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

Name
TOLBUTAMIDE
EINECS 200-594-3
CAS No. 64-77-7
Article Data88
CAS DataBase
Density 1.184 g/cm³
Solubility 0.14g/L(25 oC)
Melting Point 128-130°C
Formula C₁₂H₁₈N₂O₃S
Boiling Point white crystalline powder
Molecular Weight 270.353
Flash Point
Transport Information
Appearance white crystalline powder
Safety 26-36/37/39
Risk Codes 20/21/22-40-43
Molecular Structure
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;
PSA 83.65000
LogP 3.64560

Synthetic route

: 70-55-3
toluene-4-sulfonamide

: 111-36-4
n-butyl isocyanide

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions

Conditions	Yield
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

Conditions	Yield
at 150℃; for 8h; Product distribution; other time;;	A 94.5% B n/a
at 150℃; for 5h;	A 94.5% B n/a

...Expand

: 4083-64-1
Tosyl isocyanate

: 109-73-9
N-butylamine

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In water; N,N-dimethyl-formamide	18%

: 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

Conditions	Yield
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

Conditions	Yield
und Erwaermen des Reaktionsprodukts mit wss.HCl;

: 18522-92-4
sodium p-toluenesulfonamide

: 111-36-4
n-butyl isocyanide

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 111-36-4
n-butyl isocyanide

potassium-salt of toluene-4-sulfonamide: potassium-salt of toluene-4-sulfonamide

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 592-31-4
1-butyl-urea

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: und Erwaermen des Reaktionsprodukts mit wss.HCl View Scheme

: 98-59-9
p-toluenesulfonyl chloride

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide / water; acetonitrile / 0.33 h / 20 °C / Schlenk technique 2: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme

: 941-55-9
4-toluenesulfonyl azide

: 201230-82-2
carbon monoxide

: 109-73-9
N-butylamine

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

Conditions

Conditions	Yield
With palladium diacetate In acetonitrile at 20℃; under 15 Torr; Schlenk technique; Sealed tube;

...Expand

: 85-44-9
phthalic anhydride

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

A: 1515-72-6
N-butylphthalimide

B: 70-55-3
toluene-4-sulfonamide

Conditions

Conditions	Yield
With pyridine; dmap for 4h; Heating;	A 86% B 50%

...Expand

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

A: 1515-72-6
N-butylphthalimide

B: 70-55-3
toluene-4-sulfonamide

Conditions

Conditions	Yield
With pyridine; dmap; phthalic anhydride for 4h; Heating;	A 86% B 50%

: 3878-67-9
N-phenyl-N'-cyclohexyl carbodiimide

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 51757-93-8
N-Cyclohexyl-N'-phenyl-N''-(4-toluolsulfonyl)guanidin

Conditions

Conditions	Yield
With pyridine Heating;	84%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 175970-03-3
N-(4'-methylphenylsulfonyl)aziridino[2'3':1,2][60]fullerene

: C72H16N2O3S

Conditions

Conditions	Yield
With 1-methyl-1H-imidazole In chlorobenzene at 120℃; for 7h; Catalytic behavior; Reagent/catalyst; Temperature;	84%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

A: 592-31-4
1-butyl-urea

B: 613-33-2
(4,4'-dimethyl-1,1'-biphenyl)

C: 108-88-3
toluene

Conditions

Conditions	Yield
In diethyl ether for 2h; Product distribution; Mechanism; Irradiation; var. solvents, time;	A 80% B 10% C 34%
In methanol for 32h; Product distribution; Mechanism; Irradiation; λ=254 nm; other solvents, other time; also in the presence of O2 and xanthone;	A 25.7% B 0.9% C 29.6%

...Expand

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 108-24-7
acetic anhydride

A: 1119-49-9
N-butylacetamide

B: 1888-33-1
N-acetyl-(4-methylbenzene)sulfonamide

Conditions

Conditions	Yield
With pyridine for 0.0833333h;	A 40% B 76%

...Expand

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 543-90-8
cadmium(II) acetate

