Product Name

  • Name

    dilithium acetylide

  • EINECS
  • CAS No. 1070-75-3
  • Article Data12
  • CAS DataBase
  • Density g/cm3
  • Solubility
  • Melting Point
  • Formula C2Li2
  • Boiling Point °Cat760mmHg
  • Molecular Weight 37.904
  • Flash Point °C
  • Transport Information
  • Appearance
  • Safety Ignites and burns vigorously in fluorine, chlorine, phosphorus, selenium, or sulfur vapors. Ignites when heated in bromine or iodine vapors. When heated to decomposition it emits acrid smoke and fumes. See also LITHIUM COMPOUNDS and ACETYLIDES.
  • Risk Codes
  • Molecular Structure Molecular Structure of 1070-75-3 (dilithium acetylide)
  • Hazard Symbols
  • Synonyms Dilithioacetylene;Dilithium acetylide; Dilithium carbide; Lithium acetylide; Lithium carbide(Li2(C2))
  • PSA 0.00000
  • LogP 0.38760

Synthetic route

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine
56862-34-1

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine

A

N-(α-methylbenzyl)pentylamine
149529-74-8

N-(α-methylbenzyl)pentylamine

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: n-butyllithium; N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine at 20℃;
Stage #2: With methanol
A 80%
B n/a
thiophene
188290-36-0

thiophene

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine
56862-34-1

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine

A

N,N'-(thiophene-2,5-diylbis(methylene))bis(α-methylbenzylamine)

N,N'-(thiophene-2,5-diylbis(methylene))bis(α-methylbenzylamine)

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: thiophene; N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine With lithium diisopropyl amide In diethyl ether at 0 - 20℃;
Stage #2: With methanol
A 78%
B n/a
2-Methylthiophene
554-14-3

2-Methylthiophene

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine
56862-34-1

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine

A

N-(α-methylbenzyl)(5-methylthiophen-2-yl)methylamine

N-(α-methylbenzyl)(5-methylthiophen-2-yl)methylamine

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: 2-Methylthiophene; N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine With lithium diisopropyl amide In diethyl ether at 0 - 20℃;
Stage #2: With methanol
A 77%
B n/a
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

N-(α-methylbenzyl)-3-(trimethylsilyl)-2-propynylamine

N-(α-methylbenzyl)-3-(trimethylsilyl)-2-propynylamine

A

N-(α-methylbenzyl)pentylamine
149529-74-8

N-(α-methylbenzyl)pentylamine

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: n-butyllithium; N-(α-methylbenzyl)-3-(trimethylsilyl)-2-propynylamine at 20℃;
Stage #2: With methanol
A 71%
B n/a
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

N-(prop-2-yn-1-yl)cyclohexanamine
18292-76-7

N-(prop-2-yn-1-yl)cyclohexanamine

A

N,N-cyclohexyl-n-pentylamine
35152-42-2

N,N-cyclohexyl-n-pentylamine

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: n-butyllithium; N-(prop-2-yn-1-yl)cyclohexanamine at 20℃;
Stage #2: With methanol
A 70%
B n/a
tetrachloromethane
56-23-5

tetrachloromethane

lithium
7439-93-2

lithium

A

CLi4

CLi4

B

ethenetetrayl-tetrakis-lithium
38827-81-5

ethenetetrayl-tetrakis-lithium

C

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
In neat (no solvent) reaction of an excess of gaseous Li with gaseous CCl4 at 800-1000°C (high vac.);;A 10-18
B 61%
C 20%
furan
110-00-9

furan

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine
56862-34-1

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine

A

N,N'-(furan-2,5-diylbis(methylene))bis(α-methylbenzylamine)

N,N'-(furan-2,5-diylbis(methylene))bis(α-methylbenzylamine)

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: furan; N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine With lithium diisopropyl amide In diethyl ether at 0 - 20℃;
Stage #2: With methanol
A 58%
B n/a
N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine
56862-34-1

