26130

Sigma-Aldrich

3-Chloropropionaldehyde diethylacetal

technical, ≥90% (GC)

Synonym(s):
3-Chloro-1,1-diethoxypropane
Linear Formula:
ClCH2CH2CH(OC2H5)2
CAS Number:
Molecular Weight:
166.65
Beilstein/REAXYS Number:
1698609
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

technical

assay

≥90% (GC)

contains

~0.5% CaCO3 as stabilizer

refractive index

n20/D 1.42 (lit.)
n20/D 1.420

bp

84 °C/25 mmHg (lit.)

density

0.995 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(CCCl)OCC

InChI

1S/C7H15ClO2/c1-3-9-7(5-6-8)10-4-2/h7H,3-6H2,1-2H3

InChI key

NXHONHDWVLPPCS-UHFFFAOYSA-N

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Application

3-Chloropropionaldehyde diethylacetal has been used in the synthesis of:
  • N-[4-[[3-(2, 4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]amino]benzoyl]-L-glutamic acid, an acyclic analog of 5,6,7,8-tetrahydrofolic acid
  • 1-(D,L)-(3′-amino, 3′-carboxypropyl)uracil, nucleoamino acid
  • 7-methoxychromanone
  • grignard reagent

Packaging

25, 100 mL in glass bottle

Other Notes

Masked 3-chloropropionaldehyde; preparation of Grignard reagent

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1993C 3 / PGIII

WGK Germany

WGK 3

Flash Point(F)

129.2 °F - closed cup

Flash Point(C)

54 °C - closed cup

An Efficient Preparation of 7-Methoxychromanone.
Cao Z and Liehr JG.
Synthetic Communications, 26(6), 1233-1245 (1996)
J L Kelley et al.
Journal of medicinal chemistry, 33(2), 561-567 (1990-02-01)
The synthesis and biological evaluation of N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]amino]- benzoyl]-L-glutamic acid (1) (5-DACTHF, 543U76), an acyclic analogue of 5,6,7,8-tetrahydrofolic acid (THFA), are described. The key intermediate, hemiaminal 8, was prepared in four stages from 3-chloropropionaldehyde diethyl acetal. Reaction of 8 with dimethyl...
Masoomeh Shirzad et al.
Assay and drug development technologies, 17(5), 231-239 (2019-05-14)
This study aimed to synthesize methoxy polyethylene glycol propionaldehyde (mPEG20,000-ALD) for the preparation of PEGylated nanoliposomal cisplatin. Nanocarriers such as liposomes are developed for a wide range of drug delivery systems. PEG with high molecular weight (Mw) is used to...
A. Greiner
Tetrahedron Letters, 30, 3547-3547 (1989)
A B Cheikh et al.
Journal of molecular evolution, 30(4), 315-321 (1990-04-01)
We have prepared the nucleoamino acids 1-(3'-amino,3'-carboxypropyl)uracil (3) and 9-(3'-amino,3'-carboxypropyl)adenine (4) as (L)-enantiomers and as racemic mixtures. When 3 or 4 is suspended in water and treated with N,N'-carbonyldiimidazole, peptides are formed in good yield. The products formed from the...

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