
• 5058-19-5 2-butylpyridine 
• 29460-91-1 2-Butylpyrazine 
• 41806-40-0 1-methyl-1H-imidazole-5-carboxylic acid 
• 20485-43-2 1-methyl-2-imidazolecarboxylic acid 

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Material BehaviourEffect of enthalpy of polar modifiers interaction with n-Butyllithium (cas 109-72-8) on the reaction enthalpy, kinetics and chain microstructure during anionic polymerization of 1,3-butadiene08/20/2019

The influence of interaction enthalpy (ΔHMOD/BuLi) of μ, σ, σ+μ and σ-μ complexing polar modifiers with n-butyllithium on the 1,3-butadiene anionic polymerization enthalpy (ΔHBD), polymerization reaction rate (kp) and polybutadiene microstructure was studied. It has been found that entha...detailed

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Relative Reactivities and Mechanistic Aspects of the Reactions of Organic Halides with Alkali Metals in Alcohol Environments

The relative reactivities of organic halides over wide concentration ranges have been determined with limited amounts of lithium, sodium, and potassium in 2-ethoxyethanol (1) at 0 deg C.Under these conditions the organometallics formed protonate to their hydrocarbons rather than undergo exchange, elimination, and simple or crossed coupling.In dilute solution in 1 the relative reactivities (r1/r2) of varied halides with lithium are essentially structure independent.However, as the concentrations of the halides increase, their relative reactivities become significantly different and depend on the total concentrations T (M) = 1X> + 2X>> of the organic halides.With lithium at increased halide concentrations (1) the reactivities are iodides > bromides > chlorides, (2) halides of lower molecular weight react more rapidly than their higher homologues, and (3) the reactivity orders of chlorides are (a) allyl > primary > secondary > tertiary > neopentyl, (b) 2-buten-1-yl > 1-buten-3-yl, (c) benzyl > phenyl, and (d) p-chlorotolyl > o-chlorotolyl > m-chlorotolyl.As examples, the relative reactivities of 1-chlorobutane/2-chloro-2-methylpropane (CT = 5.83 M), 3-chloropropene/1-bromobutane (CT = 4.60 M), bromobenzene/p-chlorotoluene (CT = 4.37 M), and benzyl chloride/chlorobenzene (CT = 4.02 M) are 6.71, 5.43, 24.1, and 22.1, respectively.Additions of aprotic solvents to 1-chlorobutane and 2-chloro-2-methylpropane in 1 decrease the relative reactivities of the halides.The effectiveness of cosolvents in lowering the relative reactivities of lithium with 1-chlorobutane and 2-chloro-2-methylbutane is tetrahydrofuran > dioxane ca. 2-ethoxyethanol (1) > cyclohexene ca. benzene.The relative reactivities of halides with sodium and with potassium in 1 at 0 deg C are also total halide concentration (CT) dependent.Under comparable concentrations the relative reactivity differences of halides are greater with lithium than sodium than potassium.The reactivities of halides under conditions of chemical control can be correlated with the ionization potentials of the alkali metals, and the kinetically controlling features of these systems are different from those with magnesium.The behavior of the alkali metals, the effects of concentration, and the roles of solvents on the reactivities of halides are discussed on the basis of (1) the active sites on the metal surfaces as modified by induction and (2) steric and electronic factors in the organic substrates.The kinetically controlled reactions of lithium with sp3 halides may be interpreted to invole formation of lithio organohalide radical anions (R.-X(1-), Li(1+)), electron transfer to the lithio radical anions on the metal surface, or unsymmetrical four-center carbanionic processes on the metal.In addition to incorporating an electron into the lowest unoccupied ? level of its C-X bond, an sp2 halide offers the possibility for kinetically controlling electron transfer into the ? system of its carbon-carbon double bond(s).

Inhibitors of viral replication, their process of preparation and their therapeutical uses

The present invention relates to compounds, their use in the treatment or the prevention of viral disorders, including HIV.

Fine-tuning the oxidative ability of persistent radicals: Electrochemical and computational studies of substituted 2-pyridylhydroxylamines

N-tert-Butyl-N-2-pyridylhydroxylamines were synthesized from 2-halopyridines and 2-methyl-2-nitrosopropane using magnesium-halogen exchange. The use of Turbo Grignard generated the metallo-2-pyridyl intermediate more reliably than alkyllithium reagents. The hydroxylamines were characterized using NMR, electrochemistry, and density functional theory. Substitution of the pyridyl ring in the 3-, 4-, and 5-positions was used to vary the potential of the nitroxyl/oxoammonium redox couple by 0.95 V. DFT computations of the electrochemical properties agree with experiment and provide a toolset for the predictive design of pyridyl nitroxides.

