CAS 4420-74-0 (3-Mercaptopropyl)trimethoxysilane (HCID 20473)

Overview

See also: 1-Propanethiol, 3-(trimethoxysilyl)-, homopolymer (annotation moved to).

Names & identifiers

Preferred name: (3-Mercaptopropyl)trimethoxysilane
IUPAC: 3-trimethoxysilylpropane-1-thiol
English name: Trimethoxysilylpropanethiol
Molecular formula: C6H16O3SSi
Molecular weight: 196.34

Names & synonyms

4420-74-0(3-Mercaptopropyl)trimethoxysilane3-Mercaptopropyltrimethoxysilane3-(Trimethoxysilyl)propanethiol1-Propanethiol, 3-(trimethoxysilyl)-Silquest A 1893-(Trimethoxysilyl)-1-PropanethiolProsil 196Silane A 189(3-Thiopropyl)trimethoxysilaneNUCA 1893-(Sulfanylpropyl)trimethoxysilane

Show more names

Mercaptopropyltrimethoxysilaneγ-Mercaptopropyltrimethoxysilanekbm803kbe803Dynasylan MTMOgf70m8500A 189

M 8500 (coupling agent)3-(Trimethoxysilyl)propyl mercaptanA 189 (silicone)KBE 803KBM 803GF 70TSL 8380(gamma-mercaptopropyl)trimethoxysilane

Database identifiers

CAS: 4420-74-0
PubChem CID: 20473
DTXSID: DTXSID2044428
ChEMBL: CHEMBL3185147
UNII: 8CB1M08OIW
EC Number: 224-588-5
Nikkaji: J8.721A

Properties

Computed structural properties

Topological polar surface area: 28.7 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 6
Heavy atoms: 11
Formal charge: 0
Complexity: 89.6

Experimental & physicochemical properties

Chemical ClassesMetals -> Metalloid Compounds (Silicon)

Density1.015 @25 °C

Physical Description · 2 items

Liquid

Colorless liquid with a stench; [Alfa Aesar MSDS]

Physicochemical properties

Melting point: -50 °C · <-50°C
Boiling point: 213 · 213-215 °C(lit.)
Density: 1.057 g/mL · 1.057 g/mL at 25 °C(lit.)
vapor pressure: 0.2 hPa · 0.2 hPa (20 °C)
refractive index: 20 · n20/D 1.444(lit.)
Flash point: 204 °F · 204 °F
storage temp.: 2 · 2-8°C
solubility: Miscible with methanol, ethanol, isopropanol, acetone, benzene, toluene and xylene.
pka: 10.47 · 10.47±0.10(Predicted)
form: Liquid
color: Clear colorless to light yellow
Specific Gravity: 1.04 · 1.04
Odor: Slightly mercaptan odor
Viscosity: 1.8 mm2/s · 1.8mm2/s
Water Solubility: decomposes
Sensitive: Air & Moisture Sensitive
Hydrolytic Sensitivity: 7 · 7: reacts slowly with moisture/water
BRN: 2038119 · 2038119
Stability: Stable, but moisture sensitive - may decomposes on exposure to moist air. Incompatible with water, alcohols, strong oxidizing agents, strong acids.
Cosmetics Ingredients Functions: NAIL CONDITIONING
InChI: 1S/C6H16O3SSi/c1-7-11(8-2,9-3)6-4-5-10/h10H,4-6H2,1-3H3
InChIKey: UUEWCQRISZBELL-UHFFFAOYSA-N
SMILES: CO[Si](CCCS)(OC)OC
LogP: -1.4 · -1.4-1.7 at 20℃
CAS DataBase Reference: 4420 · 4420-74-0(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 8 CB1M08OIW · 8CB1M08OIW
NIST Chemistry Reference: 1 · 1-Propanethiol, 3-(trimethoxysilyl)-(4420-74-0)
EPA Substance Registry System: 1 · 1-Propanethiol, 3-(trimethoxysilyl)- (4420-74-0)
UNSPSC Code: 12352103 · 12352103
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07,GHS09
Signal word: Warning
Hazard statements: 302 · H302-H317-H411
Precautionary statements: 273 · P273-P280-P301+P312+P330-P302+P352
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn,N
Risk Statements: 22 · 22-43-51/53
Safety Statements: 24 · 24/25-36/37-61-57-37-24
RIDADR: 3082 · UN 3082 9/PG 3
WGK Germany: 2 · 2
RTECS: 7800000 · TZ7800000
F: 1 · 1-10-13
Autoignition Temperature: 235 °C · 235 °C
TSCA: TSCA listed
HazardClass: 9 · 9
PackingGroup: III
HS Code: 29310095 · 29310095
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2Skin Sens. 1
Toxicity: 50 orally · LD50 orally in Rabbit: 774 mg/kg LD50 dermal Rabbit 2268 mg/kg
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 4.4% (21 of 481) of reports.

