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benfurodil hemisuccinate

Product Name
benfurodil hemisuccinate
CAS No.
3447-95-8
Chemical Name
benfurodil hemisuccinate
Synonyms
CB4091;Eudilat;Eucilat;4091C.B.;4091 C.B.;Benfurodil;Benzofurodil;benfurodil hemisuccinate;Butanedioic acid, 1-[1-[5-(2,5-dihydro-5-oxo-3-furanyl)-3-methyl-2-benzofuranyl]ethyl] ester;Butanedioic acid hydrogen 1-[1-[5-(2,5-dihydro-5-oxofuran-3-yl)-3-methyl-2-benzofuryl]ethyl] ester
CBNumber
CB9902659
Molecular Formula
C19H18O7
Formula Weight
358.34
MOL File
3447-95-8.mol
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benfurodil hemisuccinate Property

Melting point:
144°
Boiling point:
611.1±55.0 °C(Predicted)
Density 
1.364±0.06 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
Soluble in DMSO
pka
4.35±0.17(Predicted)
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Safety

Toxicity
LD50 in mice: 550 mg/kg orally (Schmitt)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

American Custom Chemicals Corporation
Product number
API0016055
Product name
BENFURODIL HEMISUCCINATE
Purity
95.00%
Packaging
5MG
Price
$500.25
Updated
2021/12/16
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benfurodil hemisuccinate Chemical Properties,Usage,Production

Originator

Eucilat,Clin Midy,France,1970

Manufacturing Process

(A) Preparation of 4-(3-Acetyl-4-Hydroxyphenyl)-2-Oxo-2,5-Dihydrofuran (1567 CB): A solution of 57 grams of 4-(4-methoxyphenyl)-2-oxo-2,5- dihydrofuran (0.3 mol) in 300 ml of methylene chloride is added slowly to 200 grams of anhydrous powdered aluminum chloride, while stirring and cooling in a bath of iced water. When this is completed, one removes the bath and leaves the reagents in contact for 10 minutes, and then introduces 72 grams of acetyl chloride at a speed sufficient to maintain refluxing of the solvent. One subsequently heats under reflux for 3 hours 30 minutes, decomposes by pouring on to crushed ice, filters off the crystalline product and washes it with water. 56 g, MP = 200°C. Yield: 80%. The product is recrystallized from acetic acid and then melts at 201°-202°C.
(B) Preparation of 4-[3-Acetyl-4-(2-Oxopropyloxy)Phenyl]-2-Oxo-2,5- Dihydrofuran: 5.45 grams (0.025 mol) of compound 1567 CB prepared according to (A) dissolved in 50 ml of dimethyl formamide is stirred at room temperature for 15 minutes with 5 grams of potassium carbonate and 1 gram of sodium iodide, and 5 grams of chloracetone are then added drop by drop. The temperature spontaneously rises a few degrees. The disappearance of the phenolic compound is checked by testing with an alcoholic solution of ferric chloride; this test should be negative at the end of the reaction (approximately 2 hours). One then dilutes with 10 volumes of water, filters the product which crystallizes out under these conditions and recrystallizes it from acetic acid. It has the form of yellow needles (4 grams yield: 63%). MP, = 155°-157°C.
(C) Preparation of 2-Acetyl-3-Methyl-5-(2-Oxo-2,5-Dihydro-4- Furyl)Benro[b]Furan (3556 CB): (1) A suspension of 2 grams of the compound prepared according to (B) in 20 ml of concentrated hydrochloric acid, is heated to about 50°C, just until it dissolves. There after it is heated for 2 minutes to 70°C, just until precipitation commences. The mixture is allowed to cool, diluted with water, filtered, the residue washed, dried, and sublimed at 200°C and 0.1 mm pressure. 1.4 grams of product (Yield: 70%) is obtained. MPc=218°-221°C. A second sublimation produces a chemically pure product. MPc= 221°-222°C. (2) Compound 1567 CB and chloracetone are caused to react as in (B), the mineral salts subsequently filtered, 12 ml of concentrated hydrochloric acid are added to the solution in dimethyl formamide without dilution with water, and the mixture heated for 40 minutes on a water bath. The product crystallizes in the warm mixture, the mixture is cooled to room temperature, filtered, the residue washed with water and crystallized from acetic acid. MPc= 222°C. Yield: 60% based on compound 1567 CB. (D) Preparation of 2-(1-Hydroxyethyl)-3-Methyl-5-(2-Oxo-2,5-Dihydro-4- Furyl)Benzo[b]-Furan (3574 CB): 13.2 grams of compound 3556 CB of which the preparation is described in (C) are treated successively with 66 ml of methylene chloride, 27 ml of methanol and, with stirring, 1.6 grams of sodium borohydride added in stages. The reaction takes 1 hour. The mixture is poured into water acidified with a sufficient amount of acetic acid, the solvents are stripped under vacuum, the crystalline product removed, washed with water, and recrystallized from ethyl acetate. Yield: 90%. MPk= 158°C.
(E) Preparation of 2-(1-Succinyloxyethyl)-3-Methyl-5-(2-Oxo--2,5-Dihydro-4-Furyl)Benzo[b]-Furan (4091, CB): 8.65 grams of compound 3574 CB in 43 ml of pyridine are warmed for 30 minutes, on a water bath, with succinic anhydride. At the end of this, the pyridine is stripped off in vacuo. The mixture is treated with dilute sulfuric acid and with ether, the crystalline product filtered off, washed with water and with ether, and recrystallized from ethyl acetate (9.35 grams). MPc=144°C (measured after drying at 90°C and 0.1 mm). Yield: 77%. The product yields an equimolecular compound with morpholine. MPc=136°C (from ethyl acetate).

Therapeutic Function

Coronary vasodilator; Cardiotonic

benfurodil hemisuccinate Preparation Products And Raw materials

Raw materials

Preparation Products

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benfurodil hemisuccinate Suppliers

Beijing Jin Ming Biotechnology Co., Ltd.
Tel
010-60605840 15801484223;
Email
psaitong@jm-bio.com
Country
China
ProdList
29774
Advantage
58
TargetMol Chemicals Inc.
Tel
4008200310
Email
marketing@tsbiochem.com
Country
China
ProdList
24644
Advantage
58

3447-95-8, benfurodil hemisuccinate Related Search:


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  • 4091C.B.
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  • Eucilat
  • Eudilat
  • CB4091
  • Benzofurodil
  • Butanedioic acid, 1-[1-[5-(2,5-dihydro-5-oxo-3-furanyl)-3-methyl-2-benzofuranyl]ethyl] ester
  • 3447-95-8