112-67-4

Basic information

• Product Name: Palmitoyl chloride
• Synonyms: Palmitoyl chloride,98%;Palmitoyl chloride,92%,tech.;PalMitoyl chloride, 98% 100ML;PALMITOYL CHLORIDE FOR SYNTHESIS;Palm acetyl chlorine(14 acetyl chlorine);hexadecanoicacid,chloride;HEXADECANOYL CHLORIDE;CETYLOYL CHLORIDE
• CAS NO: 112-67-4
• Molecular Formula: C₁₆H₃₁ClO
• Molecular Weight: 274.87
• EINECS: 203-996-7
• Product Categories: ACID CHLORIDES;Acid Halides;Bioactive Small Molecules;Building Blocks;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Organic Building Blocks;P
• Mol File: 112-67-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 11-13 °C(lit.)
• Boiling Point: 88-90 °C0.2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear/Liquid
• Density: 0.906 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: −20°C
• Water Solubility: Decomposition
• Sensitive: Moisture Sensitive
• BRN: 972409
• CAS DataBase Reference: Palmitoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Palmitoyl chloride(112-67-4)
• EPA Substance Registry System: Palmitoyl chloride(112-67-4)

Safety Data

• Hazard Codes: C
• Statements: 14-34-29
• Safety Statements: 26-36/37/39-43-45-8
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 1
• F: 9-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 112-67-4(Hazardous Substances Data)

Usage

Air & Water Reactions

Decomposes rather slowly in water to form hydrochloric acid and palmitic acid, a fatty acid that is not soluble in water.

Uses

A compound which has been used as a polymeric carrier for plasmid DNA delivery to 293T cells

General Description

A clear colorless to light yellow liquid with a pungent odor. Freezing point 11-12°C. Irritates skin, eyes, and mucous membranes. May be toxic by ingestion, inhalation and skin absorption.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Uses

Palmitoyl Chloride was used as a polymeric carriers for plasmid DNA (pDNA) delivery to 293T cells.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 6101, 1989 DOI: 10.1021/jo00287a023

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Chemical Properties

clear liquid

Reactivity Profile

HEXADECANOYL CHLORIDE is incompatible with bases (including amines), with strong oxidizing agents, and with alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Synthetic route

1-hexadecylcarboxylic acid (57-10-3) → n-hexadecanoyl chloride (112-67-4)

Conditions	Yield
With thionyl chloride Reflux;	100%
With thionyl chloride In N,N-dimethyl-formamide for 3h; Reflux;	97%
With thionyl chloride; N,N-dimethyl-formamide for 3h; Reflux;	97%

hexadecanoic acid methyl ester (112-39-0) → methylene chloride (74-87-3) + n-hexadecanoyl chloride (112-67-4) + WOCl4

Conditions	Yield
With tungsten(VI) chloride In benzene at 20℃; for 90h; Product distribution;

sodium palmitate (408-35-5) → n-hexadecanoyl chloride (112-67-4)

Conditions	Yield
With thionyl chloride at 20℃;

oxalyl dichloride (79-37-8) + 1-hexadecylcarboxylic acid (57-10-3) → n-hexadecanoyl chloride (112-67-4)

Conditions	Yield
With N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
In dichloromethane for 12h; Inert atmosphere;

DL-3,4,5,6-Tetra-O-benzyl-3,5/4,6-tetrahydroxycyclohex-1-ene-1-methanol (130277-53-1, 130324-58-2) + n-hexadecanoyl chloride (112-67-4) → methyl Hexadecanoate (130277-54-2, 130324-59-3)

Conditions	Yield
With pyridine; dmap In dichloromethane for 2h; Ambient temperature;	100%

9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-2-{[(4-methoxyphenyl)diphenylmethyl]amino}-6,9-dihydro-1H-purin-6-one (88110-81-0) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid 3-hexadecanoyloxy-2-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-propyl ester (88110-83-2)

Conditions	Yield
With pyridine; dmap In dichloromethane for 20h; Ambient temperature;	100%

1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxymethyl-3-propanol (190505-04-5) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid 2-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester (190505-07-8)

Conditions	Yield
With dmap In pyridine for 2h; Heating;	100%

7,11,15,28-tetrakis(4-aminophenyl)-1,21,23,25-tetraundecyl 2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5',4'-i']benzo[1,2-d:5,4-d']bis[1,3]benzodioxin + n-hexadecanoyl chloride (112-67-4) → 7,11,15,28-tetrakis(4-palmitoylamidophenyl)-1,21,23,25-tetraundecyl 2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5',4'-i']benzo[1,2-d:5,4-d']bis[1,3]benzodioxin

Conditions	Yield
With potassium carbonate In water; ethyl acetate for 2h; Ambient temperature;	100%

N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine (177898-40-7) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid octyl-((3aS,4R,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-amide (218924-27-7)

Conditions	Yield
In pyridine for 1h; Ambient temperature;	100%

pyrrolidine (123-75-1) + n-hexadecanoyl chloride (112-67-4) → 1-(pyrrolidin-1-yl)hexadecan-1-one (70974-48-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With pyridine at 20℃; for 3h; Acylation;	4.5 g
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;

