26960-77-0

Basic information

• Product Name: sodium dodecane-1-thiolate
• Synonyms: sodium dodecane-1-thiolate;Sodium 1-dodecanethiolate
• CAS NO: 26960-77-0
• Molecular Formula: C₁₂H₂₅S*Na
• Molecular Weight: 224.38167
• EINECS: 248-141-9
• Mol File: 26960-77-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 275.3 °C at 760 mmHg
• Flash Point: 87.8 °C
• Appearance: /
• Vapor Pressure: 0.00861mmHg at 25°C
• CAS DataBase Reference: sodium dodecane-1-thiolate(CAS DataBase Reference)
• NIST Chemistry Reference: sodium dodecane-1-thiolate(26960-77-0)
• EPA Substance Registry System: sodium dodecane-1-thiolate(26960-77-0)

Safety Data

• Hazardous Substances Data: 26960-77-0(Hazardous Substances Data)

Usage

General Description

Sodium dodecane-1-thiolate is a chemical compound that consists of sodium and dodecane-1-thiolate. It is a white to slightly yellow solid and is commonly used as a reagent in organic and inorganic chemical reactions. It is known for its strong nucleophilic properties and is often used as a catalyst in various reactions. Sodium dodecane-1-thiolate is also used in the production of surfactants and lubricants, and as a stabilizer in the synthesis of nanoparticles. It is considered to be a useful and versatile chemical in the field of organic synthesis and industrial applications.

InChI:InChI=1/C12H26S.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13;/h13H,2-12H2,1H3;/q;+1/p-1

Synthetic route

1-dodecylthiol (112-55-0) → sodium dodecanethiolate (26960-77-0)

Conditions	Yield
With sodium hydride In diethyl ether
With sodium hydride In N,N-dimethyl-formamide at 5 - 25℃; for 1h; Inert atmosphere; Schlenk technique;
With sodium hydride In diethyl ether; mineral oil at 5℃; for 0.166667h;

sodium methylate (124-41-4) + 1-dodecylthiol (112-55-0) → sodium dodecanethiolate (26960-77-0)

Conditions	Yield
In methanol at 20℃; for 0.25h;

sodium dodecanethiolate (26960-77-0) + 1,2,4-Trichlorobenzene (120-82-1) → 1,2,4-tris(n-dodecylthio)benzene

Conditions	Yield
In various solvent(s) at 180℃; for 20h;	96%
In various solvent(s) at 180℃; for 20h; Product distribution; Mechanism; var. temp.; var. solvents; other subst. chlorobenzenes; other thiolates;

9,10-dichloroanthracene (605-48-1) + sodium dodecanethiolate (26960-77-0) → 9,10-bis(1-dodecylthio)anthracene

Conditions	Yield
In various solvent(s) at 169℃; for 23h;	95%

hexachlorobenzene (118-74-1) + sodium dodecanethiolate (26960-77-0) → hexakis(n-dodecylthio)benzene (99147-89-4)

Conditions	Yield
In various solvent(s) at 128℃; for 24h;	95%
In N,N,N,N,N,N-hexamethylphosphoric triamide Yield given;

sodium dodecanethiolate (26960-77-0) + 1-nitro-1,2-diphenyl-2-phenylthioethene (85296-24-8) → 1,2-diphenyl-2-dodecylthio-1-nitroethene

Conditions	Yield
In methanol at 20℃; for 1.25h;	91%

carbon monoxide (201230-82-2) + 4-iodo-biphenyl (1591-31-7) + sodium dodecanethiolate (26960-77-0) → S-dodecyl biphenyl-4-carbothioate (1213298-47-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1-dodecylthiol In tetrahydrofuran at 60℃; under 7600.51 Torr; for 24h; Autoclave;	90%

carbon monoxide (201230-82-2) + para-iodoanisole (696-62-8) + sodium dodecanethiolate (26960-77-0) → S-(n-dodecyl) 4-methoxybenzothioate (86763-33-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1-dodecylthiol In tetrahydrofuran at 60℃; under 7600.51 Torr; for 24h; Autoclave;	88%

1,2,4,5-tetrachlorobenzene (95-94-3) + sodium dodecanethiolate (26960-77-0) → 1,2,4,5-tetrakis(n-dodecylthio)benzene

Conditions	Yield
In various solvent(s) at 162℃; for 22h;	86%

sodium dodecanethiolate (26960-77-0) + 2,3-dibromopropionic acid ethyl ester (3674-13-3) → ethyl 2,3-bis(n-dodecylthio)propionate

Conditions	Yield
In ethanol at 70℃; for 4h; Substitution;	82%

C44H56Fe2N4 + sodium dodecanethiolate (26960-77-0) → C46H77FeN2S2(1-)*Na(1+)

