DL-Benzoin

Base Information

• Chemical Name: DL-Benzoin
• CAS No.: 579-44-2
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.248
• Hs Code.: 2914399090
• Mol file: 579-44-2.mol

Synonyms:579-44-2

Chemical Property of DL-Benzoin

Chemical Property:

• Appearance/Colour: Off-white crystals, with a light camphor odor.
• Vapor Pressure: 2.78E-05mmHg at 25°C
• Melting Point: 134-138oC(lit.)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 343oC at 760 mmHg
• Flash Point: 154.8oC
• PSA: 37.30000
• Density: 1.179 g/cm3
• LogP: 2.60290
• Water Solubility.: 0.3g/L(25 oC)

Purity/Quality:

99.5% ^*data from raw suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• 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.
• 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.

Technology Process of DL-Benzoin

There total 705 articles about DL-Benzoin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

cis-stilben (645-49-8) → (1S,2R)-1,2-diphenylethane-1,2-diol (579-43-1) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzaldehyde (100-52-7)

Guidance literature:

With 4-methylmorpholine N-oxide; polyaniline-supported Os; In water; acetone; acetonitrile; at 20 ℃; for 3h;

DOI:10.1002/adsc.200606077

Reference yield: 75.0%

α-(2-cyanoethyl)benzoin (174869-02-4) → 4-oxo-4-phenylbutanenitrile (5343-98-6) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzaldehyde (100-52-7)

Guidance literature:

With tetra-n-butylammonium cyanide; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1248/cpb.46.6

Reference yield: 60.0%

benzyl alcohol (100-51-6,185532-71-2) → 1,2-diphenyl-1,2-ethanediol (492-70-6,655-48-1,2325-10-2,38270-73-4,52340-78-0,579-43-1) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzaldehyde (100-52-7) + benzil (134-81-6)

Guidance literature:

With air; 2,2'-thiobis(2,4-di-tert-butylphenol); triethylamine; copper(l) chloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/(SICI)1521-3773(19980904)37:16<2217::AID-ANIE2217>3.0.CO;2-D

upstream raw materials:

ortho-tolylmagnesium bromide

(R)-benzoin

piperonal

ethanol

Downstream raw materials:

2,2'-Dinitro-4,4'-azoxytoluene

(1RS,2SR)-(+/-)-1,2-diphenyl-1,2-propandiol

(1RS,2RS)-(+/-)-1,2-diphenyl-1,2-propandiol

1,2-diphenylpropan-1,2-diol

Refernces

• 1、 Shen, Jun,Ikai, Tomoyuki,Shen, Xiande,Okamoto, Yoshio. "Synthesis and immobilization of amylose derivatives bearing a 4-terf-butylbenzoate group at the 2-position and 3,5-dichlorophenylcarbamate/3- (triethoxysilyl)propylcarbamate groups at 3- And 6-positions as chiral packing material for HPLC". . p. 442 - 444. Retrieved 2010.
• 2、 Oda, Shinobu,Isshiki, Kunio. "Asymmetric reduction of benzil to (S)-benzoin with Penicillium claviforme IAM 7294 in a liquid-liquid interface bioreactor (L-L IBR)". . p. 1364 - 1367. Retrieved 2008.
• 3、 Enders, Dieter,Breuer, Klaus,Teles, J. Henrique. "105. A novel asymmetric benzoin reaction catalyzed by a chiral triazolium salt: Preliminary communication". . p. 1217 - 1221. Retrieved 1996.
• 4、 Hoyos, Pilar,Quezada, M. Alberto,Sinisterra, Jose Vicente,Alcantara, Andres R.. "Optimised dynamic kinetic resolution of benzoin by a chemoenzymatic approach in 2-MeTHF". . p. 20 - 24. Retrieved 2011.
• 5、 Ohgo, Yoshiaki,Takeuchi, Seiji,Natori, Yukikazu,Yoshimura, Juji. "Asymmetric Reactions. X. Asymmetric Hydrogenation Catalyzed by Bis(dimethylglyoximato)cobalt(II)-Chiral Cocatalyst (Amino Alcohol) System". . p. 2124 - 2135. Retrieved 1981.
• 6、 Adam, Waldemar,Saha-Moeller, Chantu R.,Zhao, Cong-Gui. "Enantioselective oxidation of vic-diols to optically active α-hydroxy ketones by a fructose-derived dioxirane". . p. 4117 - 4122. Retrieved 1998.
• 7、 Keul, Felix,Mardyukov, Artur,Schreiner, Peter R.. "Generation and reactivity of phenylhydroxycarbenes in solution". supporting information. . Retrieved 2022/01/19.
• 8、 Chen, Yujie,Dai, Chenyang,Huang, Zhibin,Jiang, Yaqiqi,Shu, Sai,Yang, Shan,Zhao, Yingsheng. "Ruthenium(II)-Catalyzed Cross-Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2-Phenylacetophenones". . p. 2955 - 2961. Retrieved 2021/07/22.