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26235

Sigma-Aldrich

2-(3-Chloropropyl)-1,3-dioxolane

≥97.0% (GC)

Synonym(s):

4-Chlorobutyraldehyde ethylene acetal

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About This Item

Empirical Formula (Hill Notation):
C6H11ClO2
CAS Number:
16686-11-6
Molecular Weight:
150.60
Beilstein/REAXYS Number:
1236588
MDL number:
MFCD00043135
UNSPSC Code:
12352100
PubChem Substance ID:
57648166
NACRES:
NA.22

Quality Level

100

assay

≥97.0% (GC)

form

liquid

refractive index

n20/D 1.453

bp

93-94 °C/12 mmHg (lit.)

density

1.142 g/mL at 20 °C (lit.)

SMILES string

ClCCCC1OCCO1

InChI

1S/C6H11ClO2/c7-3-1-2-6-8-4-5-9-6/h6H,1-5H2

InChI key

ZBPUNVFDQXYNDY-UHFFFAOYSA-N

Related Categories

Application

2-(3-Chloropropyl)-1,3-dioxolane (2-(3′-chloropropyl)-1,3-dioxolane) is a masked γ-chlorobutyraldehyde and was used for the introduction of 3-(1,3-dioxolan-2-yl)propyl moiety. It was also used in the synthesis of:
  • (±)-histrionicotoxin and (±)-histrionicotoxin 235A using a two-directional strategy
  • 4-iodobutyraldehyde, 5-iodovaleraldehyde and 5-iodo-2-petanone
  • corresponding phosphonate

Other Notes

Masked γ-chlorobutyraldehyde, useful for the introduction of the 3-(1,3-dioxolan-2-yl)propyl moiety; Preparation and use of the corresponding phosphonate

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

174.2 °F - closed cup

flash_point_c

79 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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C.P. Forbes et al.
Journal of the Chemical Society. Perkin Transactions 1, 2353-2353 (1977)
R.E. Abbott et al.
The Journal of Organic Chemistry, 45, 5398-5398 (1980)
Two-directional synthesis. Part 1: A short formal synthesis of (?)-histrionicotoxin and (?)-histrionicotoxin 235A.
Stockman RA.
Tetrahedron Letters, 41(47), 9163-9165 (2000)
S.A. Bal et al.
The Journal of Organic Chemistry, 47, 5045-5045 (1982)
A Nagy et al.
Proceedings of the National Academy of Sciences of the United States of America, 93(6), 2464-2469 (1996-03-19)
A convenient, high yield conversion of doxorubicin to 3'-deamino-3'-(2''-pyrroline-1''-yl)doxorubicin is described. This daunosamine-modified analog of doxorubicin is 500-1000 times more active in vitro than doxorubicin. The conversion is effected by using a 30-fold excess of 4-iodobutyraldehyde in anhydrous dimethylformamide. The
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