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Chloropropamide

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Name

Chloropropamide

EINECS 202-314-5
CAS No. 94-20-2 Density 1.334 g/cm3
PSA 83.65000 LogP 3.60050
Solubility Insoluble in water Melting Point 128 °C
Formula C10H13ClN2O3S Boiling Point 302°C (rough estimate)
Molecular Weight 276.76 Flash Point
Transport Information Appearance white crystalline powder
Safety 22-36 Risk Codes 20/21/22-40
Molecular Structure Molecular Structure of 94-20-2 (1-(4-Chlorophenyl)sulfonyl-3-propylurea) Hazard Symbols HarmfulXn
Synonyms

Urea,1-[(p-chlorophenyl)sulfonyl]-3-propyl- (8CI);1-(p-Chlorobenzenesulfonyl)-3-propylurea;1-Propyl-3-(p-chlorobenzenesulfonyl)urea;Adiaben;Asucrol;Catanil;Chloronase;Diabaril;Diabechlor;Diabenal;Diabenese;Diabeneza;Diabet-Pages;Diabetoral;Diabinese;Glisema;Meldian;Melitase;Millinese;N-(p-Chlorobenzenesulfonyl)-N'-propylurea;NSC 44634;NSC 626720;P 607;Stabinol;U 9818;

 

Chloropropamide Synthetic route

110-78-1

Propyl isocyanate

98-64-6

4-Chlorobenzenesulfonamide

94-20-2

chlorpropamide

Conditions
ConditionsYield
With copper(l) chloride In nitromethane at 20℃; for 2h; Milling;92%
With boron trifluoride diethyl etherate In diethyl ether Ambient temperature;67%
98-64-6

4-Chlorobenzenesulfonamide

14549-38-3

phenyl N-(n-propyl)carbamate

94-20-2

chlorpropamide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Reflux; Green chemistry;85%
98-64-6

4-Chlorobenzenesulfonamide

39078-44-9

S-Methyl N-propyl(thiocarbamate)

94-20-2

chlorpropamide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 4h; Substitution;75%

2-chlorobenzene sulphonamide

6948-23-8

(2-hydroxy-ethyl)-carbamic acid propyl ester

94-20-2

chlorpropamide

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide46%
96-49-1

[1,3]-dioxolan-2-one

98-64-6

4-Chlorobenzenesulfonamide

94-20-2

chlorpropamide

Conditions
ConditionsYield
With propylamine In water; N,N-dimethyl-formamide
94-20-2

chlorpropamide

C10H12(2)HClN2O3S

Conditions
ConditionsYield
With Kerr's catalyst; deuterium In chlorobenzene at 120℃; for 1h; Reagent/catalyst; Temperature;96%
94-20-2

chlorpropamide

407-25-0

trifluoroacetic anhydride

98922-57-7

4-Chloro-N-(2,2,2-trifluoro-acetyl)-benzenesulfonamide

Conditions
ConditionsYield
In chloroform for 1.5h;94%
94-20-2

chlorpropamide

108-24-7

acetic anhydride

A

5331-48-6

n-propylacetamide

B

55379-05-0

N-((4-chlorophenyl)sulfonyl)acetamide

Conditions
ConditionsYield
With pyridine for 0.0833333h;A 27%
B 83%
94-20-2

chlorpropamide

N,N'-Bis-(4-chlorphenylsulfonyl)-N''-n-propylguanidin

Conditions
ConditionsYield
With pyridine; p-toluenesulfonyl chloride Heating;81%
94-20-2

chlorpropamide

1600-27-7

mercury(II) diacetate

mercury bis{N-((propylamino)carbonyl)-4-chlorobenzenesulfonamide}

Conditions
ConditionsYield
With KOH In ethanol byproducts: CH3COO(1-), H2O; addn. of suspension of Hg(CH3CO2)2 in ethanol to soln. of ligand and KOH, mixt.stirred for 20 min; pptn. on cooling to -10°C, filtered, washed (EtOH, Et2O), dried in vac., elem. anal.;70%
94-20-2

