10193-99-4

Basic information

• Product Name: Pentaerythritol tetrakis(2-mercaptoacetate)
• Synonyms: PENTAERYTHRITOL TETRAKIS(2-MERCAPTOACETATE);PENTAERYTHRITOL TETRATHIOGLYCOLATE;PENTAERYTHRITOL TETRAKIS(MERCAPTOACETATE);PENTAERYTHRITOL TETRA(MERCAPTOACETATE);ACETIC ACID, MERCAPTO-, 2,2-BIS [[(MERCAPTOACETYL) OXY] METHYL] -1,3-PROPANEDIYL ESTER;aceticacid,mercapto-,2,2-bis[[(mercaptoacetyl)oxy]methyl]-1,3-propanediyles;ter;2,2-bis[[(mercaptoacetyl)oxy]methyl]-1,3-propanediyl bis(mercaptoacetate)
• CAS NO: 10193-99-4
• Molecular Formula: C₁₃H₂₀O₈S₄
• Molecular Weight: 432.55
• EINECS: 233-482-8
• Product Categories: Chain Transfer Agents;Polymer Additives;Polymer Science
• Mol File: 10193-99-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 250 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.385 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.001Pa at 25℃
• Refractive Index: n20/D 1.547(lit.)
• Solubility: Practically insoluble in water
• PKA: 7.19±0.10(Predicted)
• Water Solubility: 693mg/L at 21℃
• CAS DataBase Reference: Pentaerythritol tetrakis(2-mercaptoacetate)(CAS DataBase Reference)
• NIST Chemistry Reference: Pentaerythritol tetrakis(2-mercaptoacetate)(10193-99-4)
• EPA Substance Registry System: Pentaerythritol tetrakis(2-mercaptoacetate)(10193-99-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37
• WGK Germany: 3
• Hazardous Substances Data: 10193-99-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to almost colorless liquid

Uses

Pentaerythritol Tetrakis(2-mercaptoacetate) can be used for agrochemical composition.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C13H20O8S4/c1-12(2,7-18-8(14)3-22)13(19-9(15)4-23,20-10(16)5-24)21-11(17)6-25/h22-25H,3-7H2,1-2H3

Synthetic route

Pentaerythritol (115-77-5) + mercaptoacetic acid (68-11-1) → 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	52%
With toluene-4-sulfonic acid In toluene at 110 - 120℃; for 4h;
With toluene-4-sulfonic acid In toluene at 130℃; for 9h; Dean-Stark; Inert atmosphere;	76 %Chromat.

Pentaerythritol (115-77-5) + Dipentaerythritol (126-58-9) + mercaptoacetic acid (68-11-1) → 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4)

Conditions	Yield
toluene-4-sulfonic acid In water; toluene at 104 - 121℃; for 5h; Product distribution / selectivity; Heating / reflux;

Pentaerythritol (115-77-5) + mercaptoacetic acid (68-11-1) → pentaerythritol tris(thioglycolate) (82575-20-0) + 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 130℃; for 9h; Dean-Stark; Inert atmosphere;	A 79 %Chromat. B 20 %Chromat.

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + di(n-butyl)tin oxide (818-08-6) → 7,7,21,21-tetrabutyl-2,12,16,26-tetraoxa-6,8,20,22-tetrathia-7,21-distanna-spiro[13.13]heptacosane-3,11,17,25-tetraone

Conditions	Yield
In toluene at 110℃; for 29h; Dean-Stark;	96%

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) → pentaerythritol tetracetate (597-71-7)

Conditions	Yield
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 20℃; UV-irradiation;	94%
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation;	94%

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) → 2,2-bis((acetoxy-2-d)methyl)propane-1,3-diylbis(acetate-2, 2’-d2)

Conditions	Yield
With di-tert-butyl peroxide; water-d2; ethydiphenylphosphine oxide In dichloromethane at 20℃; for 10h; Solvent; Irradiation; Green chemistry;	94%

4-(diphenylamino)benzaldehyde N-2,3-epoxypropyl-N-phenylhydrazone (634607-40-2) + 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) → C125H120N12O12S4

Conditions	Yield
triethylamine In tetrahydrofuran for 12h; Heating / reflux;	73%

C20H19NO4 (909781-41-5) + 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) → C93H96N4O24S4 (877614-05-6)

Conditions	Yield
tributyl-amine In dichloromethane at 20℃; for 72h;	72%

MoCl(CO)2(1,10-phenanthroline)(η(3)-CH2C(COCl)C=CH2) (156842-95-4) + dichloromethane (75-09-2) + 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) → C(MoCl(CO)2(C12H8N2)CH2CCCH2COSCH2COOCH2)4*CH2Cl2

Conditions	Yield
With triethylamine In dichloromethane (N2); addn. of amine to a soln. of molybdenum complex in CH2Cl2, addn. of a soln. of thiol in CH2Cl2, stirring for 3 h; filtration, washing with cold CH2Cl2, recrystn. (CH2Cl2/petrol); elem. anal.;	46%

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + 1-chloroacetophenone (532-27-4) → C45H44O12S4

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 18h;	45%

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + propargyl alcohol methyl ether (627-41-8) → 6,19-Bis-methoxymethyl-2,11,15,24-tetraoxa-5,8,18,21-tetrathia-spiro[12.12]pentacosane-3,10,16,23-tetraone

