19224-26-1

Basic information

• Product Name: 1,2-PROPANEDIOL DIBENZOATE
• Synonyms: 1,2-PROPANEDIOL DIBENZOATE;propane-1,2-diyl dibenzoate;Propylene glycol dibenzoate;1,2-PROPANEDIOL DIBENZOATE 96%;Bis(benzoic acid)propane-1,2-diyl ester;1,2-Propanediol,1,2-dibenzoate
• CAS NO: 19224-26-1
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31
• EINECS: 242-894-7
• Product Categories: C12 to C63;Carbonyl Compounds;Esters
• Mol File: 19224-26-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: −3 °C(lit.)
• Boiling Point: 232 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.16 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.8E-06mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Water Solubility: 7.7mg/L at 20℃
• CAS DataBase Reference: 1,2-PROPANEDIOL DIBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-PROPANEDIOL DIBENZOATE(19224-26-1)
• EPA Substance Registry System: 1,2-PROPANEDIOL DIBENZOATE(19224-26-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19224-26-1(Hazardous Substances Data)

Usage

Chemical Properties

Propylene glycol dibenzoate has virtually no odor.

InChI:InChI=1/C17H16O4/c1-13(21-17(19)15-10-6-3-7-11-15)12-20-16(18)14-8-4-2-5-9-14/h2-11,13H,12H2,1H3

Synthetic route

propylene glycol (57-55-6) + benzoic acid (65-85-0) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With Sb2(OCH2CH2O)3 at 180℃; for 30h;	94%
sulfonic acid at 120 - 225℃;
at 120 - 225℃;

benzoyl cyanide (613-90-1) + propylene glycol (57-55-6) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With dmap; 1-ethylene glycol monomethyl ether-3-methylimidazolium methanesulfonate at 25 - 35℃;	92%

propylene glycol (57-55-6) + benzoic acid anhydride (93-97-0) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; for 8h;	85%

propylene glycol (57-55-6) + diethyl benzoylphosphonate (3277-27-8) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.333333h; Product distribution; Ambient temperature;	A 17 % Spectr. B 83 % Spectr. C 8%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.333333h; Ambient temperature;	A 17 % Spectr. B 83 % Spectr. C 8%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.333333h; Ambient temperature; Title compound not separated from byproducts;	A 17 % Spectr. B 83 % Spectr. C 8%

1,2-Dibromopropane (78-75-1) + silver benzoate (532-31-0) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield

silver benzoate (532-31-0) → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With iodine; benzene anschliessend Behandeln mit Propen;

propylene glycol (57-55-6) + N-benzoyloxybenzotriazole (54769-36-7) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With triethylamine In dichloromethane for 24h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

propylene glycol (57-55-6) + benzoyl chloride (98-88-4) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
multistep reaction: monoacylation of diols with reversed chemoselectivity; other diols; quenching with chlorosilanes;
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

propylene glycol (57-55-6) + benzoic acid (65-85-0) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 1h; Product distribution; Mechanism; other asymmetric 1,2-diol;

propylene glycol (57-55-6) + dibenzoyl peroxide (94-36-0) → 1-hydroxyprop-2-yl benzoate (51591-52-7) + 2-hydroxypropyl benzoate (37086-84-3) + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With triphenylphosphine In dichloromethane for 1h; Product distribution; Mechanism; Ambient temperature; other diols, other benzoylating agent;

benzoyl chloride (98-88-4) + (+-)-propylene glycol → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With pyridine

benzoyl chloride (98-88-4) + lead sulfide → 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / Et3N / CH2Cl2 / 0.33 h 2: Et3N / CH2Cl2 / 24 h / Ambient temperature View Scheme

benzoyl fluoride (455-32-3) + C21H26O2Si → 2-((1,3-diphenylprop-2-yn-1-yl)oxy)propyl benzoate + 1,2-bis-benzoyloxy-propane (19224-26-1)

Conditions	Yield
With dmap In chloroform-d1 at 20℃; Inert atmosphere; Overall yield = 30.6 mg;

1,2-bis-benzoyloxy-propane (19224-26-1) → [(1R)-2-hydroxy-1-methyl-ethyl]benzoate (113566-74-8) + (S)-1-hydroxypropan-2-yl benzoate (113566-73-7)

Conditions	Yield
With octanol; Pseudomonas sp. lipase PS*celite In di-isopropyl ether at 20℃; Product distribution; Further Variations:; Reagents;

Upstream product

• 78-75-1 1,2-Dibromopropane 
• 532-31-0 silver benzoate 
• 57-55-6 propylene glycol 
• 3277-27-8 diethyl benzoylphosphonate 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 94-36-0 dibenzoyl peroxide 
• 613-90-1 benzoyl cyanide 
• 455-32-3 benzoyl fluoride 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 113566-74-8 [(1R)-2-hydroxy-1-methyl-ethyl]benzoate 
• 113566-73-7 (S)-1-hydroxypropan-2-yl benzoate 

Relevant articles and documents

Mechanistic Implications of 1,3,2λ5-Dioxaphospholanes in the Mitsunobu Reaction

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Catalytic Alkynylation of Cyclic Acetals and Ketals Enabled by Synergistic Gold(I)/Trimethylsilyl Catalysis

A completely regioselective and challenging gold(I)-catalyzed ring-opening of cyclic 1,3-dioxolanes and dioxanes by trimethylsilyl alkynes to set diol-derived propargyl trimethylsilyl bis-ethers is reported. This unprecedented and not trivial transformation does not operate with the catalytic methodologies recently reported for catalytic alkynylation of acyclic acetals/ketals, and is uniquely enabled by the application of a recently introduced synergistic gold(I)-silicon catalysis concept capable of producing simultaneously catalytic amounts of two key players, a silicon-based Lewis superacid and a nucleophilic gold acetylide.

Personal care products containing high refractive index esters and methods of preparing the same

The invention includes personal care compositions and methods of preparing these personal care compositions that include incorporation of a polyol polyester that is the reaction product of an aliphatic polyol that does not contain an ether group, and benzoic acid, wherein the resultant polyol polyester has a refractive index at 25° C. of greater than about 1.5. The aliphatic polyol may have two to three carbon atoms. Alternatively, the invention includes personal care compositions and methods of preparing personal care compositions including incorporating a polyol polyester into a personal care formulation. The polyol polyester is represented by formula (I): wherein R is an aliphatic alkyl group that does not contain an ether group and has a refractive index of greater than about 1.5 at 25° C. Also described are methods of preparing personal care compositions comprising a first phase and a second phase, wherein the second phase contains any of the polyol polyesters described above.