33007-83-9

Basic information

• Product Name: TRIMETHYLOLPROPANE TRIS(3-MERCAPTOPROPIONATE)
• Synonyms: p33ING1b;p47;p47ING1a;Propanoic acid,3-mercapto-, 1,1'-[2-ethyl-2-[(3-mercapto-1-oxopropoxy)methyl]-1,3-propanediyl]ester;opanediylester;propanoicacid,3-mercapto-,2-ethyl-2-[(3-mercapto-1-oxopropoxy)methyl]-1,3-pr;PROPANOIC ACID, 3-MERCAPTO-, 2-ETHYL-2- [(3-MERCAPTO-1-OXOPROPOXY) METHYL]-1, 3-PROPANEDIYL ESTER;TRIMETHYLOLPROPANE TRI(3-MERCAPTO PROPIONATE)
• CAS NO: 33007-83-9
• Molecular Formula: C₁₅H₂₆O₆S₃
• Molecular Weight: 398.56
• EINECS: 251-336-1
• Product Categories: Self Assembly&Contact Printing;Self-Assembly Materials;Sulfur Compounds;Thiols/Mercaptans;ThiolsOrganic Building Blocks;Chain Transfer Agents;Building Blocks;Chemical Synthesis;Materials Science;Organic Building Blocks;Polymer Additives;Polymer Science;Sulfur Compounds
• Mol File: 33007-83-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 220 °C0.3 mm Hg(lit.)
• Flash Point: 205 °F
• Appearance: /
• Density: 1.21 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.3E-09mmHg at 25°C
• Refractive Index: n20/D 1.518(lit.)
• Storage Temp.: -70°C
• PKA: 9.14±0.10(Predicted)
• Water Solubility: 320mg/L at 20℃
• CAS DataBase Reference: TRIMETHYLOLPROPANE TRIS(3-MERCAPTOPROPIONATE)(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLOLPROPANE TRIS(3-MERCAPTOPROPIONATE)(33007-83-9)
• EPA Substance Registry System: TRIMETHYLOLPROPANE TRIS(3-MERCAPTOPROPIONATE)(33007-83-9)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-61
• Safety Statements: 26-37/39-45-53
• RIDADR: UN 3334
• WGK Germany: 3
• Hazardous Substances Data: 33007-83-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liquid

Uses

Different sources of media describe the Uses of 33007-83-9 differently. You can refer to the following data:
1. Trimethylolpropane tris(3-Mercaptopropanoate) can be used to prepare UV curing environmentally friendly nail polish.
2. Trimethylolpropane tris(3-mercaptopropionate) may be used in the following studies:Preparation of hydrogels, via crosslinking inulin derivatives. Construction of porous hybrid monolithic materials. As monomer for the preparation of a new thiol-ene based polymeric fluorescence sensor, via photo initiated polymerization.

General Description

Trimethylolpropane tris(3-mercaptopropionate) is reported as a multi-thiol crosslinking reagent.

InChI:InChI=1/C15H26O6S3/c1-2-15(9-19-12(16)3-6-22,10-20-13(17)4-7-23)11-21-14(18)5-8-24/h22-24H,2-11H2,1H3

Synthetic route

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 3-mercaptopropionic acid (107-96-0) → 2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9)

Conditions	Yield
With sulfuric acid In toluene at 130℃; for 4h; Dean-Stark;	92%
With SO42-/ Al2O3-ZrO2 at 80 - 100℃;	199.1 g
In toluene at 120℃; for 24h; Dean-Stark;
With p-toluenesulfonylanhydride In toluene at 90 - 130℃; for 5h;	398 g

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + (E)-1-(4-(allyloxy)phenyl)ethan-1-one oxime (2089-30-7) → C48H65N3O12S3

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; UV-irradiation;	100%

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + glycerol 1,3-dimethacrylate 2-vinyl sulfonate → C54H80O27S6

Conditions	Yield
With DBN In chloroform at 20℃; for 0.5h; Michael Addition;	98%

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + C18H19NO2S5 → C54H68O12S15 (1109094-74-7)

Conditions	Yield
In dichloromethane Inert atmosphere;	93%

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + 2-Isocyanatoethyl methacrylate (30674-80-7) → C36H53N3O15S3 (1008528-94-6)

Conditions	Yield
With dibutyltin dilaurate In toluene at 28℃; for 6.5h;	81%

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + 4-(diphenylamino)benzaldehyde N-2,3-epoxypropyl-N-phenylhydrazone (634607-40-2) → C99H101N9O9S3

Conditions	Yield
triethylamine In tetrahydrofuran for 12h; Heating / reflux;	71%

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + (2,4,6-triethylbenzene-1,3,5-triyl)tris(methylene) triacrylate → C39H56O12S3

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -78℃; for 1.41667h; Reagent/catalyst; Solvent; Concentration; Temperature; Inert atmosphere;	55%

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + (+/-)-(E)-1-((1RS,2SR)-2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one → (±)-2,2-bis({[3-({4-oxo-4-[(1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl]butan-2-yl}sulfanyl)propanoyl]oxy}methyl)butyl 3-({4-oxo-4-[(1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl]butan-2-yl}sulfanyl)propanoate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 384h; Michael Addition;	35%

