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598-30-1

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598-30-1 Usage

Chemical Properties

sec-Butyllithium is a colorless crystalline solid or clear yellowish solution. It is more reactive than n-butyllithium. Its solutions are unstable and decompose about 10 to 15 times as fast as n-butyllithium under the same conditions.

Uses

sec-Butyllithium is used almost exclusively as a polymerization catalyst. It is more expensive than n-butyllithium and is used mainly because of its greater reactivity and faster polymerization initiation.

Preparation

sec-Butyllithium is produced by the reaction of sec-butyl chloride with lithium metal dispersion in hydrocarbon solvents. The lithium metal should contain catalytic amounts of up to 2 % sodium metal to attain a rapid reaction with the chloride and to minimize coupling. Massive substitution of sodium metal for lithium metal as is done in the preparation of n-butyllithium results in lower yields. Isopentane, hexane and cyclohexahe are typical solvents. Industrial and laboratory preparations are similar.

Check Digit Verification of cas no

The CAS Registry Mumber 598-30-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 8 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 598-30:
(5*5)+(4*9)+(3*8)+(2*3)+(1*0)=91
91 % 10 = 1
So 598-30-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H9.Li/c1-4(2)3;/h4H,1H2,2-3H3;/rC4H9Li/c1-4(2)3-5/h4H,3H2,1-2H3

598-30-1 Well-known Company Product Price

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  • Alfa Aesar

  • (43028)  sec-Butyllithium, 1.3M in cyclohexane, packaged under Argon in resealable ChemSeal? bottles   

  • 598-30-1

  • 0.1mole

  • 336.0CNY

  • Detail
  • Alfa Aesar

  • (43028)  sec-Butyllithium, 1.3M in cyclohexane, packaged under Argon in resealable ChemSeal? bottles   

  • 598-30-1

  • 0.5mole

  • 1772.0CNY

  • Detail

598-30-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name SEC-BUTYLLITHIUM

1.2 Other means of identification

Product number -
Other names lithium,butane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Process regulators
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:598-30-1 SDS

598-30-1Synthetic route

s-butyl chloride
78-86-4, 53178-20-4

s-butyl chloride

s-butylmagnesium chloride
15366-08-2

s-butylmagnesium chloride

lithium
7439-93-2

lithium

A

sec.-butyllithium
598-30-1

sec.-butyllithium

B

di-sec-butylmagnesium
17589-14-9

di-sec-butylmagnesium

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 20 - 25℃; for 3.75 - 4.58333h; Product distribution / selectivity;A n/a
B 97.8%
In tetrahydrofuran at 10 - 35℃; for 3.41667 - 4.58333h; Product distribution / selectivity;A n/a
B 93%
s-butyl chloride
78-86-4, 53178-20-4

s-butyl chloride

sec.-butyllithium
598-30-1

sec.-butyllithium

Conditions
ConditionsYield
With sodium; lithium In hexane at 20 - 40℃; under 217.522 Torr; for 6.5h;41.8%
With lithium; Petroleum ether
With lithium In cyclohexane at 0℃; for 0.5h;
With lithium In tert-butyl methyl ether; cyclohexane; pentane at 20 - 50℃; Inert atmosphere;
With lithium; Petroleum ether
s-butyl chloride
78-86-4, 53178-20-4

s-butyl chloride

lithium

lithium

petroleum ether

petroleum ether

sec.-butyllithium
598-30-1

sec.-butyllithium

1,5-dichlorohexamethyltrisiloxane
3582-71-6

1,5-dichlorohexamethyltrisiloxane

sec.-butyllithium
598-30-1

sec.-butyllithium

1,5-di-sec-butylhexamethyltrisiloxane

1,5-di-sec-butylhexamethyltrisiloxane

Conditions
ConditionsYield
In diethyl ether at -78℃; for 2.5h;100%
sec.-butyllithium
598-30-1

sec.-butyllithium

1,1-bis{3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl}ethylene

1,1-bis{3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl}ethylene

(chain-end-(3-bromomethyl)phenyl)polystyrene

(chain-end-(3-bromomethyl)phenyl)polystyrene

polystyrene, functionalized with two 3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl groups at one end

polystyrene, functionalized with two 3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl groups at one end