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine

tert.-butyl lithium
594-19-4

tert.-butyl lithium

A

N-(α-methylbenzyl)-2,2-dimethylpropylamine

N-(α-methylbenzyl)-2,2-dimethylpropylamine

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine; tert.-butyl lithium at 20℃;
Stage #2: With methanol
A 50%
B n/a
N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine
56862-34-1

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine

phenyllithium
591-51-5

phenyllithium

A

N-benzyl-1-phenylethylamine
3193-62-2, 17480-69-2, 19302-20-6, 38235-77-7

N-benzyl-1-phenylethylamine

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine; phenyllithium at 20℃;
Stage #2: With methanol
A 39%
B n/a
2-thienyl lithium
2786-07-4

2-thienyl lithium

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine
56862-34-1

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine

A

(RS)-N-(thiophen-2-ylmethyl)-N-(α-methylbenzyl)amine

(RS)-N-(thiophen-2-ylmethyl)-N-(α-methylbenzyl)amine

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: 2-thienyl lithium; N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine at 20℃;
Stage #2: With methanol
A 38%
B n/a
2-lithiofuran
2786-02-9

2-lithiofuran

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine
56862-34-1

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine

A

(RS)-N-(furan-2-ylmethyl)-N-(α-methylbenzyl)amine
161119-98-8

(RS)-N-(furan-2-ylmethyl)-N-(α-methylbenzyl)amine

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Stage #1: 2-lithiofuran; N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine With lithium diisopropyl amide In diethyl ether at 0 - 20℃;
Stage #2: With methanol
A 29%
B n/a
methyllithium
917-54-4

methyllithium

A

methane
34557-54-5

methane

B

dilithiomethane
21473-62-1

dilithiomethane

C

propadienetetrayl-tetrakis-lithium
69815-14-1

propadienetetrayl-tetrakis-lithium

D

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
at 223 - 226℃; Yield given. Yields of byproduct given;
cis-1,2-Dilithioethylen
65801-58-3, 75620-60-9, 171562-29-1

cis-1,2-Dilithioethylen

A

vinyllithium
917-57-7

vinyllithium

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Title compound not separated from byproducts;
trans-1,2-Dilithioethylen
65801-58-3, 75620-60-9, 171562-29-1

trans-1,2-Dilithioethylen

A

vinyllithium
917-57-7

vinyllithium

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
Title compound not separated from byproducts;
lithium acetylide
70277-75-7

lithium acetylide

A

vinyllithium
917-57-7

vinyllithium

B

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
With dilithiumethylene Title compound not separated from byproducts;
Trichloroethylene
79-01-6

Trichloroethylene

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; diethyl ether for 2h; Ambient temperature;
With n-butyllithium In tetrahydrofuran
acetylene
74-86-2

acetylene

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
With n-butyllithium In hexane at -10℃; for 0.75h; Yield given;
graphite

graphite

lithium chloride

lithium chloride

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
In melt Electrolysis; graphite electrodes, graphite dissoln. in molten Li (temp.>600°C);
graphite

graphite

lithium
7439-93-2

lithium

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
In neat (no solvent, solid phase) heated at 900°C for 12 h in Nb ampoule;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

acetylene
74-86-2

acetylene

dilithium acetylide
1070-75-3

dilithium acetylide

Conditions
ConditionsYield
In hexane inert atmosphere, diln. of soln. of n-BuLi with freshly distilled hexane, cooling to -15°C, passing of HCCH through the soln. at a temp. below -10°C, further bubbling of HCCH through the soln. (0.5 h), warming to room temp., reflux (2 h); filtration, reduction of volume (vacuum), washing (hexane), filtration, drying (60°C, 0.5 Torr), yield 82%;
niobium

niobium

niobium pentachloride
10026-12-7

niobium pentachloride

dilithium acetylide
1070-75-3

dilithium acetylide

Li(1+)*Nb6Cl19(1-)=LiNb6Cl19

Li(1+)*Nb6Cl19(1-)=LiNb6Cl19

Conditions
ConditionsYield
In melt byproducts: LiCl, NbCl4; compds. melted in quartz-glass ampoule at 530°C for 15 h; slowly (36 h) cooled to 300°C, washed with i-PrOH;90%
1,5-dichlorodecamethylpentasilane
5586-42-5