Catalyst component, catalyst for olefin polymerization, and process for producing olefin polymer using catalyst

A polymer having high catalyst activity, excellent hydrogen response, high stereoregularity and high yield can be obtained by polymerizing olefins in the presence of a catalyst for olefin polymerization comprising (A) a solid catalyst component containing magnesium, titanium, a halogen, and an electron donor compound, (B) an organoaluminum compound shown by the formula R6pAlQ3-p(R1R2N)m, and (C) an aminosilane compound shown by the formula (R3HN)nR4pSi(OR5)q.

MATERIAL FOR ORGANIC ELECTRO-OPTICAL DEVICE HAVING FLUORENE DERIVATIVE COMPOUND AND ORGANIC ELECTRO-OPTICAL DEVICE INCLUDING THE SAME

The present invention relates to a material for an organic electro-optical device and an organic electro-optical device including the same. More particularly, the present invention relates to a material having thermal stability of a glass transition temperature of 120° C. or more and a thermal decomposition temperature of 450° C. or more, and being capable of providing an organic electro-optical device having high efficiency and a long life-span due to less crystallization and improved amorphous properties in a material for an organic electro-optical device. The material for an organic electro-optical device can be used singularly or as a host material in combination with a dopant, and includes an asymmetric fluorene derivative compound. An organic electro-optical device including the material for an organic electro-optical device is also provided.

PROCESS OF MAKING ALUMINUM ALKYLS

The present invention generally relates to a new process of making a trialkyl aluminum compound in which at least one alkyl group is a primary alkyl derived from an internal olefin or alpha-olefin. The process employs an isomerization/hydroalumination catalyst.

Reactivity of individual organolithium aggregates: A RINMR study of n-butyllithium and 2-methoxy-6-(methoxymethyl)phenyllithium

Low-temperature rapid injection NMR (RINMR) experiments were performed on two lithium reagents, n-butyllithium and 2-methoxy-6-(methoxymethyl)phenyllithium (5), with the goal of measuring the relative reactivity of the different aggregates (dimer, mixed dimer, and tetramer for n-BuLi, monomer and tetramer for 5) toward typical electrophiles. The reaction of the n-BuLi dimer with (trimethylsilyl)acetylene first forms the mixed dimer n-BuLi·Me3SiC≡CLi, which is about 1/60 as reactive as the n-BuLi homodimer. The tetramer does not react. In the deprotonation of (phenylthio)acetylene, the n-BuLi dimer was found to be 3.5 × 108 as reactive as the tetramer, and in the addition to p-diethylaminobenzaldehyde, the relative reactivity was at least 2 × 104. In the deprotonation of (p-tolylsulfonyl)acetylene, the monomer of 5 was at least 1014 times as reactive as the tetramer. These measurements show that the difference in reactivity between the lower and higher aggregates of organolithium reagents can be many orders of magnitude higher than all previous estimates. Copyright

Use of sulfur containing initiators for anionic polymerization of monomers

An initiator is presented for anionically polymerizing monomers, to provide a functional head group on the polymer. A polymer having a functional head group derived from a sulfur containing anionic initiator, and optionally as additional functional group resulting from the use of a functional terminating reagent, coupling agent or linking agent is also provided. A method is presented for anionically polymerizing monomers comprising the step of polymerizing the monomers with a sulfur containing anionic initiator to provide a functional head group on the polymer. An elastomeric compound, comprising a functional polymer and filler is also described. Also provided is a tire having decreased rolling resistance resulting from a tire component containing a vulcanizable elastomeric compound.

Novel processes for the preparation of (R)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol

The present invention provides various processes for the preparation of (R)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol. These processes may be characterized by the following scheme:

METHOD FOR PRODUCING ALKYL LITHIUM COMPOUNDS AND ARYL LITHIUM COMPOUNDS BY MONITORING THE REACTION BY MEANS OF IR-SPECTROSCOPY

The invention relates to a method for producing alkyl lithium compounds and aryl lithium compounds by reacting lithium metal with alkyl or aryl halogenides in a solvent, the concentration of the alkyl/aryl halogenide and the alkyl/aryl lithium compound being detected according to an in-line measurement in the reactor by means of IR spectroscopy, and an exact recognition of the end point of the dosing of the halogenide constituents being carried out by evaluation of the IR measurement. Said method enables an optimum reactive process and reaction yield. The identification of the respective concentration of the educt and the product is a reliable reactive process. The yield of the reaction is also optimised by determining the end point of the halogenide dosing, as is the purity of the product due to a lower concentration thereof during the reaction.