Warning

H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P317, P321, P330, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 481 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 1-Propanethiol, 3-(trimethoxysilyl)-

1-Propanethiol, 3-(trimethoxysilyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Propanethiol, 3-(trimethoxysilyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 03-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/23529

3-(Trimethoxysilyl)-1-propanethiol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

Hazards SummaryA mild skin irritant; [RTECS] A skin and strong eye irritant; Harmful by ingestion; [Alfa Aesar MSDS] See 3-Chloropropyltrimethoxysilane.

Hazard Classes and CategoriesAcute Tox. 4 (94%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

2.2 [mg/m3]

24 [mg/m3]

150 [mg/m3]

Safety data

F: 1-10-13
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 2
tsca: TSCA listed
rtecs: TZ7800000
ridadr: UN 3082 9/PG 3
hs_code: 29310095
Toxicity: LD50 orally in Rabbit: 774 mg/kg LD50 dermal Rabbit 2268 mg/kg
risk_code: 22-43-51/53
Signal word: Warning
Symbol(GHS): GHS07,GHS09
hazard_code: Xn,N
safety_code: 24/25-36/37-61-57-37-24
hazard_class: 9
Storage Class: 10 - Combustible liquids
packing_group: III
Hazard statements: H302-H317-H411
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralAquatic Chronic 2Skin Sens. 1
Autoignition Temperature: 235 °C
Precautionary statements: P273-P280-P301+P312+P330-P302+P352

Chemistry & industry

Uses & manufacturing

UsesUsed as a coupling agent in polysulfide and polyurethane caulks and sealants; [REPROTOX]

U.S. Production2023: 75,000 - <100,000 lb

Industry UsesAdhesion/cohesion promoter

General Manufacturing Information · 2 items

Rubber Product Manufacturing

1-Propanethiol, 3-(trimethoxysilyl)-: ACTIVE

Applications · 3 items

UsesTrimethoxysilylpropanethiol is a bifunctional organosilane possessing a reactive organic mercapto and a hydrolyzable inorganic methoxysilyl group. Trimethoxysilylpropanethiol is a clear, colorless to light yellow liquid with a slightly mercaptan odor. It is soluble in alcohols, ketones and aliphatic or aromatic hydrocarbons. Applications: Trimethoxysilylpropanethiol can be used as coupling agent to improve the adhesion of sulfur cured elastomers (polysulfide, polyurethane sealants) to inorganic fillers (such as silica, clay, glass, mica and talc etc.), fiberglass and surfaces. Mineral-reinforced articles such as shoe soles, rubber rollers and wheels, white sidewalls, and wire and cable insulation also can be produced with lower silane loadings. Used to improve properties of mineral filled elastomer, including modulus, tensile and tear strength, heat buildup, abrasion resistance, resilience, compression set and cure time. Used as a pretreatment on minerals or added at the time of compounding. Used to improve low-rolling resistance in silica-reinforced tire tread compounds.

Uses(3-Mercaptopropyl)trimethoxysilane is used as a capping molecule for cadmium sulphide nanocrystals. It is used in the preparation of multi-walled carbon nanotubes and bilayer modified gold electrode. It acts as a linker molecule used in the preparation of gold multilayers and as a molecular adhesive in the fabrication of vapor-deposited gold electrodes on glass substrates. It is also used as a precursor for silica.

General Description(3-mercaptopropyl)trimethoxysilane (MPTMS) is an organosilane with a thiol group, which can be used as a self-assembled monolayer (SAM). It can be used as a conjunction reagent to immobilize a variety of nanoparticles.

Preparation methods

Preparation(3-Mercaptopropyl)trimethoxysilane was prepared by using thiourea and 3-chloropropyltrimethoxysilane as raw materials, petroleum ether as solvent, KI as catalyst, and ethylenediamine as neutraliser.