ALPHA-BENZOIN OXIME Chemical Properties

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

pka

10.92±0.40(Predicted)

form 

Crystalline Powder

color 

White to almost white

Odor

Odorless

optical activity

0.2°(C=0.01g/mI, CHCL3, 20°C, 589nm)

Water Solubility 

Slightly soluble in water

Sensitive 

Light Sensitive

Merck 

14,1094

BRN 

2051941

Stability:

Stable, but may be light sensitive. Incompatible with strong oxidizing agents.

CAS DataBase Reference

441-38-3(CAS DataBase Reference)

EPA Substance Registry System

Ethanone, 2-hydroxy-1,2-diphenyl-, oxime (441-38-3)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

DI1750000

F 

8

TSCA 

Yes

HS Code 

29280000

Toxicity

LD orl-rat: >500 mg/kg NCNSA6 5,9,53

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

ALPHA-BENZOIN OXIME Usage And Synthesis

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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