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1569-69-3

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1569-69-3 Usage

Chemical Properties

CLEAR LIQUID

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 6057, 1994 DOI: 10.1016/0040-4039(94)88074-3

General Description

A colorless liquid with a strong disagreeable odor. Insoluble in water and less dense than water. Vapors heavier than air. Flash point near 50°F.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Cyclohexyl mercaptan is incompatible with the following: Oxidizers, reducing agents, strong acids, alkali metals .

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Flammable

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion, subcutaneous, and intramuscular routes. Mildly toxic by skin contact. Human systemic effects by inhalation: conjunctiva irritation and changes in the olfactory and respiratory systems. Has caused damage to kidneys, liver, and blood vessels in experimental animals. Experimental reproductive effects. Human mutation data reported. A severe eye irritant. Narcotic-like action. Flammable when exposed to heat or flame; can react with oxiduing materials. Iptes on contact with chromium trioxide. Violent reaction with HNO3. Incompatible with oxidants. To fight fire, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also ALCOHOLS.

Check Digit Verification of cas no

The CAS Registry Mumber 1569-69-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,6 and 9 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1569-69:
(6*1)+(5*5)+(4*6)+(3*9)+(2*6)+(1*9)=103
103 % 10 = 3
So 1569-69-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H12S/c7-6-4-2-1-3-5-6/h6-7H,1-5H2

1569-69-3 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Aldrich

  • (C105600)  Cyclohexanethiol  97%

  • 1569-69-3

  • C105600-25G

  • 341.64CNY

  • Detail
  • Aldrich

  • (C105600)  Cyclohexanethiol  97%

  • 1569-69-3

  • C105600-100G

  • 587.34CNY

  • Detail

1569-69-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclohexanethiol

1.2 Other means of identification

Product number -
Other names Cyclohexanethiol

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:1569-69-3 SDS

1569-69-3Synthetic route

S-cyclohexyl ethanethioate
10039-63-1

S-cyclohexyl ethanethioate

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With palladium diacetate In methanol for 1h; Heating;96%
With polymer-supported potassium thiophenolate In tetrahydrofuran; methanol at 20℃; for 2.5h;94%
With potassium hydroxide
(pentacarbonylchromium)(C(C6H5)SC6H11)

(pentacarbonylchromium)(C(C6H5)SC6H11)

dimethyl amine
124-40-3

dimethyl amine

A

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

B

pentacarbonyl[(N,N-dimethylamino)(phenyl)carbene]chromium(0)
30971-68-7

pentacarbonyl[(N,N-dimethylamino)(phenyl)carbene]chromium(0)

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether under inert gas; soln. of Cr-complex ether, addn. of 40% aq. Me2NH soln., addn. of NaOH, color change from deep brown to yellow; ether phase dried (Na2SO4), evapn. (20°C/15 Torr); elem. anal.;A n/a
B 92%
1,2-dicyclohexyl disulfide
2550-40-5

1,2-dicyclohexyl disulfide

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With tetrabutylammonium borohydride In tert-butyl alcohol for 5h; Heating;90%
With cobalt-polysulfide at 150 - 185℃; under 47808 Torr; Hydrogenolyse;
With molybdenum-polysulfide at 150 - 185℃; under 47808 Torr; Hydrogenolyse;
S-Cyclohexylisothiuroniumbromid
51350-51-7

S-Cyclohexylisothiuroniumbromid

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
In water; acetic acid electroreduction on Hg-cathode, 0.8 A;81%
ferrocene
102-54-5

ferrocene

1-oxa-4-thiaspiro-<4,5>decan-2-one
1564-39-2

1-oxa-4-thiaspiro-<4,5>decan-2-one

A

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

B

η5-cyclopentadienyl(4',7'-dihydro-4'-oxo-η-4'a-7'a-spiro{cyclohexane-1,1'(3'H)-cyclopenta{c}thiopyran}yl)iron

η5-cyclopentadienyl(4',7'-dihydro-4'-oxo-η-4'a-7'a-spiro{cyclohexane-1,1'(3'H)-cyclopenta{c}thiopyran}yl)iron

