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1066-26-8

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1066-26-8 Usage

Description

Sodium acetylide is an unstable powder, a salt of acetylene. It is a severe explosion risk when shocked or heated. It is used in the manufacture of detonators.

Chemical Properties

brown slurry

Uses

Different sources of media describe the Uses of 1066-26-8 differently. You can refer to the following data:
1. Sodium acetylide suspension has been used in the preparation of: 2-ethynyladamantan-2-ol1 apical-equatorial (ae) isomer of (Et4N)3[1-(2′-B10H9)-2-NH3B10H8]2 trimethylsilylacetylene3
2. Sodium Acetylide Suspension is a reagent used in the synthesis of rhodium(I) amidinate complexes.

Definition

ChEBI: The salt formed from the acetylide monoanion and a single sodium cation.

Purification Methods

It sometimes contains diluents, e.g. xylene, butyl ether or dioxane which can be removed by filtration followed by a vacuum at 65-60o/5mm. Alternatively the acetylide is purged with HCCH at 100-125o to remove diluent. NaC2H adsorbs 2.2x, 2.0x and 1.6x its wt of xylene, butyl ether and dioxane, respectively. Powdered NaC2H is yellow or yellow-gray in colour and is relatively stable. It can be heated to ca 300o in the absence of air. Although no explosion or evolution of gas occurs, it turns brown due to disproportionation. At 170-190o in air it ignites slowly and burns smoothly. At 215-235o in air it “flash-ignites” and burns quickly. It can be dropped into a slight excess of H2O without flashing or burning, but vigorous evolution of HC CH (HIGHLY FLAMMABLE IN AIR) occurs. The sample had been stored in the absence of air for one year without deterioration. Due to the high flammability of HCCH, the salt should be stored dry and should be treated with care. After long storage, NaCCH can be redissolved in liquid NH3 and used for the same purposes as the fresh material. However it may be slightly turbid due to the presence of moisture. [Rutledge J Org Chem 22 649 1957, Greenlee & Henne J Am Chem Soc 77 5013 1955, Campbell & Campbell Inorg Synth II 76, 81 1946, Org Synth 30 15 1950, Beilstein 1 H 238.] It is available commercially under N2 in Sure/Seal bottles as an 18 wt% solution in xylene/mineral oil. See “Aliphatic Compounds”, Chapter 4, for its prepartion.

Check Digit Verification of cas no

The CAS Registry Mumber 1066-26-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,6 and 6 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1066-26:
(6*1)+(5*0)+(4*6)+(3*6)+(2*2)+(1*6)=58
58 % 10 = 8
So 1066-26-8 is a valid CAS Registry Number.
InChI:InChI=1/C2H.Na/c1-2;/h1H;/rC2HNa/c1-2-3/h1H

1066-26-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Alfa Aesar

  • (L09656)  Sodium acetylide, ca 18% slurry in xylene   

  • 1066-26-8

  • 100g

  • 629.0CNY

  • Detail
  • Alfa Aesar

  • (L09656)  Sodium acetylide, ca 18% slurry in xylene   

  • 1066-26-8

  • 500g

  • 2024.0CNY

  • Detail
  • Aldrich

  • (249572)  Sodiumacetylidesuspension  18 wt. % slurry in xylene: light mineral oil, 95% (Purity of contained acetylide)

  • 1066-26-8

  • 249572-100G

  • 560.43CNY

  • Detail
  • Aldrich

  • (249572)  Sodiumacetylidesuspension  18 wt. % slurry in xylene: light mineral oil, 95% (Purity of contained acetylide)

  • 1066-26-8

  • 249572-500G

  • 2,397.33CNY

  • Detail

1066-26-8SDS

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 monosodium acetylide

1.2 Other means of identification

Product number -
Other names Sodium acetylide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:1066-26-8 SDS

