31121-11-6

Basic information

• Product Name: N-(3-Hydroxypropyl)aniline
• Synonyms: 3-Anilino-1-propanol;3-Phenylamino-1-propanol;N-(3-Hydroxypropyl)aniline;3-Anilino-1-propanol, N-(3-Hydroxypropyl)aniline
• CAS NO: 31121-11-6
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• Mol File: 31121-11-6.mol

Chemical Properties

• Boiling Point: 140°C/0.4mmHg(lit.)
• Flash Point: 156.7°C
• Appearance: /
• Density: 1.084g/cm³
• Vapor Pressure: 0.000195mmHg at 25°C
• Refractive Index: 1.5710-1.5750
• Storage Temp.: 0-10°C
• PKA: 14.88±0.10(Predicted)
• CAS DataBase Reference: N-(3-Hydroxypropyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-Hydroxypropyl)aniline(31121-11-6)
• EPA Substance Registry System: N-(3-Hydroxypropyl)aniline(31121-11-6)

Safety Data

• Hazardous Substances Data: 31121-11-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-(3-Hydroxypropyl)aniline is used as a building block for the synthesis of various organic compounds. Its hydroxypropyl group allows for further functionalization and modification, making it a versatile intermediate in the preparation of dyes, pharmaceuticals, and other specialty chemicals.
Used in Material Science:
N-(3-Hydroxypropyl)aniline is used as a component in the development of new materials with specific properties. Its unique structure can contribute to the formation of polymers, coatings, or other materials with tailored characteristics for various applications.
Used in Pharmaceutical Industry:
N-(3-Hydroxypropyl)aniline is used as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its presence in the molecular structure can influence the biological activity and pharmacological properties of the final drug product.
Used in Dye Industry:
N-(3-Hydroxypropyl)aniline is used as a precursor in the production of dyes. Its ability to form various chemical bonds and structures makes it suitable for creating dyes with specific color properties and stability.
It is important to handle and use N-(3-Hydroxypropyl)aniline with caution due to its potential hazards, such as skin and eye irritation, and its toxic effects if ingested or inhaled.

InChI:InChI=1/C9H13NO/c11-8-4-7-10-9-5-2-1-3-6-9/h1-3,5-6,10-11H,4,7-8H2

Upstream product

• 6065-69-6 3-bromopropyl benzoate 
• 62-53-3 aniline 
• 627-30-5 1-chloro-3-hydroxypropane 
• 503-30-0 trimethylene oxide 
• 589-09-3 N-allyl-N-phenylamine 
• 7507-38-2 phenyl-carbamic acid-(3-chloro-propyl ester) 
• 109-78-4 3-Hydroxypropionitrile 
• 2453-03-4 trimethylene carbonate 
• 591-50-4 iodobenzene 
• 156-87-6 propan-1-ol-3-amine 
• 504-63-2 trimethyleneglycol 
• 107-18-6 allyl alcohol 
• 103-84-4 Acetanilid 
• 7617-76-7 3-phenoxypropanamine 

Downstream Products

• 65869-15-0 3-((hydroxyethyl)(phenyl)amino)propan-1-ol 
• 19097-22-4 N-(3-hydroxy-propyl)-N,N-dimethyl-anilinium; iodide 
• 66559-03-3 2-phenoxy-3-phenyl-[1,3,2]oxazaphosphinane 2-sulfide 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 1584642-06-7 (S)-5-chloro-6-(2,6-difluoro-4-(3-(phenylamino)propoxy)phenyl)-N-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 56535-86-5 3-phenyl-1,3-oxazinan-2-one 
• 28819-48-9 2,3-diphenyl-1,3-oxazinane 
• 28819-40-1 tetrahydro-3-phenyl-1,3-oxazine 
• 50-00-0 formaldehyd 
• 74-85-1 ethene 
• 62-53-3 aniline 
• 86651-96-9 2-Chloro-3-phenyl-1,3,2-oxazaphosphorinane 

Relevant articles and documents

Manganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis

Controlling the selectivity in a hydroamination reaction is an extremely challenging yet highly desirable task for the diversification of amines. In this article, a selective formal anti-Markovnikov hydroamination of allyl alcohols is presented. It enables the versatile synthesis of valuable γ-amino alcohol building blocks. A phosphine-free Earth's abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of aliphatic, aromatic amines, drug molecules, and natural product derivatives underwent successful hydroamination with primary and secondary allylic alcohols with excellent functional group tolerance (57 examples). The catalysis could be performed on a gram scale and has been applied for the synthesis of drug molecules. The mechanistic studies revealed the metal-ligand bifunctionality as well as hemilability of the ligand backbone as the key design principle for the success of this catalysis.