(+)-1-O-[12-N-(benzyloxycarbonyl)aminododecanoyl]-3-O-(4-methoxybenzyl)-sn-glycerol (345287-87-8) + n-hexadecanoyl chloride (112-67-4) → (+)-1-O-[12-N-(benzyloxycarbonyl)aminododecanoyl]-2-O-hexadecanoyl-3-O-(4-methoxybenzyl)-sn-glycerol (345287-88-9)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃;	100%
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	100%
With pyridine; dmap In dichloromethane	90%
Stage #1: (+)-1-O-[12-N-(benzyloxycarbonyl)aminododecanoyl]-3-O-(4-methoxybenzyl)-sn-glycerol With pyridine; dmap In dichloromethane at 0℃; for 0.5h; Stage #2: n-hexadecanoyl chloride In dichloromethane at 20℃; Further stages.;	70%

1-O-hexanoyl-3-pmethoxybenzyl-sn-glycerol + n-hexadecanoyl chloride (112-67-4) → 1-O-hexanoyl-2-O-palmitoyl-3-O-p-methoxybenzyl-sn-glycerol

Conditions	Yield
With dmap In pyridine at 20℃; for 20h;	100%

3-[4-(3α-hydroxynortropanylazo)phenoxy]propyloxymethylpolystyrene + n-hexadecanoyl chloride (112-67-4) → 3-palmitoylnortropine

Conditions	Yield
Stage #1: 3-[4-(3α-hydroxynortropanylazo)phenoxy]propyloxymethylpolystyrene; n-hexadecanoyl chloride With dmap; triethylamine In dichloromethane at 20℃; for 12h; Stage #2: With trifluoroacetic acid In dichloromethane at 0℃; Further stages.;	100%

3-[3-(4-hydroxypiperidinylazo)phenoxy]propyloxymethylpolystyrene + n-hexadecanoyl chloride (112-67-4) → 4-palmitoyloxypiperidine

Conditions	Yield
Stage #1: 3-[3-(4-hydroxypiperidinylazo)phenoxy]propyloxymethylpolystyrene; n-hexadecanoyl chloride With dmap; triethylamine In dichloromethane at 20℃; for 12h; Stage #2: With trifluoroacetic acid In dichloromethane at 0℃; Further stages.;	100%

diethylaminopropylamine (104-78-9) + n-hexadecanoyl chloride (112-67-4) → N,N-diethyl-N'-hexadecanoyl-1,3-propanediamine

Conditions	Yield
In methanol; sodium hydroxide; dichloromethane; chloroform	100%

2-(2-Aminoethoxy)ethanol (929-06-6) + n-hexadecanoyl chloride (112-67-4) → N-(ω-hydroxyethoxyethyl)hexadecanamide (20138-27-6)

Conditions	Yield
Stage #1: 2-(2-Aminoethoxy)ethanol With magnesium oxide In tetrahydrofuran; water at 5℃; for 0.5h; Stage #2: n-hexadecanoyl chloride In tetrahydrofuran; water at 5 - 10℃; for 2h;	100%
With triethylamine In dichloromethane at 0℃; for 4h;	92%
With magnesium oxide In tetrahydrofuran; water

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + n-hexadecanoyl chloride (112-67-4) → palmitic acid N-succinimide ester (14464-31-4)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 8h; Cooling with ice;	100%
With triethylamine In chloroform at 20℃; for 8h; Cooling with ice;	100%

2-amino-5,10,15,20-tetraphenylporphyrin (82945-59-3) + n-hexadecanoyl chloride (112-67-4) → C60H61N5O

Conditions	Yield
Stage #1: 2-amino-5,10,15,20-tetraphenylporphyrin With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: n-hexadecanoyl chloride In dichloromethane at 20℃; for 3h;	100%

(3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid (R)-1-(2-oxo-2-phenyl-ethoxycarbonylmethyl)-dodecyl ester (339316-64-2)

Conditions	Yield
With dmap In pyridine; dichloromethane Ambient temperature;	99.4%

methylamine (74-89-5) + n-hexadecanoyl chloride (112-67-4) → N-methylhexadecanamide (7388-58-1)

Conditions	Yield
In dichloromethane; water at 20℃; for 12h;	99%
In dichloromethane; water at 20℃; for 24h;	92%
With water

n-hexadecanoyl chloride (112-67-4) → pentadecanyl isocyanate (39633-51-7)

Conditions	Yield
With sodium azide In para-xylene for 2h; Heating;	99%
With sodium azide; benzene
With sodium azide In toluene for 5h; Reflux; Inert atmosphere;

thiazolidine-2-thione (134469-06-0) + n-hexadecanoyl chloride (112-67-4) → 1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one (74058-64-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 50℃; for 0.5h;	99%
With triethylamine In dichloromethane at 0 - 5℃; for 3h;	75%

