269131
2-(2-Bromoethyl)-1,3-dioxane
98%
Synonym(s):
3-Bromopropionaldehyde trimethylene acetal
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About This Item
Empirical Formula (Hill Notation):
C6H11BrO2
CAS Number:
Molecular Weight:
195.05
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
251-716-7
Beilstein/REAXYS Number:
1421628
MDL number:
Assay:
98%
Form:
liquid
InChI key
WMDHQEHPOVOEOG-UHFFFAOYSA-N
InChI
1S/C6H11BrO2/c7-3-2-6-8-4-1-5-9-6/h6H,1-5H2
SMILES string
BrCCC1OCCCO1
assay
98%
form
liquid
bp
67-70 °C/2.8 mmHg (lit.)
solubility
ethanol: soluble 50 (μg/mL)
density
1.431 g/mL at 25 °C (lit.)
functional group
bromo, ether
General description
The reaction of Grignard reagent prepared from 2-(2-bromoethyl)-1,3-dioxane and N-tert-butanesulfinyl aldimines was studied.
Application
2-(2-Bromoethyl)-1,3-dioxane was used in the synthesis of ketone adducts 2-[3-oxo-4(S)-(triphenylmethyl) amino-6-methylheptyl]-1,3-dioxane and 2-[3-oxo-4(S)-(triphenylmethyl)amino-6-methylheptyl]-1,3-dioxolane.
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Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
206.6 °F - closed cup
flash_point_c
97 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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Kristin M Brinner et al.
Organic & biomolecular chemistry, 3(11), 2109-2113 (2005-05-27)
A new method for the asymmetric synthesis of 2-substituted pyrrolidines in three steps from commercially available starting materials is described. Addition of the Grignard reagent prepared from 2-(2-bromoethyl)-1,3-dioxane to N-tert-butanesulfinyl aldimines proceeds in high yields and with good diastereoselectivities. The
R L Johnson et al.
International journal of peptide and protein research, 23(6), 581-590 (1984-06-01)
The Grignard reagents of 2-(2-bromoethyl)-1,3-dioxane and 2-(2-bromoethyl)-1,3-dioxolane readily reacted with the 2-thiopyridyl ester of N-triphenylmethyl-L-leucine to give the ketone adducts 2-[3-oxo-4(S)-(triphenylmethyl) amino-6-methylheptyl]-1,3-dioxane (8a) and 2-[3-oxo-4(S)-(triphenylmethyl) amino-6-methylheptyl]-1,3-dioxolane (8b) in near quantitative yield. When 1 equiv. of the Grignard reagent of 2-(2-bromoethyl)-1,3
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