579-44-2

Basic information

• Product Name: DL-Benzoin
• Synonyms: 2-Hydroxy-1,2-Diphenyetanone;Benzoin,99%;α-hydroxyl-α-phenylaceto-phenone;2-hydroxy-1,2-diphenylethan-1-one;2-HYDROXY-1,2-DIPHENYLETHANONE;2-HYDROXY-1,2-DIPHENYETHANONE;1,2-DIPHENYL-2-HYDROXYETHANONE;ALPHA-HYDROXY-ALPHA-PHENYLACETOPHENONE
• CAS NO: 579-44-2
• Molecular Formula: C14H12O2
• Molecular Weight: 212.24
• EINECS: 204-331-3
• Product Categories: Nutraceuticals
• Mol File: 579-44-2.mol
• Article Data: 553

Chemical Properties

• Melting Point: 134-138 °C(lit.)
• Boiling Point: 194 °C12 mm Hg(lit.)
• Flash Point: 181°C
• Appearance: /
• Density: 1,31 g/cm3
• Vapor Pressure: 2.78E-05mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Water Solubility: 0.3g/L(25 oC)
• CAS DataBase Reference: DL-Benzoin(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Benzoin(579-44-2)
• EPA Substance Registry System: DL-Benzoin(579-44-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: DI1590000
• Hazardous Substances Data: 579-44-2(Hazardous Substances Data)

Usage

Description

Benzoin（known as benzoin gum and benzoin resin），is a spice made from the resin obtained from wounding the trunk of several benzoin trees. The benzoin tree is distributed in Sumatra, Java and the Malay Peninsula in Indonesia, and the trade name is Sumatra benzoin; the Siamese benzoin tree is distributed in Thailand, Vietnam, Cambodia, China's Yunnan and Guangxi, and the trade name is Siam (Thailand) benzoin.

Chemical Properties

White or light yellow prismatic crystal, insoluble in cold water, slightly soluble in hot water and ether, soluble in ethanol. It can reduce Fehling's solution and react with concentrated sulfuric acid to generate bibenzoyl.

Uses

DL-Benzoin has anti-oxidant and anti-aging properties in medicine, and has a diuretic effect when taken orally. It can also be used as an expectorant for chronic bronchitis. It is widely used as an additive in cosmetics such as perfume, soap, detergent, vanishing cream, etc.

Synthesis

The mixtrue of benzaldehyde and ethanol was adjusted to pH 7-8 with sodium hydroxide solution, refluxed with 3% sodium cyanide at 75-80℃ for 0.5h. The solution was cooled down to -10 °C and filtered to give DL-Benzoin, 90%.

InChI:InChI=1/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H

Upstream product

• 64357-12-6 benzoin phenylhydrazone ethyl ether 
• 1035-52-5 N,N-dicyclohexylbenzamide 
• 24854-35-1 benzoin tosylhydrazone 
• 947-19-3 1-hydroxycyclohexyl phenyl ketone 
• 71292-75-6 diethyl α-benzoyl-α-<(trimethylsilyl)oxy>benzylphosphonate 
• 441-38-3 benzoin oxime 
• 579-43-1 (1S,2R)-1,2-diphenylethane-1,2-diol 
• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 884-09-3 phenyl thiobenzoate 
• 7473-98-5 2-hydroxy-2-methylpropiophenone 
• 72223-17-7 1-trimethylsilyloxy-1,2-diphenylethylene 
• 136-60-7 benzoic acid, butyl ester 
• 952-92-1 1-Benzyl-1,4-dihydronicotinamide 
• 134-81-6 benzil 

