59694-08-5

Basic information

• Product Name: 1,3-Butanediol, 1-benzoate
• CAS NO: 59694-08-5
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• Mol File: 59694-08-5.mol

Chemical Properties

• CAS DataBase Reference: 1,3-Butanediol, 1-benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Butanediol, 1-benzoate(59694-08-5)
• EPA Substance Registry System: 1,3-Butanediol, 1-benzoate(59694-08-5)

Safety Data

• Hazardous Substances Data: 59694-08-5(Hazardous Substances Data)

Upstream product

• 18826-95-4 1.3-butanediol 
• 3277-27-8 diethyl benzoylphosphonate 
• 22950-57-8 diisopropyl benzoylphosphonate 
• 65-85-0 benzoic acid 
• 10364-94-0 1-benzoylimidazole 
• 339204-85-2 Benzoic acid (R)-3-(tetrahydro-pyran-2-yloxy)-butyl ester 
• 6290-03-5 (R)-butane-1,3-diol 
• 98-88-4 benzoyl chloride 
• 644-32-6 dibenzoyl disulfide 
• 93-97-0 benzoic acid anhydride 
• 90238-20-3 N,N-diethyl-α,α-difluorobenzylamine 
• 774-44-7 4-methyl-2-phenyl-[1,3]dioxane 
• 774-44-7 (±)-(2S,4R)-2,4-dimethyl-1,3-dioxane 
• 54769-36-7 N-benzoyloxybenzotriazole 

Downstream Products

• 73842-83-8 Benzoesaeure-<3-(t-butyl-dimethylsilyloxy)-butyl>ester 
• 2867-65-4 butane-1,3-diyl dibenzoate 
• 1379680-90-6 (R)-3-(tert-butyldimethylsilyloxy)butyl benzoate 
• 135081-58-2 C₁₇H₁₈O₄⁽¹⁸⁾OS 
• 135081-59-3 C₁₇H₁₈O₄⁽¹⁸⁾OS 
• 129991-11-3 (S)-(+)-3-<(N-methyl-N-trifluoromethanesulfonyl)amino>-1-butanol benzoate 
• 2867-66-5 1-benzoyloxy-3-bromobutane 

Relevant articles and documents

Benzoxaborole Catalyst for Site-Selective Modification of Polyols

The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.

DBN-Catalyzed Regioselective Acylation of Carbohydrates and Diols in Ethyl Acetate

The 1,5-diazabicyclo[4.3.0]non-5-ene (DBN)-catalyzed regioselective acylation of carbohydrates and diols in ethyl acetate has been developed. The hydroxyl groups can be selectively acylated by the corresponding anhydride in EtOAc in the presence of a catalytic amount (as low as 0.1 equiv.) of DBN at room temperature to 40 °C. This method avoids metal catalysts and toxic solvents, which makes it comparatively green and mild, and it uses less organic base compared with other selective acylation methods. Mechanism studies indicated that DBN could catalyze the selective acylation of hydroxyl moieties through a dual H-bonding interaction.

An inexpensive catalyst, Fe(acac)3, for regio/site-selective acylation of diols and carbohydrates containing a 1,2-: Cis -diol

This work describes the [Fe(acac)3] (acac = acetylacetonate)-catalyzed, regio/site-selective acylation of 1,2- and 1,3-diols and glycosides containing a cis-vicinal diol. The iron(iii) catalysts initially formed cyclic dioxolane-type intermediates with substrates between the iron(iii) species and vicinal diols, and the efficient and selective acylation of one hydroxyl group was subsequently achieved by adding acylation reagents in the presence of diisopropylethylamine (DIPEA) under mild conditions. This reaction generally produced high selectivities and highly isolated yields with the same protection pattern as that achieved with dibutyl tinoxide-mediated schemes.

A microwave-assisted highly practical chemoselective esterification and amidation of carboxylic acids

The ubiquitousness of esters and amide functionalities makes their coupling reaction one of the most sought-after organic transformations. Herein, we have described an efficient microwave-assisted synthesis of esters and amides. Soluble triphenylphosphine, in conjugation with molecular iodine, gave the desired products without the requirement for a base/catalyst. In addition, a solid-phase synthetic route is incorporated for the said conversion, which has added advantages over solution-phase pathways, such as low moisture sensitivity, easy handling, isolation of the product by simple filtration, and reusability. In short, our method is simple, mild, green, and highly chemoselective in nature.

Diacyl Disulfide: A Reagent for Chemoselective Acylation of Phenols Enabled by 4-(N,N-Dimethylamino)pyridine Catalysis

A general and excellent acylation reagent, diacyl disulfide, was uncovered for efficient ester formation enabled by DMAP (4-(N,N-dimethylamino)pyridine) catalysis. This protocol offered a promising synthetic platform on site-selective acylation of phenolic and primary aliphatic hydroxyl groups, which greatly expanded the realm of protecting group chemistry. The importance of the reagent was also reflected by its excellent moisture tolerance, high efficiency, and potential in synthetic chemistry and biologically meaningful natural product modification.

Regioselective benzoylation of diols and carbohydrates by catalytic amounts of organobase

A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DB

A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols

An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.

Simple and practical method for selective acylation of primary hydroxy group catalyzed by N-methyl-2-phenylimidazole (Ph-NMI) or 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT)

N-Methyl-2-phenylimidazole (Ph-NMI) and 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT) catalyzed selective acylation of primary alcohols using acid anhydrides. The Ph-NMI- or Ph-IBT-catalyzed reaction using (PhCO)2O as an acylating agent could particularly acylate the primary hydroxy group of 1,n-diols (n ≥ 3) with a high, synthetically useful selectivity.

Stereoselective synthesis of ophiocerin B

A stereoselective total synthesis of ophiocerin B is reported by asymmetric synthesis, starting from L-malic acid. Of the three stereogenic centers, the vic-diols C-3, C-4 were obtained by Sharpless asymmetric dihydroxylation. ARKAT-USA, Inc.

Total synthesis of macrosphelide M from diacetone glucose

The total synthesis of macrosphelide M is described. The key steps include the preparation of the acid and alcohol fragments from diacetone glucose and (S)-malic acid, respectively, followed by Yamaguchi esterification and macrocyclization of the tris-olefin by ring-closing metathesis. Finally, one-pot deprotection of the PMB and TBS groups with TiCl4 results in the target. The C-3/C-4 stereocenters of diacetone glucose are used for the introduction of four stereocenters, whereas the fifth stereocenter is realized from (S)-malic acid. The total synthesis of macrosphelide M was achieved from diacetone glucose and (S)-malic acid. The key steps include Yamaguchi esterification and macrocyclization of the tris-olefin by the second-generation Grubbs catalyst.