Product Name

  • Name

    PENTACHLOROTHIOPHENOL

  • EINECS 205-107-8
  • CAS No. 133-49-3
  • Article Data17
  • CAS DataBase
  • Density 1.745 g/cm3
  • Solubility
  • Melting Point 223-227 °C(lit.)
  • Formula C6H Cl5 S
  • Boiling Point 351.3 °C at 760 mmHg
  • Molecular Weight 282.405
  • Flash Point 144.6 °C
  • Transport Information UN 3335
  • Appearance Off-white to White Powder
  • Safety Poison by intraperitoneal route. Mildly toxic by ingestion. Severe eye irritant. When heated to decomposition it emits very toxic fumes of SOx and Cl. See also CHLOROPHENOLS.
  • Risk Codes R20/22;
  • Molecular Structure Molecular Structure of 133-49-3 (PENTACHLOROTHIOPHENOL)
  • Hazard Symbols R20/22:Harmful by inhalation and if swallowed.;
  • Synonyms Benzenethiol,pentachloro- (6CI,7CI,8CI,9CI); AP; NSC 5578; Pentachlorobenzenethiol;Pentachlorothiophenol; RPA 6; Struktol A 95
  • PSA 38.80000
  • LogP 5.24230

Synthetic route

Quintozene
82-68-8

Quintozene

pentachlorothiophenol
133-49-3

pentachlorothiophenol

Conditions
ConditionsYield
With sodium hydroxide; hydrogen sulfide 1.) methanol, 2.) pyridine, reflux , 2h;55%
(Z,Z)-2,3,4,5-Tetrachlor-2,4-pentadienthiosaeure-S-pentachlorphenylester
76827-74-2

(Z,Z)-2,3,4,5-Tetrachlor-2,4-pentadienthiosaeure-S-pentachlorphenylester

A

pentachlorothiophenol
133-49-3

pentachlorothiophenol

B

3,4,5-trichloro-α-pyrone
5659-38-1

3,4,5-trichloro-α-pyrone

Conditions
ConditionsYield
With tin(IV) chloride for 6h; Heating;A 25%
B 55%
diethyl ether
60-29-7

diethyl ether

2-(pentachlorophenylsulfanyl)-1-phenylethanone

2-(pentachlorophenylsulfanyl)-1-phenylethanone

A

pentachlorothiophenol
133-49-3

pentachlorothiophenol

B

acetophenone
98-86-2

acetophenone

C

1-ethoxy-1-pentachlorophenylsulfanylethane

1-ethoxy-1-pentachlorophenylsulfanylethane

D

phenacylacetophenone
495-71-6

phenacylacetophenone

Conditions
ConditionsYield
for 2h; Product distribution; Irradiation;A 16%
B 30%
C 54%
D n/a
hexachlorobenzene
118-74-1

hexachlorobenzene

pentachlorothiophenol
133-49-3

pentachlorothiophenol

Conditions
ConditionsYield
With benzyltriethylammonium tetrathiomolybdate In N,N-dimethyl-formamide at 70℃; for 8h;20%
With methanol; sodium hydrogensulfide at 120 - 140℃;
With pyridine; sodium hydrogensulfide; ethylene glycol
With methanol; sodium sulfide; sulfur
With sodium hydroxide; sodium hydrogensulfide; concentrated aqueous hydrochloric acid In N-methyl-acetamide; water
2,3,4,5,6-pentachloroaniline
527-20-8