Conditions
ConditionsYield
Stage #1: sec.-butyllithium; 1,1-bis{3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl}ethylene
Stage #2: (chain-end-(3-bromomethyl)phenyl)polystyrene
100%
sec.-butyllithium
598-30-1

sec.-butyllithium

1,1-bis{3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl}ethylene

1,1-bis{3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl}ethylene

polystyrene functionalized with four 3-(bromomethyl)phenyl groups at one end

polystyrene functionalized with four 3-(bromomethyl)phenyl groups at one end

polystyrene, functionalized with 8 3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl groups at one end

polystyrene, functionalized with 8 3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl groups at one end

Conditions
ConditionsYield
Stage #1: sec.-butyllithium; 1,1-bis{3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl}ethylene
Stage #2: polystyrene functionalized with four 3-(bromomethyl)phenyl groups at one end
100%
sec.-butyllithium
598-30-1

sec.-butyllithium

1,1-bis{3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl}ethylene

1,1-bis{3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl}ethylene

polystyrene functionalized with two 3-(bromomethyl)phenyl groups at one end

polystyrene functionalized with two 3-(bromomethyl)phenyl groups at one end

polystyrene, functionalized with 4 3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl groups at one end

polystyrene, functionalized with 4 3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl groups at one end

Conditions
ConditionsYield
Stage #1: sec.-butyllithium; 1,1-bis{3-[(tert-butyl(dimethyl)silyloxy)methyl]phenyl}ethylene
Stage #2: polystyrene functionalized with two 3-(bromomethyl)phenyl groups at one end
100%
1,1-bis(4-trimethylsilylphenyl)ethylene

1,1-bis(4-trimethylsilylphenyl)ethylene

vinyl-4-tolylsulfoxide
36832-47-0

vinyl-4-tolylsulfoxide

sec.-butyllithium
598-30-1

sec.-butyllithium

poly(4-methylphenyl vinyl sulfoxide), Mn=12400, Mw/Mn=1.07; monomer(s): 4-methylphenyl vinyl sulfoxide; 1,1-bis(4-trimethylsilylphenyl)ethylene; sec-butyllithium

poly(4-methylphenyl vinyl sulfoxide), Mn=12400, Mw/Mn=1.07; monomer(s): 4-methylphenyl vinyl sulfoxide; 1,1-bis(4-trimethylsilylphenyl)ethylene; sec-butyllithium

Conditions
ConditionsYield
Stage #1: 1,1-bis(4-trimethylsilylphenyl)ethylene; sec.-butyllithium In tetrahydrofuran at -78℃; under 1E-05 Torr; for 0.5h;
Stage #2: With lithium bromide In tetrahydrofuran at -78℃; under 1E-06 Torr; for 0.166667h;
Stage #3: vinyl-4-tolylsulfoxide In tetrahydrofuran at -78℃; under 1E-06 Torr; for 20h;
100%
1,1-bis(4-trimethylsilylphenyl)ethylene

1,1-bis(4-trimethylsilylphenyl)ethylene

vinyl-4-tolylsulfoxide
36832-47-0

vinyl-4-tolylsulfoxide

sec.-butyllithium
598-30-1

sec.-butyllithium

poly(4-methylphenyl vinyl sulfoxide), Mn=12500, Mw/Mn=1.11; monomer(s): 4-methylphenyl vinyl sulfoxide; 1,1-bis(4-trimethylsilylphenyl)ethylene; sec-butyllithium

poly(4-methylphenyl vinyl sulfoxide), Mn=12500, Mw/Mn=1.11; monomer(s): 4-methylphenyl vinyl sulfoxide; 1,1-bis(4-trimethylsilylphenyl)ethylene; sec-butyllithium

