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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:
112-67-4
Molecular Weight:
274.87
Beilstein:
972409
EC Number:
203-996-7
MDL number:
MFCD00000742
UNSPSC Code:
12352100
PubChem Substance ID:
24898879
NACRES:
NA.22

Quality Level

200

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
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

WGK

WGK 1

Flash Point(F)

320.0 °F

Flash Point(C)

160 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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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
Regioselective opening of an oxirane system with trifluoroacetic anhydride. A general method for the synthesis of 2-monoacyl-and 1, 3-symmetrical triacylglycerols
Stamatov SD and Stawinski J
Tetrahedron, 61(15), 3659-3669 (2005)
Synthesis and studies of catechol-containing mycobactin S and T analogs
Walz AJ, et al.
Organic & Biomolecular Chemistry, 5(10), 1621-1628 (2007)
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)
View All Related Papers

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