Conditions	Yield
With tripropylborane In methanol; hexane; benzene at 20℃;	42%

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + hex-1-yne (693-02-7) → 6,19-Dibutyl-2,11,15,24-tetraoxa-5,8,18,21-tetrathia-spiro[12.12]pentacosane-3,10,16,23-tetraone

Conditions	Yield
With tripropylborane In methanol; hexane; benzene at 20℃;	25%

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + (+/-)-(E)-1-((1RS,2SR)-2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one → (±)-3-{[({4-oxo-4-[(1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl]butan-2-yl}sulfanyl)-acetyl]oxy}-2,2-bis({[({4-oxo-4-[(1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl]butan-2-yl}sulfanyl)acetyl]oxy}methyl)propyl ({4-oxo-4-[(1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl]butan-2-yl}sulfanyl)acetate

Conditions	Yield
at 20℃; for 336h; Michael Addition;	23%

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + 1,3-Phenylene diisocyanate (123-61-5) → poly(thioglycolic acid pentaerythritol ester)-co-(m-xylene diisocyanate)

Conditions	Yield
With Zerec UN (acidic phosphate ester); BioSorb 583 (UV absorber); dibutyltin chloride at 10 - 120℃; for 18h; Product distribution / selectivity; Heating / reflux;

C10H10ClNO5S (1390628-51-9) + 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) → C53H56N4O28S8 (1390628-52-0)

Conditions	Yield
With triethylamine In 1,2-dimethoxyethane; tert-butyl methyl ether at 0℃; for 3h;

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + (E)-1-((1RS,2SR)-2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one (359865-01-3) → 2-((2-mercaptoacetoxy)methyl)-2-((2-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)acetoxy)methyl)propane-1,3-diyl bis(2-mercaptoacetate) + 2-((2-mercaptoacetoxy)methyl)-2-((2-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)acetoxy)methyl)propane-1,3-diyl bis(2-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)acetate) + 2,2-bis((2-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)acetoxy)methyl)propane-1,3-diyl bis(2-mercaptoacetate)

Conditions	Yield
at 20℃; for 336h;

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + (E)-1-((1RS,2SR)-2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one (359865-01-3) → 2-((2-mercaptoacetoxy)methyl)-2-((2-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)acetoxy)methyl)propane-1,3-diyl bis(2-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)acetate)

Conditions	Yield
at 20℃; for 192h;

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) → 2,15,19,32-tetraoxa-6,11,23,28-tetrathia-spiro[16.16]tritriacontan-3,7,10,14,20,24,27,31-octaone

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 29 h / 110 °C / Dean-Stark 2: [2,2]bipyridinyl / chloroform / Reflux View Scheme

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + 2'-acryloyl taxol → C63H73NO23S4

Conditions	Yield
In N,N-dimethyl-formamide

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + 5-acryloxymethyl-5-ethyl-1,3-dioxacyclohexane → C23H36O12S4

Conditions	Yield
With triethylamine In ethyl acetate at 50℃; for 10h; Temperature;

hexamethylene glycol diacrylate (13048-33-4) + 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) → C38H58O20S8

Conditions	Yield
With triethylamine In ethyl acetate at 50℃; for 10h; Temperature;

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) + 2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate (15625-89-5) → C51H74O30S12

Conditions	Yield
With triethylamine In ethyl acetate at 50℃; for 10h; Temperature; Michael Addition; Green chemistry;

Upstream product

• 115-77-5 Pentaerythritol 
• 68-11-1 mercaptoacetic acid 
• 126-58-9 Dipentaerythritol 

Downstream Products

• 597-71-7 pentaerythritol tetracetate 
• 1390628-52-0 C₅₃H₅₆N₄O₂₈S₈ 

Relevant articles and documents

POLYTHIOL COMPOSITION FOR A PLASTIC OPTICAL LENS

The embodiments relate to a polythiol composition for a plastic optical lens and a polythiourethane-based plastic optical lens prepared therefrom. In the embodiments, a first polythiol compound having an ester group and a mercapto group only as a hydrogen-bondable functional group and a second polythiol compound having an ester group and a hydrogen-bondable functional group other than a mercapto group are used in an appropriate amount. Thus, it is possible to control the viscosity of a polymerizable composition at the initial stage of polymerization at a low temperature of 5 to 15℃ and to stabilize the rate of increase in the viscosity of the composition and the reaction rate thereof, thereby preventing the generation of striae, bubbles, and the like. Further, various plastic lenses such as eyeglass lenses, camera lenses, and the like having excellent appearance characteristics (without striae and bubbles) and excellent optical characteristics can be obtained from the composition.

PROCESS FOR PRODUCING PENTAERYTHRITOL MERCAPTOCARBOXYLIC ACID ESTER, PENTAERYTHRITOL MERCAPTOCARBOXYLIC ACID ESTER OBTAINED BY THE SAME, AND USE THEREOF

Pentaerythritol which contains none of the alkali metals and alkaline earth metals or which contains at least one of these in a total amount of 1.0 wt.% or smaller is reacted with a mercaptocarboxylic acid to produce a pentaerythritol mercaptocarboxylic acid ester.