Conditions
ConditionsYield
Stage #1: 1,1-bis(4-trimethylsilylphenyl)ethylene; sec.-butyllithium In tetrahydrofuran at -78℃; under 1E-05 Torr; for 0.5h;
Stage #2: With lithium chloride In tetrahydrofuran at -78℃; under 1E-06 Torr; for 0.166667h;
Stage #3: vinyl-4-tolylsulfoxide In tetrahydrofuran at -78℃; under 1E-06 Torr; for 16h;
100%
1,1-bis(4-trimethylsilylphenyl)ethylene

1,1-bis(4-trimethylsilylphenyl)ethylene

vinyl-4-tolylsulfoxide
36832-47-0

vinyl-4-tolylsulfoxide

sec.-butyllithium
598-30-1

sec.-butyllithium

poly(4-methylphenyl vinyl sulfoxide), Mn=9300, Mw/Mn=1.16; monomer(s): 4-methylphenyl vinyl sulfoxide; 1,1-bis(4-trimethylsilylphenyl)ethylene; sec-butyllithium

poly(4-methylphenyl vinyl sulfoxide), Mn=9300, Mw/Mn=1.16; monomer(s): 4-methylphenyl vinyl sulfoxide; 1,1-bis(4-trimethylsilylphenyl)ethylene; sec-butyllithium

Conditions
ConditionsYield
Stage #1: 1,1-bis(4-trimethylsilylphenyl)ethylene; sec.-butyllithium In tetrahydrofuran at -78℃; under 1E-05 Torr; for 0.5h;
Stage #2: With lithium bromide In tetrahydrofuran at -78℃; under 1E-06 Torr; for 0.166667h;
Stage #3: vinyl-4-tolylsulfoxide In tetrahydrofuran at -78℃; under 1E-06 Torr; for 20h;
100%
8,9-dioxa-8a-borabenzo[fg]tetracene

8,9-dioxa-8a-borabenzo[fg]tetracene

sec.-butyllithium
598-30-1

sec.-butyllithium

C22H20BO2(1-)*Li(1+)

C22H20BO2(1-)*Li(1+)

Conditions
ConditionsYield
In tetrahydrofuran; cyclohexane at -78 - 20℃; for 0.166667h; Inert atmosphere;100%
In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
sec.-butyllithium
598-30-1

sec.-butyllithium

methyldiphenylphosphine borane complex

methyldiphenylphosphine borane complex

α-lithium methylenediphenylphosphine borane
452969-86-7

α-lithium methylenediphenylphosphine borane

Conditions
ConditionsYield
In tetrahydrofuran BuLi adding into THF soln. of phosphine borane at -78°C, according to Imamoto et al. J. Am. Chem. Soc. 112 (1990) 5244;99%
1-aza-5-stanna-5-chloro-bicyclo{3.3.3}undecane
93253-73-7

1-aza-5-stanna-5-chloro-bicyclo{3.3.3}undecane

sec.-butyllithium
598-30-1

sec.-butyllithium

5-(1-methylpropyl)-1-aza-5-stannabicyclo[3.3.3]undecane
142509-27-1

5-(1-methylpropyl)-1-aza-5-stannabicyclo[3.3.3]undecane

Conditions
ConditionsYield
In diethyl ether; cyclohexane at -78℃; for 3h; Inert atmosphere;99%
In tetrahydrofuran at 0 - 20℃; for 12.25h; Inert atmosphere;
4-methyl-pent-3-en-2-one
141-79-7