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + acrylic acid (79-10-7) + Desyl chloride (447-31-4) → 3-[(3-{2,2-bis[({3-[(2-oxo-1,2-diphenylethyl)sulfanyl]propanoyl}oxy)methyl]butoxy}-3-oxopropyl)sulfanyl]propanoic acid

Conditions	Yield
Stage #1: 2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) With triethylamine In acetonitrile at 20℃; Stage #2: acrylic acid In acetonitrile at 25℃; for 3h; Stage #3: Desyl chloride In acetonitrile at 25℃; for 2h;	11%

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + pentaerythritol triallyl ether (1471-17-6) → polymer, product of frontal polymerization; monomer(s): pentaerythritol triallyl ether; trimethylolpropane tris(3-mercaptopropionate)

Conditions	Yield
With 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Heating;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + hexamethylene glycol diacrylate (13048-33-4) → polymer, product of frontal polymerization; monomer(s): 1,6-hexanediol diacrylate; trimethylolpropane tris(3-mercaptopropionate)

Conditions	Yield
With 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Heating;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + vinyl propionate (105-38-4) → polymer, product of photopolymerization; monomer(s): trimethylolpropane tris(3-mercaptopropionate); vinyl propionate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone Irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + vinyl acrylate (2177-18-6) → polymer, product of photopolymerization; monomer(s): trimethylolpropane tris(3-mercaptopropionate); vinyl acrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone Irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + ethyl acrylate (140-88-5) → polymer, product of photopolymerization; monomer(s): trimethylolpropane tris(3-mercaptopropionate); ethyl acrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone Irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + vinyl propionate (105-38-4) + ethyl acrylate (140-88-5) → polymer, product of photopolymerization; monomer(s): trimethylolpropane tris(3-mercaptopropionate); ethyl acrylate; vinyl propionate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone Irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) → C15H25NO7S3

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) → trimethylolpropane tris(3-sulfenylchloropropionate)

Conditions	Yield
With N-chloro-succinimide In tetrachloromethane at 27℃; Inert atmosphere;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + triallyl isocyanurate (1025-15-6) → poly[triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione-co-trimethylolpropane tris(3-mercaptopropionate)]

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone for 0 - 0.0138889h; Conversion of starting material; UV-irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + trimethylolpropane trivinyl ether → poly[trimethylolpropane tris(3-mercaptopropionate)-co-trimethylolpropane trivinyl ether]

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone UV-irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + trimethylolpropane trivinyl ether → poly[trimethylolpropane tris(3-mercaptopropionate)-co-trimethylolpropane trivinyl ether]

Conditions	Yield
for 0 - 0.0833333h; Conversion of starting material; UV-irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + pentaerythritol triallyl ether (1471-17-6) → poly[pentaerythritol triallyl ether-co-trimethylolpropane tris(3-mercaptopropionate)]

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone UV-irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + 4-vinyl-1,3-dioxolan-2-one (4427-96-7) → 2-ethyl-2-(((3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoyl)oxy)methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) (1287759-42-5)

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone for 1h; UV-irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + (E)-1-((1RS,2SR)-2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one (359865-01-3) → 2-ethyl-2-(((3-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)propanoyl)oxy)methyl)propane-1,3-diyl bis(3-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)propanoate) + 2-ethyl-2-(((3-mercaptopropanoyl)oxy)methyl)propane-1,3-diyl bis(3-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)propanoate) + 2-ethyl-2-(((3-((4-oxo-4-((1RS,2SR)-2,6,6-trimethylcyclohex-3-en-1-yl)butan-2-yl)thio)propanoyl)oxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 16h;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) → C15H25O6S3(1-)

Conditions	Yield
With C18H29NO7 Michael Addition;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + D-limonene (5989-27-5) → C45H74O6S3

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In ethyl acetate UV-irradiation;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + 3-(trimethoxysilyl)propyl isocyanate (15396-00-6) → C22H41NO10S3Si

Conditions	Yield
With dioctyltin(IV) oxide at 80℃;
With dioctyltin(IV) oxide at 80℃; for 2h;
With dioctyltin(IV) oxide at 80℃; for 2h;

2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) (33007-83-9) + sodium 4-methylbenzenesulfinate (824-79-3) → C36H44O12S6

Conditions	Yield
Stage #1: 2-ethyl-2-((3-mercaptopropanoyloxy)methyl)propane-1,3-diyl bis(3-mercaptopropanoate) With N-chloro-succinimide In tetrachloromethane at 25℃; for 4h; Inert atmosphere; Stage #2: sodium 4-methylbenzenesulfinate In tetrahydrofuran for 15h;	18 g

Upstream product

• 77-99-6 1,1,1-tri(hydroxymethyl)propane 
• 107-96-0 3-mercaptopropionic acid 

Downstream Products

• 1287759-42-5 2-ethyl-2-(((3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoyl)oxy)methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) 
• 1109094-74-7 C₅₄H₆₈O₁₂S₁₅ 

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