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Sigma-Aldrich

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:
33884-43-4
Molecular Weight:
195.05
Beilstein:
1421628
EC Number:
251-716-7
MDL number:
MFCD00006567
UNSPSC Code:
12352100
PubChem Substance ID:
24856313
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.481 (lit.)

bp

67-70 °C/2.8 mmHg (lit.)

solubility

ethanol: soluble 50 (μg/mL)

density

1.431 g/mL at 25 °C (lit.)

SMILES string

BrCCC1OCCCO1

InChI

1S/C6H11BrO2/c7-3-2-6-8-4-1-5-9-6/h6H,1-5H2

InChI key

WMDHQEHPOVOEOG-UHFFFAOYSA-N

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

206.6 °F - closed cup

Flash Point(C)

97 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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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