3-HYDROXY-P-BUTYROPHENETIDINE Chemical Properties

Melting point:

160 °C

Boiling point:

364.56°C (rough estimate)

Density 

1.1223 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

pka

14.07±0.70(Predicted)

color 

White to Off-White

Merck 

14,1458

CAS DataBase Reference

1083-57-4

EPA Substance Registry System

Butanamide, N-(4-ethoxyphenyl)-3-hydroxy- (1083-57-4)

Safety Information

Hazard Codes 

T

Risk Statements 

45-46-20/21/22

Safety Statements 

53-22-36/37/39-45

WGK Germany 

3

RTECS 

EU0900000

HS Code 

2924.29.7790

Toxicity

LD50 in mice (mg/kg): 790 i.p., 2800 orally (Fujimura)

MSDS

• Language:English Provider:SigmaAldrich

3-HYDROXY-P-BUTYROPHENETIDINE Usage And Synthesis

Originator

Bucetin,ZYF Pharm Chemical

Uses

Bucetin is an antipyretic and analgesic drug that is chemically similar to phenacetin. The use of Bucetin has been withdrawn due to renal toxicity.

Uses

3-Hydroxy-p-butyrophenetidine is an antipyretic and analgesic drug that is chemically similar to phenacetin (P294580). The use of 3-Hydroxy-p-butyrophenetidine has been withdrawn due to renal toxicity.

Definition

ChEBI: Bucetin is an organic molecular entity.

Manufacturing Process

Bucetin may be prepared from acetoacetic acid p-phenetidide as follows: 5.5 parts of acetoacetic acid p-phenetidide, suspended in 600 parts by volume of methanol, are hydrogenated at 80°-85°C with a nickel catalyst supported on kiesel-guhr. When the theoretical quantity of hydrogen has been absorbed, the solution is cooled, then filtered, and the filtrate is concentrated. The solid residue is recrystallized from six times its weight of isopropanol. β- Hydroxybutyric acid p-phenetidide is obtained in an almost quantitative yield in the form of white crystals which melt at 160°C.
55 parts of acetoacetic acid p-phenetidide, suspended in 500 parts by volume of methanol, are hydrogenated with Raney nickel at 70°C. When the theoretical quantity of hydrogen has been absorbed, the solution is cooled, then filtered, and the filtrate is concentrated. The solid residue is recrystallized from six times its weight of isopropanol. 51 parts (93 % of the theoretical yield) of β-hydroxybutyric acid p-phenetidide are obtained in the form of white crystals, which are sparingly soluble in water and melt at 160°C.
A mixture of 5 g of aluminum amalgam, 5 g of acetoacetic acid p-phenetidide and 50 ml of ethanol are gently heated for 30 minutes. After filtering off the reducing agent with suction, water is added to the filtrate, and the latter is then acidified with 2 N hydrochloric acid. β-Hydroxybutyric acid p-phenetidide melting at 160°C crystallizes in almost quantitative yield in the form of white crystals.

brand name

Beelin;Bonanza;Haitmin;Hoe 15239;New isomidon;Ringl-s.

Therapeutic Function

Analgesic

World Health Organization (WHO)

Bucetin is an analogue of phenacetin. See WHO comment for phenacetin.

3-HYDROXY-P-BUTYROPHENETIDINE(1083-57-4)Related Product Information

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