sec-Butyllithium supplier | CasNO.598-30-1

Name
sec-Butyllithium
EINECS 209-927-7
CAS No. 598-30-1
Article Data16
CAS DataBase
Density 0.769 g/mL at 25 °C
Solubility Soluble in cyclohexane or mixture of cyclohexane and heptane
Melting Point
Formula C₄H₉Li
Boiling Point
Molecular Weight 64.0565
Flash Point -17 °C
Transport Information UN 3394 4.2/PG 1
Appearance clear yellowish solution
Safety 26-36/37/39-43-45-60-61-62-33-16
Risk Codes 11-15-17-34-50/53-65-67-66
Molecular Structure
Hazard Symbols F,C,N
Synonyms Lithium,sec-butyl- (6CI,8CI);(1-Methylpropyl)lithium;2-Butyllithium;Lithium,(1-methylpropyl)-;Butan-2-yllithium;
PSA 0.00000
LogP 1.75410

Synthetic route

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

: 15366-08-2
s-butylmagnesium chloride

: 7439-93-2
lithium

A: 598-30-1
sec.-butyllithium

B: 17589-14-9
di-sec-butylmagnesium

Conditions

Conditions	Yield
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%

...Expand

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

: 598-30-1
sec.-butyllithium

Conditions

Conditions	Yield
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

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

lithium: lithium

petroleum ether: petroleum ether

: 598-30-1
sec.-butyllithium

...Expand

: 3582-71-6
1,5-dichlorohexamethyltrisiloxane

: 598-30-1
sec.-butyllithium

: 1,5-di-sec-butylhexamethyltrisiloxane

Conditions

Conditions	Yield
In diethyl ether at -78℃; for 2.5h;	100%

: 598-30-1
sec.-butyllithium

: 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

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

...Expand

: 598-30-1
sec.-butyllithium

: 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

Conditions	Yield
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%

...Expand

: 598-30-1
sec.-butyllithium

: 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

Conditions	Yield
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%

...Expand

: 1,1-bis(4-trimethylsilylphenyl)ethylene

: 36832-47-0
vinyl-4-tolylsulfoxide

: 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

Conditions	Yield
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%

...Expand

: 1,1-bis(4-trimethylsilylphenyl)ethylene

: 36832-47-0
vinyl-4-tolylsulfoxide

: 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

Conditions	Yield
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%

...Expand

: 1,1-bis(4-trimethylsilylphenyl)ethylene

: 36832-47-0
vinyl-4-tolylsulfoxide

: 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

Conditions	Yield
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%

...Expand

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

: 598-30-1
sec.-butyllithium

: C22H20BO2(1-)*Li(1+)

Conditions

Conditions	Yield
In tetrahydrofuran; cyclohexane at -78 - 20℃; for 0.166667h; Inert atmosphere;	100%
In tetrahydrofuran at -78 - 20℃; Inert atmosphere;

: 598-30-1
sec.-butyllithium

: methyldiphenylphosphine borane complex

: 452969-86-7
α-lithium methylenediphenylphosphine borane

Conditions

Conditions	Yield
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%

: 93253-73-7
1-aza-5-stanna-5-chloro-bicyclo{3.3.3}undecane

: 598-30-1
sec.-butyllithium

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

Conditions

Conditions	Yield
In diethyl ether; cyclohexane at -78℃; for 3h; Inert atmosphere;	99%
In tetrahydrofuran at 0 - 20℃; for 12.25h; Inert atmosphere;

: 141-79-7
4-methyl-pent-3-en-2-one

: 598-30-1
sec.-butyllithium

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

Conditions

Conditions	Yield
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;

: 598-30-1
sec.-butyllithium

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

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

Conditions

Conditions	Yield
In tetrahydrofuran Ambient temperature;	98%

: 598-30-1
sec.-butyllithium

: 98-86-2
acetophenone

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

Conditions

Conditions	Yield
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;

: 221343-17-5
1-(4-(3-bromopropyl)phenyl)-1-phenylethylene

: 292638-84-7
styrene

: 530-48-3
1,1-Diphenylethylene

: 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

Conditions	Yield
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%

...Expand

: 292638-84-7
styrene

: 1066-35-9
dimethylmonochlorosilane

: 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

Conditions	Yield
Stage #1: styrene; sec.-butyllithium In cyclohexane; benzene for 12h; Stage #2: dimethylmonochlorosilane In cyclohexane; benzene for 11h; Further stages.;	98%

...Expand

: 5419-55-6
Triisopropyl borate

: 598-30-1
sec.-butyllithium

A: sec-butyldiisopropoxyborane

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

Conditions

Conditions	Yield
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%

...Expand

: ferrocenyl p-tolyl sulphide

: 7789-20-0
water-d2

: 598-30-1
sec.-butyllithium

A: Fe(C5H4(2)H)(C5H4SC6H4CH3)