2,3,4,5,6-pentachloroaniline

pentachlorothiophenol
133-49-3

pentachlorothiophenol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; sodium nitrite anschliessend Behandeln mit einer wss. Loesung von Kalium-<O-aethyl-dithiocarbonat> und Natriumcarbonat und Erwaermen des danach erhaltenen Reaktionsprodukts mit einer wss.-aethanol. Natronlauge;
pentachlorophenylsulphenyl chloride
19815-92-0

pentachlorophenylsulphenyl chloride

Isobutane
75-28-5

Isobutane

A

pentachlorothiophenol
133-49-3

pentachlorothiophenol

B

di(pentachlorophenyl)disulfide
22441-21-0

di(pentachlorophenyl)disulfide

C

t-Bu-pentachlorphenylsulfid
42325-67-7

t-Bu-pentachlorphenylsulfid

D

iso-Bu-pentachlorphenylsulfid
42325-68-8

iso-Bu-pentachlorphenylsulfid

Conditions
ConditionsYield
With CFC-112a In tetrachloromethane Irradiation;
pentachlorophenylsulphenyl chloride
19815-92-0

pentachlorophenylsulphenyl chloride

cyclohexane
110-82-7

cyclohexane

A

pentachlorothiophenol
133-49-3

pentachlorothiophenol

B

cyclohexyl chloride
542-18-7

cyclohexyl chloride

C

di(pentachlorophenyl)disulfide
22441-21-0

di(pentachlorophenyl)disulfide

D

Cyclohexyl-pentachlorphenyl-sulfid
91399-09-6

Cyclohexyl-pentachlorphenyl-sulfid

Conditions
ConditionsYield
In tetrachloromethane Irradiation; Further byproducts given;
pentachlorofluorobenzene
319-87-9

pentachlorofluorobenzene

pentachlorothiophenol
133-49-3

pentachlorothiophenol

Conditions
ConditionsYield
With pyridine; sodium hydrogensulfide
sodium pentachlorobenzenethiolate
22441-28-7

sodium pentachlorobenzenethiolate

pentachlorothiophenol
133-49-3

pentachlorothiophenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / diethyl ether / 1 h / Ambient temperature
2: 25 percent / tin(IV) chloride / 6 h / Heating
View Scheme
pentachlorothiophenol
133-49-3

pentachlorothiophenol

5-t-butyl-7-methyl-1-oxaspiro<2,5>octa-5,7-dien-4-one
78074-81-4

5-t-butyl-7-methyl-1-oxaspiro<2,5>octa-5,7-dien-4-one

6-t-butyl-1,2,3,4-tetrachloro-8-methylphenoxathiin
78074-84-7

6-t-butyl-1,2,3,4-tetrachloro-8-methylphenoxathiin

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 1.5h; Mechanism; Heating;95%
With sodium hydroxide In ethanol for 1.5h; Heating;95%
With sodium hydroxide In ethanol Yield given;
pentachlorothiophenol
133-49-3

pentachlorothiophenol

1,2-bis(diphenylphosphino)ethane nickel(II) chloride
14647-23-5

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

C38H24Cl10NiP2S2

C38H24Cl10NiP2S2

Conditions
ConditionsYield
Stage #1: pentachlorothiophenol With methyllithium In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere; Schlenk technique;
Stage #2: 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; diethyl ether for 2h; Inert atmosphere; Schlenk technique;
93%
pentachlorothiophenol
133-49-3

pentachlorothiophenol

triphenylbismuthane
603-33-8

triphenylbismuthane

[Bi(SC6Cl5)3]

[Bi(SC6Cl5)3]

Conditions
ConditionsYield
In toluene byproducts: C6H6; (Ar); standard Schlenk technique; HSC6Cl5 (3 equiv.) was added to soln. of Bi compd. in toluene; mixt. was refluxed for 96 h; solvent removed (vac., room temp.); residue washed (hexane); dried (vac.); elem. anal.;91%
pentachlorothiophenol
133-49-3

pentachlorothiophenol

diphenylantimony(III) acetate
5613-52-5

diphenylantimony(III) acetate

(C6H5)2SbSC6Cl5
5035-71-2

(C6H5)2SbSC6Cl5

Conditions
ConditionsYield
In toluene82%
In toluene82%
In toluene
In toluene
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

