D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL

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

CAS NO.：716-61-0
Empirical Formula: C9H12N2O4
Molecular Weight: 212.2
MDL number: MFCD00078126
EINECS: 211-938-7
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-25 23:13:37

D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL Structural

What is D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL?

Chemical properties

light yellow powder

The Uses of D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL

D-threo-(-)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol is an impurity of Chloramphenicol (C325030), a broad spectrum antibiotic agent obtained from cultures of the soil bacterium Streptomyces venezuel ae.

The Uses of D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL

Chloramphenicol base is the parent 4-nitrophenylpropylamine formed by the hydrolysis of the dichloroacetamide of chloramphenicol and is a degradation product commonly encountered with commercial production of chloramphenicol. Chloramphenicol base has no antibiotic activity but has played an integral role in the synthesis and SAR of new generation antibiotics, notably thiamphenicol and experimental analogues, bromamphenicol and methamphenicol.

The Uses of D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL

(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].

Definition

ChEBI: A diol that is propane 1,3-diol bearing additional amino and 4-nitrophenyl substituents at positions 2 and 1 respectively.

Properties of D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL

Melting point:	163-165 °C(lit.)
Boiling point:	352.03°C (rough estimate)
Density	1.3136 (rough estimate)
refractive index	-30.5 ° (C=1, 6mol/L HCl)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Water Solubility	almost transparency in hot Water
solubility	DMSO (Slightly), Methanol (Slightly)
pka	10.98±0.45(Predicted)
form	Powder
color	Light yellow
optical activity	[α]25/D 30°, c = 1 in 6 M HCl

Safety information for D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.