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156876

Sigma-Aldrich

N-(2-Hydroxyethyl)aniline

98%

Synonym(s):

2-(Phenylamino)ethanol, 2-Anilinoethanol, N-Phenylethanolamine

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About This Item

Linear Formula:
C6H5NHCH2CH2OH
CAS Number:
122-98-5
Molecular Weight:
137.18
Beilstein:
774672
MDL number:
MFCD00002832
UNSPSC Code:
12352100
PubChem Substance ID:
24849642
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

200

vapor pressure

<0.01 mmHg ( 20 °C)

Assay

98%

form

liquid

refractive index

n20/D 1.578 (lit.)

bp

278-282 °C/760 mmHg (lit.)

density

1.094 g/mL at 25 °C (lit.)

SMILES string

OCCNc1ccccc1

InChI

1S/C8H11NO/c10-7-6-9-8-4-2-1-3-5-8/h1-5,9-10H,6-7H2

InChI key

MWGATWIBSKHFMR-UHFFFAOYSA-N

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Application

N-(2-Hydroxyethyl)aniline was employed as substrate for human olfactory UDP-glucuronosyltransferase.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Dam. 1 - STOT RE 2 - STOT SE 1

Target Organs

Blood, Blood,hematopoietic system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBL0248V
1433059V
1433059
1384616
1195456

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M Amat et al.
Organic letters, 3(21), 3257-3260 (2001-10-12)
[reaction: see text]. The phenylglycinol-derived 2-pyridone 1 undergoes m-CPBA oxidation steroselectively leading to the chiral nonracemic unsaturated bicyclic hydroxylactam 2, from which the enantioselective synthesis of (3R,5R)-3,4,5-trihydroxypiperidine (16) and the formal synthesis of the azasugar epiisofagomine are described. The enantioselective
Mercedes Amat et al.
Natural product communications, 6(4), 515-526 (2011-05-13)
This review is focused on recent synthetic achievements and ongoing work in our laboratory using phenylglycinol-derived oxazolopiperidone lactams as starting materials for the enantioselective synthesis of piperidine-containing alkaloids: madangamines, 2,5-disubstituted decahydroquinoline and 1-substituted tetrahydroisoquinoline alkaloids, the indole alkaloids 20S- and
Mercedes Amat et al.
Organic & biomolecular chemistry, 9(7), 2175-2184 (2011-02-08)
The double cyclocondensation of symmetric pyridyl bis(oxoacids) 2b and 3b with (R)-phenylglycinol stereoselectively gave access to bis-phenylglycinol-derived oxazolopyrrolidine 9 and oxazolopiperidone 10, respectively. Application of the stereocontrolled cyclocondensation reaction to phenyl bis-γ-oxoacid 4b provided 11, which was converted to the
Mercedes Amat et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(28), 7724-7732 (2011-06-15)
Phenylglycinol-derived, unsaturated oxazolopiperidone lactams are extremely useful building blocks that undergo stereoselective conjugate addition reactions with organocuprates, enolates, and sulfur-stabilized anions, allowing the stereocontrolled introduction of substituents at the piperidine 4-position. The factors governing the exo- or endo-facial selectivity are
Mercedes Amat et al.
The Journal of organic chemistry, 71(10), 3804-3815 (2006-05-06)
The stereochemical outcome of the alkylation of a variety of phenylglycinol-derived oxazolopiperidone lactams is studied. The influence of the configuration of the C-8a stereocenter and the effect of the substituents at the C-8 and C-8a positions on the stereoselectivity of
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