Conditions	Yield
In tetrahydrofuran-d8 at 20℃; for 3h; Inert atmosphere; Glovebox;	82%

1-Bromonaphthalene (90-11-9) + sodium dodecanethiolate (26960-77-0) → 1-(1-dodecylthio)naphthalene

Conditions	Yield
In various solvent(s) at 175℃; for 22h;	81%

sodium dodecanethiolate (26960-77-0) + 2-p-chlorophenylthio-1-nitro-1,2-diphenylethene (137908-45-3) → 1,2-diphenyl-2-dodecylthio-1-nitroethene

Conditions	Yield
In methanol at 20℃; for 1.08333h;	81%

sodium dodecanethiolate (26960-77-0) + 1-nitro-1,2-diphenyl-2-(4-tolylsulfonyl)ethene → 1,2-diphenyl-2-dodecylthio-1-nitroethene

Conditions	Yield
In methanol at 20℃; for 1.58333h;	80%

8-bromoquinoline (16567-18-3) + sodium dodecanethiolate (26960-77-0) → 8-(dodecylthio)quinoline (113749-84-1)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20 - 80℃; Inert atmosphere; Sealed tube;	80%

ortho-methylphenyl iodide (615-37-2) + carbon monoxide (201230-82-2) + sodium dodecanethiolate (26960-77-0) → S-(n-dodecyl) 2-methylbenzothioate (1213298-48-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1-dodecylthiol In tetrahydrofuran at 60℃; under 7600.51 Torr; for 24h; Autoclave;	79%

iodobenzene (591-50-4) + carbon monoxide (201230-82-2) + sodium dodecanethiolate (26960-77-0) → S-(n-dodecyl) benzothioate (86763-30-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1-dodecylthiol In tetrahydrofuran at 60℃; under 7600.51 Torr; for 24h; Autoclave;	78%

sodium dodecanethiolate (26960-77-0) + 1-nitro-2-p-tolylsulfonyl-1,2-diphenylethene → 1,2-diphenyl-2-dodecylthio-1-nitroethene

Conditions	Yield
In methanol at 20℃; for 1h;	76%

1,2,4-trifluorobenzene (367-23-7) + sodium dodecanethiolate (26960-77-0) → 1,2,4-tris(n-dodecylthio)benzene

Conditions	Yield
In various solvent(s) at 150℃; for 19h;	75%

1,2,4-tribromobenzene (615-54-3) + sodium dodecanethiolate (26960-77-0) → 1,2,4-tris(n-dodecylthio)benzene

Conditions	Yield
In various solvent(s) at 157℃; for 20h;	68%

sodium dodecanethiolate (26960-77-0) + 2-(6-ethoxy-2-benzothiazolylthio)-1-nitro-1-phenylethene (629628-19-9) → 2-dodecylthio-1-nitro-1-phenylethene

Conditions	Yield
In methanol at 20℃; for 0.5h;	68%

sodium dodecanethiolate (26960-77-0) + 2-(2-benzothiazolylthio)-1-nitro-1,2-diphenylethene → 1,2-diphenyl-2-dodecylthio-1-nitroethene

Conditions	Yield
In methanol at 20℃; for 1h;	67%

1,3-dibromo-2-hydroxypropane (96-21-9) + sodium dodecanethiolate (26960-77-0) → 1,3-Bis-(dodecylmercapto)-propyl-1-phosphoric acid monocholine ester + 1,3-bis-(dodecylmercapto)-2-propanol (59852-53-8)

Conditions	Yield
In N-methyl-acetamide	A 67% B n/a

pentaerythritol tetrabromide (3229-00-3) + sodium dodecanethiolate (26960-77-0) → 1,3-bis-dodecylmercapto-2,2-bis-(dodecylmercapto-methyl)-propane (105198-24-1)

Conditions	Yield
In methanol; water for 5h; Heating;	63%

para-dichlorobenzene (106-46-7) + sodium dodecanethiolate (26960-77-0) → 1,4-bis(n-dodecylthio)benzene (4115-60-0)

Conditions	Yield
In various solvent(s) at 157℃; for 20h;	63%

sodium dodecanethiolate (26960-77-0) + 3-(bromomethyl)-3-(dodecylthiomethyl)thietane (105198-26-3) → 3,3-bis(dodecylthiomethyl)thietane (105198-27-4)

