CAS 1576-37-0 p-Toluenesulfonamide, N-benzyl- (HCID 95801)

Overview

4-methyl-N-(phenylmethyl)benzenesulfonamide is a sulfonamide.

Names & identifiers

Preferred name: p-Toluenesulfonamide, N-benzyl-
IUPAC: N-benzyl-4-methylbenzenesulfonamide
English name: BTS
Molecular formula: C14H15NO2S
Molecular weight: 261.34

Names & synonyms

N-Benzyl-p-toluenesulfonamideN-TosylbenzylamineBenzenesulfonamide, 4-methyl-N-(phenylmethyl)-p-Toluenesulfonamide, N-benzyl-BRN 2217277AI3-30867NSC 371233-12-00-02328 (Beilstein Handbook Reference)DTXSID40166290RefChem:858212DTXCID20887811576-37-0

Show more names

BTSCLN3BatteninBTS, 10 mM in DMSON-Benzyl-p-tosylaMideLABOTEST-BB LT00786416N-TosylphenylmethanamineN-Tosylbenzenemethaneamine

N-Benzyl-4-methylbenzenesulfonamideN-Benzyl-4-methyl-benzenesulfonamideN-benzyl-4-methylbenzene-1-sulfonamideMFCD00159328Oprea1_691087Oprea1_824524N-Benzyl-p-toluene sulphonamideCHEMBL1332361

Database identifiers

CAS: 1576-37-0
PubChem CID: 95801
DTXSID: DTXSID40166290
ChEMBL: CHEMBL1332361
ChEBI: CHEBI:114205
Nikkaji: J426.785K

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 54.6 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 18
Formal charge: 0
Complexity: 333

Experimental & physicochemical properties

Solubility25.9 [ug/mL] (The mean of the results at pH 7.4)

Physicochemical properties

Melting point: 115 °C · 115 °C
Boiling point: 419.1 · 419.1±48.0 °C(Predicted)
Density: 1.204 · 1.204±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Chloroform (Slightly), Dichloromethane, Ethyl Acetate (Slightly)
pka: 11.54 · 11.54±0.30(Predicted)
form: White crystalline solid
color: White to Off-White
Sensitive: Light Sensitive
InChI: InChI=1S/C14H15NO2S/c1-12-7-9-14(10-8-12)18(16,17)15-11-13-5-3-2-4-6-13/h2-10,15H,11H2,1H3
InChIKey: WTHKAJZQYNKTCJ-UHFFFAOYSA-N
SMILES: C1(S(NCC2=CC=CC=C2)(=O)=O)=CC=C(C)C=C1
CAS DataBase Reference: 1576 · 1576-37-0(CAS DataBase Reference)
UNSPSC Code: 12352200 · 12352200
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
WGK Germany: 3 · WGK 3
RTECS: 5490000 · XT5490000
HS Code: 2935.9 · 2935.90.9500
Storage Class: 11 · 11 - Combustible Solids
Toxicity: 500 mg/kg · rat,LD,oral,> 500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 41, 1953.

Safety & regulation

Safety data

wgk: WGK 3
rtecs: XT5490000
hs_code: 2935.90.9500
Toxicity: rat,LD,oral,> 500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 41, 1953.
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 3 items

DescriptionBTS is an inhibitor of skeletal muscle myosin II ATPase activity that reduces the affinity of ADP-myosin for actin. It inhibits calcium-stimulated ATPase activity of rabbit muscle myosin subfragment 1 (S1) in an actin-independent manner with an IC50 value of approximately 5 μM. It is selective for calcium-stimulated myosin II over human platelet myosin II, kinesin, pyruvate kinase, and lactate dehydrogenase at 100 μM. BTS (2 μM) inhibits the activity of skeletal muscle myosin, reversibly reducing the sliding velocity of heavy meromyosin in a gliding-filament assay. It inhibits isometric calcium-activated tension in isolated fast-twitch rabbit psoas muscle fibers (IC50 = ~3 μM) but not in isolated slow-twitch rat trabeculae and papillary cardiac muscle. BTS is also an intermediate in the synthesis of sulfonamides.

UsesA potent inhibitor of skeletal muscle Ca2+-stimulated myosin S1 ATPase (IC50 approx. 5uM) activity. Reversible blocks the gliding motility. Also weakens myosin interaction with F-actin. Does not affect platelet myosin II

UsesA potent inhibitor of calcium-stimulated myosin S1 ATPase