B: Fe(C5H5)(C5H3(2)HSC6H4CH3)

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

Conditions

Conditions	Yield
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%

...Expand

: 90-11-9
1-Bromonaphthalene

: 598-30-1
sec.-butyllithium

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

Conditions

Conditions	Yield
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%

: 1973-22-4
1-bromo-2-ethylbenzene

: 598-30-1
sec.-butyllithium

: 1-sec-butyl-2-ethylbenzene

Conditions

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

: 75-15-0
carbon disulfide

: 530-48-3
1,1-Diphenylethylene

: 598-30-1
sec.-butyllithium

: 100-39-0
benzyl bromide

: 1433762-83-4
C26H28S2

Conditions

Conditions	Yield
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%

...Expand

: 598-30-1
sec.-butyllithium

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

: 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

Conditions	Yield
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%

...Expand

: 598-30-1
sec.-butyllithium

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

: 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

Conditions	Yield
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%

...Expand

: 930-30-3
cyclopent-2-enone

: 598-30-1
sec.-butyllithium

: 91523-76-1
3-sec-butylcyclopentanone

Conditions

Conditions	Yield
With s-Bu(Me)Cu(CN)Li2 In tetrahydrofuran at 0℃; for 0.5h;	97%

: 598-30-1
sec.-butyllithium

: (+/-)-(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

Conditions

Conditions	Yield
In diethyl ether at -78℃; for 0.5h;	97%

: 598-30-1
sec.-butyllithium

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

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

Conditions

Conditions	Yield
In tetrahydrofuran; hexane at -78℃;	97%

: 598-30-1
sec.-butyllithium

: (-)-(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

Conditions

Conditions	Yield
In tetrahydrofuran at -20 - 0℃;	97%

: 598-30-1
sec.-butyllithium

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

A: 14905-79-4
1-methylpropyl phenyl sulfide

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

Conditions

Conditions	Yield
In tetrahydrofuran; cyclohexane at -45℃; for 1h;	A 89.7% B 96.2%

...Expand

: 598-30-1
sec.-butyllithium

: 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

: 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

Conditions	Yield
In tetrahydrofuran; hexane at -78℃; for 0.75h;	96%

: 2855-19-8
Decyl-oxiran

: 598-30-1
sec.-butyllithium

: (E)-3-methyl-4-pentadecene

Conditions

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

sec-Butyllithium Specification

sec-Butyllithium is an organic compound with the formula C₄H₉Li, and its IUPAC name is the same with the product name. With the CAS registry number 598-30-1, it is also named as (1-Methylpropyl)lithium. What's more, its systematic name is Butan-2-yllithium. It belongs to the product categories of Straight Chain Compounds; Metal Alkyl. Its EINECS number is 209-927-7. In addition, the molecular weight is 64.06. This chemical is sensitive to air and water. The product should be sealed and stored in nitrogen-filled containers which are placed at the temperature of 4 °C. It is used as lithium reagent, and it is also used in the polymerization of isoprene and butadiene.

Preparation: this chemical can be prepared by the reaction of sec-butyl halides with lithium metal.

CH₃CHClCH₂CH₃ + 2 Li → CH₃CHLiCH₂CH₃ + LiCl

Uses of sec-Butyllithium: it can be used to produce 2-methyl-1-phenyl-butan-1-one at the temperature of 0 - 25 °C. It will need solvent tetrahydrofuran with the reaction time of 2 hours. The yield is about 81%.

sec-Butyllithium can be used to produce 2-methyl-1-phenyl-butan-1-one at the temperature of 0 - 25 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable, so you should keep it away from sources of ignition - No smoking. It is spontaneously flammable in air and can cause burns. Moreover, if contact with water, it will liberate extremely flammable gases. This substance is very toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. What's more, it is harmful as it may cause lung damage if swallowed. Repeated exposure may cause skin dryness or cracking and its vapours may cause drowsiness and dizziness. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. You must take precautionary measures against static discharges. In case of fire use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water). In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible). This material and its container must be disposed of as hazardous waste. You must avoid releasing it to the environment, and you need to refer to special instructions/safety data sheet. If swallowed, it will not induce vomiting, but you must seek medical advice immediately and show this container or label.

You can still convert the following datas into molecular structure:
(1)SMILES: CC([Li])CC
(2)Std. InChI: InChI=1S/C4H9.Li/c1-3-4-2;/h3H,4H2,1-2H3;
(3)Std. InChIKey: VATDYQWILMGLEW-UHFFFAOYSA-N

Product Name

sec-Butyllithium

Synthetic route

sec-Butyllithium Specification

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