4-methyl-pent-3-en-2-one

sec.-butyllithium
598-30-1

sec.-butyllithium

4,4,5-trimethyl-heptan-2-one
66018-00-6

4,4,5-trimethyl-heptan-2-one

Conditions
ConditionsYield
Stage #1: sec.-butyllithium With tellurium In tetrahydrofuran; hexane at -78 - 20℃;
Stage #2: 4-methyl-pent-3-en-2-one With boron trifluoride diethyl etherate at -78 - 20℃;
98%
(i) CuBr*Me2S, Me2S, Et2O, cyclohexane, (ii) /BRN= 1361550/, Et2O; Multistep reaction;
sec.-butyllithium
598-30-1

sec.-butyllithium

2-(2-methoxy-1-naphthyl)oxazoline
94321-29-6

2-(2-methoxy-1-naphthyl)oxazoline

2-(2-sec-butyl-1-naphthyl)oxazoline
137869-12-6

2-(2-sec-butyl-1-naphthyl)oxazoline

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;98%
sec.-butyllithium
598-30-1

sec.-butyllithium

acetophenone
98-86-2

acetophenone

3-methyl-2-phenyl-pentan-2-ol
33484-93-4

3-methyl-2-phenyl-pentan-2-ol

Conditions
ConditionsYield
With cerium(III) triiodide In tetrahydrofuran; hexane at -65℃; for 3h; Product distribution; var. temp., time; also without CeI3;98%
With cerium(III) triiodide In tetrahydrofuran; hexane at -65℃; for 3h;98%
With cerium(III) triiodide in THF, 1) -65 deg C, 30 min., 2) -65 deg C, 3h; Yield given. Multistep reaction;
1-(4-(3-bromopropyl)phenyl)-1-phenylethylene
221343-17-5

1-(4-(3-bromopropyl)phenyl)-1-phenylethylene

styrene
292638-84-7

styrene

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

sec.-butyllithium
598-30-1

sec.-butyllithium

DPE-chain-end-functionalized polystyrene, Mn=9600, Mw/Mn=1.02; monomer(s): styrene; sec-butyllithium; 1,1-diphenylethylene; 1-(4-(3-bromopropyl)phenyl)-1-phenylethylene

DPE-chain-end-functionalized polystyrene, Mn=9600, Mw/Mn=1.02; monomer(s): styrene; sec-butyllithium; 1,1-diphenylethylene; 1-(4-(3-bromopropyl)phenyl)-1-phenylethylene

Conditions
ConditionsYield
Stage #1: styrene; sec.-butyllithium In tetrahydrofuran at -78℃; under 1E-06 Torr; for 0.5h;
Stage #2: 1,1-Diphenylethylene In tetrahydrofuran at -78℃; under 1E-06 Torr; for 1h;
Stage #3: 1-(4-(3-bromopropyl)phenyl)-1-phenylethylene In tetrahydrofuran at -78℃; under 1E-06 Torr; for 0.166667h;
98%
styrene
292638-84-7

styrene

dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

sec.-butyllithium
598-30-1

sec.-butyllithium

polystyrene, α-dimethylsilyl-terminated, ω-(but-2-yl)-terminated, Mn 2.2E3 g/mol, Mw/Mn 1.04; monomer(s): sec-butyllithium; styrene; chlorodimethylsilane

polystyrene, α-dimethylsilyl-terminated, ω-(but-2-yl)-terminated, Mn 2.2E3 g/mol, Mw/Mn 1.04; monomer(s): sec-butyllithium; styrene; chlorodimethylsilane

Conditions
ConditionsYield
Stage #1: styrene; sec.-butyllithium In cyclohexane; benzene for 12h;
Stage #2: dimethylmonochlorosilane In cyclohexane; benzene for 11h; Further stages.;
98%
Triisopropyl borate
5419-55-6

Triisopropyl borate

sec.-butyllithium
598-30-1

sec.-butyllithium

A

sec-butyldiisopropoxyborane

sec-butyldiisopropoxyborane

B

(C2H5CH(CH3))2B(OCH(CH3)2)
148058-17-7

(C2H5CH(CH3))2B(OCH(CH3)2)

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added BuLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR;A 98%
B 2%
ferrocenyl p-tolyl sulphide

ferrocenyl p-tolyl sulphide

water-d2
7789-20-0

water-d2

sec.-butyllithium
598-30-1

sec.-butyllithium

A

Fe(C5H4(2)H)(C5H4SC6H4CH3)