: potassium tris{N-((butylamino)carbonyl)-4-methylbenzenesulfonamido}cadmate

Conditions

Conditions	Yield
With KOH In ethanol byproducts: CH3COOK; 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.;	75%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 111182-41-3
N-n-Butyl-N',N''-bis-(4-toluolsulfonyl)guanidin

Conditions

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride for 1h; Heating;	67%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 407-25-0
trifluoroacetic anhydride

: 81005-28-9
N-(trifluoroacetyl)-p-toluenesulfonamide

Conditions

Conditions	Yield
In chloroform for 1.5h;	62%

: 50-00-0
formaldehyd

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

A: 27117-97-1
3,5-di-n-butyl-2-oxo-1-p-tosyl-perhydro-1,3,5-triazine

B: N-morpholinomethyl-p-toluenesulfonylcarbamic acid

C: 1-Butyl-3,5-bis-(toluene-4-sulfonyl)-[1,3,5]triazinan-2-one

Conditions

Conditions	Yield
With morpholine In methanol; water at 60℃; for 1h;	A 61% B n/a C 18%
With morpholine In methanol; water at 60℃; for 1h; Mechanism; other reagents and solvents, var. temp.;	A 61% B n/a C 18%

...Expand

: 108-30-5
succinic acid anhydride

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: N-n-Butyl-N'-4-toluolsulfonyl-bernsteinsaeurediamid

Conditions

Conditions	Yield
With pyridine; dmap for 5h;	51%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: silver nitrate

: potassium bis{N-((butylamino)carbonyl)-4-methylbenzenesulfonamido}argentate

Conditions

Conditions	Yield
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.;	50%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 538-75-0
dicyclohexyl-carbodiimide

: 908-18-9
N-(bis(cyclohexylamino)methylene)-4-methylbenzenesulfonamide

Conditions

Conditions	Yield
With pyridine for 2h; Heating;	43%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 5719-85-7
4-hydroxytolbutamide

Conditions

Conditions	Yield
With SoLo-D241G unspecific peroxygenase; dihydrogen peroxide; ascorbic acid In aq. phosphate buffer; acetonitrile at 30℃; for 1h; pH=7; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;	21%
With rat liver microsomes at 37℃; for 0.333333h; pH=7.4; Enzyme kinetics; Oxidation; Enzymatic reaction;
With α-D-glucose 6-phosphate; human liver microsomes; NADP In phosphate buffer at 37℃; for 0.5h; pH=7.4; Enzyme kinetics;

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0
fullerene-C60

: C72H16N2O3S

Conditions

Conditions	Yield
With 1,10-Phenanthroline; copper diacetate In chlorobenzene at 140℃; for 4.5h; Reagent/catalyst; Temperature;	21%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 100254-89-5
N-(tosylcarbamoyl)butyramide

Conditions

Conditions	Yield
In acetonitrile pH=10; Electrolysis;	19%

: 14041-89-5
N-isopropyl-N'-phenylcarbodiimide

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: N-Isopropyl-N'-phenyl-N''-(4-toluolsulfonyl)guanidin

Conditions

Conditions	Yield
With pyridine Heating;	17%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 88241-95-6
1-butyl-3-(p-formylphenyl)sulphonylurea

Conditions

Conditions	Yield
With SoLo-D241G unspecific peroxygenase; dihydrogen peroxide; ascorbic acid In aq. phosphate buffer; acetonitrile at 30℃; for 1h; pH=7; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;	16%

: 64-77-7
N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

: 693-13-0
diisopropyl-carbodiimide

: 965-31-1
N-(bis(isopropylamino)methylene)-4-methylbenzenesulfonamide

Conditions

Conditions	Yield
With pyridine Heating;	10%

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 NO_x and SO_x.
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).

Product Name

TOLBUTAMIDE

Synthetic route

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

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

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

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

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

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