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Sigma-Aldrich

1-Iododecane

98%

Synonym(s):

Decyl iodide

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About This Item

Linear Formula:
CH3(CH2)9I
CAS Number:
2050-77-3
Molecular Weight:
268.18
Beilstein:
1735228
EC Number:
218-104-1
MDL number:
MFCD00001085
UNSPSC Code:
12352100
PubChem Substance ID:
24854150
NACRES:
NA.22

vapor density

>5 (vs air)

vapor pressure

0.01 mmHg ( 20 °C)

Assay

98%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.485 (lit.)

bp

132 °C/15 mmHg (lit.)

density

1.257 g/mL at 25 °C (lit.)

SMILES string

CCCCCCCCCCI

InChI

1S/C10H21I/c1-2-3-4-5-6-7-8-9-10-11/h2-10H2,1H3

InChI key

SKIDNYUZJPMKFC-UHFFFAOYSA-N

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General description

Electrochemical reduction of 1-iododecane at mercury cathodes in DMF containing tetra-n-butylammonium perchlorate or tetramethyl ammonium perchlorate (supporting electrolyte) has been investigated.

Application

1-Iododecane has been used in the preparation of 9-nonadecanone via palladium-catalyzed carbonylative cross-coupling reaction with 9-octyl-9-borabicyclo[3.3.l]nonane.

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)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Electrochemical reduction of 1-iododecane and 1-bromodecane at a mercury cathode in dimethylformamide.
McNamee GM, et al.
Journal of the American Chemical Society, 99(6), 1831-1835 (1977)
Palladium-catalyzed carbonylative cross-coupling reaction of iodoalkanes with 9-alkyl-9-BBN derivatives. A direct and selective synthesis of ketones.
Ishiyama T and Miyaura N.
Tetrahedron Letters, 32(47), 6923-6926 (1991)
Niluksha Walalawela et al.
Photochemistry and photobiology, 95(5), 1160-1168 (2019-03-19)
In order to develop a new long alkane chain pterin that leaves the pterin core largely unperturbed, we synthesized and photochemically characterized decyl pterin-6-carboxyl ester (CapC) that preserves the pterin amide group. CapC contains a decyl-chain at the carboxylic acid
María José Sosa et al.
Photochemistry and photobiology, 97(1), 80-90 (2020-07-07)
Mono- and bis-decylated lumazines have been synthesized and characterized. Namely, mono-decyl chain [1-decylpteridine-2,4(1,3H)-dione] 6a and bis-decyl chain [1,3-didecylpteridine-2,4(1,3H)-dione] 7a conjugates were synthesized by nucleophilic substitution (SN 2) reactions of lumazine with 1-iododecane in N,N-dimethylformamide (DMF) solvent. Decyl chain coupling occurred
Thomas Bielewicz et al.
Nanotechnology, 27(35), 355602-355602 (2016-07-28)
Two-dimensional colloidal nanosheets represent very attractive optoelectronic materials. They combine good lateral conductivity with solution-processability and geometry-tunable electronic properties. In the case of PbS nanosheets, so far synthesis has been driven by the addition of chloroalkanes as coligands. Here, we
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