Fe(C5H4(2)H)(C5H4SC6H4CH3)

B

Fe(C5H5)(C5H3(2)HSC6H4CH3)

Fe(C5H5)(C5H3(2)HSC6H4CH3)

C

Fe(C5H5)(C5H3(2)HSC6H4CH3)
693833-12-4

Fe(C5H5)(C5H3(2)HSC6H4CH3)

Conditions
ConditionsYield
In tetrahydrofuran to soln. of ferrocenyl sulfide-pTol in anhydrous THF under Ar added dropwise at -10°C soln. of s-BuLi; soln. stirred at 0°C for 7 h; trapping with D2O gave deuterated compds.; not isolated, detected by NMR(2)H;A n/a
B n/a
C 98%
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

sec.-butyllithium
598-30-1

sec.-butyllithium

2-(1-naphthyl)butane
1680-58-6

2-(1-naphthyl)butane

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In cyclohexane at 20℃; for 0.00555556h; pH=6; Schlenk technique;98%
With bis(tri-t-butylphosphine)palladium(0) In toluene at 20℃; for 1h;90%
With Pd-PEPPSI-IPent-Acenapht In toluene at -62℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere;89%
Stage #1: 1-Bromonaphthalene With bis(tri-t-butylphosphine)palladium(0); oxygen In toluene at 20℃; for 0.0166667h; Schlenk technique;
Stage #2: sec.-butyllithium In toluene at 20℃; for 0.0333333h; Schlenk technique;
61%
1-bromo-2-ethylbenzene
1973-22-4

1-bromo-2-ethylbenzene

sec.-butyllithium
598-30-1

sec.-butyllithium

1-sec-butyl-2-ethylbenzene

1-sec-butyl-2-ethylbenzene

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In cyclohexane at 20℃; for 0.00555556h; pH=6; Schlenk technique;98%
carbon disulfide
75-15-0

carbon disulfide

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

sec.-butyllithium
598-30-1

sec.-butyllithium

benzyl bromide
100-39-0

benzyl bromide

C26H28S2
1433762-83-4

C26H28S2

Conditions
ConditionsYield
Stage #1: 1,1-Diphenylethylene; sec.-butyllithium In tetrahydrofuran at -80℃; for 0.25h; Inert atmosphere;
Stage #2: carbon disulfide In tetrahydrofuran at -80℃; for 0.333333h; Inert atmosphere;
Stage #3: benzyl bromide In tetrahydrofuran at -80 - 20℃; for 0.5h; Inert atmosphere;
97.9%
sec.-butyllithium
598-30-1

sec.-butyllithium

buta-1,3-diene
106-99-0

buta-1,3-diene

isoprene
78-79-5

isoprene

4,1-polyisoprene-b-1,2-polybutadiene diblock copolymer, Mn 1.13E4 (SEC/NMR), PDI 1.02-1.09 (SEC), fPB 0.355 (SEC/NMR), 94.3 mol percent 4,1-polyisoprene, 98.6 mol percent 1,2-polybutadiene (NMR); monomer(s): isoprene; sec-butyllithium; 1,3-butadiene

4,1-polyisoprene-b-1,2-polybutadiene diblock copolymer, Mn 1.13E4 (SEC/NMR), PDI 1.02-1.09 (SEC), fPB 0.355 (SEC/NMR), 94.3 mol percent 4,1-polyisoprene, 98.6 mol percent 1,2-polybutadiene (NMR); monomer(s): isoprene; sec-butyllithium; 1,3-butadiene

