2-Chloromethyl 2-(trimethylsilyl)ethyl ether (HCID 2724271)

Names & identifiers

Preferred name: 2-Chloromethyl 2-(trimethylsilyl)ethyl ether
IUPAC: 2-(chloromethoxy)ethyl-trimethylsilane
English name: 2-(Trimethylsilyl)ethoxymethyl chloride
Molecular formula: C6H15ClOSi
Molecular weight: 166.72

Names & synonyms

76513-69-42-(Trimethylsilyl)ethoxymethyl chloride2-Chloromethyl 2-(trimethylsilyl)ethyl etherSILANE, [2-(CHLOROMETHOXY)ETHYL]TRIMETHYL-EINECS 278-483-4DTXSID10227327Silane, (2-(chloromethoxy)ethyl)trimethyl-RefChem:470470DTXCID10149818Silane, 2-(chloromethoxy)ethyltrimethyl-278-483-4(2-(CHLOROMETHOXY)ETHYL)TRIMETHYLSILANE

Show more names

SEM-CI(2-trimethylethylsilylethoxy)methyl chloride2-(CHLOROMETHOXY)ETHYLTRIMETHYLSILANE(Trimethylsilyl)ethoxymethyl chloride{2-[(chloromethyl)oxy]ethyl}(trimethyl)silaneDK8912-(Trime

SEM-chloride2-(Trimethylsilyl)ethoxymethylchlorideSEM-Cl[2-(chloromethoxy)ethyl]trimethylsilane2-(chloromethoxy)ethyl-trimethylsilaneMFCD00009919C6H15ClOSiSEM chloride

Database identifiers

CAS: 76513-69-4
PubChem CID: 2724271
DTXSID: DTXSID10227327
UNII: G8Q8Y64LT8
EC Number: 278-483-4
Nikkaji: J319.335G

Properties

Computed structural properties

Topological polar surface area: 9.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 4
Heavy atoms: 9
Formal charge: 0
Complexity: 69.9

Physicochemical properties

Boiling point: 170 · 170-172 °C (lit.) 57-59 °C/8 mmHg (lit.)
Density: 0.942 g/mL · 0.942 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.435(lit.)
Flash point: 116 °F · 116 °F
storage temp.: 2 · 2-8°C
solubility: Sol most organic solvents (pentane, CH2Cl2, Et2O, THF, DMF, DMPU, HMPA)
form: Liquid
color: Clear colorless
Specific Gravity: 0.95 · 0.95
Water Solubility: decomposes
Sensitive: Moisture Sensitive
Hydrolytic Sensitivity: 7 · 7: reacts slowly with moisture/water
BRN: 3587289 · 3587289
Stability: Unstable in Solution
InChI: 1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3
InChIKey: BPXKZEMBEZGUAH-UHFFFAOYSA-N
SMILES: C[Si](C)(C)CCOCCl
CAS DataBase Reference: 76513 · 76513-69-4(CAS DataBase Reference)
UNSPSC Code: 12352101 · 12352101
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS05
Signal word: Danger
Hazard statements: 226 · H226-H314
Precautionary statements: 280 · P280-P305+P351+P338-P310
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: C
Risk Statements: 10 · 10-34
Safety Statements: 26 · 26-28-36/37/39-45-16
RIDADR: 2920 · UN 2920 8/PG 2
WGK Germany: 3 · 3
F: 8 · 8-10-21
TSCA: No
HazardClass: 3.2 · 3.2
PackingGroup: III
HS Code: 29319090 · 29319090
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 Skin · Flam. Liq. 3Skin Corr. 1B
REACH Registrations: Inactive
Limited Quantities: 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

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

P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 27-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/34974

Silane, 2-(chloromethoxy)ethyltrimethyl-: Does not have an individual approval but may be used under an appropriate group standard

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

Safety data

F: 8-10-21
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
tsca: No
ridadr: UN 2920 8/PG 2
hs_code: 29319090
risk_code: 10-34
Signal word: Danger
Symbol(GHS): GHS02,GHS05
hazard_code: C
safety_code: 26-28-36/37/39-45-16
hazard_class: 3.2
Storage Class: 3 - Flammable liquids
packing_group: III
Hazard statements: H226-H314
Limited Quantities: 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations: Inactive
Hazard Classifications: Flam. Liq. 3Skin Corr. 1B
Precautionary statements: P280-P305+P351+P338-P310

Chemistry & industry

Applications · 3 items

Uses2-(Trimethylsilyl)ethoxymethyl Chloride is a reagent used in the protection of alcohols, secondary aryl amines, and imidazole, indole, and pyrrole nitrogens;electrophilic formaldehyde equivalent; acyl anion equivalent,used in One-carbon Homologations, Cyclizations etc.

Uses2-(Chloromethoxy)ethyltrimethylsilane is used in the preparation of SEM [2-(trimethylsilyl)ethoxy]methyl]-ethers. It serves as a phenol protecting group in the synthesis of laterifluorones. Further, it reacts with 1H-imidazole to prepare 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole.

General Description2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is a widely used reagent for the preparation protection groups for amines, alcohols, phenols, and carboxy groups. The nitrogen of amides and sulfonamides groups are also protected by using SEM-Cl reagent.