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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/REAXYS Number:
774672
MDL number:
MFCD00002832
UNSPSC Code:
12352100
PubChem Substance ID:
24849642
NACRES:
NA.22

vapor density

>1 (vs air)

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.

signalword

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

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

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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.
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.
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
Alok K Awasthi et al.
The Journal of organic chemistry, 70(14), 5387-5397 (2005-07-02)
[reaction: see text] A practical, large-scale synthesis of a beta-amino ester 1 was developed. A chiral imine derived from (S)-phenylglycinol and 3-trimethylsilylpropanal was coupled with the Reformatsky reagent 3 with high diastereoselectivity (de > 98%) to give (SS)-4a as 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
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