10335-95-2

Basic information

• Product Name: 1,2-Ethanediol, 1-phenyl-, 2-benzoate
• CAS NO: 10335-95-2
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• Mol File: 10335-95-2.mol
• Article Data: 37

Chemical Properties

• CAS DataBase Reference: 1,2-Ethanediol, 1-phenyl-, 2-benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanediol, 1-phenyl-, 2-benzoate(10335-95-2)
• EPA Substance Registry System: 1,2-Ethanediol, 1-phenyl-, 2-benzoate(10335-95-2)

Safety Data

• Hazardous Substances Data: 10335-95-2(Hazardous Substances Data)

Upstream product

• 96-09-3 styrene oxide 
• 93-56-1 phenylethane 1,2-diol 
• 3277-27-8 diethyl benzoylphosphonate 
• 93-97-0 benzoic acid anhydride 
• 10534-59-5 tetrabutylammonium acetate 
• 98-88-4 benzoyl chloride 
• 61040-98-0 3,6-diphenyl-1,2,4-trioxane 
• 65-85-0 benzoic acid 
• 128733-27-7 Benzoic acid 1-phenyl-2-trimethylsilanyloxy-ethyl ester 
• 53574-78-0 2-hydroxy-1-phenylethyl benzoate 
• 100-42-5 styrene 
• 10364-94-0 1-benzoylimidazole 
• 54826-37-8 2-iodo-1-phenylethyl benzoate 
• 33868-50-7 phenacyl benzoate 

Downstream Products

• 93-56-1 phenylethane 1,2-diol 
• 155831-70-2 5-ethyl-1-<<1'-phenyl-2'-(t-butyldimethylsilyloxy)ethoxy>methyl>-6-(phenylseleno)uracil 
• 155831-66-6 5-ethyl-1-<<1'-phenyl-2'(t-butyldimethylsilyloxy)ethoxy>methyl>-6-(phenylthio)uracil 
• 155831-69-9 1-<<1'-phenyl-2'-(t-butyldimethylsilyloxy)ethoxy>methyl>-6-(phenylseleno)thymine 
• 155831-65-5 1-<<1'-phenyl-2'(t-butyldimethylsilyloxy)ethoxy>methyl>-6-(phenylthio)thymine 
• 155831-68-8 1-<<1'-phenyl-2'-(t-butyldimethylsilyloxy)ethoxy>methyl>-6-(phenylseleno)uracil 
• 155831-64-4 1-<<1'-phenyl-2'(t-butyldimethylsilyloxy)ethoxy>methyl>-6-(phenylthio)uracil 
• 155831-58-6 5-ethyl-1-<<(1'-phenyl-2'-benzyloxy)ethoxy>methyl>uracil 
• 155831-57-5 1-<<(1'-phenyl-2'-benzyloxy)ethoxy>methyl>thymine 
• 155831-63-3 5-ethyl-1-<<1'-phenyl-2'-(t-butyldimethylsilyloxy)ethoxy>methyl>uracil 
• 155831-62-2 1-<<1'-phenyl-2'-(t-butyldimethylsilyloxy)ethoxy>methyl>thymine 
• 155831-56-4 1-<<(1'-phenyl-2'-benzyloxy)ethoxy>methyl>uracil 
• 155831-61-1 1-<<1'-phenyl-2'-(t-butyldimethylsilyloxy)ethoxy>methyl>uracil 
• 155831-60-0 5-ethyl-1-<<(1'-phenyl-2'-hydroxy)ethoxy>methyl>uracil 

Relevant articles and documents

DIALKYL ACYLPHOSPHONATES: A NEW ACYLATING AGENT OF ALCOHOLS

Diethyl benzoylphosphonate (1) underwent facile benzoylation of alcohols in the presence of DBU.Reactions of diols containing primary and secondary hydroxyl groups with 1 gave predominantly monobenzoates in which primary hydroxyl groups were highly selectively benzoylated.Related acylations were also described.

Selective Benzoylation of Diols with 1-(Benzoyloxy)benzotriazole

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An Efficient Method for the Chemoselective Preparation of Benzoylated 1,2-Diols from Epoxides

A very efficient and highly regioselective ring-opening reaction of epoxides with benzoic acid and its derivatives in the presence of cat. amount of tetrabutylammonium bromide (TBAB) in anhydrous acetonitrile has been developed. This effective method is useful for the preparation of selectively protected diols as precursor for many organic syntheses such as those of acyclic nucleosides and other synthetic purposes. The advantages of this method are efficiency, selectivity, low cost, and the applicability in large-scale synthesis of β-benzoyloxyalkanols.

Direct esterification of carboxylic acids with alcohols catalyzed by Iron(III) acetylacetonate complex

Direct condensation of carboxylic acids and alcohols with electronic, steric, and functional group variations was carried out using the environmentally benign, moisture-stable, inexpensive, and recoverable iron(III) acetylacetonate [Fe(acac)3] as catalyst (5 mol%). This iron salt efficiently catalyzed the esterification of several primary and secondary alcohols in refluxing xylene, without the need for a dehydration reagent. The chemoselectivity of the proposed protocol was demonstrated by the selective esterification of primary alcohol functionality in racemic 1-phenylethane-1,2- diol with benzoic acid. The esterification was also applicable to unmasked α-hydroxyacid, guasiaromatic, heterocyclic, and N-protected amino acids. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study

A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism studies indicated that FeCl3 initially formed [Fe(btfa)3] (btfa = benzoyl trifluoroacetonate) with twice the amount of Hbtfa under basic conditions in the solvent acetonitrile at room temperature. Then, Fe(btfa)3 and two hydroxyl groups of the substrates formed a five- or six-membered ring intermediate in the presence of the base. The subsequent reaction between the cyclic intermediate and a sulfonylation reagent led to the selective sulfonylation of the substrate. All key intermediates were captured in the high-resolution mass spectrometry assay, therefore demonstrating this mechanism for the first time.

Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope

This work reports stannous chloride (SnCl2)-catalyzed regio-/site-selective acylation with unusually broad substrate scope. In addition to 1,2- and 1,3-diols and glycosides containing cis-vicinal diol, the substrate scope also includes glycosides without cis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84-97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst for regio-/site-selective acylation compared with any previously reported reagents. This journal is