C

1,1'-{cyclohexylidenethio(2-oxoethylene)}ferrocene

1,1'-{cyclohexylidenethio(2-oxoethylene)}ferrocene

D

1,2-dicyclohexyl disulfide
2550-40-5

1,2-dicyclohexyl disulfide

Conditions
ConditionsYield
aluminium trichloride In carbon disulfide excess ferrocene, mixture is stirred for 24 h at room temp.; addn. of 10% HCl soln., extn. with CHCl3 and CH2Cl2, ext. is washed with water, aq. Na2CO3 soln., water; dried over MgSO4, solvent is removed by distn. under reduced pressure, HPLC, preparative thin layer chromy.;A 2%
B 5%
C 80%
D 2%
cyclohexene
110-83-8

cyclohexene

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With dicyclohexyl sulfide; hydrogen sulfide In acetonitrile at 25℃; for 2h; Reagent/catalyst; Electrolysis;77%
With hydrogen sulfide; boron trifluoride; pentane at 30 - 40℃; weitere Reagenzien: fluessiger HF, Phosphorsaeure;
With hydrogen sulfide; boron trifluoride; pentane at 30 - 40℃; weitere Reagenzien: fluessiger HF, Phosphorsaeure;
1,4-dithiaspiro[4.5]decane
177-16-2

1,4-dithiaspiro[4.5]decane

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With n-butyllithium In diethyl ether at 25℃; for 6h;73%
1-oxa-4-thiaspiro-<4,5>decan-2-one
1564-39-2

1-oxa-4-thiaspiro-<4,5>decan-2-one

benzene
71-43-2

benzene

A

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

B

1,2-dicyclohexyl disulfide
2550-40-5

1,2-dicyclohexyl disulfide

C

cyclohexyl phenyl sulphide
7570-92-5

cyclohexyl phenyl sulphide

D

2-cyclohexylthioacetic acid
52363-15-2

2-cyclohexylthioacetic acid

E

spiro-4'-one
141622-49-3

spiro-4'-one

F

<<1-(phenyl)-cyclohexyl>thio>acetic acid
141622-63-1

<<1-(phenyl)-cyclohexyl>thio>acetic acid

Conditions
ConditionsYield
With aluminium trichloride for 24h; Product distribution; Mechanism; Ambient temperature; other arenes;A 2%
B 3%
C 2%
D 5%
E 70%
F 6%
(triphenylsilylthio)cyclohexane

(triphenylsilylthio)cyclohexane

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With naphthalene; lithium In tetrahydrofuran; methanol at 20℃; for 1.5h;51%
cyclohexylamine
108-91-8

cyclohexylamine

A

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

B

cyclohexylcyclohexane
92-51-3

cyclohexylcyclohexane

C

cyclohexane
110-82-7

cyclohexane

D

1,2-dicyclohexyl disulfide
2550-40-5

1,2-dicyclohexyl disulfide

E

dicyclohexyl sulfide
7133-46-2

dicyclohexyl sulfide

F

cyclohexene
110-83-8

cyclohexene

G

starting material (15.4 g)

starting material (15.4 g)

Conditions
ConditionsYield
With hydrogen sulfide; hydrogen; sulphided Ni-W at 300℃; for 6h; Product distribution; Heating;A 4.9%
B 0.03%
C 0.6%
D 0.8%
E 0.04%
F 0.3%
G n/a
aniline
62-53-3

aniline

A

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

B

cyclohexylcyclohexane
92-51-3

cyclohexylcyclohexane

C

cyclohexane
110-82-7

cyclohexane

D

diphenylamine
122-39-4

diphenylamine

E

cyclohexene
110-83-8

cyclohexene

F

benzene
71-43-2

benzene

Conditions
ConditionsYield
With hydrogen sulfide; hydrogen; sulphided Ni-W at 300℃; under 116259 Torr; for 6h; Product distribution; Heating;A 0.27%
B 0.002%
C 0.14%
D 1.7%
E 0.03%
F 0.04%
cyclohexane
110-82-7