1066-26-8Synthetic route

acetylene
74-86-2

acetylene

sodium acetylide
1066-26-8

sodium acetylide

Conditions
ConditionsYield
With sodium; xylene at 60 - 110℃;
With dibutyl ether; sodium at 60 - 110℃;
With diethylene glycol dibutyl ether; sodium at 60 - 110℃;
diethyl ether
60-29-7

diethyl ether

1,2-dibutoxy-1,2-dichloro-ethene
232269-26-0

1,2-dibutoxy-1,2-dichloro-ethene

sodium

sodium

A

sodium acetylide
1066-26-8

sodium acetylide

B

sodium butanolate
2372-45-4

sodium butanolate

2-Adamantanone
700-58-3

2-Adamantanone

sodium acetylide
1066-26-8

sodium acetylide

2-Ethynyl-2-hydroxyadamantane
70887-49-9

2-Ethynyl-2-hydroxyadamantane

Conditions
ConditionsYield
In tetrahydrofuran; xylene 1.) 18 h, room temp., 2.) 1 h, 70 deg C;100%
In tetrahydrofuran; xylene a) RT, 18 h, b) 70 deg C, 1 h;5.30 g
sodium acetylide
1066-26-8

sodium acetylide

3a-hydroxy-1e,3e-dimethyl-4-piperidone
36106-49-7, 52899-10-2, 56029-53-9

3a-hydroxy-1e,3e-dimethyl-4-piperidone

3a,4a-dihydroxy-1e,3e-dimethyl-4e-ethynyl-6e-phenylpiperidine
84687-60-5, 84687-62-7, 84714-91-0, 98114-75-1

3a,4a-dihydroxy-1e,3e-dimethyl-4e-ethynyl-6e-phenylpiperidine

Conditions
ConditionsYield
In ammonia for 1h;100%
sodium acetylide
1066-26-8

sodium acetylide

3a-hydroxy-3e-methyl-1-benzyl-4-piperidone
56642-31-0, 56642-34-3

3a-hydroxy-3e-methyl-1-benzyl-4-piperidone

3a,4e-dihydroxy-3e-methyl-1e-benzyl-4a-ethynyl-6e-phenylpiperidine
84714-87-4, 84714-89-6, 84714-95-4, 84714-97-6

3a,4e-dihydroxy-3e-methyl-1e-benzyl-4a-ethynyl-6e-phenylpiperidine

Conditions
ConditionsYield
In ammonia for 1h;100%
bis((4S,5S)-4-(azidomethyl)-5-phenyl-4,5-dihydrooxazol-2-yl)methane
1453106-63-2

bis((4S,5S)-4-(azidomethyl)-5-phenyl-4,5-dihydrooxazol-2-yl)methane

sodium acetylide
1066-26-8

sodium acetylide

bis((4S,5S)-4-((1H-1,2,3-triazol-1-yl)methyl)-5-phenyl-4,5-dihydrooxazol-2-yl)methane
1453106-70-1

bis((4S,5S)-4-((1H-1,2,3-triazol-1-yl)methyl)-5-phenyl-4,5-dihydrooxazol-2-yl)methane

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; dimethyl sulfoxide at 20℃; for 18h; Inert atmosphere; Schlenk technique;100%
sodium acetylide
1066-26-8

sodium acetylide

3,3-(ethylenedioxy)-5β,10β-epoxyestra-9(11)-ene-17-one
39931-88-9

3,3-(ethylenedioxy)-5β,10β-epoxyestra-9(11)-ene-17-one

3,3-(ethylenedioxy)-17α-ethynyl-17β-hydroxy-5β,10β-epoxyestr-9(11)-ene

3,3-(ethylenedioxy)-17α-ethynyl-17β-hydroxy-5β,10β-epoxyestr-9(11)-ene

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;100%
1-bromo-20-(methoxymethoxy)icosane

1-bromo-20-(methoxymethoxy)icosane

sodium acetylide
1066-26-8

sodium acetylide

22-(methoxymethoxy)docos-1-yne

22-(methoxymethoxy)docos-1-yne

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;100%
2,4-dimethoxy-4'-fluorobenzophenone
7359-15-1

