22038-87-5

Basic information

• Product Name: (R)-1-(4-NITRO-PHENYL)-ETHYLAMINE
• Synonyms: (R)-4-NITRO-ALPHA-METHYLBENZYLAMINE;(R)-A-METHYL-4-NITROBENZYLAMINE;(R)-1-(4-NITRO-PHENYL)-ETHYLAMINE;R-P-NITRO-ALPHA-METHYLBENZYLAMINE;4-Nitro-alpha-methylbenzylamine;R-P-NITRO-A-METHYLBENZYLAMINE;Benzenemethanamine, α-methyl-4-nitro-, (αR)-;(R)-alpha-Methyl-4-nitrobenzylamine
• CAS NO: 22038-87-5
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• Product Categories: API intermediates
• Mol File: 22038-87-5.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 288.8 ºC at 760 mmHg
• Flash Point: 128.4 ºC
• Appearance: /
• Density: 1.199 g/cm³
• Vapor Pressure: 0.00229mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• PKA: 8.31±0.10(Predicted)
• CAS DataBase Reference: (R)-1-(4-NITRO-PHENYL)-ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(4-NITRO-PHENYL)-ETHYLAMINE(22038-87-5)
• EPA Substance Registry System: (R)-1-(4-NITRO-PHENYL)-ETHYLAMINE(22038-87-5)

Safety Data

• Hazardous Substances Data: 22038-87-5(Hazardous Substances Data)

Usage

Description

(R)-1-(4-NITRO-PHENYL)-ETHYLAMINE, also known as R-(+)-α-Methyl-4-nitrobenzylamine, is an organic compound that serves as an essential intermediate in the synthesis of various pharmaceuticals. It is characterized by its unique molecular structure, which features a nitro group attached to a phenyl ring and an ethylamine group, making it a valuable building block in the development of new drugs.

Uses

Used in Pharmaceutical Industry:
(R)-1-(4-NITRO-PHENYL)-ETHYLAMINE is used as a key intermediate in the synthesis of Tamsulosin (T006351) for the treatment of benign prostatic hyperplasia (BPH) and other related conditions. Tamsulosin is a selective α1A-adrenoceptor antagonist that helps relax the muscles in the prostate and bladder neck, improving urine flow and reducing symptoms associated with BPH.
In the synthesis of Tamsulosin, (R)-1-(4-NITRO-PHENYL)-ETHYLAMINE plays a crucial role in the formation of the final product, contributing to its effectiveness in managing BPH symptoms and improving the quality of life for patients suffering from this condition.

InChI:InChI=1/C8H10N2O2/c1-6(9)7-2-4-8(5-3-7)10(11)12/h2-6H,9H2,1H3/t6-/m1/s1

Upstream product

• 42142-15-4 1-(4-nitro-phenyl)-ethylamine 
• 142068-38-0 (S)-1-p-nitrophenyl-1-(2-benzoylhydrazino)ethane 
• 4187-54-6 (S)-N-[1-(4-nitrophenyl)ethyl]acetamide 
• 1434603-08-3 (Z)-1-(4-nitrophenyl)ethanone O-benzyloxime 
• 73744-35-1 (Z)-1-(4-nitrophenyl)ethanone oxime 
• 99-81-0 4-Nitrophenacyl bromide 
• 36283-44-0 N-acetyl-1-phenylethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 100-19-6 (4-nitrophenyl)ethanone 
• 4187-54-6 (R)-N-acetyl-1-(4-nitrophenyl)ethylamine 
• 1121583-62-7 isopropyl 2-propoxyacetate 
• 124-20-9 N-(3-aminopropyl)-1,4-diaminobutane 
• 70249-37-5 3-aminocyclohexa-1,5-dienecarboxylic acid 
• 2354-91-8 (S)-2,2,2-trifluoro-(α-methylbenzyl)acetamide 

Downstream Products

• 3976-22-5 N-[(R)-1-(4-nitro-phenyl)-ethyl]-benzamide 
• 4187-54-6 (R)-N-acetyl-1-(4-nitrophenyl)ethylamine 
• 1621151-93-6 C₂₄H₃₁N₃O₄S 
• 1621508-96-0 C₂₄H₃₁N₃O₄S 
• 1621151-98-1 C₂₆H₃₅N₃O₄S 
• 1621151-99-2 C₂₆H₃₅N₃O₄S 
• 1621152-02-0 C₂₈H₃₉N₃O₄S 
• 1621152-03-1 C₂₈H₃₉N₃O₄S 
• 1621152-16-6 C₂₄H₃₃N₃O₂S 

Relevant articles and documents

Widely applicable background depletion step enables transaminase evolution through solid-phase screening

Directed evolution of transaminases is a widespread technique in the development of highly sought-after biocatalysts for industrial applications. This process, however, is challenged by the limited availability of effective high-throughput protocols to evaluate mutant libraries. Here we report a rapid, reliable, and widely applicable background depletion method for solid-phase screening of transaminase variants, which was successfully applied to a transaminase from Halomonas elongata (HEWT), evolved through rounds of random mutagenesis towards a series of diverse prochiral ketones. This approach enabled the identification of transaminase variants in viable cells with significantly improved activity towards para-substituted acetophenones (up to 60-fold), as well as tetrahydrothiophen-3-one and related substrates. Rationalisation of the mutants was assisted by determination of the high-resolution wild-type HEWT crystal structure presented herein.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

Biocatalytic transamination with near-stoichiometric inexpensive amine donors mediated by bifunctional mono- and di-amine transaminases

The discovery and characterisation of enzymes with both monoamine and diamine transaminase activity is reported, allowing conversion of a wide range of target ketone substrates with just a small excess of amine donor. The diamine co-substrates (putrescine, cadaverine or spermidine) are bio-derived and the enzyme system results in very little waste, making it a greener strategy for the production of valuable amine fine chemicals and pharmaceuticals.