Conditions	Yield
In ethanol	60%

1-Chloro-4-iodobenzene (637-87-6) + carbon monoxide (201230-82-2) + sodium dodecanethiolate (26960-77-0) → S-(n-dodecyl) 4-chlorobenzothioate (4906-36-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1-dodecylthiol In tetrahydrofuran at 60℃; under 7600.51 Torr; for 24h; Autoclave;	54%

sodium dodecanethiolate (26960-77-0) + N,N-didesmethylvenlafaxine (93413-77-5, 272788-06-4, 273720-73-3) → N,N-Didesmethyldesvenlafaxine (149289-29-2) + dodecyl methyl sulfide (3698-89-3) + O-desmethylvenlafaxine (93413-62-8) + 1-dodecylthiol (112-55-0)

Conditions	Yield
In decaethylene glycol at 190℃; for 3h; Product distribution / selectivity;	A 52% B n/a C n/a D n/a

tetrahydrofuran (109-99-9) + C44H56Fe2N4 + sodium dodecanethiolate (26960-77-0) → C60H87Fe2N4NaO4S

Conditions	Yield
at 20℃; for 5h; Inert atmosphere; Glovebox;	51.1%

sodium dodecanethiolate (26960-77-0) + 2-(4-chlorophenylthio)-1-nitro-1-phenylethene (137908-43-1) → didodecyl disulfide (2757-37-1) + 2-p-chlorophenylthio-2-dodecylthio-1-nitro-1-phenylethane

Conditions	Yield
In methanol at -10 - 0℃; for 1h;	A 40% B 50%

Umemoto's reagent (129946-88-9) + sodium dodecanethiolate (26960-77-0) → didodecyl disulfide (2757-37-1) + 1-[(trifluoromethyl)thio]dodecane (129922-44-7)

Conditions	Yield
In tetrahydrofuran for 0.5h; Ambient temperature;	A 30% B 47%

sodium dodecanethiolate (26960-77-0) + 2-(4-chlorophenylthio)-1-nitro-1-phenylethene (137908-43-1) → didodecyl disulfide (2757-37-1) + 2-dodecylthio-1-nitro-1-phenylethene + 2-p-chlorophenylthio-2-dodecylthio-1-nitro-1-phenylethane

Conditions	Yield
In methanol at 20℃; for 0.0833333h;	A 7% B 33% C 44%

Upstream product

• 112-55-0 1-dodecylthiol 
• 124-41-4 sodium methylate 

Downstream Products

• 1462-55-1 n-dodecyl mercaptoethanol 
• 1656-63-9 Tri-n-dodecyl phosphorotrithioite 
• 14019-39-7 tridodecyltetrathiophosphate 
• 26960-81-6 (4-(dodecylthio)phenyl)(phenyl)methanone 
• 16139-89-2 Cyclohexandithiophosphonsaeure-S_.S-didodecylester 
• 102315-51-5 4-Brom-ω-n-dodecylmercapto-acetophenon 
• 4115-60-0 1,4-bis(n-dodecylthio)benzene 
• 2883-70-7 9-(1-dodecyl)anthracene 
• 2757-37-1 didodecyl disulfide 
• 2169-02-0 1-ethylsulfinyldodecane 
• 40520-14-7 4-Dodecylmercapto-buttersaeure 
• 110877-57-1 4-(4-bromo-phenyl)-5-dodecylsulfanyl-3H-thiazol-2-one 
• 102466-46-6 2-bromo-1-(4-bromo-phenyl)-2-dodecylsulfanyl-ethanone 
• 114305-52-1 4-Brom-ω-n-dodecylmercapto-ω-thiocyanato-acetophenon 

Relevant articles and documents

CO2-Activated Reversible Transition between Polymersomes and Micelles with AIE Fluorescence

Fluorescent polymersomes with both aggregation-induced emission (AIE) and CO2-responsive properties were developed from amphiphilic block copolymer PEG-b-P(DEAEMA-co-TPEMA) in which the hydrophobic block was a copolymer made of tetraphenylethene functionalized methacrylate (TPEMA) and 2-(diethylamino)ethyl methacrylate (DEAEMA) with unspecified sequence arrangement. Four block copolymers with different DEAEMA/TPEMA and hydrophilic/hydrophobic ratios were synthesized, and bright AIE polymersomes were prepared by nanoprecipitation in THF/water and dioxane/water systems. Polymersomes of PEG45-b-P(DEAEMA36-co-TPEMA6) were chosen to study the CO2-responsive property. Upon CO2 bubbling vesicles transformed to small spherical micelles, and upon Ar bubbling micelles returned to vesicles with the presence of a few intermediate morphologies. These polymersomes might have promising applications as sensors, nanoreactors, or controlled release systems.

Processes for the synthesis of O-desmethylvenlafaxine

The present invention describes processes for the preparation of O-desmethylvenlafaxine and tridesmethylvenlafaxine, which may be used as an intermediate in preparing O-desmethylvenlafaxine.