33528-63-1

Basic information

• Product Name: 1,12-DIMERCAPTODODECANE
• Synonyms: 1,12-DODECANEDITHIOL;1,12-DIMERCAPTODODECANE
• CAS NO: 33528-63-1
• Molecular Formula: C₁₂H₂₆S₂
• Molecular Weight: 234.46
• Mol File: 33528-63-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 346.8°C (estimate)
• Flash Point: 131.1°C
• Appearance: /
• Density: 0.9469 (estimate)
• Vapor Pressure: 0.000335mmHg at 25°C
• Refractive Index: 1.4943 (estimate)
• CAS DataBase Reference: 1,12-DIMERCAPTODODECANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,12-DIMERCAPTODODECANE(33528-63-1)
• EPA Substance Registry System: 1,12-DIMERCAPTODODECANE(33528-63-1)

Safety Data

• Hazardous Substances Data: 33528-63-1(Hazardous Substances Data)

Usage

General Description

1,12-Dimercaptododecane is a chemical compound with the molecular formula C12H26S2. It belongs to the class of organic compounds known as alkylthiols, which are sulfur analogs of alcohols. 1,12-DIMERCAPTODODECANE is a colorless liquid with a strong odor and is commonly used as a reagent in chemical reactions. It is known for its ability to bind to heavy metals such as mercury, lead, and arsenic, making it useful in the treatment of heavy metal poisoning. Due to its mercapto groups, 1,12-dimercaptododecane can also act as a reducing agent in certain chemical processes. It is important to handle this compound with care, as it can be toxic if ingested or inhaled, and it may cause skin irritation upon contact.

InChI:InChI=1/C12H26S2/c13-11-9-7-5-3-1-2-4-6-8-10-12-14/h13-14H,1-12H2

Synthetic route

thioacetic acid S-(12-acetylsulfanyldodecyl) ester (676251-48-2) → dodecane-1,12-dithiol (33528-63-1)

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃; for 4h;	56%

1,12-dibromododecane (3344-70-5) → dodecane-1,12-dithiol (33528-63-1)

Conditions	Yield
With methanol; ammonium sulfide
With sodium hydrogensulfide; diethyl ether; ethanol; hydrogen sulfide zuletzt unter Erwaermen;
Multi-step reaction with 2 steps 1: 21 percent / dimethylformamide / 24 h / 20 °C 2: 56 percent / NaOH / H2O; acetone / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: H2O / 20 h / Heating 2: 0.42 mmol / aq. NaOH / 6 h / Heating View Scheme

diethyl ether (60-29-7) + ethanol (64-17-5) + 1,12-dibromododecane (3344-70-5) + hydrogen sulfide (7783-06-4) + NaHS → dodecane-1,12-dithiol (33528-63-1)

C14H32N4S2(2+)*2Br(1-) → dodecane-1,12-dithiol (33528-63-1)

Conditions	Yield
With sodium hydroxide for 6h; Heating;	0.42 mmol

1,12-bis-carbamimidoylmercapto-dodecane (62476-83-9) → dodecane-1,12-dithiol (33528-63-1)

Conditions	Yield
With sodium hydroxide Heating;

1,12-dodecandiol (5675-51-4) → dodecane-1,12-dithiol (33528-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HBr / Heating 2: aq. NaOH / Heating View Scheme

dodecane-1,12-dithiol (33528-63-1) + 16,20-bis(bromomethyl)[14]paracyclophane (512857-00-0) → 2,15-dithia[16][14]metaparacyclophane (512857-01-1)

Conditions	Yield
With caesium carbonate In ethanol; benzene for 6h;	82%

dodecane-1,12-dithiol (33528-63-1) + trityl chloride (76-83-5) → 1,12-Bis(triphenylmethylthio)dodecan (102435-91-6)

Conditions	Yield
With aluminum oxide In 1,4-dioxane for 24h;	81%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + dodecane-1,12-dithiol (33528-63-1) → 3-Methylene-1,5-dithia-cycloheptadecane (128183-81-3)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 55 - 60℃;	75%

dodecane-1,12-dithiol (33528-63-1) + 1,2-Bis<3-(bromomethyl)phenyl>-4,4-dimethyl-3,5-pyrazolidinedione (121012-95-1) → 23,24-(Dimethylmalonyl)-2,15-dithia-23,24-diaza<16.2>metacyclophan (121013-05-6)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In tetrahydrofuran for 50h; Heating;	64%

dodecane-1,12-dithiol (33528-63-1) → 1,2-Dithia-cyclotetradecane (69466-45-1)

Conditions	Yield
Multistep reaction;	61%

dodecane-1,12-dithiol (33528-63-1) + N-(bromododecanoyl)aza-18-crown-6 → 1,12-dithia-(N-dodecanoylaza-18-crown-6)dodecane (141279-85-8)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 96h; Heating;	57%

dodecane-1,12-dithiol (33528-63-1) + 2,3-Dimethoxyanthracene (51790-19-3) → C26H32S2

