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P78

Sigma-Aldrich

Palmitoyl chloride

98%

Synonym(s):

Hexadecanoyl chloride

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About This Item

Linear Formula:
CH3(CH2)14COCl
CAS Number:
Molecular Weight:
274.87
Beilstein/REAXYS Number:
972409
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

refractive index

n20/D 1.452 (lit.)

bp

88-90 °C/0.2 mmHg (lit.)

mp

11-13 °C (lit.)

density

0.906 g/mL at 25 °C (lit.)

SMILES string

CCCCCCCCCCCCCCCC(Cl)=O

InChI

1S/C16H31ClO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3

InChI key

ARBOVOVUTSQWSS-UHFFFAOYSA-N

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Application

Palmitoyl chloride can be used:
  • To introduce carbon chain in glycosphingolipid galactosyl ceramide through stereoselective olefin cross-metathesis.
  • To prepare monoacyl and 1,3-symmetrical triacylglycerols via regioselective ring opening of an oxirane.

It can also be used in the total synthesis of:
  • Hericenone J and 5′ -deoxohericenone C (hericene A).
  • Seminolipid.
  • Mycobactin S and T equivalents having catechol-glycine group instead of phenol-oxazoline of the naturally occurring mycobactins.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

supp_hazards

wgk_germany

WGK 1

flash_point_f

320.0 °F

flash_point_c

160 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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Total syntheses of seminolipid and its analogues by using 2, 6-bis (trifluoromethyl) phenylboronic acid as protective reagent
Shimada N, et al.
Organic & Biomolecular Chemistry, 17(31), 7325-7329 (2019)
Synthesis of the glycosphingolipid β-galactosyl ceramide and analogues via olefin cross metathesis
Rai AN and Basu A
The Journal of Organic Chemistry, 70(20), 8228-8230 (2005)
Nrupa Borkar et al.
The Journal of pharmacy and pharmacology, 69(9), 1110-1115 (2017-06-18)
Apomorphine is used to symptomatically treat Parkinson's disease (PD). Oral delivery of apomorphine is generally limited by its short plasma half-life and a hepatic first-pass metabolism. This study was aimed at evaluating the behavioural response of apomorphine and its prodrug
Synthesis and studies of catechol-containing mycobactin S and T analogs
Walz AJ, et al.
Organic & Biomolecular Chemistry, 5(10), 1621-1628 (2007)
Kyoung-Hwa Choi et al.
Carbohydrate polymers, 246, 116487-116487 (2020-08-05)
The purpose of this study was to investigate the improvement in the hydrophobicity of cellulose through gas grafting treatment with long chain fatty acid chloride using high pressure during pressing at high temperature. To do this, the gas grafting treatment

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