2,4-dimethoxy-4'-fluorobenzophenone

sodium acetylide
1066-26-8

sodium acetylide

C17H15FO3
1352150-78-7

C17H15FO3

Conditions
ConditionsYield
With 18-crown-6 ether In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 20℃; for 168h;99%
sodium acetylide
1066-26-8

sodium acetylide

ethylene deltenone
5571-36-8

ethylene deltenone

(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol
5490-76-6

(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol

Conditions
ConditionsYield
In tetrahydrofuran at -2 - 0℃; for 6.5h; Inert atmosphere; Industrial scale;99%
In tetrahydrofuran at -2 - 0℃; for 6h; Inert atmosphere; Large scale;99%
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;95%
sodium acetylide
1066-26-8

sodium acetylide

hexadecanyl bromide
112-82-3

hexadecanyl bromide

1-octadecyne
629-89-0

1-octadecyne

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;98%
With ammonia at 25℃; unter Druck;
With ammonia; N,N-dimethyl-formamide nach Entfernung des Ammoniaks bei 65-70grad;
(±)-2-methyl-2-phenyl-2,3-dihydro-1H-inden-1-one
1005420-27-8, 10474-32-5, 887255-49-4

(±)-2-methyl-2-phenyl-2,3-dihydro-1H-inden-1-one

sodium acetylide
1066-26-8

sodium acetylide

(1R,2R)-1-Ethynyl-2-methyl-2-phenyl-indan-1-ol
104480-61-7, 104480-64-0

(1R,2R)-1-Ethynyl-2-methyl-2-phenyl-indan-1-ol

Conditions
ConditionsYield
In tetrahydrofuran for 15h; Ambient temperature;98%
sodium acetylide
1066-26-8

sodium acetylide

C30H50O4Si

C30H50O4Si

C32H52O4Si

C32H52O4Si

Conditions
ConditionsYield
In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 40℃; for 4.5h; Temperature;97.23%
3beta-Acetoxyandrosta-1,5-dien-17-one
16413-85-7

3beta-Acetoxyandrosta-1,5-dien-17-one

sodium acetylide
1066-26-8

sodium acetylide

3beta,17beta-Dihydroxy-17alpha-ethynylandrosta-1,5-diene
2774-17-6

3beta,17beta-Dihydroxy-17alpha-ethynylandrosta-1,5-diene

Conditions
ConditionsYield
In dimethyl sulfoxide; xylene at 20℃; for 2h;96%
[Ru(η(5)-indenyl)(=C=C=CPh2)(triphenylphosphine)2](hexafluorophosphate)

[Ru(η(5)-indenyl)(=C=C=CPh2)(triphenylphosphine)2](hexafluorophosphate)

sodium acetylide
1066-26-8

sodium acetylide

[Ru(CCC(CCH)Ph2)(η(5)-C9H7)(PPh3)2]
194924-65-7

[Ru(CCC(CCH)Ph2)(η(5)-C9H7)(PPh3)2]

Conditions
ConditionsYield
In tetrahydrofuran N2-atmosphere; -20°C to room temp.; evapn. (vac.), extg. (Et2O), filtering, evapn., chromy. (SiO2, hexane / Et2O = 4 : 1); elem. anal.;96%
1-azido-3-bromobenzene
2101-89-5

1-azido-3-bromobenzene

sodium acetylide
1066-26-8

sodium acetylide

1-(3-bromophenyl)-1H-1,2,3-triazole
85862-62-0

1-(3-bromophenyl)-1H-1,2,3-triazole

Conditions
ConditionsYield
Stage #1: 1-azido-3-bromobenzene; sodium acetylide In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: With water In dimethyl sulfoxide
96%
1-bromo-10-decanol
53463-68-6