1,5-dichlorodecamethylpentasilane

dilithium acetylide
1070-75-3

dilithium acetylide

3,3,4,4,5,5,6,6,7,7-decamethyl-3,4,5,6,7-pentasilacycloheptyne
129415-88-9

3,3,4,4,5,5,6,6,7,7-decamethyl-3,4,5,6,7-pentasilacycloheptyne

Conditions
ConditionsYield
80%
dilithium acetylide
1070-75-3

dilithium acetylide

(diethylamino)dimethylsilyl-triflat
155166-24-8

(diethylamino)dimethylsilyl-triflat

Bis<(diethylamino)dimethylsilyl>ethin

Bis<(diethylamino)dimethylsilyl>ethin

Conditions
ConditionsYield
In diethyl ether for 0.5h; Ambient temperature;78%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

dilithium acetylide
1070-75-3

dilithium acetylide

bis(trimethyltin)acetylene
2117-50-2

bis(trimethyltin)acetylene

Conditions
ConditionsYield
In pentane byproducts: LiCl; inert atmosphere, addn. of soln. of (CH3)3SnCl to suspension of Li2C2 at-25°C (40 min), warming to room temp., reflux (1 h); filtration from LiCl, concn., recrystn. (pentane, -78°C), drying (40°C, 5 Torr);76%
dilithium acetylide
1070-75-3

dilithium acetylide

6-hepten-1-yl iodide
107175-49-5

6-hepten-1-yl iodide

1,15-hexadecadien-8-yne
188525-80-6

1,15-hexadecadien-8-yne

Conditions
ConditionsYield
In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide rt, 16 h; reflux, 2 h;72%
3-(tert-butyldimethylsilyloxy)propyl bromide
89031-84-5

3-(tert-butyldimethylsilyloxy)propyl bromide

dilithium acetylide
1070-75-3

dilithium acetylide

1-(tert-butyldimethylsilyloxy)-4-pentyne
61362-77-4

1-(tert-butyldimethylsilyloxy)-4-pentyne

Conditions
ConditionsYield
In dimethyl sulfoxide at 0℃;68.5%
POC6H2-2,4,6-t-Bu3
796-62-3

POC6H2-2,4,6-t-Bu3

dilithium acetylide
1070-75-3

dilithium acetylide

C38H58Cl2O2P2

C38H58Cl2O2P2

Conditions
ConditionsYield
In diethyl ether at 25℃; for 3h;66%
1,4-dichloropermethyltetrasilane
754-75-6

1,4-dichloropermethyltetrasilane

dilithium acetylide
1070-75-3

dilithium acetylide

octamethyltetrasilacyclohexyne
138542-16-2

octamethyltetrasilacyclohexyne

Conditions
ConditionsYield
65%
trimethyltin bromide
1066-44-0

trimethyltin bromide

dilithium acetylide
1070-75-3

dilithium acetylide

bis(trimethyltin)acetylene
2117-50-2

bis(trimethyltin)acetylene

Conditions
ConditionsYield
In pentane Ar atmosphere, addn. of soln. of (CH3)3SnBr to suspension of Li2C2 at -25°C (40 min), warming to room temp., reflux (1 h); filtration from LiCl, concn., recrystn. (pentane, -78°C), drying (40°C, 5 Torr);64%
dilithium acetylide
1070-75-3