chlorpropamide

543-90-8

cadmium(II) acetate

potassium tris{N-((propylamino)carbonyl)-4-chlorobenzenesulfonamido}cadmate

Conditions
ConditionsYield
With KOH In ethanol byproducts: CH3COOK, H2O; addn. of suspension of Cd(CH3CO2)2 in EtOH to ligand and KOH in EtOH, mixt. stirred for 3h, pptn.; concd., cooled to -10°C, crystn., filtered, washed (EtOH, Et2O), dried in vac., elem. anal.;60%
94-20-2

chlorpropamide

108-24-7

acetic anhydride

55379-05-0

N-((4-chlorophenyl)sulfonyl)acetamide

Conditions
ConditionsYield
With pyridine Ambient temperature;54.8%
94-20-2

chlorpropamide

A

98-64-6

4-Chlorobenzenesulfonamide

B

99996-79-9

N,N'-Bis-propylcarbamoyl-biphenyl-disulfonamid-(4,4')

C

98273-82-6

N-(p-chlorophenylsulfonyl)formamide

Conditions
ConditionsYield
In methanol at 20℃; for 8h; Irradiation;A 13%
B 53%
C 34%
In methanol at 20℃; for 8h; Mechanism; Irradiation; in vitro phototoxicity;A 13%
B 53%
C 34%
108-30-5

succinic acid anhydride

94-20-2

chlorpropamide

N-4-Chlorphenylsulfonyl-N'-n-propyl-bernsteinsaeurediamid

Conditions
ConditionsYield
With pyridine; dmap52%
94-20-2

chlorpropamide

silver nitrate

potassium bis{N-((propylamino)carbonyl)-4-chlorobenzenesulfonamido}argentate

Conditions
ConditionsYield
With KOH In ethanol; water addn. of EtOH/H2O (80:20) soln. of AgNO3 to soln. of ligand and KOH in EtOH, mixt. stirred for 30 min, pptn.; concd., cooled to 0°C, pptn., filtered, washed (EtOH/H2O and ether), dried in vac., elem. anal.;45%
94-20-2

chlorpropamide

108-24-7

acetic anhydride

N-acetyl-N-ethyl-4-chlorobenzenesulfonamide

Conditions
ConditionsYield
With triethylamine at 130℃; for 20h;40%
94-20-2

chlorpropamide

693-13-0

diisopropyl-carbodiimide

N-(bis(isopropylamino)methylene)-4-chlorobenzenesulfonamide

Conditions
ConditionsYield
With pyridine Heating;35%
94-20-2

chlorpropamide

A

627-06-5

n-propylurea

B

623-12-1

4-chloromethoxybenzene

C

2050-68-2

4,4'-dichlorobiphenyl

D

108-90-7

chlorobenzene

E

2051-62-9

4'-biphenyl chloride

F

71-43-2

benzene

Conditions
ConditionsYield
In methanol for 76h; Product distribution; Mechanism; Irradiation; λ=254 nm;A 21.8%
B n/a
C 3.1%
D 32.8%
E n/a
F n/a
94-20-2

chlorpropamide

3-methyl-4-nitro-1-(trifluoromethoxy)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-3-ium trifluoromethanesulfonate

4-chloro-N-(propylcarbamoyl)-3-(trifluoromethoxy)benzenesulfonamide

Conditions
ConditionsYield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In acetonitrile at 23℃; for 16h; Sealed tube; Irradiation; regioselective reaction;27%
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In acetonitrile at 23℃; for 16h; Glovebox; Irradiation; Sealed tube; Inert atmosphere;27%
94-20-2

chlorpropamide

538-75-0

dicyclohexyl-carbodiimide

N-(bis(cyclohexylamino)methylene)-4-chlorobenzenesulfonamide

Conditions
ConditionsYield
With pyridine Heating;24%
94-20-2

chlorpropamide

110-78-1

Propyl isocyanate

Conditions
ConditionsYield
With COCl2 In chlorobenzene at 130℃;
94-20-2

chlorpropamide

5769-15-3

4-Chlorophenylsulfonyl isocyanate

Conditions
ConditionsYield
With COCl2 In chlorobenzene at 130℃;
94-20-2

chlorpropamide

106-95-6

allyl bromide

1-(3-propenyl)-1-[(4-chlorophenyl)sulfonyl]-3-n-propylurea

Conditions
ConditionsYield
With sodium hydride 1.) dimethylacetamide, 20 min, 2.) dimethylacetamide, 20 h; Yield given. Multistep reaction;

Chloropropamide Chemical Properties

IUPAC Name: Chloropropamide
The MF of Chlorpropamide (CAS NO.94-20-2) is C10H13ClN2O3S.

