205877-13-0

Basic information

• Product Name: Benzenemethanol, 2-amino-3-methoxy- (9CI)
• Synonyms: Benzenemethanol, 2-amino-3-methoxy- (9CI);2-Amino-3-methoxybenzenemethanol
• CAS NO: 205877-13-0
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.17844
• Product Categories: METHOXY
• Mol File: 205877-13-0.mol

Chemical Properties

• Melting Point: 38 °C
• Boiling Point: 312.6±27.0 °C(Predicted)
• Appearance: /
• Density: 1.182±0.06 g/cm3(Predicted)
• PKA: 14.28±0.10(Predicted)
• CAS DataBase Reference: Benzenemethanol, 2-amino-3-methoxy- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, 2-amino-3-methoxy- (9CI)(205877-13-0)
• EPA Substance Registry System: Benzenemethanol, 2-amino-3-methoxy- (9CI)(205877-13-0)

Safety Data

• Hazardous Substances Data: 205877-13-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Benzenemethanol, 2-amino-3-methoxy(9CI), is utilized as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for versatile reactions and the formation of a wide range of derivatives, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Benzenemethanol, 2-amino-3-methoxy(9CI), serves as a crucial component in the development of new drugs. Its unique chemical properties enable it to be incorporated into drug molecules, potentially enhancing their therapeutic effects and selectivity. Researchers leverage its reactivity and structural features to design and synthesize novel drug candidates for the treatment of various diseases and conditions.
Used in Chemical Research:
Benzenemethanol, 2-amino-3-methoxy(9CI), is also employed in chemical research to study the properties and reactions of aromatic amines. Its unique structure provides insights into the reactivity and selectivity of various functional groups, contributing to a deeper understanding of organic chemistry and the development of new synthetic methods and strategies.

Upstream product

• 53055-04-2 (3-methoxy-2-nitrophenyl)methanol 
• 3177-80-8 2-amino-3-methoxybenzoic acid 
• 4920-80-3 3-methoxy-2-nitrobenzoic acid 

Downstream Products

• 1026879-61-7 1-(2-Hydroxymethyl-6-methoxy-phenyl)-3-pentyl-urea 
• 1026637-41-1 4-(2-hydroxymethyl-6-methoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester 
• 78684-63-6 (-)-Mianserin 
• 148726-41-4 1-(2-Hydroxy-6-hydroxymethyl-phenyl)-3-pentyl-urea 

Relevant articles and documents

Synthesis and pharmacological testing of 1,2,3,4,10,14b-hexahydro-6-methoxy-2-methyldibenzo[c,f]pyrazino[1,2-a]azepin and its enantiomers in comparison with the two antidepressants mianserin and mirtazapine

The synthesis and resolution of 1,2,3,4,10,14b-hexahydro-6-methoxy-2-methy[dibenzo[c,f]pyrazino [1,2-α]azepin (6-methoxymianserin, 6) are described. Furthermore, the in vitro and in vivo effects of 6 and its enantiomers are presented. 6 displayed high aff

Metal-Free C-C/C-N/C-C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[ b]indolines

A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.

Asymmetric synthesis of isoquinolinonaphthyridines catalyzed by a chiral Br?nsted acid

A catalytic asymmetric method for the synthesis of chiral isoquinolinonaphthyridines has been developed. A chiral disulfonimide catalyzes a redox cyclization reaction between 2-methyl-3-aldehydeazaarenes and 1,2,3,4-tetrahydroisoquinolines to deliver a range of isoquinolinonaphthyridines with good to high yields (up to 91%) and up to 92:8 er.

Decarboxylative [4+2] Cycloaddition by Synergistic Palladium and Organocatalysis

A novel reaction based on synergistic catalysis, combining palladium- and organocatalysis has been developed. The palladium catalyst activates vinyl benzoxazinanones via a decarboxylation to undergo a [4+2] cycloaddition with iminium-ion activated α,β-uns

The role of methoxy substituents in regulating the activity of selenides that serve as spirodioxyselenurane precursors and glutathione peroxidase mimetics

A series of o-(hydroxymethyl)phenyl selenides containing single or multiple methoxy substituents was synthesized, and the rate at which each compound catalyzed the oxidation of benzyl thiol to its disulfide with excess hydrogen peroxide was measured. This

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.

PHOSPHONIC ACID DERIVATES AND THEIR USE AS P2Y12 RECEPTOR ANTAGONISTS

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Synthesis of new benzoxazinone derivatives as neuropeptide Y5 antagonists for the treatment of obesity

Screening of our internal chemical collection against the neuropeptide Y5 (NPY Y5) receptor allowed the identification of a benzoxazine derivative 5f as a hit that showed moderate affinity (IC50 = 300 nM). With the aim of improving the in vitro potency, a series of 2-benzoxazinone derivatives have been synthesized and tested for NPY Y5 activity. Most of the compounds were found to be potent and selective NPY Y5 antagonists having nanomolar binding affinities for the NPY Y5 receptor and showing functional antagonism in the forskolin-induced cyclic AMP test. Prelimminary studies in order to understand the structure-activity relationship were undertaken. Selected compounds were further evaluated for in vivo efficacy, affording the lead compound 2-[4-(8-methyl-2-oxo-4H-benzo[d][1,3]oxazin-1-yl)piperidin-1-yl] -N-(9-oxo-9H-fluoren-3-yl)acetamide 5p, which displayed in vivo activity reducing food intake in rodents.

Benzocarbapenems from indoles

The 8,8a-dihydroazeto[1,2-a]indol-2(1H)-ones (benzocarbapenems) 1a, 16, 17, 22, 27, 35 and 36 have been prepared by cyclodehydration of the corresponding β-amino acids, these amino acids being obtained by reduction of the analogous 2-substituted or 2,7-disubstituted indoles. The hydroxy group of compound 36 is designed to mimic the carboxylic acid function of the carbapenems on the basis of molecular modelling. The azetidinones 1a and 27, which are unsubstituted at the methylene group of the four-membered ring, are unstable and highly susceptible to ring opening by nucleophiles but the compounds 22,35 and 36 with two methyl substituents at this position are much more stable. The carbonyl stretching frequency in the IR is close to 1770 cm-1 for all the azetidinones except the phenol 36 for which the absorption is at 1735 cm-1. An X-ray crystal structure of compound 36 is reported.

Structure-activity relationship of a series of phenylureas linked to 4- phenylimidazole. Novel potent inhibitors of acyl-CoA:cholesterol O- acyltransferase with antiatherosclerotic activity. 2

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