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Key Documents

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:
Molecular Weight:
212.20
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Signal Word

Warning

Hazard Statements

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

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(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)
Development of new isothiocyanate-based chiral derivatizing agent for amino acids.
Peter M, et al.
Chromatographia, 50(5-6), 373-375 (1999)
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
D A Pearce et al.
Molecular genetics and metabolism, 66(4), 314-319 (1999-04-07)
The CLN3 gene, which encodes the protein whose absence is responsible for Batten disease, the most common inherited neurovisceral storage disease of childhood, was identified in 1995. The function of the protein, Cln3p, still remains elusive. We previously cloned the
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)

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