cyclohexane

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With carbon oxide sulfide at 20 - 25℃; for 6h; Product distribution; Irradiation; other monoatomic sulfur traps, other cosolvents;0.187%
cyclohexene sulfide
286-28-2

cyclohexene sulfide

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With lithium aluminium tetrahydride
carbon disulfide
75-15-0

carbon disulfide

cyclohexane
110-82-7

cyclohexane

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With pyridine; chlorine Irradiation.Abtrennen der bei 80grad/4 Torr fluechtigen Anteile des Reaktionsprodukts und Erhitzen des Rueckstands mit aethanol. KOH;
1-bromocyclohexane
108-85-0

1-bromocyclohexane

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With ethanol; potassium hydrosulfide
Multi-step reaction with 2 steps
1: alcohol
2: NH3; absolute alcohol
View Scheme
S-cyclohexyl O-ethyl carbonodithioate
54497-82-4

S-cyclohexyl O-ethyl carbonodithioate

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With ethanol; ammonia
cyclohexanesulfinyl-acetic acid
107347-84-2

cyclohexanesulfinyl-acetic acid

A

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

B

bis-cyclohexylmercapto-acetic acid

bis-cyclohexylmercapto-acetic acid

C

Glyoxilic acid
298-12-4

Glyoxilic acid

cyclohexylmagnesiumchloride
931-51-1

cyclohexylmagnesiumchloride

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With sulfur Behandeln des Reaktionsprodukts mit angesaeuertem Wasser;
cyclohexylmercapto-fumaric acid
879396-25-5

cyclohexylmercapto-fumaric acid

ethylene glycol
107-21-1

ethylene glycol

A

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

B

2-cyclohexylmercapto-acrylic acid
855923-25-0

2-cyclohexylmercapto-acrylic acid

C

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

1-bromocyclohexane
108-85-0

1-bromocyclohexane

thiourea
17356-08-0

thiourea

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
folgende Hydrolyse;
thiourea
17356-08-0

thiourea

cyclohexanol
108-93-0

cyclohexanol

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With hydrogen bromide Umsetzung bei Siedetemperatur und Kochen der mit NaOH neutralisierten Reaktionsloesung unter Stickstoff;
cyclohexanol
108-93-0

cyclohexanol

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With hydrogen sulfide at 300 - 360℃; beim Leiten ueber ThO2;
cyclohexanesulfonyl chloride
4837-38-1

cyclohexanesulfonyl chloride

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With hydrogenchloride; tin
cyclohexyl phenyl sulphide
7570-92-5

cyclohexyl phenyl sulphide

A

dibenzothiophene
132-65-0

dibenzothiophene

B

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

C

phenyl(propyl)sulfide
874-79-3

phenyl(propyl)sulfide

D

Ethyl phenyl sulfide
622-38-8

Ethyl phenyl sulfide

E

diphenyl sulfide
139-66-2

diphenyl sulfide

F

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
under 1 Torr; Product distribution; plasma desulfurization: 10-100 W;A 2 % Chromat.
B 2 % Chromat.
C n/a
D n/a
E 7 % Chromat.
F 7 % Chromat.
Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester
105398-69-4

Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With sulfur; sodium tetrahydroborate 1) CH2Cl2, irradiation, 0 deg C, 1 h, 2) MeOH, CH2Cl2, RT, 1 h; Yield given. Multistep reaction;
3-methyl-1,2,5-thiadiazole
5728-06-3

3-methyl-1,2,5-thiadiazole

cyclohexylmagnesium bromide
931-50-0

cyclohexylmagnesium bromide

A

3-methyl-[1,2,5]selenadiazole
17505-11-2

3-methyl-[1,2,5]selenadiazole

B

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

C

dicyclohexyl sulfide
7133-46-2

dicyclohexyl sulfide

D

3-cyclohexyl-4-methyl-1,2,5-selenadiazole
112633-33-7

3-cyclohexyl-4-methyl-1,2,5-selenadiazole

Conditions
ConditionsYield
With sulenium monochloride 1.) ether, -40 deg C, 2 h, 2.) ether, 3 h; Yield given. Multistep reaction. Yields of byproduct given;
1,2,5-thiadiazole
288-39-1, 23091-39-6