Visible light-mediated Smiles rearrangements and annulations of non-activated aromatics

We report the first examples of radical cation Smiles rearrangements. A series of aryloxy alkylamines underwent spontaneous reaction, with the amino group displacing theipso-alkoxy group through substitution, at ambient temperature and under photoactivation by visible light in the presence of an acridinium catalyst (5 mol%). The study was extended to 3-(2-methoxyphenyl)propan-1-amine derivatives, which lack an appropriateipsoleaving group. Here, efficient cyclisations resulted in displacement of the methoxy group and formation of tetrahydroquinolines.

Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols

Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.

Ruthenium-Pincer-Catalyzed Hydrogenation of Lactams to Amino Alcohols

By using the commercially available ruthenium pincer complex (Ru-MACHO-BH) as a catalyst, the challenging direct hydrogenation of lactams and analogues has been successfully accomplished to deliver corresponding value-added amino alcohols in good-to-excellent yields under mild reaction conditions. Remarkably, in addition to N-protected lactams, unprotected ones could also be readily reduced in the presence of a catalytic amount of weak base or even under neutral reaction conditions, which further highlights the broad substrate scope and the protocol efficiency.

Hydroxy Group Directed Catalytic Hydrosilylation of Amides

Chemo- and site-selective hydrosilylation of α- or β-hydroxy amides using organocatalyst B(C6F5)3 and commercially available hydrosilanes is described. This transformation is operative under mild conditions and tolerates a wide range of functional groups. The reaction was applied for selective reduction of a specific amide group of the therapeutically important cyclic peptide cyclosporin A, demonstrating the potential usefulness of this catalytic method in late-stage structural transformations of drug lead molecules.

The synthesis of new 1,3-oxazolidines and 1,3-oxazinanes containing (η6-arene)tricarbonylchromium group based on condensation between aldehydes and amino alcohols

The condensation reactions of β- and γ-amino alcohols containing phenyl or (η6-arene) tricarbonylchromium substituent with formaldehyde, acetaldehyde, benzaldehyde, and (η6-benzaldehyde)tricarbonylchromium were studied. The resulting 1,3-oxazolidine and 1,3-oxazinane products were isolated in a pure form and identified by different physicochemical methods. The effect of (η6-arene)tricarbonylchromium moiety on the reaction process was demonstrated.

The invention relates to a N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method (by machine translation)

The invention discloses a to N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method, the method uses the aromatic halides with amine compound as a raw material, in order to alcohol compound as the solvent, in order to copper or copper compound as a catalyst, in order to as formula I or formula II as shown by a N, N - disubstituted hydrazide as a ligand, the presence of a base, in the 10 - 130 °C generating C - N coupled reaction for generating N - aryl compound: the invention mild reaction conditions, high chemical selectivity, substrate and wide range of application, simplicity of operation, product is simple and easy to separation and environmental protection, the obtained product yield is higher. Wherein R1, R2 is selected from methyl, phenyl, 4 - methoxyphenyl, 4 - nitro-phenyl, 2 - methylphenyl, 2 - isopropyl phenyl; R3 is hydrogen or methoxy. (by machine translation)

Room-Temperature CuI-Catalyzed Amination of Aryl Iodides and Aryl Bromides

A general and effective CuI/N′,N′-diaryl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the amination of aryl iodides and bromides at room temperature with good chemoselectivity between -OH and -NH2 groups. Only 5 mol % of CuI and ligands was needed in this protocol to effect the amination of various aryl bromides and aryl iodides with a wide range of aliphatic and aryl amines (1.3 equiv).

Highly Efficient Mechanochemical N-Arylation of Amino Alcohols and Diamines with Cu0 Powder

Cu0-catalysed arylations have rightly acquired great importance over the last decade. This paper reports the N-arylation of amino alcohols and diamines with iodobenzene derivatives in a planetary ball mill and an investigation into the procedure. This newly developed solvent-free protocol is fast, efficient and occurs under the mechanochemical activation of metallic copper powder. It does not require additional ligands and gives excellent yields. This paper aims to broaden the scope of mechanochemical Cu0-activation and so a new one-pot, two-step synthesis that combines CuAAC and N-arylation has been successfully performed and reported herein.

BIPHENYL COMPOUNDS AND USES THEREOF

The present invention relates to biphenyl compounds and uses thereof in medicine. Specifically, the present invention relates to a compound of Formula (I), or a stereoisomer, a geometric isomer, a tautomer, a mesomer, a racemate, an enantiomer, a diastereoisomer, an N-oxide, a hydrate, a solvate, a metabolite, a hydrolysate, a pharmaceutically acceptable salt or a prodrug thereof. The compound disclosed herein is used as a therapeutic agent particularly a GPR40 agonist for treating diabetes and metabolic disease in a patient.