| Identification | More | [Name]
ALPHA-BENZOIN OXIME | [CAS]
441-38-3 | [Synonyms]
2-HYDROXY-1,2-DIPHENYLETHANONE OXIME, ALPHA-FORM
A-BENZOIN OXIME
ALPHA-BENZOIN OXIME
BENZOIN ALPHA-MONOXIME
BENZOIN-ALPHA-OXIME
BENZOIN ANTI-OXIME
BENZOIN A-OXIME
BENZOIN OXIME
CUPRON
CUPRONE
TIMTEC-BB SBB000680
2-hydroxy-1,2-diphenyl-ethanonoxime
alpha-benzoin
benzoinoxim
Cupron,2-Hydroxy-2-phenylacetophenoneoxime
Ethanone,2-hydroxy-1,2-diphenyl-,oxime
usaffa-5
2-Hydroxy-2-phenylacetophenone oxime
A-BenzoinOximeGr
2-BenzoineOxime | [EINECS(EC#)]
207-127-2 | [Molecular Formula]
C14H13NO2 | [MDL Number]
MFCD00004501 | [Molecular Weight]
227.26 | [MOL File]
441-38-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
153-155 °C(lit.)
| [Boiling point ]
368.97°C (rough estimate) | [density ]
1.13 | [vapor density ]
7.9 (vs air)
| [refractive index ]
1.5780 (estimate) | [storage temp. ]
Store below +30°C. | [solubility ]
ethanol: 0.1 g/mL, clear
| [form ]
Crystalline Powder | [pka]
10.92±0.40(Predicted) | [color ]
White to almost white | [Odor]
Odorless | [Stability:]
Stable, but may be light sensitive. Incompatible with strong oxidizing agents. | [Optical Rotation]
0.2°(C=0.01g/mI, CHCL3, 20°C, 589nm) | [Water Solubility ]
Slightly soluble in water | [Sensitive ]
Light Sensitive | [Merck ]
14,1094 | [BRN ]
2051941 | [CAS DataBase Reference]
441-38-3(CAS DataBase Reference) | [EPA Substance Registry System]
Ethanone, 2-hydroxy-1,2-diphenyl-, oxime (441-38-3) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
DI1750000
| [F ]
8 | [TSCA ]
Yes | [HS Code ]
29280000 | [Toxicity]
LD orl-rat: >500 mg/kg NCNSA6 5,9,53 |
| Hazard Information | Back Directory | [Chemical Properties]
white crystalline powder | [Safety Profile]
Poison by intraperitoneal route.Mildly toxic by ingestion. An eye irritant. When heated todecomposition it emits toxic fumes of NOx. | [Synthesis]
General procedure for the synthesis of α-benzoin oxime (copper reagent) from benzene diphosgene: benzene diphosgene (21.2 g, 0.1 mol) was dissolved with NH4OH-HCl (21 g, 0.3 mol) in 300 mL of ethanol. 41.5 mL of triethylamine was added slowly and dropwise to the reaction system, warmed to 75 °C and refluxed for 24 hours. The progress of the reaction was monitored by thin layer chromatography (TLC), and after the disappearance of the raw material point, 300 mL of water was added and extracted three times with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate and filtered, and the solvent was removed by rotary evaporation to give about 18 g of the benzene diphenoxime compound in 79% yield.
2.4 g of 10% Pd/C catalyst with a small amount of 3% hydrochloric acid-ethanol solution (10 mL HCl-EtOH) was added to the reaction flask and activated by passing hydrogen gas. Benzene coupling oxime (12.0 g, 52.5 mmol) obtained in the previous step was dissolved in 80 mL of ethanol and slowly added dropwise to the reaction flask and reacted overnight, the system was observed to become viscous. After adding 300 mL of water and filtering, the pH of the filtrate was adjusted to 8 with concentrated ammonia and 9.2 g of 1,2-diphenylamino alcohol solid was precipitated in 82% yield. | [Purification Methods]
Crystallise the oxime from diethyl ether. It is used for the spectroscopic determination of Cu2+, Pd2+, Pt4+, Rh3+ and V5+ [Singh et al. Talanta 26 425 1979, Beilstein 8 IV 1282.] | [References]
[1] Patent: CN104945345, 2017, B. Location in patent: Paragraph 0105; 0107-0109
[2] Journal of the Chemical Society, 1909, vol. 95, p. 1597
[3] Heterocycles, 2000, vol. 52, # 3, p. 1359 - 1370
[4] Oriental Journal of Chemistry, 2014, vol. 30, # 3, p. 1343 - 1348 |
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