pentachlorothiophenol
133-49-3

pentachlorothiophenol

2-chloro-3-((perchlorophenyl)thio)naphthalene-1,4-dione
1404074-65-2

2-chloro-3-((perchlorophenyl)thio)naphthalene-1,4-dione

Conditions
ConditionsYield
With sodium carbonate In ethanol for 6 - 8h;78%
pentachlorothiophenol
133-49-3

pentachlorothiophenol

5,7-di-t-butyl-1-oxaspiro<2.5>octa-5,7-dien-4-one
39117-89-0

5,7-di-t-butyl-1-oxaspiro<2.5>octa-5,7-dien-4-one

6,8-di-t-butyl-1,2,3,4-tetrachlorophenoxathiin
78074-83-6

6,8-di-t-butyl-1,2,3,4-tetrachlorophenoxathiin

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 1.5h; Heating;73%
With sodium hydroxide In ethanol Yield given;
pentachlorothiophenol
133-49-3

pentachlorothiophenol

Methyl 2-acetamidoacrylate
35356-70-8

Methyl 2-acetamidoacrylate

2-acetamido-3-(pentachlorophenylsulfanyl)propionic acid methyl ester
68671-96-5

2-acetamido-3-(pentachlorophenylsulfanyl)propionic acid methyl ester

Conditions
ConditionsYield
With Aliquat 336; potassium carbonate In tetrahydrofuran; toluene at 20℃; for 18h; sulfa-Michael addition;71%
pentachlorothiophenol
133-49-3

pentachlorothiophenol

S-difluoromethyl-S-phenyl-2,4,6-trimethoxyphenylsulfonium tetrafluoroborate

S-difluoromethyl-S-phenyl-2,4,6-trimethoxyphenylsulfonium tetrafluoroborate

(difluoromethyl)(perchlorophenyl)sulfane

(difluoromethyl)(perchlorophenyl)sulfane

Conditions
ConditionsYield
Stage #1: pentachlorothiophenol With lithium hydroxide In fluorobenzene at 20℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: S-difluoromethyl-S-phenyl-2,4,6-trimethoxyphenylsulfonium tetrafluoroborate In fluorobenzene at 20℃; Schlenk technique; Inert atmosphere; chemoselective reaction;
69%
pentachlorothiophenol
133-49-3

pentachlorothiophenol

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

pentachlorophenyl 3-chloropropyl sulfide
1227176-31-9

pentachlorophenyl 3-chloropropyl sulfide

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Inert atmosphere; Reflux;68%
pentachlorothiophenol
133-49-3

pentachlorothiophenol

propyl bromide
106-94-5

propyl bromide

propyl pentachlorophenyl sulfide

propyl pentachlorophenyl sulfide

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;60%
pentachlorothiophenol
133-49-3

pentachlorothiophenol

{Cu(C5H4NCHNNCSNH2)(CH3CO2)}2

{Cu(C5H4NCHNNCSNH2)(CH3CO2)}2

{Cu(C7H7N4S)(C6Cl5S)}2

{Cu(C7H7N4S)(C6Cl5S)}2

Conditions
ConditionsYield
In methanol; sodium hydroxide aq. NaOH; a soln. of the thiophenol in 0.1M aq.-methanolic NaOH wad added dropwise to a hot, filtered aq. soln. of the Cu-complex (molar ratio Cu-complex:Hpctp = 1 : 2);; the ppt. was immediately washed with water and diethyl ether; elem. anal.;;56%
pentachlorothiophenol
133-49-3

pentachlorothiophenol

5,6,8-trimethyl-1-oxaspiro<2,5>octa-5,7-dien-4-one
78074-82-5

5,6,8-trimethyl-1-oxaspiro<2,5>octa-5,7-dien-4-one

1,2,3,4-tetrachloro-6,7,9-trimethylphenoxathiin
78074-85-8

1,2,3,4-tetrachloro-6,7,9-trimethylphenoxathiin

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 1.5h; Heating;47%
With sodium hydroxide In ethanol Yield given;
pentachlorothiophenol
133-49-3

