138969-57-0

Basic information

• Product Name: 2,3-Dihydro-1H-indol-2-ylmethanol
• Synonyms: 2,3-Dihydro-1H-indole-2-methanol
• CAS NO: 138969-57-0
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149
• Mol File: 138969-57-0.mol

Chemical Properties

• Boiling Point: 309.1±11.0 °C(Predicted)
• Appearance: /
• Density: 1.120±0.06 g/cm3(Predicted)
• PKA: 14.42±0.10(Predicted)
• CAS DataBase Reference: 2,3-Dihydro-1H-indol-2-ylmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dihydro-1H-indol-2-ylmethanol(138969-57-0)
• EPA Substance Registry System: 2,3-Dihydro-1H-indol-2-ylmethanol(138969-57-0)

Safety Data

• Hazardous Substances Data: 138969-57-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dihydro-1H-indol-2-ylmethanol is used as a pharmaceutical candidate for its anti-inflammatory and anti-cancer properties. It has the potential to modulate various biological pathways and mechanisms involved in inflammation and cancer, offering therapeutic benefits in the treatment of these conditions.
Used in Drug Development:
2,3-Dihydro-1H-indol-2-ylmethanol is used as a scaffold for the design of new compounds with potential therapeutic applications. Its unique chemical structure and biological activities make it a valuable starting point for the development of novel drugs targeting various diseases and conditions.
Used in Antioxidant Applications:
2,3-Dihydro-1H-indol-2-ylmethanol is used as an antioxidant agent, providing protection against oxidative stress and damage caused by reactive oxygen species. Its antioxidant properties can be beneficial in the prevention and treatment of various diseases and conditions associated with oxidative stress.
Used in Antimicrobial Applications:
2,3-Dihydro-1H-indol-2-ylmethanol is used as an antimicrobial agent, exhibiting activity against various microorganisms, including bacteria and fungi. Its antimicrobial properties can be utilized in the development of new antimicrobial drugs and therapies to combat infections and drug-resistant pathogens.
Used in Synthesis of Biologically Active Compounds:
2,3-Dihydro-1H-indol-2-ylmethanol is used as a building block in the synthesis of various biologically active compounds. Its unique chemical structure and properties make it a versatile component in the development of new molecules with potential applications in medicine, agriculture, and other fields.

Upstream product

• 59040-84-5 indoline-2-carboxylic acid methyl ester 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 76182-48-4 methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate 
• 33140-80-6 methyl indol-1-ylacetate 
• 39597-68-7 (2,3-dihydro-indol-1-yl)-acetic acid methyl ester 
• 172647-94-8 methyl 7-azaindol-1-acetate 
• 172648-34-9 ethyl 1-methyl-7-azaindole-2-carboxylate 
• 50501-07-0 (S)-2,3-dihydro-1H-indole-2-carboxylic acid,ethyl ester 
• 24621-70-3 2-(hydroxymethyl)indole 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 111457-18-2 N-(2-allyl-phenyl)-benzamide 
• 32704-22-6 2-allyl-phenylamine 
• 589-09-3 N-allyl-N-phenylamine 

Downstream Products

• 150535-14-1 2-<(methoxycarbonyl)methyl>indoline 
• 135829-04-8 benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate 
• 321744-15-4 (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole 

Relevant articles and documents

Design and synthesis of novel indoline-(thio)urea hybrids

A series of novel indoline-(thio)urea were designed and prepared using indoline(s) as a new platform and tested as organocatalysts in the Michael and Morita–Baylis–Hillman reactions. Most of the compounds were found to be very active catalysts although they did not promote the enantioselectivity. As agents for the conversion of thiocarbonyl compounds into carbonyl compounds, potentials of PIFA and DDQ were also displayed. Furthermore, DFT calculations rationalized the experimentally observed non-enantioselectivity of the catalysts.

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst

The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.

Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes

Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).

Hexafluoroisopropanol: A powerful solvent for the hydrogenation of indole derivatives. Selective access to tetrahydroindoles or cis-fused octahydroindoles

Pd/C in HFIP was used to hydrogenate indole derivatives under relatively mild conditions, leading to potential synthetic intermediates of bioactive compounds. Depending on their substitution, tetrahydroindoles or octahydroindoles could selectively be obtained.