Conditions
ConditionsYield
Stage #1: sec.-butyllithium; isoprene In cyclohexane at 40℃; for 4h;
Stage #2: buta-1,3-diene With 1,2-dipiperidinoethane In cyclohexane at 18℃; for 3h;
97.6%
sec.-butyllithium
598-30-1

sec.-butyllithium

buta-1,3-diene
106-99-0

buta-1,3-diene

isoprene
78-79-5

isoprene

4,1-polyisoprene-b-1,2-polybutadiene diblock copolymer, Mn 1.18E4 (SEC/NMR), PDI 1.01-1.07 (SEC), fPB 0.284 (SEC/NMR), 94.3 mol percent 4,1-polyisoprene, >99 mol percent 1,2-polybutadiene (NMR); monomer(s): isoprene; sec-butyllithium; 1,3-butadiene

4,1-polyisoprene-b-1,2-polybutadiene diblock copolymer, Mn 1.18E4 (SEC/NMR), PDI 1.01-1.07 (SEC), fPB 0.284 (SEC/NMR), 94.3 mol percent 4,1-polyisoprene, >99 mol percent 1,2-polybutadiene (NMR); monomer(s): isoprene; sec-butyllithium; 1,3-butadiene

Conditions
ConditionsYield
Stage #1: sec.-butyllithium; isoprene In cyclohexane at 40℃; for 4h;
Stage #2: buta-1,3-diene With 1,2-dipiperidinoethane In cyclohexane at 18℃; for 3h;
97.6%
cyclopent-2-enone
930-30-3

cyclopent-2-enone

sec.-butyllithium
598-30-1

sec.-butyllithium

3-sec-butylcyclopentanone
91523-76-1

3-sec-butylcyclopentanone

Conditions
ConditionsYield
With s-Bu(Me)Cu(CN)Li2 In tetrahydrofuran at 0℃; for 0.5h;97%
sec.-butyllithium
598-30-1

sec.-butyllithium

(+/-)-(2R,3S,4S)-2-fluoro-3-tosylmethyl-2-trifluoromethyl-4-pentanolide

(+/-)-(2R,3S,4S)-2-fluoro-3-tosylmethyl-2-trifluoromethyl-4-pentanolide

(2S,3S,4R,5R)-2-sec-Butyl-3-fluoro-5-methyl-4-(toluene-4-sulfonylmethyl)-3-trifluoromethyl-tetrahydro-furan-2-ol

(2S,3S,4R,5R)-2-sec-Butyl-3-fluoro-5-methyl-4-(toluene-4-sulfonylmethyl)-3-trifluoromethyl-tetrahydro-furan-2-ol

Conditions
ConditionsYield
In diethyl ether at -78℃; for 0.5h;97%
sec.-butyllithium
598-30-1

sec.-butyllithium

3-methoxy-2,3-diphenyl-1-trimethylsilyl-1-propanone

3-methoxy-2,3-diphenyl-1-trimethylsilyl-1-propanone

6-methoxy-3-methyl-5,6-diphenyl-4-trimethylsilyl-4-hexanol

6-methoxy-3-methyl-5,6-diphenyl-4-trimethylsilyl-4-hexanol

Conditions
ConditionsYield
In tetrahydrofuran; hexane at -78℃;97%
sec.-butyllithium
598-30-1

sec.-butyllithium

(-)-(2S,4R,5S)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine-2-borane

(-)-(2S,4R,5S)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine-2-borane

(RP)-(s-butyl)[(1S,2R)-(N-ephedrino)](phenyl)phosphine-P-borane

(RP)-(s-butyl)[(1S,2R)-(N-ephedrino)](phenyl)phosphine-P-borane

Conditions
ConditionsYield
In tetrahydrofuran at -20 - 0℃;97%
sec.-butyllithium
598-30-1

sec.-butyllithium

1,1,1,6,6,6-hexakis(phenylthio)hexane
83711-09-5

1,1,1,6,6,6-hexakis(phenylthio)hexane

A

1-methylpropyl phenyl sulfide
14905-79-4

1-methylpropyl phenyl sulfide

B

1,1,6,6-tetrakis(phenylthio)hexane
70871-25-9

1,1,6,6-tetrakis(phenylthio)hexane

Conditions
ConditionsYield
In tetrahydrofuran; cyclohexane at -45℃; for 1h;A 89.7%
B 96.2%
sec.-butyllithium
598-30-1

sec.-butyllithium

(1R,2S,5S,8S,10R)-5,8,11,11-tetramethyl-7-methylene-3-oxatricyclo<8.1.1.02,8>dodecan-4-one
81550-54-1

