Product Name

  • Name

    SODIUM ACETYLIDE

  • EINECS 213-908-9
  • CAS No. 1066-26-8
  • Density g/cm3
  • Solubility Reacts with water.
  • Melting Point
  • Formula C2H Na
  • Boiling Point °Cat760mmHg
  • Molecular Weight 48.0197
  • Flash Point °C
  • Transport Information
  • Appearance brown slurry
  • Safety When heated to 150°C it decomposes to form a gas which ignites spontaneously in air. The dry powder can ignite spontaneously if a large surface area is exposed to air (e.g. on a filter paper). When heated to decomposition it emits toxic fumes of Na2O. See also ACETYLIDES.
  • Risk Codes 10-15-20/21-38-34-14/15
  • Molecular Structure Molecular Structure of 1066-26-8 (SODIUM ACETYLIDE)
  • Hazard Symbols F,Xn,C
  • Synonyms Sodiumacetylide (6CI,7CI);Sodium acetylide (Na(HC2)) (8CI);Ethynyl sodium;Monosodium acetylide;Sodium acetylenide;Sodium carbide (Na(C2H));Sodiumcarbide (Na(HC2));Sodium, ethynyl-;
  • PSA 0.00000
  • LogP 0.12640

Synthetic 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%

Monosodium Acetylide Chemical Properties

Chemistry informtion about Monosodium Acetylide (CAS NO.1066-26-8) is:
IUPAC Name: Sodium Ethyne
Synonyms: Ethynylsodium ; Sodium Acetylide ; Sodium Acetylide Suspension ; Sodium Acetylide, 18 Wt. % Slurry In Xyl Ene/Light Mineral Oil, 95% ; Sodium Acetylide Suspension, ~12% In Xylene ; Sodium Acetylide 18% Slurry In Xylene/Oil ; Sodium Acetylide, 18 Wt% Slurry In Xylene ; Sodium Acetylide 20% W/W Slurry In Xylene/Oil 85:15
MF: C2HNa
MW: 48.02
EINECS: 213-908-9 
Density: 0,865 g/cm3
Flash Point: 85 °F
Vapour Pressure: 69700 mmHg at 25°C
Enthalpy of Vaporization: 21.12 kJ/mol
Storage temp.: Refrigerator (+4°C) + Flammables area
Sensitive: Air & Moisture Sensitive
BRN: 3587232
Following is the molecular structure of Monosodium Acetylide (CAS NO.1066-26-8) is:

Monosodium Acetylide Production

Preparation Products are Linalool --> Leaf Alcohol --> Vitamin A --> 1-Ethynyl-2-Methyl Penten-2-Ol --> Propiolic Acidd -->Chlorempenthrin .

Monosodium Acetylide Safety Profile

When heated to 150°C it decomposes to form a gas which ignites spontaneously in air. The dry powder can ignite spontaneously if a large surface area is exposed to air (e.g. on a filter paper). When heated to decomposition it emits toxic fumes of Na2O. See also ACETYLIDES.
Hazard Codes:
FlammableF
HarmfulXn
Risk Statements:
R10:Flammable. 
R15:Contact with water liberates extremely flammable gases. 
R20/21:Harmful by inhalation and in contact with skin. 
R38:Irritating to skin.
Safety Statements:
S36/37:Wear suitable protective clothing and gloves. 
S43:In case of fire use ... (there follows the type of fire-fighting equipment to be used.)
RIDADR: UN 3399 4.3/PG 1
WGK Germany: 3
HazardClass: 4.3
PackingGroup: II

Monosodium Acetylide Specification

 Monosodium Acetylide (CAS NO.1066-26-8) is a brown slurry.
First Aid Measures:
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion: Get medical aid. Wash mouth out with water.
Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. 
Handling and Storage:
Handling: Use spark-proof tools and explosion proof equipment. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Use and store under nitrogen. Do not allow contact with water.
Storage: Keep away from sources of ignition. Keep refrigerated. (Store below 4°C/39°F.) Store in a tightly closed container. Store in a dry area. Flammables-area. Keep away from acidic, alkaline, combustible and oxidizing materials.

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