Benzoin

Benzoin Basic information
Product Name:Benzoin
Synonyms:PHENYLBENZOYLCARBINOL;2-hydroxy-1,2-diphenyl-ethanon;2-hydroxy-2-phenyl-acetophenon;Acetophenone, 2-hydroxy-2-phenyl-;Bitter almond oil camphor;bitteralmondoilcamphor;bitter-almond-oilcamphor;Ethanone,2-hydroxy-1,2-diphenyl
CAS:119-53-9
MF:C14H12O2
MW:212.24
EINECS:204-331-3
Product Categories:Functional Materials;Photopolymerization Initiators;Benzil and Benzoin Compounds;Organic Photoinitiators;Polymerization Initiators;Analytical Reagents;Analytical/Chromatography;B;Highly Purified Reagents;Other Categories;Zone Refined Products;Heterocyclic Compounds;Pharmaceutical Intermediates;Intermediates;Bioactive Small Molecules;Building Blocks;C13 to C14;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Derivatization Reagents;Derivatization Reagents HPLC;Ketones;Materials Science;Organic Building Blocks;Polymer Science;UV-VIS
Mol File:119-53-9.mol
Benzoin Structure
Benzoin Chemical Properties
Melting point 134-138 °C(lit.)
Boiling point 194 °C12 mm Hg(lit.)
density 1.31
vapor pressure 1.3 hPa (136 °C)
FEMA 2132 | BENZOIN
Fp 181
storage temp. Store below +30°C.
solubility 0.3g/l
pka12.28±0.20(Predicted)
form Powder
color Off-white to very slightly yellow
Odoragreeable vanilla-like odor
Odor Typebalsamic
Water Solubility Soluble in chlorine. Slightly soluble in water, ethanol and ether.
Sensitive Moisture Sensitive
Merck 14,1093
JECFA Number836
BRN 391839
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKeyISAOCJYIOMOJEB-UHFFFAOYSA-N
LogP1.84-2.13 at 25℃
CAS DataBase Reference119-53-9(CAS DataBase Reference)
NIST Chemistry ReferenceEthanone, 2-hydroxy-1,2-diphenyl-(119-53-9)
EPA Substance Registry SystemBenzoin (119-53-9)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 24/25-36-26
WGK Germany 2
RTECS DI1590000
TSCA Yes
HS Code 29144090
Hazardous Substances Data119-53-9(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 10000 mg/kg LD50 dermal Rabbit 8870 mg/kg
MSDS Information
ProviderLanguage
2-Hydroxy-2-phenylacetophenone English
SigmaAldrich English
ACROS English
ALFA English
Benzoin Usage And Synthesis
Chemical Propertieslight yellow powder or crystals with a camphor-like odour
Chemical PropertiesBenzoin has a faint, sweet, balsamic odor.
OccurrenceBenzoin is a resin from the trees of genus Styrax.
UsesBenzoin is used as a flavor, antiseptic and photopolymerization catalyst. It is also used as a raw material in organic syntheses. It serves as a precursor to benzil, which is a photoinitiator. Further, it is used as degassing agent for powder coatings. In addition to this, it is used as an additive and in powder coating to remove the pinhole phenomenon.
Usesbenzoin is a fragrant essential oil with bactericidal, anti-irritation, and anti-itching properties. It is considered a good ingredient for reducing skin redness and is a preservative of fats. Although its primary constituent is benzoic acid, it also contains canillin and an oily aromatic liquid. This balsamic resin is extracted by cutting deeply into the trunks of trees that grow primarily in Indonesia and Thailand.
UsesDegassing for powder coatings
DefinitionChEBI: A ketone that consists of acetophenone bearing hydroxy and phenyl substituents at the alpha-position. The parent of the class of benzoins.
Definitionbenzoin: A colourless crystallinecompound, C6H5CHOHCOC6H5; m.p.137°C. It is a condensation product ofbenzenecarbaldehyde (benzaldehyde),made by the action of sodiumcyanide on benzenecarbaldehyde inalcoholic solution. It also occurs naturallyas the resin of a tropical tree. Itis both a secondary alcohol and a ketone,and gives reactions characteristicof both types of compound.
Taste threshold valuesTaste characteristics at 25 ppm: spicy, balsamic, resinous, fruity with an herbal nuance.
General DescriptionOff-white to yellow-white crystalline solid with an odor of camphor. Slightly acrid taste. When broken the fresh surfaces have a milky-white color.
Air & Water ReactionsInsoluble in water.
Reactivity Profile2-Hydroxy-2-phenylacetophenone is sensitive to heat and light. 2-Hydroxy-2-phenylacetophenone is incompatible with oxidizers. 2-Hydroxy-2-phenylacetophenone reduces Fehling's solution.
HazardHighly toxic.
Fire HazardFlash point data for 2-Hydroxy-2-phenylacetophenone are not available; however, 2-Hydroxy-2-phenylacetophenone is probably combustible.
Safety ProfileSlightly toxic by ingestion andskin contact. Mutation data reported. A flammable liquid.When heated to decomposition it emits acrid smoke andirritating fumes.
SynthesisIt may be prepared by condensation of benzaldehyde with an alkali cyanide and used in organic synthesis.
Purification MethodsCrystallise benzoin from CCl4, hot EtOH (8mL/g), or 50% acetic acid. Also crystallise it from high purity *benzene, then twice from high purity MeOH, to remove fluorescent impurities [Elliott & Radley Anal Chem 33 1623 1961]. It can be sublimed. [Beilstein 8 IV 1279.]
Benzoin Preparation Products And Raw materials
Preparation ProductsBenzil-->4,5-DIPHENYL-2-IMIDAZOLETHIOL-->2-(2-Chlorophenyl)-4,5-diphenylimidazole-->2,3-DIPHENYLQUINOXALINE-->BENZOIN ISOPROPYL ETHER-->"6,7-diphenyl-2-sulfanylidene-1H-pteridin-4-one-->Tetraphenylcyclopentadienone-->2,4,5-Triphenylimidazole-->Pyridine, 4-(4,5-diphenyl-1H-imidazol-2-yl)-
CHEMBRDG-BB 5102843 BENZOIN 2-ETHYLHEXYL ETHER BENZOIN N-PROPYL ETHER 1,3-Indandione, 2-(3-tert-butyl-2-hydroxyphenyl)-2-hydroxy- AURORA KA-4111 BENZOIN ISOBUTYL ETHER 1,2-bis(4-tert-butylphenyl)-2-hydroxyethanone 4,4'-DIMETHYLBENZOIN (R)-2-HYDROXY-2-PHENYLACETOPHENONE 4,4'-DIFLUOROBENZOIN 4μ-Dimethylamino-2-hydroxy-2-phenylacetophenone,P-DIMETHYLAMINO-A-HYDROXY-A-PHENYLACETOPHENONE,4-(DIMETHYLAMINO)BENZOIN 2-Hydroxy-2-(2-hydroxy-p-tolyl)-1,3-indandione DIETHOXYPHENYLACETOPHENONE AURORA KA-3322 AURORA KA-3185 BENZOIN ETHYL ETHER 4,4'-DICHLOROBENZOIN DESYL BENZOATE

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