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4-(2-Aminoethyl)benzenesulfonamide

Product Name4-(2-Aminoethyl)benzenesulfonamide
CAS35303-76-5
MFC8H12N2O2S
MW200.26
EINECS252-501-0
MOL File35303-76-5.mol

Chemical Properties

Melting point	150-152 °C (lit.)
Boiling point	387.4±44.0 °C(Predicted)
Density	1.2581 (rough estimate)
vapor pressure	0Pa at 25℃
refractive index	1.5690 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	DMSO (Slightly), Methanol (Slightly)
pka	10.16±0.10(Predicted)
form	Solid
color	White
Water Solubility	15.5g/L at 20℃
InChI	InChI=1S/C8H12N2O2S/c9-6-5-7-1-3-8(4-2-7)13(10,11)12/h1-4H,5-6,9H2,(H2,10,11,12)
InChIKey	FXNSVEQMUYPYJS-UHFFFAOYSA-N
SMILES	C1(S(N)(=O)=O)=CC=C(CCN)C=C1
LogP	-3.1 at 19.8℃
CAS DataBase Reference	35303-76-5(CAS DataBase Reference)

Safety Information

Hazard Codes	C,Xi,Xn
Risk Statements	34-22-36/37/38-20/21/22
Safety Statements	45-36/37/39-26-36-24/25
RIDADR	UN3259
WGK Germany	3
Hazard Note	Irritant
HazardClass	8
PackingGroup	III
HS Code	29350090
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Eye Irrit. 2 Met. Corr. 1 Skin Irrit. 2

MSDS

Provider	Language
4-(2-Aminoethyl)benzenesulfonamide	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Uses

4-(2-Aminoethyl)benzenesulfonamide is used as the starting material in the synthesis of Des(5-methylpyrazinecarbonyl) trans-4-Methyl Glipizide (D292605); a degradation product of Glimepiride (G410150) which is a sulfonylurea hypoglycemic agent and an antidiabetic. 4-(2-Aminoethyl)benzenesulfonamide is also used as a reagent in the synthesis of deorphaning pyrrolopyrazines as potent multi-target antimalarial agents.

Chemical Properties

white to yellowish crystalline powder

Uses

4-(2-Aminoethyl)benzenesulfonamide was used to develop a model system to study the implementation of a microfluid chip required for Fourier transform measurements of biochemical interactions.

General Description

The human hepatocellular carcinoma (HCC) cells were treated with its inhibitor 4-(2-aminoethyl)benzenesulfonamide.

Flammability and Explosibility

Not classified

Synthesis

Benzenesulfonyl chloride, 4-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]-

223253-87-0

35303-76-5

The general procedure for the synthesis of 4-(2-aminoethyl)benzenesulfonamide from the compound (CAS:223253-87-0) was as follows: compound II was dissolved in 80 mL of acetone. Under the condition of ice water bath, 150 mL of concentrated ammonia was added to the reaction mixture and the reaction was stirred at room temperature. After completion of the reaction, the mixture was poured into 500 mL of ice water and the solid was collected by filtration. The filter cake was acidified with 200 mL of 2N hydrochloric acid. Subsequently, the mixture was heated to reflux for 6 hours and filtered. The filtrate was dissolved in hot water and the pH was adjusted to 11-12 with 2N KOH solution. after cooling in an ice bath, the solution was boiled naturally and cooled again to precipitate a pale yellow precipitate. After filtration, it was dried under vacuum to obtain 21.6 g (0.108 mol) of compound III, i.e., 4-(2-aminoethyl)benzenesulfonamide.

References

[1] Patent: CN107879955, 2018, A. Location in patent: Paragraph 0050

Preparation Products And Raw materials

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