1-bromo-10-decanol

sodium acetylide
1066-26-8

sodium acetylide

11-dodecyn-1-ol
18202-10-3

11-dodecyn-1-ol

Conditions
ConditionsYield
In ammonia; N,N-dimethyl-formamide at 50℃; for 2h;93.4%
(4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl)(phenyl)methanone

(4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl)(phenyl)methanone

sodium acetylide
1066-26-8

sodium acetylide

1-(4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl)-1-phenylprop-2-yn-1-ol

1-(4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl)-1-phenylprop-2-yn-1-ol

Conditions
ConditionsYield
In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 0 - 20℃; for 3h; Inert atmosphere;93.2%
trimethylaluminum
75-24-1

trimethylaluminum

sodium acetylide
1066-26-8

sodium acetylide

benzaldehyde
100-52-7

benzaldehyde

1-Phenyl-2-propyn-1-ol
4187-87-5

1-Phenyl-2-propyn-1-ol

Conditions
ConditionsYield
In tetrahydrofuran; toluene; xylene for 1h; Ambient temperature;93%
1-azido-3-chlorobenzene
3296-06-8

1-azido-3-chlorobenzene

sodium acetylide
1066-26-8

sodium acetylide

1-(3-chlorophenyl)-1H-1,2,3-triazole
85862-60-8

1-(3-chlorophenyl)-1H-1,2,3-triazole

Conditions
ConditionsYield
Stage #1: 1-azido-3-chlorobenzene; sodium acetylide In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: With water In dimethyl sulfoxide
93%
3-methoxyphenyl azide
3866-16-8

3-methoxyphenyl azide

sodium acetylide
1066-26-8

sodium acetylide

1-(3-methoxyphenyl)-1H-1,2,3-triazole
108429-57-8

1-(3-methoxyphenyl)-1H-1,2,3-triazole

Conditions
ConditionsYield
Stage #1: 3-methoxyphenyl azide; sodium acetylide In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: With water In dimethyl sulfoxide
93%
1,1-bis(diethylphosphono)ethylene
37465-31-9

1,1-bis(diethylphosphono)ethylene

sodium acetylide
1066-26-8

sodium acetylide

tetraethyl (3-butyn-1-ylidene)-1,1-bisphosphonate
154384-16-4

tetraethyl (3-butyn-1-ylidene)-1,1-bisphosphonate

Conditions
ConditionsYield
In tetrahydrofuran; xylene at -15 - 20℃;92%
In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at -15 - 20℃; for 19h;40%
2-(5-bromopentyl)-2-methyl-[1,3]dioxolane
37865-98-8

2-(5-bromopentyl)-2-methyl-[1,3]dioxolane

sodium acetylide
1066-26-8

sodium acetylide

2-(hept-6-ynyl)-2-methyl-1,3-dioxolane
4405-14-5

2-(hept-6-ynyl)-2-methyl-1,3-dioxolane

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;92%
sodium acetylide
1066-26-8

sodium acetylide

2-((13-bromotridecyl)oxy)tetrahydro-2H-pyran
116452-12-1

2-((13-bromotridecyl)oxy)tetrahydro-2H-pyran

1-tetrahydropyranyloxy-14-pentadecyne
159627-62-0

1-tetrahydropyranyloxy-14-pentadecyne

Conditions
ConditionsYield
In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; xylene for 36h; Ambient temperature;91%
trimethylaluminum
75-24-1

trimethylaluminum

sodium acetylide
1066-26-8

sodium acetylide

N,N-Diethyl-6-oxoheptanamide

N,N-Diethyl-6-oxoheptanamide

6-Hydroxy-6-methyl-oct-7-ynoic acid diethylamide

6-Hydroxy-6-methyl-oct-7-ynoic acid diethylamide

Conditions
ConditionsYield
In tetrahydrofuran; toluene; xylene at 0℃; for 3h;91%
trimethylaluminum
75-24-1

