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1-Butyl-3-(4-methylphenyl)sulfonylurea
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Name

1-Butyl-3-(4-methylphenyl)sulfonylurea

 EINECS 200-594-3
CAS No. 64-77-7 Density 1.184 g/cm3
PSA 83.65000 LogP 3.64560
Solubility 0.14g/L(25 oC) Melting Point 128-130°C
Formula C12H18N2O3S Boiling Point white crystalline powder
Molecular Weight 270.353 Flash Point N/A
Transport Information N/A Appearance white crystalline powder
Safety 26-36/37/39 Risk Codes 20/21/22-40-43
Molecular Structure Molecular Structure of 64-77-7 (TOLBUTAMIDE) Hazard Symbols F,Xn
Synonyms

Urea,1-butyl-3-(p-tolylsulfonyl)- (8CI);1-Butyl-3-(p-methylphenylsulfonyl)urea;1-Butyl-3-(p-tolylsulfonyl)urea;3-(p-Tolyl-4-sulfonyl)-1-butylurea;Aglicid;Arkozal;Artosin;Artozin;Butamid;Butamide;D 860;Diaben;Diabetamid;Diabetol;Diabuton;Diasulfon;Dolipol;Glyconon;HLS 831;Ipoglicone;Mobenol;N-(4-Methylbenzenesulfonyl)-N'-butylurea;N-(4-Methylphenylsulfonyl)-N'-butylurea;N-(Sulfonyl-p-methylbenzene)-N'-n-butylurea;N-(p-Methylbenzenesulfonyl)-N'-butylurea;N-(p-Tolylsulfonyl)-N'-butylcarbamide;N-Butyl-N'-(4-methylphenylsulfonyl)urea;N-Butyl-N'-(p-tolylsulfonyl)urea;N-Butyl-N'-p-toluenesulfonylurea;N-n-Butyl-N'-tosylurea;NSC 23813;NSC 87833;Orabet;Oralin;Orezan;Orinase;Orinaz;Oterben;Pramidex;Rastinon;Tolbusal;Tolbutamid;Tolbutamide;Toluina;Tolumid;Tolumide;Toluvan;U 2043;Willbutamide;

Article Data 88

1-Butyl-3-(4-methylphenyl)sulfonylurea Synthetic route

70-55-3

toluene-4-sulfonamide

111-36-4

n-butyl isocyanide

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With copper(l) chloride In nitromethane at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Milling;95%
copper(l) chloride In N,N-dimethyl-formamide for 21h; Ambient temperature;85%
With boron trifluoride diethyl etherate In diethyl ether for 2h; Ambient temperature;66%
1792-17-2

N,N'-di-n-butylurea

18522-92-4

sodium p-toluenesulfonamide

A

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

B

109-73-9

N-butylamine

Conditions
ConditionsYield
at 150℃; for 8h; Product distribution; other time;;A 94.5%
B n/a
at 150℃; for 5h;A 94.5%
B n/a
4083-64-1

Tosyl isocyanate

109-73-9

N-butylamine

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With potassium carbonate In neat (no solvent) at 20℃; for 0.5h; Glovebox;93%
Stage #1: Tosyl isocyanate; N-butylamine In dichloromethane at 0 - 20℃;
Stage #2: With 5-hydroxymethyl-2-norbornene In dichloromethane at 0 - 20℃;
Stage #3: With [{1,3-bis(mesyl)imidazolidin-2-yl}RuCl2(PCy3)(=CHPh)] In dichloromethane Heating; Further stages.;		90%
39078-72-3

S-methyl N-butylthiocarbamate

70-55-3

toluene-4-sulfonamide

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 4h; Substitution;85%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃;85%
3898-47-3

phenyl-N-butylcarbamate

70-55-3

toluene-4-sulfonamide

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Reflux; Green chemistry;80%
70-55-3

toluene-4-sulfonamide

39764-19-7

1-(1-butylaminocarbonyl)-1H-benzotriazole

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonamide; 1-(1-butylaminocarbonyl)-1H-benzotriazole at 100℃; Inert atmosphere; neat (no solvent);
Stage #2: With potassium carbonate for 0.25h; Inert atmosphere; neat (no solvent);
Stage #3: With hydrogenchloride In water at 60℃; for 0.5h;		75%
70-55-3

toluene-4-sulfonamide

27095-02-9

hydroxyethyl carbamic acid butyl ester

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide18%
41891-17-2

N-butylcarbamoyl chloride

18522-92-4

sodium p-toluenesulfonamide

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

4932-55-2

N-(4-methylphenylsulfonyl)-N'-butylthiourea

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide
98275-71-9

N-butyl-O-methyl-isourea

98-59-9

p-toluenesulfonyl chloride

64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
und Erwaermen des Reaktionsprodukts mit wss.HCl;

