(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine - CAS 167316-27-0

Name: (1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine
Brand: BOC Sciences
Rating: 5 (1 reviews)

Catalog:	BB012380
Product Name:	(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine
CAS:	167316-27-0
Synonyms:	N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide; N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide

Technical Data

IUPAC Name:	N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide
Description:	(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine (CAS# 167316-27-0) is used as a catalyst in the synthesis of keramamine C, a carboline alkaloid that is isolated from the Okinawan sponge Amphimedon sp. (1S,2S)-N-(p-Toluenesulfonyl)-1,2-diphenylethanediamine is also used as a catalyst in the synthesis of Tolvaptan (T536650), a selective oral vasopressin V2-receptor agonist that is used to treat hyponatremia.
Molecular Weight:	366.48
Molecular Formula:	C21H22N2O2S
Canonical SMILES:	CC1=CC=C(C=C1)S(=O)(=O)NC(C2=CC=CC=C2)C(C3=CC=CC=C3)N
InChI:	InChI=1S/C21H22N2O2S/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17/h2-15,20-21,23H,22H2,1H3/t20-,21-/m0/s1
InChI Key:	UOPFIWYXBIHPIP-SFTDATJTSA-N
Boiling Point:	537.3 °C / 760 mmHg
Melting Point:	130 °C
Purity:	≥ 98 %, ≥ 95 % e.e.
Density:	1.224 g/cm³
Solubility:	Soluble in hot acetonitrile (almost transparency).
Appearance:	White or pale yellow needle-like crystal
Storage:	Room temperature.
MDL:	MFCD03095684
LogP:	5.88660

GHS Hazard Statement:	H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
Precautionary Statement:	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word:	Warning

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PMID	Publication Date	Title	Journal
21589615	20101127	N-[(1S,2S)-2-Amino-1,2-diphenyl-eth-yl]-4-methyl-benzene-sulfonamide [(S,S)-TsDPEN]	Acta crystallographica. Section E, Structure reports online
20235268	20100401	Chiral eta(6)-arene/N-tosylethylenediamine-ruthenium(II) complexes: solution behavior and catalytic activity for asymmetric hydrogenation	Chemistry, an Asian journal
18567024	20080101	Biomimetic iron-catalyzed asymmetric epoxidation of aromatic alkenes by using hydrogen peroxide	Chemistry (Weinheim an der Bergstrasse, Germany)
11871912	20020308	Practical synthesis of optically active amino alcohols via asymmetric transfer hydrogenation of functionalized aromatic ketones	The Journal of organic chemistry

Complexity:	511
Compound Is Canonicalized:	Yes
Covalently-Bonded Unit Count:	1
Defined Atom Stereocenter Count:	2
Defined Bond Stereocenter Count:	0
Exact Mass:	366.14019912
Formal Charge:	0
Heavy Atom Count:	26
Hydrogen Bond Acceptor Count:	4
Hydrogen Bond Donor Count:	2
Isotope Atom Count:	0
Monoisotopic Mass:	366.14019912
Rotatable Bond Count:	6
Topological Polar Surface Area:	80.6 Å²
Undefined Atom Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
XLogP3:	3.4