pentachlorothiophenol

4-Bromo-2,3,5,6-tetrachloropyridine
23995-94-0

4-Bromo-2,3,5,6-tetrachloropyridine

tetrachloro-4-(pentachlorophenylthio)pyridine
39775-10-5

tetrachloro-4-(pentachlorophenylthio)pyridine

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide for 2h; Heating;25%
pentachlorothiophenol
133-49-3

pentachlorothiophenol

N,N'-dichloro-1,4-benzoquinone diimine
103303-10-2, 637-70-7, 68456-83-7

N,N'-dichloro-1,4-benzoquinone diimine

C18H4Cl10N2S2

C18H4Cl10N2S2

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane6%
2-furancarbonyl chloride
527-69-5

2-furancarbonyl chloride

pentachlorothiophenol
133-49-3

pentachlorothiophenol

furan-2-carbothioic acid S-pentachlorophenyl ester
112535-67-8

furan-2-carbothioic acid S-pentachlorophenyl ester

Conditions
ConditionsYield
With pyridine
pentachlorothiophenol
133-49-3

pentachlorothiophenol

thiophosgene
463-71-8

thiophosgene

trithiocarbonic acid bis-pentachlorophenyl ester
85139-17-9

trithiocarbonic acid bis-pentachlorophenyl ester

Conditions
ConditionsYield
With sodium hydroxide
pentachlorothiophenol
133-49-3

pentachlorothiophenol

2-bromoethylamine hydrobromide
2576-47-8

2-bromoethylamine hydrobromide

2-pentachlorophenylsulfanyl-ethylamine
14289-10-2

2-pentachlorophenylsulfanyl-ethylamine

Conditions
ConditionsYield
With sodium hydroxide
pentachlorothiophenol
133-49-3

pentachlorothiophenol

pentachlorophenylsulphenyl chloride
19815-92-0

pentachlorophenylsulphenyl chloride

Conditions
ConditionsYield
With tetrachloromethane; chlorine
With chlorine
With iodine; chlorine In tetrachloromethane
pentachlorothiophenol
133-49-3

pentachlorothiophenol

di(pentachlorophenyl)disulfide
22441-21-0

di(pentachlorophenyl)disulfide

Conditions
ConditionsYield
With tetrachloromethane; phosphorus pentachloride
With sodium hydroxide; potassium hexacyanoferrate(III)
With dihydrogen peroxide In water
pentachlorothiophenol
133-49-3

pentachlorothiophenol

(2-chloro-ethyl)-pentachlorophenyl sulfide
55882-17-2

(2-chloro-ethyl)-pentachlorophenyl sulfide

Conditions
ConditionsYield
With potassium hydroxide; 1,2-dichloro-ethane
pentachlorothiophenol
133-49-3

pentachlorothiophenol

pentachlorothioanisole
1825-19-0

pentachlorothioanisole

Conditions
ConditionsYield
With sodium hydroxide; dimethyl sulfate
With ethanol; sodium ethanolate; methyl iodide
pentachlorothiophenol
133-49-3

pentachlorothiophenol

ethyl-pentachlorophenyl sulfide
77876-27-8

ethyl-pentachlorophenyl sulfide

Conditions
ConditionsYield
With ethanol; sodium ethanolate; ethyl iodide
With sodium hydroxide; diethyl sulfate
pentachlorothiophenol
133-49-3

pentachlorothiophenol

pentachloro-benzenesulfenyl bromide
98139-76-5

pentachloro-benzenesulfenyl bromide

Conditions
ConditionsYield
With hexane; bromine
pentachlorothiophenol
133-49-3

pentachlorothiophenol

pentachlorophenyl-vinyl sulfide
98436-67-0

pentachlorophenyl-vinyl sulfide

Conditions
ConditionsYield
With sodium carbonate; acetylene at 190℃; under 10297.1 Torr;
pentachlorothiophenol
133-49-3

