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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:
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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

26235-INTR-F:
26235-5ML-F:
26235-BULK-F:
26235-25ML-F:
26235-VAR-F:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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