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339822

Sigma-Aldrich

(S)-α-Methyl-4-nitrobenzylamine hydrochloride

97%

Synonym(s):

(S)-1-(4-Nitrophenyl)ethylamine hydrochloride

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About This Item

Linear Formula:
O2NC6H4CH(CH3)NH2 · HCl
CAS Number:
132873-57-5
Molecular Weight:
202.64
MDL number:
MFCD00066312
UNSPSC Code:
12352116
PubChem Substance ID:
24860686
NACRES:
NA.22

Assay

97%

form

powder

optical activity

[α]25/D −6.5°, c = 1 in 0.05 M NaOH

mp

248-250 °C (lit.)

SMILES string

Cl.C[C@H](N)c1ccc(cc1)[N+]([O-])=O

InChI

1S/C8H10N2O2.ClH/c1-6(9)7-2-4-8(5-3-7)10(11)12;/h2-6H,9H2,1H3;1H/t6-;/m0./s1

InChI key

CZQQGVFHLSBEDV-RGMNGODLSA-N

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Application

(S)-α-Methyl-4-nitrobenzylamine hydrochloride can be used as:
  • A fluorescence-quenching guest in the determination of chiral recognition capabilities of binaphthocrown ether and polythiophene complex.
  • A starting material in the synthesis of chiral cyclopalladated complexes with applications in the resolution of racemic compounds.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The first orthopalladation of a primary nitrobenzylamine. Synthesis of chiral cyclopalladated complexes derived from (S)-α-methyl-4-nitrobenzylamine
Vicente J, et al.
J. Chem. Soc., Dalton Trans., 47(15), 2535-2539 (1995)
Polymer-based supramolecular sensing and application to chiral photochemistry
Fukuhara G
Polymer Journal, 47(10), 649-655 (2015)
Gaku Fukuhara et al.
Chemical communications (Cambridge, England), 48(11), 1641-1643 (2011-12-15)
Chiral recognition abilities of the title host for (R)- and (S)-α-methyl-4-nitrobenzylamine were examined in the ground and excited states to give a relative affinity (K(R)/K(S)) of 2.16 by spectral titration and a relative rate constant (k(R)/k(S)) of 2.23 by fluorescence

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