trimethylaluminum

sodium acetylide
1066-26-8

sodium acetylide

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

4-(1-hydroxyprop-2-yn-1-yl)benzonitrile
1595-70-6

4-(1-hydroxyprop-2-yn-1-yl)benzonitrile

Conditions
ConditionsYield
In tetrahydrofuran; toluene; xylene at 0℃; for 3h;90%
sodium acetylide
1066-26-8

sodium acetylide

3-(3-furyl)-1-bromopropane
98126-48-8

3-(3-furyl)-1-bromopropane

3-(pent-4-yn-1-yl)furan
187458-26-0

3-(pent-4-yn-1-yl)furan

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide at 15℃; for 2h;90%
2-(4-methoxybenzoyl)thiophene
4160-63-8

2-(4-methoxybenzoyl)thiophene

sodium acetylide
1066-26-8

sodium acetylide

1-(thiophen-2-yl)-1-(4-methoxyphenyl)-prop-2-yn-1-ol
211796-85-9

1-(thiophen-2-yl)-1-(4-methoxyphenyl)-prop-2-yn-1-ol

Conditions
ConditionsYield
In xylene for 48h; Ambient temperature;90%
In dimethyl sulfoxide at 23℃; for 2h;84.1%
RhOs(CO)3(NCCH3)H((C6H5)2PCH2P(C6H5)2)2(2+)*2BF4(1-)*CH3CN=[RhOs(CO)3NC2H4(C6H5)8P4C2H4](BF4)2*CH3CN

RhOs(CO)3(NCCH3)H((C6H5)2PCH2P(C6H5)2)2(2+)*2BF4(1-)*CH3CN=[RhOs(CO)3NC2H4(C6H5)8P4C2H4](BF4)2*CH3CN

sodium acetylide
1066-26-8

sodium acetylide

A

RhOs(CH2CN)(CO)3((C6H5)2PCH2P(C6H5)2)2

RhOs(CH2CN)(CO)3((C6H5)2PCH2P(C6H5)2)2

B

[RhOs(C2H)(CO)3((C6H5)2PCH2P(C6H5)2)2]*0.5CH2Cl2

[RhOs(C2H)(CO)3((C6H5)2PCH2P(C6H5)2)2]*0.5CH2Cl2

Conditions
ConditionsYield
In acetonitrile crystn. (CH2Cl2/Et2O); elem. anal.;A n/a
B 90%
In acetonitrile stirring (1 h); evapn. of CH2Cl2 soln. (vac., 6 h), recrystn. (Et2O/CH2Cl2); elem. anal.;A 50%
B n/a
sodium acetylide
1066-26-8

sodium acetylide

p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

1-(4-methoxyphenyl)-1H-[1,2,3]triazole
68535-49-9

1-(4-methoxyphenyl)-1H-[1,2,3]triazole

Conditions
ConditionsYield
Stage #1: sodium acetylide; p-methoxy-phenylazide In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: With water In dimethyl sulfoxide
90%
Toluene-4-sulfonic acid 2-((S)-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester
853193-64-3

Toluene-4-sulfonic acid 2-((S)-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester

sodium acetylide
1066-26-8

sodium acetylide

(R)-4-But-3-ynyl-2,2-dimethyl-[1,3]dioxane
853193-65-4

(R)-4-But-3-ynyl-2,2-dimethyl-[1,3]dioxane

Conditions
ConditionsYield
In dimethyl sulfoxide for 0.166667h; cooling;89%
7-octene-2-one
3664-60-6

7-octene-2-one

sodium acetylide
1066-26-8

sodium acetylide

3-methylnon-8-en-1-yn-3-ol

3-methylnon-8-en-1-yn-3-ol

Conditions
ConditionsYield
In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 20℃; for 16h; Inert atmosphere;89%

1066-26-8Relevant articles and documents

-

Kriz et al.

, p. 2881 (1965)

-

-

Rutledge

, p. 649 (1957)

-

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