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Synthetic route

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

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

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

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
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

...Expand

: 188290-36-0
thiophene

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

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

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
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

...Expand

: 554-14-3
2-Methylthiophene

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

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

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
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

...Expand

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

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

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

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
Stage #1: n-butyllithium; N-(α-methylbenzyl)-3-(trimethylsilyl)-2-propynylamine at 20℃; Stage #2: With methanol	A 71% B n/a

...Expand

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

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

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

B: 1070-75-3
dilithium acetylide

Conditions

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

...Expand

: 56-23-5
tetrachloromethane

: 7439-93-2
lithium

A: CLi4

B: 38827-81-5
ethenetetrayl-tetrakis-lithium

C: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
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%

...Expand

: 110-00-9
furan

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

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

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
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

...Expand

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

: 594-19-4
tert.-butyl lithium

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

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
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

...Expand

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

: 591-51-5
phenyllithium

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

B: 1070-75-3
dilithium acetylide

Conditions

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

...Expand

: 2786-07-4
2-thienyl lithium

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

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

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
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

...Expand

: 2786-02-9
2-lithiofuran

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

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

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
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

...Expand

: 917-54-4
methyllithium

A: 34557-54-5
methane

B: 21473-62-1
dilithiomethane

C: 69815-14-1
propadienetetrayl-tetrakis-lithium

D: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
at 223 - 226℃; Yield given. Yields of byproduct given;

...Expand

: 65801-58-3, 75620-60-9, 171562-29-1
cis-1,2-Dilithioethylen

A: 917-57-7
vinyllithium

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
Title compound not separated from byproducts;

: 65801-58-3, 75620-60-9, 171562-29-1
trans-1,2-Dilithioethylen

A: 917-57-7
vinyllithium

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
Title compound not separated from byproducts;

: 70277-75-7
lithium acetylide

A: 917-57-7
vinyllithium

B: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
With dilithiumethylene Title compound not separated from byproducts;

: 79-01-6
Trichloroethylene

: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; diethyl ether for 2h; Ambient temperature;
With n-butyllithium In tetrahydrofuran

: 74-86-2
acetylene

: 1070-75-3
dilithium acetylide

Conditions

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

: graphite

: lithium chloride

: 1070-75-3
dilithium acetylide

Conditions

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

: graphite

: 7439-93-2
lithium

: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
In neat (no solvent, solid phase) heated at 900°C for 12 h in Nb ampoule;

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

: 74-86-2
acetylene

: 1070-75-3
dilithium acetylide

Conditions

Conditions	Yield
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

: 10026-12-7
niobium pentachloride

: 1070-75-3
dilithium acetylide

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

Conditions

Conditions	Yield
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%

...Expand

: 5586-42-5
1,5-dichlorodecamethylpentasilane

: 1070-75-3
dilithium acetylide

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

Conditions

Conditions	Yield
	80%

: 1070-75-3
dilithium acetylide

: 155166-24-8
(diethylamino)dimethylsilyl-triflat

: Bis<(diethylamino)dimethylsilyl>ethin

Conditions

Conditions	Yield
In diethyl ether for 0.5h; Ambient temperature;	78%

: 1066-45-1
trimethyltin(IV)chloride

: 1070-75-3
dilithium acetylide

: 2117-50-2
bis(trimethyltin)acetylene

Conditions

Conditions	Yield
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%

: 1070-75-3
dilithium acetylide

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

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

Conditions

Conditions	Yield
In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide rt, 16 h; reflux, 2 h;	72%

