Benzoin
Title: Benzoin
CAS Registry Number: 119-53-9
CAS Name: 2-Hydroxy-1,2-diphenylethanone
Additional Names: benzoylphenylcarbinol; a-hydroxy-a-phenylacetophenone; bitter-almond-oil camphor
Molecular Formula: C14H12O2
Molecular Weight: 212.24
Percent Composition: C 79.23%, H 5.70%, O 15.08%
Literature References: Prepd by treating an alcoholic soln of benzaldehyde with an alkali cyanide: Adams, Marvel, Org. Synth. vol. 1, p 33 (1921); coll. vol. I, 88; Arnold, Fuson, J. Am. Chem. Soc. 58, 1295 (1936); L. F. Fieser, Organic Experiments (D. C. Heath & Co., Boston, 1964) pp 211-214.
 
Derivative Type: dl-Form
Properties: Six-sided monoclinic prisms from alcohol, mp 137°. bp768 344°. bp12 194°. Reduces Fehling's soln. uv max (ethanol): 247 nm (e 14500); infrared in chloroform: 2.88; 5.93; 6.21; 6.28, 6.85 m. Soluble in 3335 parts water, more in hot water, in 5 parts pyridine; sol in acetone, in boiling alc; slightly in ether.
Melting point: mp 137°
Boiling point: bp768 344°; bp12 194°
Absorption maximum: uv max (ethanol): 247 nm (e 14500)
 
Derivative Type: Methyl ether
Molecular Formula: C15H14O2
Molecular Weight: 226.27
Percent Composition: C 79.62%, H 6.24%, O 14.14%
Properties: Needles, mp 49°.
Melting point: mp 49°
 
Derivative Type: Ethyl ether
Molecular Formula: C16H16O2
Molecular Weight: 240.30
Percent Composition: C 79.97%, H 6.71%, O 13.32%
Properties: Needles, mp 62°.
Melting point: mp 62°
 
Derivative Type: l-Form
Properties: Needles, mp 132°. [a]D12 -118° (c = 1.2 in acetone).
Melting point: mp 132°
Optical Rotation: [a]D12 -118° (c = 1.2 in acetone)
 
Derivative Type: d-Form
Properties: Needles, mp 132°. [a]D12 +120.5° (c = 1.2 in acetone).
Melting point: mp 132°
Optical Rotation: [a]D12 +120.5° (c = 1.2 in acetone)
 
NOTE: Not to be confused with Gum Benzoin.
Use: In organic syntheses.

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