dilithium acetylide

1,2-bis<2-(chlorodimethylsilyl)ethyl>-1,1,2,2-tetramethyldisilane
172538-40-8

1,2-bis<2-(chlorodimethylsilyl)ethyl>-1,1,2,2-tetramethyldisilane

3,3,6,6,7,7,10,10-octamethyl-3,6,7,10-tetrasilacyclodecyne
172538-42-0

3,3,6,6,7,7,10,10-octamethyl-3,6,7,10-tetrasilacyclodecyne

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;62.2%
tetra(μ-N,N'-2-anilinopyridinate)diruthenium(II,III) chloride

tetra(μ-N,N'-2-anilinopyridinate)diruthenium(II,III) chloride

dilithium acetylide
1070-75-3

dilithium acetylide

bis((tetraμ-N,N'-2-anilinopyridinate)diruthenium(II,III))ethynediyl

bis((tetraμ-N,N'-2-anilinopyridinate)diruthenium(II,III))ethynediyl

Conditions
ConditionsYield
In tetrahydrofuran (Ar), at room temp. for 12 h; washed (brine), evapd., rinzed (CH2Cl2), recrystd.(THF), elem. anal.;42%
Ru2(2-anilinopyridinate)4Cl

Ru2(2-anilinopyridinate)4Cl

dilithium acetylide
1070-75-3

dilithium acetylide

bis((tetraμ-N,N'-2-anilinopyridinate)diruthenium(II,III))ethynediyl

bis((tetraμ-N,N'-2-anilinopyridinate)diruthenium(II,III))ethynediyl

Conditions
ConditionsYield
In tetrahydrofuran under Ar atm. using Schlenk techniques; LiCCLi transferred to THF soln. of Ru complex; stirred at room temp. overnight; to the ice-chilled soln. added satd. aq. soln. of NaCl; org. layer sepd.; washed aq. satd. soln. of NaCl; dried (Na2SO4); solvent removed; ppt. collected by filtration; washed (CH2Cl2); residue dried (vac.) overnight; elem. anal.;42%
1,2-bis[2-(chlorodimethylgermyl)ethyl]-1,1,2,2-tetramethyldigermane
172538-41-9

1,2-bis[2-(chlorodimethylgermyl)ethyl]-1,1,2,2-tetramethyldigermane

dilithium acetylide
1070-75-3

dilithium acetylide

3,3,6,6,7,7,10,10-octamethyl-3,6,7,10-tetragermacyclodecyne
172538-43-1

3,3,6,6,7,7,10,10-octamethyl-3,6,7,10-tetragermacyclodecyne

Conditions
ConditionsYield
In tetrahydrofuran mixing of solns. of Li salt and Ge compound (room temp., 5 h), stirring (overnight); Kugelrohr distillation;23%
bis(cyclopentadienyl)titanium dichloride
1271-19-8

bis(cyclopentadienyl)titanium dichloride

dilithium acetylide
1070-75-3

dilithium acetylide

trimethylphosphane
594-09-2

trimethylphosphane

μ-(η1:η1-ethendiylidnene)-bis{bis(η5-cyclopentadienyl)(trimethylphosphane)titanium}
142895-81-6

μ-(η1:η1-ethendiylidnene)-bis{bis(η5-cyclopentadienyl)(trimethylphosphane)titanium}

Conditions
ConditionsYield
With Mg In tetrahydrofuran Ar atmosphere; addn. of Li2C2 in THF to soln. of Ti compd. in THF (20°C), stirring (20°C, 12 h), addn. of PMe3 and Mg, warming (27°C), stirring (24 h); removal of solvent (0.5 Torr), addn. of toluene, filtration, removal of toluene (0.5 Torr), addn. of THF, standing (2 d), sepn., drying (Ar stream); not pure;20%
V(C6H2(CH3)3)3C4H8O*0.25C4H8O

V(C6H2(CH3)3)3C4H8O*0.25C4H8O

dilithium acetylide
1070-75-3

dilithium acetylide

Dilithium-μ-ethindiyl-hexamesityl-divanadat-terahydrofuran(1/8)