1,2,5-thiadiazole

cyclohexylmagnesium bromide
931-50-0

cyclohexylmagnesium bromide

A

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

B

dicyclohexyl sulfide
7133-46-2

dicyclohexyl sulfide

C

3-Cyclohexyl-[1,2,5]selenadiazole
112633-29-1

3-Cyclohexyl-[1,2,5]selenadiazole

D

1,2,5-selenadiazole
288-40-4

1,2,5-selenadiazole

Conditions
ConditionsYield
With sulenium monochloride 1.) ether, -40 deg C, 2 h, 2.) ether, 3 h; Yield given. Multistep reaction. Yields of byproduct given;
1-iodocyclohexane
626-62-0

1-iodocyclohexane

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
With palladium diacetate; thioacetate exchange resin 1.) MeOH, 65 deg C, 18 h, 2.) MeOH, reflux, 1 h; Yield given. Multistep reaction;
cyclohexanone
108-94-1

cyclohexanone

CS2

CS2

hydrogen

hydrogen

cobalt sulfide

cobalt sulfide

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
at 150℃; under 73550.8 Torr;
cyclohexanone
108-94-1

cyclohexanone

CS2

CS2

hydrogen

hydrogen

iron sulfide

iron sulfide

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Conditions
ConditionsYield
at 150℃; under 73550.8 Torr;
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

1,2-dicyclohexyl disulfide
2550-40-5

1,2-dicyclohexyl disulfide

Conditions
ConditionsYield
With 2,2'-bipyridylchromium peroxide In benzene for 0.7h; Product distribution; Heating; effect of various chromium(VI) based oxidants;100%
With 2,2'-bipyridylchromium peroxide In benzene for 0.7h; Heating;100%
With tris paraperiodate In benzene for 1h; Heating;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

tetramethyl ammoniumhydroxide
75-59-2

tetramethyl ammoniumhydroxide

Cyclohexanethiolatetetramethyl-ammonium;
138555-12-1

Cyclohexanethiolatetetramethyl-ammonium;

Conditions
ConditionsYield
In benzene at 6 - 10℃; for 1h;100%
7-azabicyclo[4.1.0]heptane
286-18-0

7-azabicyclo[4.1.0]heptane

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

trans-2-cyclohexylsulfanylcyclohexylamine

trans-2-cyclohexylsulfanylcyclohexylamine

Conditions
ConditionsYield
In methanol for 7h; Heating;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

gallium(II) bromide

gallium(II) bromide

(GaBr2SC6H11)2
97092-88-1

(GaBr2SC6H11)2

Conditions
ConditionsYield
In further solvent(s) byproducts: H2; dry thiol was condensed on to cooled solid Ga2Br4 in vac., warmed for 5min; crystd. on standing;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

In2I4

In2I4

(InI2(SC6H11))2
97092-69-8

(InI2(SC6H11))2

Conditions
ConditionsYield
In further solvent(s) thiol was condensed on to cooled solid In2I4 in vac., warmed for 12 h;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Ga2I4

Ga2I4

(GaI2SC6H11)2
97092-89-2

(GaI2SC6H11)2

Conditions
ConditionsYield
In further solvent(s) byproducts: H2; dry thiol was condensed on to cooled solid Ga2I4 in vac., warmed for 5 min; crystd. on standing;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Br4In2

Br4In2

(InBr2(SC6H11))2
97092-68-7

(InBr2(SC6H11))2

Conditions
ConditionsYield
In further solvent(s) thiol was condensed on to cooled solid In2Br4 in vac., warmed for 12 h;100%
digallium tetrachloride

digallium tetrachloride

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

(GaCl2SC6H11)2
97092-87-0

(GaCl2SC6H11)2

Conditions
ConditionsYield
In further solvent(s) byproducts: H2; dry thiol was condensed on to cooled solid Ga2Cl4 in vac., warmed for 5min; crystd. on standing;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

