Basic information
- CAS
86864-60-0- Standard SMILES
CC(C)(C)[Si](C)(C)OCCBr- InChIKey
JBKINHFZTVLNEM-UHFFFAOYSA-N- Molecular formula
- C8H19BrOSi
- Average molar mass
- 239.22 g/mol
- Monoisotopic mass
- 238.03885
Names & identifiers
- Preferred name
- (2-Bromoethoxy)-tert-butyldimethylsilane
- IUPAC
- 2-bromoethoxy-tert-butyl-dimethylsilane
- English name
- (2-Bromoethoxy)-tert-butyldimethylsilane
- Molecular formula
- C8H19BrOSi
- Molecular weight
- 239.23
Names & synonyms
86864-60-0(2-Bromoethoxy)-tert-butyldimethylsilaneDTXSID30394126RefChem:68573DTXCID50344986675-780-4(2-Bromoethoxy)(tert-butyl)dimethylsilane2-bromoethoxy-tert-butyl-dimethylsilaneMFCD00209550C8H19BrOSi2-bromoethoxy-tert-butyl-dimethyl-silane2-Bromoethoxy-t-butyldimethylsilane
Show more names
2-Bromoethyloxy(tert-butyl)dimethylsilane2-Bromoethyl tert-butyldimethylsilyl etherDK933DK417DKSI039OZAN-008DKFELEX02492-bromethanolTBDMSether2-(t-butyldimethylsiloxy)ethylbromide
2-Bromoethoxy-tert-butyldimethylsilane(2-bromoethoxy)-t-butyldimethylsilaneS028952-bromoethoxy-t-butyl dimethylsilaneSilane, (2-bromoethoxy)(1,1-dimethylethyl)dimethyl-BrCH2CH2OTBSSCHEMBL57968SCHEMBL19210228
Database identifiers
- CAS
86864-60-0- PubChem CID
- 3608067
Properties
Computed structural properties
- Topological polar surface area
- 9.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 4
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 118
Physicochemical properties
- Boiling point
- 70 · 70-75 °C2.5 mm Hg(lit.)
- Density
- 1.115 g/mL · 1.115 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.444(lit.)
- Flash point
- 163 °F · 163 °F
- storage temp.
- 2 · 2-8°C
- form
- Liquid
- Specific Gravity
- 1.115 · 1.115
- color
- White to pale yellow
- Hydrolytic Sensitivity
- 7 · 7: reacts slowly with moisture/water
- InChI
- InChI=1S/C8H19BrOSi/c1-8(2,3)11(4,5)10-7-6-9/h6-7H2,1-5H3
- InChIKey
- JBKINHFZTVLNEM-UHFFFAOYSA-N
- SMILES
- [Si](OCCBr)(C(C)(C)C)(C)C
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (97.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (97.8%)
Safety data
- wgk
- 3
- hs_code
- 29319090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Storage Class
- 10 - Combustible liquids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
Chemistry & industry
Applications
Uses(2-Bromoethoxy)-tert-butyldimethylsilane was used in the synthesis of 4-(3-hydroxypropyl)-4′-methyl-2,2′-bipyridine.It may be used as a reagent for the selective N-alkylation of 5-piperazin-1-yl-1H-indole and (1H-indol-2-yl)-piperazin-1-yl-methanone and also in the synthesis of 2-[3-[(3,4,5-trimethoxyphenyl)thio]-1H-indol-5-yloxy]ethanol.
Uses(2-Bromoethoxy)-tert-butyldimethylsilane can be used in N-alkylation with 5-piperazin-1-yl-1H-indole to synthesize 5-(4-(2-((tert-butyldimethylsilyl)oxy)ethyl)piperazin-1-yl)-1H-indole.
General Description(2-Bromoethoxy)-tert-butyldimethylsilane is a silane derivative.
Preparation methods
PreparationIn a round-bottom flask, TBDMSC1 (10.61 g, 70.42 mmol) and imidazole (6.23 g, 91.55 mmol) were dissolved in DMF (12.5 mL) and the solution was stirred at 30 mmat rt. Then, 2-bromoethanol (5 mL, 70.42 mmol) was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was partitioned between Et20 and water. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give 17 g of (2-Bromoethoxy)-tert-butyldimethylsilane (quantitative yield, colorless oil).
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
444 records
Compound notes
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