2271-58-1

Usage

Molecular Structure

A derivative of 1,3-propanediol with an amino group and a nitrophenyl group, as well as a hydrochloride salt.

Industrial Applications

Used in various industrial applications.

Reagent Usage

Sometimes used as a reagent in organic synthesis and pharmaceutical research.

Potential Applications

May have potential applications in the production of certain polymers and materials.

Versatility

A versatile compound with a range of potential uses in research and industry.

Context-Dependence

Its precise properties and uses depend on the specific context and industry in which it is being employed.

Upstream product

• 103-64-0 bromostyrene 
• 2425-28-7 2-Bromo-1-phenylethanol 
• 77940-37-5 5-bromo-4-phenyl-[1,3]dioxane 
• 100-42-5 styrene 
• 54299-23-9 (+/-)-threo-5-amino-4-phenyl-1,3-dioxane 

Downstream Products

• 1194708-89-8 (S)-((R)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol 
• 109162-23-4 (1RS,2SR)-1,3-diacetoxy-2-amino-1-(4-nitro-phenyl)-propane; hydrochloride 
• 40958-11-0 (1RS,2SR)-3-acetoxy-2-acetylamino-1-(4-nitro-phenyl)-propan-1-ol 
• 109162-23-4 (1RS,2RS)-1,3-diacetoxy-2-amino-1-(4-nitro-phenyl)-propane; hydrochloride 

Relevant academic research and scientific papers

STEREOSELECTIVE SYNTHESIS OF (+/-)-threo-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL

Addition of hypobromic acid to styrene afforded styrene bromohydrin (I) which was dehydrated to ω-bromostyrene (II).Prince reaction of II with aqueous formaldehyde gave 5-bromo-4-phenyl-1,3-dioxane (III).The bromine atom in III was replaced with amino group by treatment with methanolic ammonia at 150 deg C and 6 - 8 MPa and the obtained threo-5-amino-4-phenyl-1,3-dioxane (IVa) was hydrolyzed to give (+/-)-threo-2-amino-1-phenyl-1,3-propanediol (V).Suitably chosen method of nitration converted the free base IVa or its N-acetyl derivative IVb into 5-amino-4-(4-nitrophe nyl)-1,3-dioxane (VIa) or its N-acetyl derivative VIb which without isolation were hydrolyzed to threo-2-amino-1-(4-nitrophenyl)-1,3-propanediol (VII), isolated as hydrochloride.The liberated base was resolved into enantiomers and dichloroacetylated in the known manner to give D-(-)-threo-2-dichloroacetylamino-1-(4-nitrophenyl)-1,3-propanediol (chloramphenicol).