In2Cl4

In2Cl4

(InCl2(SC6H11))2
97092-67-6

(InCl2(SC6H11))2

Conditions
ConditionsYield
In further solvent(s) thiol was condensed on to cooled solid In2Cl4 in vac., warmed for 12 h;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

ethyl 2-bromo-4-(trifluoromethyl)oxazole-5-carboxylate
1227934-69-1

ethyl 2-bromo-4-(trifluoromethyl)oxazole-5-carboxylate

ethyl 2-(cyclohexylthio)-4-trifluoromethyloxazole-5-carboxylate
1227935-01-4

ethyl 2-(cyclohexylthio)-4-trifluoromethyloxazole-5-carboxylate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 80℃; for 5h;100%
With potassium carbonate In tetrahydrofuran; water100%
3-isobutylglutaric anhydride
185815-59-2

3-isobutylglutaric anhydride

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

(-)-3-cyclohexylsulfanylcarbonylmethyl-5-methyl-hexanoic acid
1237492-10-2

(-)-3-cyclohexylsulfanylcarbonylmethyl-5-methyl-hexanoic acid

Conditions
ConditionsYield
In tert-butyl methyl ether at 20℃; for 72h; Product distribution / selectivity; Inert atmosphere;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

but-3-enyl 4-methylbenzenesulfonate
778-29-0

but-3-enyl 4-methylbenzenesulfonate

but-3-en-1-yl(cyclohexyl)sulfane
1256168-89-4

but-3-en-1-yl(cyclohexyl)sulfane

Conditions
ConditionsYield
Stage #1: Cyclohexanethiol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: but-3-enyl 4-methylbenzenesulfonate In N,N-dimethyl-formamide at 0 - 20℃; for 20h; Inert atmosphere;
100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

sodium cyclohexanethiolate
50729-68-5

sodium cyclohexanethiolate

Conditions
ConditionsYield
With sodium In ethanol at 20℃; for 3h; Inert atmosphere;100%
With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; Inert atmosphere;
With sodium hydride In tetrahydrofuran
methanol
67-56-1

methanol

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

methyl cyclohexanesulfinate

methyl cyclohexanesulfinate

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane at 0 - 25℃; for 1h;100%
With N-Bromosuccinimide In ethyl acetate at 20℃; for 0.5h; Sonication; Green chemistry;97%
With N-Bromosuccinimide at 0 - 25℃; for 12h;86%
formaldehyd
50-00-0

formaldehyd

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

(bromomethyl)(cyclohexyl)sulfide

(bromomethyl)(cyclohexyl)sulfide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 20℃;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

(5-bromothiazol-2-yl)methylcarbamic acid tert-butyl ester
713107-42-7

(5-bromothiazol-2-yl)methylcarbamic acid tert-butyl ester

tert-butyl ((5-(cyclohexylthio)-1,3-thiazol-2-yl)methyl)carbamate

tert-butyl ((5-(cyclohexylthio)-1,3-thiazol-2-yl)methyl)carbamate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene; tert-butyl alcohol at 110℃; for 18h; Inert atmosphere;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

2,2-difluoroacetic anhydride
401-67-2

2,2-difluoroacetic anhydride

C8H12F2OS

C8H12F2OS

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 2h;100%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

cyclohexyl(1-(4-methoxyphenyl)ethyl)sulfane

cyclohexyl(1-(4-methoxyphenyl)ethyl)sulfane

Conditions
ConditionsYield
In neat (no solvent) at 60℃; for 3h; Catalytic behavior; Solvent; Green chemistry;99.6%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

benzaldehyde
100-52-7

benzaldehyde

benzaldehyde dicyclohexyldithioacetal
110466-18-7

benzaldehyde dicyclohexyldithioacetal

Conditions
ConditionsYield
With lithium bromide at 75 - 80℃; for 0.333333h;99%
With lithium trifluoromethanesulfonate at 90℃; for 0.833333h; Alkylation;99%
With lithium trifluoromethanesulfonate at 90℃; for 0.8h;99%
With eosin y at 20℃; for 12h; Irradiation; Schlenk technique; Inert atmosphere;99%
With polyphosphoric acid trimethylsilyl ester In dichloromethane at 20℃; for 2h;91%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