                            
The MW of Chlorpropamide (CAS NO.94-20-2) is 276.74.
Synonyms of Chlorpropamide (CAS NO.94-20-2): 1-(4-chlorophenyl)sulfonyl-3-propyl-urea ; 4-Chlor-N-(propylcarbamoyl)benzolsulfonamid ; Benzenesulfonamide, 4-chloro-N-((propylamino)carbonyl)- ; Oradian
Appearance: white crystalline powder
Stability: Stable. Combustible
Index of Refraction: 1.552 
EINECS: 202-314-5
Density: 1.334 g/ml 
Melting Point: 128 °C
Merck: 2186

Chloropropamide Uses

  Chlorpropamide (CAS NO.94-20-2) is sulfonylurea oral hypoglycemic agents which mainly selectively act on the pancreatic islet-β-cells, promoting insulin secretion.Chlorpropamide has a relatively large side-effects, so the using of the drug are decreasing trend.

Chloropropamide Production

 Chlorobenzene sulfonamide reacts with chlorobenzene sulfonyl amide,generating C urea sodium salt. Then hydrochloric acid, refined to derive. Another method is based on chlorobenzene sulfonamide, isopropyl isocyanate, triethylamine as raw materials.

Chloropropamide Toxicity Data With Reference

1.    

sce-mus-orl 177 mg/kg

    MUREAV    Mutation Research. 77 (1980),349.
2.    

sce-ham-ipr 7100 µg/kg

    MUREAV    Mutation Research. 77 (1980),349.
3.    

orl-wmn TDLo:25 mg/kg/5D-I:BLD

    DICPBB    Drug Intelligence and Clinical Pharmacy. 18 (1984),981.
4.    

orl-wmn TDLo:300 mg/kg:CNS

    CTOXAO    Clinical Toxicology. 11 (1977),13.
5.    

orl-man TDLo:83 mg/kg/25D-I:GIT

    AJGAAR    American Journal of Gastroenterology. 80 (1985),381.
6.    

orl-rat LD50:2150 mg/kg

    FATOAO    Farmakologiya i Toksikologiya (Moscow). 25 (1962),93.
7.    

ipr-rat LD50:580 mg/kg

    TXAPA9    Toxicology and Applied Pharmacology. 18 (1971),185.
8.    

ivn-rat LD50:590 mg/kg

    PMDCAY    Progress in Medical Chemistry. 1 (1961),187.
9.    

orl-mus LD50:1546 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 153 (1965),379.
10.    

ivn-mus LD50:500 mg/kg

    PMDCAY    Progress in Medical Chemistry. 1 (1961),187.

Chloropropamide Consensus Reports

NCI Carcinogenesis Bioassay (feed); No Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-45 ,1978. . EPA Genetic Toxicology Program.

Chloropropamide Safety Profile

Moderately toxic by ingestion, intraperitoneal, and intravenous routes. Human systemic effects by ingestion: hemolysis with or without anemia, ulceration or bleeding from large intestine, cholestatic jaundice. Human teratogenic effects by ingestion: fetal death. Human reproductive effects by ingestion and possibly other routes: stillbirth, reduced viability and abnormal characteristics of newborn at birth. An experimental teratogen. Experimental reproductive effects. Mutation data reported. An antidiabetic agent. When heated to decomposition it emits very toxic fumes of Cl, NOx, and SOx.Safety information of Chlorpropamide (CAS NO.94-20-2):
Hazard Codes  HarmfulXn
Risk Statements 
20/21/22 Harmful by inhalation, in contact with skin and if swallowed
40 Limited evidence of a carcinogenic effect
Safety Statements 
22 Do not breathe dust
36 Wear suitable protective clothing
WGK Germany  3
RTECS  YS6650000

Chloropropamide Specification

A halogenated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

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