597-71-7

Basic information

• Product Name: PENTAERYTHRITOL TETRAACETATE
• Synonyms: 1,3-Propanediol, 2,2-bis[(acetyloxy)methyl]-, diacetate;1,3-Propanediol,2,2-bis[(acetyloxy)methyl]-,diacetate;3-(Acetyloxy)-2,2-bis[(acetyloxy)methyl]propyl acetate;3-propanediol,2,2-bis((acetyloxy)methyl)-diacetate;PENTAERYTHRITOL TETRAACETATE 98+%;tetra-O-acetyl pentaerythritol;Pentaerythrityl tetraacetate,95%;Pentaerythritol Teraacetate
• CAS NO: 597-71-7
• Molecular Formula: C₁₃H₂₀O₈
• Molecular Weight: 304.29
• EINECS: 209-907-8
• Mol File: 597-71-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 78-83 °C
• Boiling Point: 325 °C
• Flash Point: 160.5 °C
• Appearance: white crystalline powder
• Density: 1.2730
• Vapor Pressure: 0.000139mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• CAS DataBase Reference: PENTAERYTHRITOL TETRAACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAERYTHRITOL TETRAACETATE(597-71-7)
• EPA Substance Registry System: PENTAERYTHRITOL TETRAACETATE(597-71-7)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 24/25-45-36/37/39-26-16
• RTECS: RZ2600000
• Hazardous Substances Data: 597-71-7(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white powder

Safety Profile

Moderately toxic by ingestion.Slightly toxic by intraperitoneal route. When heated todecomposition it emits acrid smoke and irritating vapors

Purification Methods

Crystallise pentaerythritol tetraacetate from hot water, then leach it with cold water until the odour of acetic acid is no longer detectable. It also crystallises from 95% EtOH after dissolving in CHCl3, washing with saturated NaHCO3, then H2O, drying over anhydrous CaCl2 and evaporating. It has been prepared by acetolysis of the tetranitrate in 95% yield [Wolfrom et al. J Am Chem Soc 73 874 1951]. [Breusch & Oguzer Chem Ber 88 1511 1955, LeFèvre et.al. J Chem Soc 16 1958, Beilstein 1 IV 1812, 2 IV 264.]

InChI:InChI=1/C13H20O8/c1-18-9(14)5-13(6-10(15)19-2,7-11(16)20-3)8-12(17)21-4/h5-8H2,1-4H3

Synthetic route

Pentaerythritol (115-77-5) + acetic anhydride (108-24-7) → pentaerythritol tetracetate (597-71-7)

Conditions	Yield
With methanesulfonic acid at 25℃; for 2h; Inert atmosphere;	98%
With aluminum triflate at 20℃; for 0.00833333h;	95%
aluminium dodecatungsten phosphate at 20℃; for 0.583333h;	94%

3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate (10193-99-4) → pentaerythritol tetracetate (597-71-7)

Conditions	Yield
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 20℃; UV-irradiation;	94%
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation;	94%

2,2-bis(iodomethyl)-1,3-propanediol (3296-88-6) + silver(I) acetate (563-63-3) → pentaerythritol tetracetate (597-71-7)

Conditions	Yield
With acetic acid at 140 - 150℃; man kocht das Reaktionsprodukt mit Acetanhydrid und einer Spur Zinkchlorid;

pentaerythritol bisacetate (5419-74-9) → Pentaerythritol (115-77-5) + pentaerythritol triacetate (13051-30-4) + pentaerythritol tetracetate (597-71-7)

Conditions	Yield
beim Aufbewahren;

Pentaerythritol (115-77-5) + acetic acid (64-19-7) → pentaerythritol tetracetate (597-71-7)

pentaerythritol tetracetate (597-71-7) → pentaerythritol triacetate (13051-30-4)

Conditions	Yield
With sodium acetate at 170℃; for 2h; Inert atmosphere;	41%

pentaerythritol tetracetate (597-71-7) + saccharin (81-07-2) → C18H21NO9S

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) at 150℃; for 24h; Sealed tube;	30%

Pentaerythritol (115-77-5) + pentaerythritol tetracetate (597-71-7) → monoacetyl pentaerythritol (13051-29-1)