n-octyne
629-05-0

n-octyne

carbon monoxide
201230-82-2

carbon monoxide

2-Methylene-octanethioic acid S-cyclohexyl ester

2-Methylene-octanethioic acid S-cyclohexyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine)platinum In acetonitrile at 120℃; under 22800 Torr; for 2h; Product distribution; reactant ratio dependence;99%
tetrakis(triphenylphosphine)platinum In acetonitrile at 120℃; under 22501.8 Torr; for 2h;99%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

4-Iodoacetophenone
13329-40-3

4-Iodoacetophenone

1-(4-cyclohexylmercapto-phenyl)-ethanone
100971-72-0

1-(4-cyclohexylmercapto-phenyl)-ethanone

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; L-proline In N,N-dimethyl-formamide at 80℃; for 40h;99%
With CuMoO4; caesium carbonate In dimethyl sulfoxide at 30℃; for 7h; Inert atmosphere;91%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

4-tolyl iodide
624-31-7

4-tolyl iodide

(4-methylphenyl)cyclohexyl sulfane
59693-93-5

(4-methylphenyl)cyclohexyl sulfane

Conditions
ConditionsYield
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; sodium t-butanolate In 1,2-dimethoxyethane at 70℃; for 6h; Inert atmosphere;99%
With pyridine; zinc; CoI2(dppe) In toluene at 70℃; for 10h;91%
With pyridine; (1,2-dimethoxyethane)dichloronickel(II); Ir[dF(CF3)ppy]2(dtbbpy)PF6; 4,4′-di-(tert-butyl)-2,2′-bipyridyl In acetonitrile at 23 - 25℃; for 24h; Irradiation; chemoselective reaction;88%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

(2R-trans)-2-<<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-methyl>-2,3-dihydro-3-hydroxy-4H-pyran-4-one
84010-44-6

(2R-trans)-2-<<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-methyl>-2,3-dihydro-3-hydroxy-4H-pyran-4-one

C18H34O4SiS

C18H34O4SiS

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran at 0℃; for 0.166667h;99%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

N-tosyldiphenylmethylamine
853-83-8

N-tosyldiphenylmethylamine

diphenylmethyl cyclohexyl thioether

diphenylmethyl cyclohexyl thioether

Conditions
ConditionsYield
With chloro-trimethyl-silane; zinc(II) chloride In dichloromethane at 20℃; for 1.5h;99%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

2-methylphenyl cyclohexyl sulfide
59693-92-4

2-methylphenyl cyclohexyl sulfide

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In toluene for 6h; Inert atmosphere; Reflux;99%
With [(C6H3(OP(i-Pr)2)2)RhHCl]; sodium t-butanolate In toluene at 110℃; for 24h; Sealed tube; Inert atmosphere;30 %Spectr.
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

ethyl 2-butoxy-3,4-dihydro-6-phenyl-2H-pyran-5-carboxylate
1256543-90-4

ethyl 2-butoxy-3,4-dihydro-6-phenyl-2H-pyran-5-carboxylate

ethyl 2-benzoyl-5,5-bis(cyclohexylthio)pentanoate
1266617-51-9

ethyl 2-benzoyl-5,5-bis(cyclohexylthio)pentanoate

Conditions
ConditionsYield
With manganese(II) bromide In nitromethane at 80℃; for 6h;99%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