Downstream Products

• 110247-84-2 (1RS,2RS)-1,2-diphenyl-1-o-tolyl-ethane-1,2-diol 
• 873381-94-3 7-bromo-1,2-diphenyl-naphtho[2,1-b]furan 
• 36715-46-5 2-(benzo[d][1,3]dioxol-5-yl)-2-hydroxy-2-phenylethanone 
• 110247-84-2 L-1cat_F.2cat_F-diphenyl-1r_F-o-tolyl-ethanediol-(1t_F.2t_F) 
• 100978-99-2 [4-(α'-oxo-bibenzyl-α-ylamino)-phenyl]-acetic acid 
• 114302-68-0 N-(2,3-diphenyl-indol-5-yl)-N-methyl-acetamide 
• 30935-14-9 (+/-)-1cat_F,2c_F-diphenyl-butanediol-(1r_F,2t_F) 
• 40103-57-9 2,5-Bis-(α-hydroxy-benzyl)-3,4-diphenyl-furan 
• 579-43-1 (1S,2R)-1,2-diphenylethane-1,2-diol 
• 50353-99-6 1,2-diphenyl-2-p-tolylethanone 
• 23181-79-5 2,3,5,6-tetraphenyl-1,4-dithia-2,5-cyclohexadiene 
• 106141-91-7 2-ethoxy-2,3,5,6-tetraphenyl-2,3-dihydro-[1,4]dithiin 
• 805252-19-1 2-Methoxy-2,3,5,6-tetraphenyl-2,3-dihydro-[1,4]dioxin 
• 863-81-0 trans-2,5-dimethoxy-2,3,5,6-tetraphenyl-1,4-dioxane 

Relevant articles and documents

Asymmetric Hydrogenation Cazalyzed by Bis(disubstitiuted glyoximato)cobalt(II)-Chiral Cocatalyst System. Effect of Structural Variation of Ligands and Hydrogen Pressure

The reaction rate was extremely enhanced by increasing the basicity of the axial ligand of and by increasing the hydrogen pressure without decreasing the enantioselectivity.Substituting one and two methyl groups of the dimethylglyoxime liga

Benzaldehyde lyase (BAL)-catalyzed enantioselective CC bond formation in deep-eutectic-solvents-buffer mixtures

Deep-eutectic-solvents (DES) have emerged in the last decades as promising bio-based and biodegradable neoteric solvents for biocatalysis, with examples covering different enzymes (mostly hydrolases) and whole-cells (baker's yeast). This paper explores fo

A holoenzyme model of thiamin dependent enzyme; asymmetrical acyloin condensation using a lipid catalyst in a bilayer membrane

Within a DPPC bilayer membrane, the lipid catalyst 1, having a thiazolium salt unit in the head group, exhibited catalytic activity and enantioselectivity in the acyloin condensation of benzaldehyde. The activity and enantioselectivity were strongly depen

Fungal deracemization of benzoin

An enzyme system of Rhizopus oryzae (ATCC 9363) catalyzes the inversion of the chirality of benzoin via a deracemization reaction and, depending on the pH of the medium, both enantiomers of benzoin are obtained in good yield and high ee starting from rac-

SmI2-(Chiral Auxiliary)-Induced Asymmetric Reduction

Benzyl was reduced to benzoin with 56.2 percent ee by a system of SmI2-THF-HMPA in the presence of quinidine.

Efficient and Selective Carboligation with Whole-Cell Biocatalysts in Pickering Emulsion

Pickering emulsions (PEs) are particle-stabilized multiphase systems with promising features for synthetic applications. Described here is a novel, simplified set-up employing catalytically active whole cells for simultaneous emulsion stabilization and sy

Purification and covalent immobilization of benzaldehyde lyase with heterofunctional chelate-epoxy modified magnetic nanoparticles and its carboligation reactivity

In this work, histidine-tagged recombinant benzaldehyde lyase from Pseudomonas fluorescens Biovar I (BAL, EC 4.1.2.38) was immobilized on the magnetically responsive epoxy-chelate magnetic support following a two-step mechanism; that is, the protein is ph

Direct Synthesis of Vinylene Carbonates from Aromatic Aldehydes**

Substituted vinylene carbonates were directly prepared from aromatic aldehydes following a one-pot Benzoin condensation/transcarbonation sequence under solvent-free conditions. The combination of a N-phenyl substituted triazolium salt NHC precursor and 4-dimethylaminopyridine (DMAP) was found essential to reach high yield and selectivity. The reaction scope was investigated with a range of aromatic aldehydes and the corresponding vinylene carbonates were obtained with 32–86 % isolated yields (14 examples).

Visible Light Enabled Formal Cross Silyl Benzoin Reaction as an Access to α-Hydroxyketones

In this work, a visible-light enabled coupling of acylsilanes with aldehydes to give a range of cross-benzoin type products α-hydroxyketones is described. The reaction could proceed at ambient temperature, with the irradiation of low energy visible light, and without addition of photosensitizer or any other additives. (Figure presented.).