pentachlorothiophenol

bis-pentachlorophenyl trisulfide
80303-92-0

bis-pentachlorophenyl trisulfide

Conditions
ConditionsYield
With carbon disulfide; sulfur dichloride

PENTACHLOROTHIOPHENOL Chemical Properties

MF: C6HCl5S
MW: 282.402 g/mol 
EINECS: 205-107-8
Sensitive: Stench
Density: 1.745 g/cm3
Flash Point: 144.6 °C
Index of Refraction: 1.648
Melting Point: 223-227 °C(lit.)
Enthalpy of Vaporization: 57.24 kJ/mol 
Boiling Point: 351.3 °C at 760 mmHg 
Vapour Pressure: 8.41E-05 mmHg at 25°C 
IUPAC Name: 2,3,4,5,6-Pentachlorobenzenethiol
Synonyms: Pentachlorothiophenol;Pentachlorobenzenethiol;2,3,4,5,6-Pentachlorobenzenethiol;Akrochem Peptizer PTP;Benzenethiol, pentachloro-;Pctp;Pentachloro-benzenethio;Pentachlorthiofenol
Product Categories: Organics;Phenol&Thiophenol & Mercaptan
Following is the molecular structure of Pentachlorothiophenol (133-49-3):

PENTACHLOROTHIOPHENOL Uses

Pentachlorothiophenol (133-49-3) is natural rubber, neoprene, nitrile rubber, styrene-butadiene rubber and butyl rubber, and plastic refining accelerator, as well as with Synthetic rubber composition of the regeneration of the higher doses. Applicable to high temperature and low temperature plastic plastic refining refining, sulfur may terminate the role of plastic solution. The product toxicity, no pollution, no smell vulcanized rubber, the rubber physical properties and aging properties of no effect. The product with the zinc sulfate solution, the reaction of thiophenol five zinc chloride can be used as natural rubber plasticating accelerator, high, low use of technology showed a significant catalytic role, suitable for open mill and mixer. 5 Chloro thiophenol zinc vulcanizate physical properties, aging properties, as well as chlorine taste and so no effect can be used for light-colored products. The product of real material with mineral mixtures nearly equal weight, then adding a small amount of organic activator, that is composed of five chloro-thiophenol compound, also be used as natural rubber, polybutadiene rubber, isoamyl rubber, styrene-butadiene rubber, NBR rubber, neoprene, butyl rubber and other unsaturated bond-containing rubber peptizer, low temperatures can also have a good solution of the role of plastic. The role of a small amount of sulfur solution for termination of its plastic effects.

PENTACHLOROTHIOPHENOL Production

Manufacturing methd of Pentachlorothiophenol (133-49-3):Pentachlorothiophenol is formed by HCB reaction with sodium hydrosulfide, with dimethyl formamide and other organic solvents as solvent. Reaction of the five chlorine thiophenol in the reaction system and then with sodium hydrosulfide, resulting in five thiophenol sodium chloride and hydrogen sulfide. Then, hydrochloric acid 5 sodium chloride precipitates thiophenol thiophenol pentachlorophenol, and then filtering, washing, drying, that is to be finished five chlorine thiophenol.

PENTACHLOROTHIOPHENOL Toxicity Data With Reference

1.    

eye-rbt 500 mg/24H SEV

    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,168.
2.    

orl-rat LD50:11,900 g/kg

    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,168.
3.    

ipr-mus LD50:100 mg/kg

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .

PENTACHLOROTHIOPHENOL Consensus Reports

Chlorophenol compounds are on The Community Right-To-Know List. Reported in EPA TSCA Inventory.

PENTACHLOROTHIOPHENOL Safety Profile

Poison by intraperitoneal route. Mildly toxic by ingestion. Severe eye irritant. When heated to decomposition it emits very toxic fumes of SOx and Cl.
Safety Information of Pentachlorothiophenol (133-49-3):
RIDADR: UN 3335
WGK Germany: 3
RTECS: DC1925000
Hazard Note: Harmful/Stench
Hazardous Substances Data: 133-49-3(Hazardous Substances Data)

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