1-chloro-2-methylnaphthalene
5859-45-0

1-chloro-2-methylnaphthalene

cyclohexyl(2-methylnaphthalen-1-yl)sulfane
1360571-27-2

cyclohexyl(2-methylnaphthalen-1-yl)sulfane

Conditions
ConditionsYield
Stage #1: 1-chloro-2-methylnaphthalene With dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II); lithium isopropoxide In toluene at 80℃; for 0.5h; Inert atmosphere;
Stage #2: Cyclohexanethiol With potassium tert-butylate In toluene at 40℃; for 24h; Inert atmosphere;
99%
styrene
292638-84-7

styrene

Cyclohexanethiol
1569-69-3

Cyclohexanethiol

1-(1-cyclohexylthio)-2-phenylethane
1411816-37-9

1-(1-cyclohexylthio)-2-phenylethane

Conditions
ConditionsYield
With tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In acetonitrile for 8h; Sealed tube; Irradiation;99%
With Benzoylformic acid In tetrahydrofuran for 4h; Irradiation; Green chemistry;98%
With zinc diacetate In toluene at 100℃; for 36h; regioselective reaction;79%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

Triethoxysilane
998-30-1

Triethoxysilane

S-cyclohexyl O,O,O-triethyl orthosilicothioate
1443045-47-3

S-cyclohexyl O,O,O-triethyl orthosilicothioate

Conditions
ConditionsYield
With [RuCl(η5-(3-phenyl)indenyl)(PPh3)2] In toluene at 110℃; for 16h; Glovebox;99%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-cyanophenyl cyclohexyl sulfide
288588-24-9

4-cyanophenyl cyclohexyl sulfide

Conditions
ConditionsYield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; (1,2-dimethoxyethane)dichloronickel(II); diisopropylammonium bis(catecholato)(3-mercaptopropyl)silicate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 27℃; for 36h; Reagent/catalyst; Irradiation; Inert atmosphere;99%

1569-69-3Relevant articles and documents

Thiolation of cycloalkenes C5, C6 by redox-activation of hydrogen sulfide

Shinkar, Elena V.,Kudryavtsev, Daniil A.,Pashchenko, Konstantin P.,Berberova, Nadezhda T.,Okhlobystina, Alexandra V.

, p. 180 - 182 (2017)

Direct and indirect redox-activation of H2S in the presence of cyclopentene or cyclohexene in MeCN at 25?°C affords the corresponding cycloalkanethiols.

The benzyl can be selectively removed by visible light or near visible light. Method for protecting allyl and propargyl group

-

Paragraph 0031, (2021/10/16)

The invention provides a method for selectively removing benzyl, allyl and propargyl protecting groups by visible light or near visible light, namely a substrate containing benzyl, allyl or propargyl protecting groups. The method has the advantages of simple operation, safe and clean visible light or near visible light as excitation conditions, cheap and easily available reagents, high reaction yield, high reaction chemistry and regional selectivity, and is suitable for selective removal of benzyl, allyl and propargyl protecting groups in various substrates.

Insight into the Mechanism of Reversible Ring-Opening of 1,3-Benzoxazine with Thiols

Urbaniak, Tobias,Soto, Marc,Liebeke, Manuel,Koschek, Katharina

, p. 4050 - 4055 (2017/04/27)

The reversible ring-opening addition and fragmentation reaction of p-cresol-based N-phenylbenzoxazine with aliphatic and aromatic thiols was investigated in solvent-mediated and solvent-free reactions. Independently of the used thiol, N-phenylbenzoxazine and the thiols reacted to equilibrium with comparable amounts of reactants and products in aprotic solvent, whereas in protic solvent almost full conversions were reached. In contrast, thiol reactivity was a crucial factor in solvent-free reactions yielding fast and complete conversions for a more acidic thiol and balanced equilibrium concentrations in case of thiols with high pKa values. The strong influence of thiols with low pKa values emphasizes the relevance of the protonation step in the ring-opening reactions of 1,3-benzoxazines with thiols in absence of solvents where acidity predominates nucleophilicity. The reverse reactions, namely adduct dissociation and benzoxazine recovery, were successfully conducted at elevated temperatures and reduced pressure facilitated by the removal of the formed thiols yielding up to 95% recovered 1,3-benzoxazine. These results provide deeper understanding of the reversible ring-opening reaction mechanism of 1,3-benzoxazine with thiols.

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