Kinetic resolutions of lndolines by a nonenzymatic acylation catalyst

The first method for the kinetic resolution of indolines through catalytic N-acylation is described. To improve the selectivity factor, new planar-chiral PPY-derived catalysts were synthesized, wherein the chiral environment was systematically modified. This work provides a rare example of a nonenzyme-based acylation catalyst for the kinetic resolution of amines. Copyright

PYRIMIDINE-5-CARBOXAMIDE COMPOUNDS, PROCESS FOR PRODUCING THE SAME AND USE THEREOF

A compound of the formula wherein R1 is a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 nitrogen atom(s), which heterocycle is attached by a secondary nitrogen atom constituting the heterocycle; X is an oxygen atom, a nitrogen atom optionally substituted by a hydrocarbon group having 1 to 5 carbon atom(s) or a sulfur atom optionally oxidized with 1 or 2 oxygen, Y is a bond or a C1-5 alkylene group, R2 is (1) a hydrogen atom, (2) a hydroxy group, (3) a C1-5 alkoxy group, (4) a C1-5 alkylthio group, (5) a carbocycle having 3 to 15 carbon atoms or (6) a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 heteroatom(s), provided that when Y is a bond, R2 is a carbocycle having 3 to 15 carbon atoms or a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 heteroatom(s) and; one of R3 and R4 is a hydrogen atom or a group of the formula: -Z-R5 (Z is a bond or C1-10 alkylene group optionally having substituent(s) and R5 is (1) a hydrogen atom, (2) a hydroxy group, (3) a C1-5 alkoxy group, (4) a nitrile group, (5) a C1-5 alkoxy-carbonyl group, (6) a carboxyl group, (7) a carbamoyl group, (8) a (mono or di-C1-5 alkyl)carbamoyl group, (9) an amino group, (10) a (di or mono-C1-5 alkyl)amino group, (11) a (C1-5 alkoxy-carbonyl)amino group, (12) a C1-5 alkylthio group, (13) a carbocycle having 3 to 15 carbon atoms or (14) a heterocycle having a skeleton consisting of 3 to 15 atoms including 1 to 5 heteroatom(s)); the other is a group of the formula: -Z-R5 (Z and R5 are as defined above); and R3 and R4 may form, together with the adjacent nitrogen atom, a heterocycle having a skeleton consisting of 3 to 15 atoms, which heterocycle is attached by a secondary nitrogen atom constituting the heterocycle, wherein the above-mentioned heterocycle and a carbocycle having 3 to 15 carbon atoms are each optionally substituted by substituent(s) selected from the group consisting of C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C7-16 aralkyl, C3-8 cycloalkyl, C3-8 cycloalkenyl, C6-14 aryl, C1-8 alkoxy, C1-3 alkylenedioxy, hydroxy, halogen atom, amino, (di or mono-C1-5 alkyl)amino, (C1-5 alkoxy-carbonyl)amino, (C1-5 acyl)amino, (C1-5 acyl) (C1-5 alkyl)amino, C1-5 alkylthio, nitrile, nitro, C1-5 alkoxy-carbonyl, carboxyl, C1-5 alkyl-carbonyloxy, oxo, thioxo, C1-6 acyl group, sulfamoyl and (di or mono-C1-5 alkyl)sulfamoyl, or a salt thereof or a prodrug thereof have a superior cGMP specific phosphodiesterase (PDE) inhibitory activity, and can be used as an agent for the prophylaxis or treatment of cardiovascular diseases such as angina pectoris, heart failure, cardiac infarction, hypertension, arteriosclerosis and the like, allergic diseases such as asthma, or disorders of male or female genital function and the like.

Heterocycle carboxamides as antiviral agents

The present invention provides a compound of formula I which is useful as antiviral agents, in particular, as agents against viruses of the herpes family.

Heterocyclic compounds having anti-diabetic activity and their use

Compounds of formula (I): STR1 [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.

Tricyclic quinoxalinediones

Tricyclic quinoxalinediones of the formula: STR1 wherein X is alkyl, halogen, cyano, trifluoromethyl, nitro, hydroxy, amino, etc.; R 1 is H, etc.; R 2 is H, alkyl, cycloalkyl, alkenyl, alkynyl, cycloalkylalkyl, arylalkyl, substituted arylalkyl, aryl, or substituted aryl; W is H, CO 2 R 3, CO 2 Y, CONR 3 R 4, CONR 3 Y, CON(OR 3)R 4, COR 3, CN, tetrazolyl, or substituted alkyl; R 3 and R 4 independently are H, alkyl, cycloalkyl, alkenyl, alkynyl, etc.; Y is mono-substituted alkyl or di-substituted alkyl; and n is an integer 0 or 1, or a pharmaceutically acceptable salt thereof, which are useful as a selective antagonist of glutamate receptor for the treatment or prevention of various diseases in animals including human being, for example, minimizing damage of central nervous system induced by ischaemic or hypoxylic conditions, treatment and/or prevention of neurodegenerative disorders, and further analgesics, antidepressants, anxiolitics, and anti-schizophrenics.

AMINO-SUBSTITUTED PYRAZOLES HAVING CRF ANTAGONISTIC ACTIVITY

The invention relates to compounds of the formula I STR1 and to pharmaceutically acceptable salts thereof, wherein Z, A, Y, X 1, R. sub.1, R 2, and R 3 are as defined herein. The invention further relates to pharmaceutical compositions containing, and to