N-hydroxy-N-methylbenzenecarbothioamide (89861-45-0) + n-hexadecanoyl chloride (112-67-4) → N-methyl-N-palmitoyloxythiobenzamide (89861-46-1)

Conditions	Yield
With pyridine In diethyl ether for 0.5h; Ambient temperature;	99%

DL-(1,2,4/3,5,6)-2,5,6-Tri-O-benzyl-2,3,4,5,6-pentahydroxy-3,4-bis-O-(4-methoxybenzyl)cyclohexane-1-methanol, DL-(1,2,3,5/4,6)-2,3,6-Tri-O-benzyl-2,3,4,5,6-pentahydroxy-4,5-bis-O-(4-methoxybenzyl)cyclohexane-1-methanol (130277-63-3, 130324-67-3) + n-hexadecanoyl chloride (112-67-4) → methyl Hexadecanoate, methyl Hexadecanoate (130277-66-6, 130324-68-4)

Conditions	Yield
With pyridine; dmap In dichloromethane at 25℃; for 1h;	99%

rac-1-O-hexadecyl-3-O-benzylglycerol (103475-80-5) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid 2-benzyloxy-1-hexadecyloxymethyl-ethyl ester (95895-49-1)

Conditions	Yield
With pyridine In benzene at 70℃;	99%

RETINOL (68-26-8) + n-hexadecanoyl chloride (112-67-4) → retinyl palmitate (79-81-2)

Conditions	Yield
In toluene at 35℃; for 1h;	99%
With pyridine In 1,2-dichloro-ethane

6,7dihydroxy-3methyl-4-thiaheptanoic acid t-butyl ester (167768-03-8) + n-hexadecanoyl chloride (112-67-4) → 6,7-bis(palmitoyloxy)-3-methyl-4-thiaheptanoic acid t-butyl ester (167768-04-9)

Conditions	Yield
With dmap In dichloromethane for 1h; Ambient temperature;	99%
With 2-(Dimethylamino)pyridine; sodium bicarbonate; triethylamine; citric acid In chloroform; water	99%

(S)-2-(4-{[3-(3-Hexadecanoylamino-2-hydroxy-propylsulfanyl)-propionylamino]-methyl}-benzoylamino)-pentanedioic acid di-tert-butyl ester (204583-04-0) + n-hexadecanoyl chloride (112-67-4) → (S)-2-(4-{[3-(3-Hexadecanoylamino-2-hexadecanoyloxy-propylsulfanyl)-propionylamino]-methyl}-benzoylamino)-pentanedioic acid di-tert-butyl ester (204583-05-1)

Conditions	Yield
With dmap In dichloromethane for 0.5h; Ambient temperature;	99%

methyl furan-2-ylacetate (4915-22-4) + n-hexadecanoyl chloride (112-67-4) → (5-hexadecanoylfuran-2-yl)acetic acid methyl ester (852152-07-9)

Conditions	Yield
With tin(IV) chloride In dichloromethane at -5℃; for 1h;	99%
With tin(IV) chloride In dichloromethane at -5℃; for 1h; Friedel-Crafts acylation;	98%
With tin(IV) chloride In dichloromethane at -5℃; for 1h; Substitution; Friedel-Crafts reaction;
With tin(IV) chloride In dichloromethane at -5℃; Friedel-Crafts acylation;

3-O-Benzyl-1-O-octadecanoyl-sn-glycerin (4145-51-1, 6236-22-2, 116947-35-4, 988-76-1) + n-hexadecanoyl chloride (112-67-4) → 3-O-benzyl-2-O-hexadecanoyl-1-O-octadecanoyl-sn-glycerol (282532-76-7)

Conditions	Yield
With dmap In pyridine; dichloromethane at 0 - 20℃; Acylation;	99%

(S)-3-Hydroxy-2-(2-tetradecanoylamino-acetylamino)-propionic acid benzyl ester (260785-43-1) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid (S)-2-benzyloxycarbonyl-2-(2-tetradecanoylamino-acetylamino)-ethyl ester

Conditions	Yield
With triethylamine In chloroform at 20℃; for 6h; Acylation;	99%

O-(5-Acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (94458-63-6) + n-hexadecanoyl chloride (112-67-4) → (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-hexadecanamino-4-octadecene-1,3-diol

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 2h;	99%
With sodium acetate In tetrahydrofuran; water Acylation;

glycine ethyl ester hydrochloride (5680-79-5) + n-hexadecanoyl chloride (112-67-4) → N-hexadecanoyl glycine methyl ester (214706-34-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	99%
With sodium hydrogencarbonate In chloroform; water at 20℃; for 2h;
Stage #1: glycine ethyl ester hydrochloride With potassium carbonate In dichloromethane; water at 0℃; for 0.0833333h; Stage #2: n-hexadecanoyl chloride In dichloromethane; water at 20℃; for 16h;	1.48 g

Upstream product

• 57-10-3 Palmitic acid 

Downstream Products

• 137-66-6 L-Ascorbyl 6-palmitate 
• 36653-82-4 1-Hexadecanol 
• 530-43-8 Chloramphenicol palmitate 

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