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A70704

Sigma-Aldrich

(1R,2R)-(−)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

99%

Synonym(s):

D-(−)-threo-2-Amino-1-(p-nitrophenyl)-1,3-propanediol, Chloramphenicol base

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About This Item

Linear Formula:
HOCH2CH(NH2)CH(C6H4NO2)OH
CAS Number:
716-61-0
Molecular Weight:
212.20
EC Number:
211-938-7
MDL number:
MFCD00078126
UNSPSC Code:
12352116
PubChem Substance ID:
24891170
NACRES:
NA.22

Assay

99%

form

powder

optical activity

[α]25/D −30°, c = 1 in 6 M HCl

mp

163-165 °C (lit.)

SMILES string

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

InChI

1S/C9H12N2O4/c10-8(5-12)9(13)6-1-3-7(4-2-6)11(14)15/h1-4,8-9,12-13H,5,10H2/t8-,9-/m1/s1

InChI key

OCYJXSUPZMNXEN-RKDXNWHRSA-N

Application

(1R,2R)-(-)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol may be used in the preparation of (1R,2R)-(-)-2-dimethylamino-1-(4-nitrophenyl)-1,3-propanediol via N,N-dimethylation. It may also be used as a starting material to synthesize (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propylisothioeyanate [(R,R)-DANI].

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

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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Development of new isothiocyanate-based chiral derivatizing agent for amino acids.
Peter M, et al.
Chromatographia, 50(5-6), 373-375 (1999)
(1R, 2R)-(-)-2-Dimethylamino-1-(4-nitrophenyl)-1, 3-propanediol/l-proline cocatalyzed enantioselective Morita-Baylis-Hillman reaction.
Tang H, et al.
Catalysis Communications, 8(11), 1811-1814 (2007)
D K Zheng et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 25(6), 430-434 (1990-01-01)
Threo (-) or (+)-1-(p-nitrophenyl)-1,3-dihydroxypropylamine-2 was found to be a useful resolving agent for racemic gossypol. The optical and chemical stability of the condensate of enantiomeric gossypols with the titled amine and the great difference in the Rf values on TLC
Induced synthesis of phosphatases in Anacystis nidulans by p-NO2-phenylserinal.
M L Muñoz-Calvo et al.
The Journal of antibiotics, 33(5), 520-522 (1980-05-01)
W A Korfmacher et al.
Journal of chromatographic science, 28(5), 236-238 (1990-05-01)
The thermospray (TS) liquid chromatographic-mass spectrometric analysis of the antibiotic chloramphenicol and three related compounds is presented. The three additional compounds are dehydrochloramphenicol, aminodehydrochloramphenicol, and nitrophenylaminopropanediol. Baseline separation of the four compounds is achieved. The TS mass spectrum of each
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