: 89031-84-5
3-(tert-butyldimethylsilyloxy)propyl bromide

: 1070-75-3
dilithium acetylide

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

Conditions

Conditions	Yield
In dimethyl sulfoxide at 0℃;	68.5%

: 796-62-3
POC6H2-2,4,6-t-Bu3

: 1070-75-3
dilithium acetylide

: C38H58Cl2O2P2

Conditions

Conditions	Yield
In diethyl ether at 25℃; for 3h;	66%

: 754-75-6
1,4-dichloropermethyltetrasilane

: 1070-75-3
dilithium acetylide

: 138542-16-2
octamethyltetrasilacyclohexyne

Conditions

Conditions	Yield
	65%

: 1066-44-0
trimethyltin bromide

: 1070-75-3
dilithium acetylide

: 2117-50-2
bis(trimethyltin)acetylene

Conditions

Conditions	Yield
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%

: 1070-75-3
dilithium acetylide

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

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

Conditions

Conditions	Yield
In tetrahydrofuran Ambient temperature;	62.2%

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

: 1070-75-3
dilithium acetylide

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

Conditions

Conditions	Yield
In tetrahydrofuran (Ar), at room temp. for 12 h; washed (brine), evapd., rinzed (CH2Cl2), recrystd.(THF), elem. anal.;	42%

: Ru2(2-anilinopyridinate)4Cl

: 1070-75-3
dilithium acetylide

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

Conditions

Conditions	Yield
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%

: 172538-41-9
1,2-bis[2-(chlorodimethylgermyl)ethyl]-1,1,2,2-tetramethyldigermane

: 1070-75-3
dilithium acetylide

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

Conditions

Conditions	Yield
In tetrahydrofuran mixing of solns. of Li salt and Ge compound (room temp., 5 h), stirring (overnight); Kugelrohr distillation;	23%

: 1271-19-8
bis(cyclopentadienyl)titanium dichloride

: 1070-75-3
dilithium acetylide

: 594-09-2
trimethylphosphane

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

Conditions

Conditions	Yield
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%

...Expand

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

: 1070-75-3
dilithium acetylide

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

Conditions

Conditions	Yield
With THF In tetrahydrofuran 30 min stirring, under Ar; concg., pptn. with diethylether, washing with ether, drying in vac.; elem.anal.;	18%

: 1066-45-1
trimethyltin(IV)chloride

: 1070-75-3
dilithium acetylide

: 74-86-2
acetylene

: 2117-50-2
bis(trimethyltin)acetylene

Conditions

Conditions	Yield
In hexane excess of C2H2;	10%

...Expand

: 994-31-0
chlorotriethylstannane

: 1070-75-3
dilithium acetylide

: 74-86-2
acetylene

A: 994-39-8
triethylethynylstannane

B: 994-99-0
bis(triethylstannyl)ethyne

Conditions

Conditions	Yield
In hexane excess of C2H2;	A 10% B n/a

...Expand

: 358-23-6
trifluoromethylsulfonic anhydride

: 1070-75-3
dilithium acetylide

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

: C18H12F6O4S2

Conditions

Conditions	Yield
In diethyl ether at -20℃;	1.3%

...Expand

: 1116-61-6
tripropylborane

: 1070-75-3
dilithium acetylide

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

Conditions

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

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Zhuozhou Wenxi import and Export Co., Ltd

Shanghai Upbio Tech Co.,Ltd

Qingdao Beluga Import and Export Co., LTD

Shandong Hanjiang Chemical Co., Ltd.

Henan Wentao Chemical Product Co., Ltd.

Zibo Hangyu Biotechnology Development Co., Ltd

Hangzhou J&H Chemical Co., Ltd.

Xi`an Eastling Biotech Co., Ltd.

Henan Tianfu Chemical Co., Ltd.

Xian Changyue Biological Technology Co., Ltd.

Chemsigma International Co.,Ltd.

Antimex Chemical Limied

DB BIOTECH CO., LTD

BOC Sciences

Henan Kanbei Chemical Co.,LTD

Shanghai Chinqesen Biotechnology Co., Ltd.

Hebei Muhuang Technology Co., Ltd

ZHEJIANG JIUZHOU CHEM CO.,LTD

HuBei Ipure Biotech CO.,ltd

Cerametek Materials（ShenZhen）Co., Ltd.

Shanghai Run-Biotech Co., Ltd.

Nanjing Raymon Biotech Co., Ltd.

Hebei Ruishun Trade Co.,Ltd

Chemical Co.Ltd

Prochemtech International, Inc

Sluyter Company Ltd

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