Conditions	Yield
With trifluorormethanesulfonic acid In toluene Heating;	43%

dodecane-1,12-dithiol (33528-63-1) + acetic anhydride (108-24-7) → thioacetic acid S-(12-sulfanyldodecyl) ester (117581-30-3)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	41%

dodecane-1,12-dithiol (33528-63-1) + 1,2-Bis<4-(brommethyl)phenyl>-4,4-dimethyl-3,5-pyrazolidindion (114038-66-3) → N,N'-dimethylmalonyl-2,15-dithia-23,24-diaza-<16.2>paracyclophane (114038-74-3)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In benzene for 50h; Heating;	25%

dodecane-1,12-dithiol (33528-63-1) + 1-tridecene (2437-56-1) → 1,12-bis-tridecylmercapto-dodecane

Conditions	Yield
With dihydrogen peroxide at 180℃;

dodecane-1,12-dithiol (33528-63-1) + 2,4-dinitrobenzenesulfenyl chloride (528-76-7) → 1,12-bis-(2,4-dinitro-phenyldisulfanyl)-dodecane

Conditions	Yield
With 1,2-dichloro-ethane

dodecane-1,12-dithiol (33528-63-1) + 2-nitrobenzenesulfenyl chloride (7669-54-7) → 1,12-bis-(2-nitro-phenyldisulfanyl)-dodecane

Conditions	Yield
With 1,2-dichloro-ethane

dodecane-1,12-dithiol (33528-63-1) + 1-chloro-2,4-dinitro-benzene (97-00-7) → 1,12-bis-(2,4-dinitro-phenylsulfanyl)-dodecane

Conditions	Yield
With potassium hydroxide

dodecane-1,12-dithiol (33528-63-1) + anthracenylmethyl chloride (24463-19-2) → 1,12-Bis-(9-anthranylmethylthio)dodecan

Conditions	Yield
With potassium hydroxide In ethanol; benzene

dodecane-1,12-dithiol (33528-63-1) + benzyl chloroformate (501-53-1) → thiocarbonic acid O-benzyl ester S-(12-mercapto-dodecyl) ester

Conditions	Yield
With sodium hydroxide; water In acetone at 20℃; Substitution;

dodecane-1,12-dithiol (33528-63-1) + acetic anhydride (108-24-7) → thioacetic acid S-(12-acetylsulfanyldodecyl) ester (676251-48-2)

Conditions	Yield
With sodium hydrogencarbonate Heating;

dodecane-1,12-dithiol (33528-63-1) → 2,2,15,15-tetraoxo-2,15-dithia[16][14]metaparacyclophane (512857-02-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / cesium carbonate / ethanol; benzene / 6 h 2: 97 percent / 30 percent hydrogen peroxide; acetic acid / 2 h / 0 °C View Scheme

dodecane-1,12-dithiol (33528-63-1) → C50H54S2*C21H42 (102435-92-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Al2O3 / dioxane / 24 h 2: 0.35 percent / p-Me-C6H6-SO3H / toluene / 0.5 h / 130 °C View Scheme

dodecane-1,12-dithiol (33528-63-1) → C50H54S2*C22H44 (102435-93-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Al2O3 / dioxane / 24 h 2: 0.5 percent / p-Me-C6H6-SO3H / toluene / 0.5 h / 130 °C View Scheme

dodecane-1,12-dithiol (33528-63-1) → C50H54S2*C23H46 (102435-94-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Al2O3 / dioxane / 24 h 2: 0.75 percent / p-Me-C6H6-SO3H / toluene / 0.5 h / 130 °C View Scheme

dodecane-1,12-dithiol (33528-63-1) → C50H54S2*C24H48 (102435-95-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Al2O3 / dioxane / 24 h 2: 0.9 percent / p-Me-C6H6-SO3H / toluene / 0.5 h / 130 °C View Scheme

dodecane-1,12-dithiol (33528-63-1) → C50H54S2*C26H52 (102435-96-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Al2O3 / dioxane / 24 h 2: 1.2 percent / p-Me-C6H6-SO3H / toluene / 0.5 h / 130 °C View Scheme

dodecane-1,12-dithiol (33528-63-1) → <2>-<1,12-Bis(triphenylmethylthio)dodecan>--Rotaxan (102435-97-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Al2O3 / dioxane / 24 h 2: 3.8 percent / p-Me-C6H6-SO3H / toluene / 0.5 h / 130 °C View Scheme

dodecane-1,12-dithiol (33528-63-1) → C50H54S2*C29H58 (102492-30-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / Al2O3 / dioxane / 24 h 2: 6.8 percent / p-Me-C6H6-SO3H / toluene / 0.5 h / 130 °C View Scheme

Upstream product

• 3344-70-5 1,12-dibromododecane 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 7783-06-4 hydrogen sulfide 
• 676251-48-2 thioacetic acid S-(12-acetylsulfanyldodecyl) ester 
• 62476-83-9 1,12-bis-carbamimidoylmercapto-dodecane 
• 5675-51-4 1,12-dodecandiol 

Downstream Products

• 102492-30-8 C₅₀H₅₄S₂*C₂₉H₅₈ 
• 102435-97-2 <2>-<1,12-Bis(triphenylmethylthio)dodecan>--Rotaxan 
• 102435-96-1 C₅₀H₅₄S₂*C₂₆H₅₂ 
• 102435-95-0 C₅₀H₅₄S₂*C₂₄H₄₈ 
• 102435-94-9 C₅₀H₅₄S₂*C₂₃H₄₆ 
• 102435-93-8 C₅₀H₅₄S₂*C₂₂H₄₄ 
• 102435-92-7 C₅₀H₅₄S₂*C₂₁H₄₂ 

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