156957

Sigma-Aldrich

Hexanoyl chloride

97%

Synonym(s):
Caproyl chloride
Linear Formula:
CH3(CH2)4COCl
CAS Number:
Molecular Weight:
134.60
Beilstein/REAXYS Number:
506332
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

refractive index

n20/D 1.426 (lit.)

bp

150-153 °C (lit.)

solubility

chloroform: soluble(lit.)
diethyl ether: soluble(lit.)

density

0.963 g/mL at 25 °C (lit.)

SMILES string

CCCCCC(Cl)=O

InChI

1S/C6H11ClO/c1-2-3-4-5-6(7)8/h2-5H2,1H3

InChI key

YWGHUJQYGPDNKT-UHFFFAOYSA-N

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Application

Hexanoyl chloride was used in:
  • total synthesis of (±)-7-butyl-6,8-dihydroxy-3-pentyl-3,4-dihydroisochromen-1-one
  • asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth
  • preparation of hexanoyl-coated nanofibers dispersible in several organic solvents
  • total synthesis of natural isocarbostyril ruprechstyril (3-n-pentyl-6-methoxy-8-hydroxy-1(2H)-isoquinolinone), isolated from Ruprechtia tangarana
  • synthesis of 5-chloro-8-hydroxy-6-methoxy-3-pentylisocoumarin, the 5-chloro analog of naturally occurring 7-chloro-8-hydroxy-6-methoxy-3-pentylisocoumarin, isolated from Tessmannia densiflora

Packaging

25, 100, 500 mL in glass bottle

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2920 3(8) / PGII

WGK Germany

WGK 1

Flash Point(F)

122.0 °F - closed cup

Flash Point(C)

50 °C - closed cup

Aamer Saeed
Journal of Asian natural products research, 13(6), 505-511 (2011-05-31)
The synthesis of title isocoumarin, the 5-chloro analog of naturally occurring 7-chloro-8-hydroxy-6-methoxy-3-pentylisocoumarin, isolated from Tessmannia densiflora is described. Chlorination of ethyl 2-(2-ethoxy-2-oxoethyl)-4,6-dimethoxybenzoate (2) afforded 3-chloro ester (3) followed by hydrolysis to furnish the 2-(carboxymethyl)-3-chloro-4,6-dimethoxybenzoic acid (4) that was converted to...
Tao Zhang et al.
Molecules (Basel, Switzerland), 18(5), 5201-5208 (2013-05-09)
An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. The target molecule was synthesized in six linear steps and in 30.3% overall yield from commercially available hexanoyl chloride, (S)-4-benzyloxazolidin-2-one and 1,9-nonanediol. The hexanoyl...
Aamer Saeed et al.
Journal of Asian natural products research, 15(10), 1112-1122 (2013-07-23)
A new total synthesis of ( ± )-7-butyl-6,8-dihydroxy-3-pentyl-3,4-dihydroisochromen-1-one, isolated as R-enantiomer from Geotrichum sp., has been described. Reaction of 4-butyl-3,5-dimethoxyhomophthalic anhydride with hexanoyl chloride in the presence of 1,1,3,3-tetramethyl guanidine and triethyl amine afforded 7-butyl-6,8-dimethoxy-3-pentylisochromen-1-one, which was converted into corresponding 3,4-dihydroisochromen-1-one by...
Aamer Saeed
Natural product research, 27(13), 1153-1158 (2012-08-14)
A short total synthesis of natural isocarbostyril ruprechstyril (3-n-pentyl-6-methoxy-8-hydroxy-1(2H)-isoquinolinone) isolated from Ruprechtia tangarana is reported. 6,8-Dimethoxy-3-pentylisocoumarin obtained by condensation of 3,5-dimethoxyhomophthalic anhydride with hexanoyl chloride was smoothly converted to O-methylruprechstyril by refluxing with methanamide. Regioselective demethylation of the latter using...
Pei Huang et al.
ChemSusChem, 5(12), 2319-2322 (2012-11-28)
Got a crush: Native cellulose can be dispersed as nanofibers in organic solvents by ball milling with esterification agents. Milling with hexanoyl chloride/DMF gives hexanoyl-coated nanofibers dispersible in several organic solvents. Milling with succinic anhydride/DMSO results water-dispersible nanofibers. The results...

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