1-Butyl-3-(4-methylphenyl)sulfonylurea Chemical Properties

IUPAC Name: 1-Butyl-3-(4-methylphenyl)sulfonylurea
CAS: 64-77-7
Formula  : C12H18N2O3S
Molecular Weight: 270.35
Molecular Structure of 1-Butyl-3-(4-methylphenyl)sulfonylurea (64-77-7): 
 
Density: 1.184 g/cm3 
Melting Point: 128-130°C 
Appearance: white crystalline powder
Index of Refraction: 1.532
Molar Refractivity: 70.76 cm3 
Molar Volume: 228.2 cm3 
Polarizability: 28.05×10-24cm3 
Surface Tension: 42.7 dyne/cm 
Water Solubility: 182.6(mg/L) at 25°C
Product Categories: potassium channel

1-Butyl-3-(4-methylphenyl)sulfonylurea Toxicity Data With Reference

1.    

sce-mus-orl 28,600 µg/kg

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

sce-ham-ipr 28,600 µg/kg

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

orl-wmn LDLo:1 g/kg:GIT:SYS

     ATXKA8    Archiv fuer Toxikologie. 23 (1968),153.
4.    

orl-rat LD50:2490 mg/kg

     PMDCAY    Progress in Medical Chemistry. 1 (1961),187.
5.    

ipr-rat LD50:860 mg/kg

     FRPSAX    Farmaco, Edizione Scientifica. 12 (1957),268.
6.    

ivn-rat LD50:700 mg/kg

     PMDCAY    Progress in Medical Chemistry. 1 (1961),187.
7.    

orl-mus LD50:490 mg/kg

     IJCREE    International Journal of Crude Drug Research. 26 (1988),81.
8.    

ipr-mus LD50:650 mg/kg

     TXAPA9    Toxicology and Applied Pharmacology. 4 (1962),631.
9.    

scu-mus LD50:980 mg/kg

     NATUAS    Nature. 193 (1962),891.
10.    

ivn-mus LD50:770 mg/kg

     PMDCAY    Progress in Medical Chemistry. 1 (1961),187.
11.    

ipr-mus LD50:700 mg/kg

1-Butyl-3-(4-methylphenyl)sulfonylurea 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-31 (1977). . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

1-Butyl-3-(4-methylphenyl)sulfonylurea Safety Profile

Moderately toxic by ingestion and several other routes. A human teratogen. Human reproductive effects by ingestion and possibly other routes: stillbirth, developmental abnormalities of the cardiovascular (circulatory) system and urogenital system, and unspecified neonatal effects. Human systemic effects by ingestion: nausea or vomiting, hypoglycemia. Other experimental teratogenic and reproductive effects. Mutation data reported. Implicated in aplastic anemia. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Safety Information about 1-Butyl-3-(4-methylphenyl)sulfonylurea (64-77-7):
Risk Statements about 1-Butyl-3-(4-methylphenyl)sulfonylurea (64-77-7):
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R40: Limited evidence of a carcinogenic effect.
R43: May cause sensitization by skin contact.
Safety Statements about 1-Butyl-3-(4-methylphenyl)sulfonylurea (64-77-7):
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 2
RTECS: YS4550000

1-Butyl-3-(4-methylphenyl)sulfonylurea Specification

  The chemical synonyms of 1-Butyl-3-(4-methylphenyl)sulfonylurea (64-77-7) are Labotest-bb lt00772316 ; 3-[P-tolyl-4-sulfonyl]-1-butylurea ; 1-Butyl-3-(p-tolylsulfonyl)urea ; 1-Butyl-3-(4-methylbenzenesulfonyl)urea ; 1-Butyl-3-(4-methylphenylsulfonyl)urea ; 1-N-butyl-3-(p-tolylsulfonyl)urea ; Toluina ; Tolbutamide .Tolbutamide is an amide. 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. Imides are less basic yet and in fact react with strong bases to form salts. 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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