CAS 2916-68-9 2-(Trimethylsilyl)ethanol (HCID 18013)

Names & identifiers

Preferred name: 2-(Trimethylsilyl)ethanol
IUPAC: 2-trimethylsilylethanol
English name: 2-(Trimethylsilyl)ethanol
Molecular formula: C5H14OSi
Molecular weight: 118.25

Names & synonyms

2-(Trimethylsilyl)ethanol2916-68-9ETHANOL, 2-(TRIMETHYLSILYL)-GF24TDM0VONSC-96784DTXSID80183421RefChem:849112-TMSEDTXCID90105912220-844-5(2-Hydroxyethyl)trimethylsilane2-trimethylsilylethanol

Show more names

trimethylsilylethanolDK254DK717DKSI0330.825 g/MLDKFELEX01842-(TrimethyLTIMTEC-BB SBB009030

2-(trimethylsilyl)ethan-1-ol2-HYDROXYETHYLTRIMETHYLSILANESilane, (2-hydroxyethyl)trimethyl-C5H14OSi2-(trimethylsily)ethanolMFCD000028252-Trimethylsilanyl-ethanol2-(trimethylsilyl)-ethanol

Database identifiers

CAS: 2916-68-9
PubChem CID: 18013
DTXSID: DTXSID80183421
ChEMBL: CHEMBL25482
UNII: GF24TDM0VO
EC Number: 220-844-5
Nikkaji: J49.849A

Properties

Computed structural properties

Topological polar surface area: 20.2 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 2
Heavy atoms: 7
Formal charge: 0
Complexity: 46.5

Experimental & physicochemical properties

SpringerMaterials Properties29Si nuclear magnetic resonance spectrum

Physicochemical properties

Boiling point: 71 · 71-73 °C35 mm Hg(lit.)
Density: 0.825 g/mL · 0.825 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.423(lit.)
Flash point: 123 °F · 123 °F
storage temp.: 2 · Sealed in dry,2-8°C
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
pka: 15.38 · 15.38±0.10(Predicted)
form: Liquid
color: Clear colorless
Specific Gravity: 0.825 · 0.825
Water Solubility: soluble
Hydrolytic Sensitivity: 4 · 4: no reaction with water under neutral conditions
BRN: 1732034 · 1732034
Stability: Hygroscopic
InChI: 1S/C5H14OSi/c1-7(2,3)5-4-6/h6H,4-5H2,1-3H3
InChIKey: ZNGINKJHQQQORD-UHFFFAOYSA-N
SMILES: C[Si](C)(C)CCO
CAS DataBase Reference: 2916 · 2916-68-9(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 24 TDM0VO · GF24TDM0VO
NIST Chemistry Reference: -2 · Trimethyl-2-hydroxyethylsilane(2916-68-9)
UNSPSC Code: 12352000 · 12352000
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02
Signal word: Warning
Hazard statements: 226 · H226
Precautionary statements: 210 · P210
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi,F
Risk Statements: 10 · 10-36/37/38
Safety Statements: 16 · 16-37/39-26-24/25
RIDADR: 1987 · UN 1987 3/PG 3
WGK Germany: 3 · 3
RTECS: 5480000 · KM5480000
Hazard Note: Flammable
TSCA: No
HazardClass: 3 · 3
PackingGroup: III
HS Code: 29310095 · 29310095
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 · Flam. Liq. 3
Toxicity: 50 · mouse,LD50,intraperitoneal,1122mg/kg (1122mg/kg),Doklady Akademii Nauk SSSR. Proceedings of the Academy of Sciences of the USSR. For English translation, see DBIOAM and DKBSAS. Vol. 229, Pg. 1011, 1976.

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 57 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information2-(Trimethylsilyl)-ethanol: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: No
rtecs: KM5480000
ridadr: UN 1987 3/PG 3
hs_code: 29310095
Toxicity: mouse,LD50,intraperitoneal,1122mg/kg (1122mg/kg),Doklady Akademii Nauk SSSR. Proceedings of the Academy of Sciences of the USSR. For English translation, see DBIOAM and DKBSAS. Vol. 229, Pg. 1011, 1976.
risk_code: 10-36/37/38
Signal word: Warning
Symbol(GHS): GHS02
hazard_code: Xi,F
hazard_note: Flammable
safety_code: 16-37/39-26-24/25
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: III
Hazard statements: H226
Hazard Classifications: Flam. Liq. 3
Precautionary statements: P210

Chemistry & industry

Applications · 3 items

Uses2-(Trimethylsilyl)ethanol is a protecting reagent for carboxyl, phosphoryl, hydroxyl, and amino groups. It participates in the reactions of Phenol and Acid Protection, Alcohol Protection, Hemiacetal Protection, Amine Protection, Enol Ether Synthesis, Carbohydrate Chemistry etc.

Uses2-(Trimethylsilyl)ethanol is used as a protecting reagent for carboxyl, phosphoryl, hydroxyl and amino group in organic synthesis. It is used as a precursor to prepare trimethyl(2-phenoxyethyl)silanes by reacting with aromatic fluoride. It is also used in the synthesis of teoc-protected amines by using the corresponding isocyanates.

UsesUsed to synthesize Teoc-protected amines via alcoholysis of the corresponding isocyanates.

Preparation methods · 1 item

PreparationThree methods of preparation have been reported: (a) from the treatment of ethyl bromoacetate with zinc followed by the reaction with chlorotrimethylsilane1 and subsequent reduction of the resultant ethyl trimethylsilylacetate with lithium aluminum hydride2,3 or borane¨Ctetrahydrofuran(eq 1); (b) from the hydroboration/oxidation or oxymercuration/demercuration of vinyltrimethylsilane (eq 2); and (c)most conveniently, by the reaction of the Grignard reagent formed from (chloromethyl)trimethylsilane with paraformaldehyde (eq 3).