Dilithium-μ-ethindiyl-hexamesityl-divanadat-terahydrofuran(1/8)

Conditions
ConditionsYield
With THF In tetrahydrofuran 30 min stirring, under Ar; concg., pptn. with diethylether, washing with ether, drying in vac.; elem.anal.;18%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

dilithium acetylide
1070-75-3

dilithium acetylide

acetylene
74-86-2

acetylene

bis(trimethyltin)acetylene
2117-50-2

bis(trimethyltin)acetylene

Conditions
ConditionsYield
In hexane excess of C2H2;10%
chlorotriethylstannane
994-31-0

chlorotriethylstannane

dilithium acetylide
1070-75-3

dilithium acetylide

acetylene
74-86-2

acetylene

A

triethylethynylstannane
994-39-8

triethylethynylstannane

B

bis(triethylstannyl)ethyne
994-99-0

bis(triethylstannyl)ethyne

Conditions
ConditionsYield
In hexane excess of C2H2;A 10%
B n/a
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

dilithium acetylide
1070-75-3

dilithium acetylide

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

C18H12F6O4S2

C18H12F6O4S2

Conditions
ConditionsYield
In diethyl ether at -20℃;1.3%
tripropylborane
1116-61-6

tripropylborane

dilithium acetylide
1070-75-3

dilithium acetylide

4,5-dipropyl-4-octene
57984-32-4

4,5-dipropyl-4-octene

Conditions
ConditionsYield
(i) , (ii) BrCN, NaOMe, (iii) EtCO2H; Multistep reaction;

Lithium acetylide Chemical Properties

IUPAC:  Dilithium acetylide
 Lithium acetylide with CAS NO.of 1070-75-3 is also called for EINECS 213-980-1 ; CID66115 ; 1070-75-3 ; 1,2-Dilithioacetylene ; Dilithioacetylene ; Ethyne-1,2-diylbislithium ; Ethynylenebislithium and so on.
CAS: 1070-75-3
Molecular Formula: C2Li2
Molecular Weight: 37.9034
EINECS: 213-980-1
ACD/LogP: 0.37
ACD/LogD (pH 5.5): 0.37 
ACD/LogD (pH 7.4): 0.37 
ACD/BCF (pH 5.5): 1.13 
ACD/BCF (pH 7.4): 1.13 
ACD/KOC (pH 5.5): 37.87 
ACD/KOC (pH 7.4): 37.87 
H bond acceptors: 0 
H bond donors: 0 
Freely Rotating Bonds: 0 
Heavy Atom Count: 4
Formal Charge: 0
Complexity: 12
Isotope Atom Count: 0
Defined Atom StereoCenter Count: 0
Undefined Atom StereoCenter Count: 0
Defined Bond StereoCenter Count: 0
Undefined Bond StereoCenter Count: 0
Covalently-Bonded Unit Count: 3
Enthalpy of Vaporization: 21.12 kJ/mol 
Vapour Pressure: 69700 mmHg at 25°C
Density: 1.3 g/cm3
Melting Point: > 550°C
The molecular structure of  Lithium acetylide with CAS NO.of  1070-75-3:

Lithium acetylide Uses

 Lithium acetylide (CAS NO.1070-75-3) can be used in radiocarbon dating.

Lithium acetylide Production

 Lithium acetylide (CAS NO.1070-75-3) can be prepared from the following two ways:
1.molten lithium + graphite are reacted at high temperature
2.carbon dioxide + molten lithium

Lithium acetylide Safety Profile

Ignites and burns vigorously in fluorine, chlorine, phosphorus, selenium, or sulfur vapors. Ignites when heated in bromine or iodine vapors. When heated to decomposition it emits acrid smoke and fumes. See also LITHIUM COMPOUNDS and ACETYLIDES.

Lithium acetylide Specification

 Lithium acetylide with CAS NO.of 1070-75-3 is an ionic salt, it will transform reversibly to a cubic anti-fluorite structure at high temperatures.
 

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