Conditions	Yield
With potassium carbonate at 180℃;

tetra(n-butoxy)silane (4766-57-8) + pentaerythritol tetracetate (597-71-7) → 3,3-bis-acetoxymethyl-18,18-dibutoxy-1,5,7,11,13,17,19,22,23,26-decaoxa-6,12,18-trisila-tetraspiro[5.2.2.2.5.2.2.2]hexacosane (6192-21-8)

Conditions	Yield
With toluene-4-sulfonic acid at 170 - 200℃;

pentaerythritol tetracetate (597-71-7) → carbon dioxide (124-38-9) + carbon monoxide (201230-82-2) + H2

Conditions	Yield
With oxygen at 170℃; Rate constant; Product distribution; Mechanism; Eact, lgA; further temperatures;

Pentaerythritol (115-77-5) + pentaerythritol tetracetate (597-71-7) → pentaerythritol diacetate

aluminium trichloride (7446-70-0) + pentaerythritol tetracetate (597-71-7) → pentaerythritol dichlorohydrin diacetate

Conditions	Yield
at 150 - 160℃;

aluminium trichloride (7446-70-0) + pentaerythritol tetracetate (597-71-7) → pentaerythritol monochlorohydrin triacetate

Conditions	Yield
at 150 - 160℃;

Pentaerythritol (115-77-5) + pentaerythritol tetracetate (597-71-7) → pentaerythritol triacetate

aluminium trichloride (7446-70-0) + pentaerythritol tetracetate (597-71-7) → pentaerythritol trichlorohydrin acetate

Conditions	Yield
at 150 - 160℃;

Pentaerythritol (115-77-5) + pentaerythritol tetracetate (597-71-7) → pentaerythritol bisacetate (5419-74-9)

Conditions	Yield
With sodium acetate

pentaerythritol tetracetate (597-71-7) → 2-(acetoxymethyl)-2-(bromomethyl)propane-1,3-diyl diacetate (3492-42-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate / 2 h / 170 °C / Inert atmosphere 2: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 18 h / 0 °C / Inert atmosphere View Scheme

pentaerythritol tetracetate (597-71-7) → 2-(acetoxymethyl)-2-(mercaptomethyl)propane-1,3-diyl diacetate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium acetate / 2 h / 170 °C / Inert atmosphere 2: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 18 h / 0 °C / Inert atmosphere 3: NaS*5H2O; carbon disulfide / N,N-dimethyl-formamide / 0.17 h / 25 °C / Inert atmosphere View Scheme

Upstream product

• 5419-74-9 pentaerythritol bisacetate 
• 115-77-5 Pentaerythritol 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 10193-99-4 3-[(sulfanylacetyl)oxy]-2,2-bis{[(sulfanylacetyl)oxy]methyl}propyl sulfanylacetate 
• 3296-88-6 2,2-bis(iodomethyl)-1,3-propanediol 
• 563-63-3 silver(I) acetate 

Downstream Products

• 13051-29-1 monoacetyl pentaerythritol 

Relevant articles and documents

A Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light

A visible-light-induced metal-free desulfurization method for thiols and disulfides has been explored. This radical desulfurization features mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small molecules, but also to peptides.

Synthesis of dipentaerythritol from pentaerythritol under acidic conditions

The direct synthesis of dipentaerythritol (DPE) from pentaerythritol (PE) was studied under acidic conditions. After optimization of the reaction parameters in a batch reactor, DPE was obtained with 50% selectivity when 50% PE was converted. This process, using PE in suspension in sulfolane (PE/sulfolane ratio = 2333 g/L) at 175 °C for 60 min, required a low amount of sulfuric acid (0.5 mol %). The optimized conditions were transposed to a 140 grams scale process. Finally, DPE was isolated with 16% yield (72% gas chromatography, GC purity) for 28% conversion of PE that corresponds to 57% DPE selectivity.

Folding control of a non-natural glycopeptide using saccharide-coded structural information for polypeptides

We synthesized "glyco-arylopeptides", whose folding structure significantly changes depending on the kind of saccharide in their side chain. The saccharide moiety interacts with the main chain via hydrogen bonding, and the non-natural polypeptides form two well-defined architectures - (P)-31- and (M)-41-helices - depending on the length of the saccharide chains and even the configuration of a single stereo-genic center in the epimers.