(1R,2S,5S,8S,10R)-5,8,11,11-tetramethyl-7-methylene-3-oxatricyclo<8.1.1.02,8>dodecan-4-one

(1R,2S,5S,8S,10R)-5,8,11,11-tetramethyl-7-methylene-4-(1-methylpropyl)-3-oxatricyclo<8.1.1.02,8>dodecan-4-ol
83152-48-1

(1R,2S,5S,8S,10R)-5,8,11,11-tetramethyl-7-methylene-4-(1-methylpropyl)-3-oxatricyclo<8.1.1.02,8>dodecan-4-ol

Conditions
ConditionsYield
In tetrahydrofuran; hexane at -78℃; for 0.75h;96%
Decyl-oxiran
2855-19-8

Decyl-oxiran

sec.-butyllithium
598-30-1

sec.-butyllithium

(E)-3-methyl-4-pentadecene

(E)-3-methyl-4-pentadecene

Conditions
ConditionsYield
In tetrahydrofuran -70 deg C to -50 deg C, 20 min;96%

598-30-1Relevant articles and documents

Complex-Induced Proximity Effects and Dipole-Stabilized Carbanions: Kinetic Evidence for the Role of Complexes in the α'-Lithiations of Carboxamides

Hay, David R.,Song, Zhiguo,Smith, Stanley G.,Beak, Peter

, p. 8145 - 8153 (1988)

The kinetics of the α'-lithiations of N,N-dimethyl-2,4,6-triisopropylbenzamide (4) and N,N-diethyl-2,4,6-triisopropylbenzamide (5) by sec-butyllithium (s-BuLi) in cyclohexane have been investigated.Direct observation of the reactant amide, the intermediate amide-lithium reagent complex(es), and the α'-lithiated products by stopped-flow infrared spectroscopy was used to investigate the initial rate constants as a fuction of reactant concentrations.At constant amide concentration the initial rate constant decreases sharply with increasing concentration of s-BuLi.This behavior is also observed in the presence of tetramethylethylene diamine (TMEDA).The major interaction of TMEDA with s-BuLi in cyclohexane is shown by cryoscopic measurements to be an addition of TMEDA to aggregated s-BuLi.Semiquantitative schemes constructed on the basis of the kinetic data suggest the presence of at least two reactive complexes and that complexes with more ligands are more reactive.The implications of these results are discussed.

Method for industrially producing sec-butyl lithium

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Paragraph 0019; 0026-0030, (2021/12/07)

The invention provides a method for industrially producing sec-butyl lithium. The method for industrially producing sec-butyl lithium comprises (1) replacing air with argon gas in a reaction kettle and adding a solvent. (2) The lithium particles are charged into a feeder, air is replaced with argon, and all the lithium particles are placed in the reaction vessel. (3) On stirring, 2 - chlorobutane and metallic lithium are added dropwise through a metering pump to control the reaction temperature through the reaction kettle jacket and 2 - chlorobutane feeding speed. (4) After incubation 2 - 4h, the reaction is hydraulically introduced into the intermediate tank with argon, and the excess metal lithium is left in the reaction vessel. (5) The material in the intermediate tank was passed to a filter to remove lithium chloride solids with argon gas, and the resulting colorless to pale yellow transparent clear liquid, i.e. sec-butyllithium solution. The method adopts excess metal lithium particles and 2 - chlorobutane in a solvent to react at a certain temperature to produce sec-butyl lithium, so that side reactions are effectively avoided, and the yield is improved.

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

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Page/Page column 14-15, (2008/06/13)

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.

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