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234478

Sigma-Aldrich

1-Chloro-3-iodopropane

99%

Synonym(s):

Trimethylene chloroiodide

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About This Item

Linear Formula:
Cl(CH2)3I
CAS Number:
6940-76-7
Molecular Weight:
204.44
Beilstein/REAXYS Number:
1731115
EC Number:
230-088-8
MDL number:
MFCD00001096
UNSPSC Code:
12352100
PubChem Substance ID:
24854043
NACRES:
NA.22

vapor density

6.8 (vs air)

vapor pressure

2 mmHg ( 20 °C)

assay

99%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.548 (lit.)

bp

170-172 °C (lit.)

density

1.904 g/mL at 25 °C (lit.)

SMILES string

ClCCCI

InChI

1S/C3H6ClI/c4-2-1-3-5/h1-3H2

InChI key

SFOYQZYQTQDRIY-UHFFFAOYSA-N

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General description

1-Chloro-3-iodopropane undergoes asymmetric α-alkylation with N-sulfinyl imidates to yield 2-substituted N-tert-butanesulfinyl-5-chloropentanimidates. Electroreduction of 1-chloro-3-iodopropane at glassy carbon electrode in dimethylformamide containing tetra-n-butylammonium perchlorate has been investigated by cyclic voltammetry. It also participates in conjugate addition of alkyl iodides to α,β-unsaturated nitriles in water.

Application

1-Chloro-3-iodopropane has been used in the synthesis of:
  • N-[4-[5-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-2-(2,2,2-trifluoroacetyl)pentyl]benzoyl]-L-glutamic acid, an inhibitor of glycinamide ribonucleotide transformylase (GAR Tfase) and aminoimidazole carboxamide ribonucleotide transformylase (AICAR Tfase)
  • interesting ″proton sponge″ type molecule quino[7,8-h]quinoline

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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Synthesis of 1, 2, 3, 4-tetrahydroquinolines and 1, 2, 3, 4-tetrahydro-1, 6-naphthyridines by a directed lithiation reaction.
Reed JN, et al.
Tetrahedron Letters, 29(45), 5725-5728 (1988)
Filip Colpaert et al.
The Journal of organic chemistry, 76(1), 234-244 (2010-12-02)
α-Alkylation of N-sulfinyl imidates with 1-chloro-3-iodopropane successfully led to 2-substituted N-tert-butanesulfinyl-5-chloropentanimidates in acceptable diastereomeric ratios (dr 67/33 to 72/28) and good yields (74-86%). Subsequent reduction with NaBH(4) led to the corresponding 2-substituted N-tert-butanesulfinyl-5-chloropentylamines, which could be cyclized to a range
Fraser F Fleming et al.
The Journal of organic chemistry, 72(18), 6961-6969 (2007-08-10)
A new silica-supported zinc-copper matrix reagent promotes the conjugate addition of alkyl iodides to cyclic and acyclic alkenenitriles in water. X-ray diffraction and electron microscopy techniques suggest that the active copper species generated from elemental zinc and copper(I) iodide is
Electrochemical Reduction of 1, 3-Dihalopropanes at Carbon Cathodes in Dimethylformamide.
Pritts WA and Peters DG.
Journal of the Electrochemical Society, 141(4), 990-995 (1994)
Heng Cheng et al.
Bioorganic & medicinal chemistry, 13(10), 3593-3599 (2005-04-26)
The synthesis and evaluation of N-[4-[5-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-2-(2,2,2-trifluoroacetyl)pentyl]benzoyl]-L-glutamic acid (2) as an inhibitor of glycinamide ribonucleotide transformylase (GAR Tfase) and aminoimidazole carboxamide ribonucleotide transformylase (AICAR Tfase) are reported. The inhibitor 2 was prepared in a convergent synthesis involving C-alkylation of methyl 4-(4,4,4-trifluoro-3-dimethylhydrazonobutyl)benzoate

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