16452-01-0

Basic information

• Product Name: 3-METHOXY-4-METHYLANILINE
• Synonyms: 3-methoxy-4-methyl-benzenamin;o-cresidine;2-METHYL-5-ANISIDINE;2-METHOXY-4-AMINOTOLUENE;4-AMINO-2-METHOXYTOLUENE;3-METHOXY-4-METHYLBENZENAMINE;3-METHOXY-4-METHYLANILINE;Benzenamine, 3-methoxy-4-methyl-
• CAS NO: 16452-01-0
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 240-500-8
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Anilines, Amides & Amines;Anisoles, Alkyloxy Compounds & Phenylacetates;NULL
• Mol File: 16452-01-0.mol

Chemical Properties

• Melting Point: 56-60°C
• Boiling Point: 252.03°C (rough estimate)
• Flash Point: >113℃
• Appearance: Brown chunky solid
• Density: 1.0630 (rough estimate)
• Vapor Pressure: 0.021mmHg at 25°C
• Refractive Index: 1.5647 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 4.61±0.10(Predicted)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: 3-METHOXY-4-METHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXY-4-METHYLANILINE(16452-01-0)
• EPA Substance Registry System: 3-METHOXY-4-METHYLANILINE(16452-01-0)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• RIDADR: UN2811
• WGK Germany: 3
• RTECS: CY0888000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 16452-01-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxy-4-methylaniline is used as a key intermediate in the synthesis of 8-methoxy-7-methylalloxazine, a compound with potential applications in the pharmaceutical industry. Its role in the production of this alloxazine derivative highlights its importance in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
3-Methoxy-4-methylaniline serves as a valuable building block in various chemical synthesis processes. Its unique structure allows for further functionalization and modification, making it a versatile component in the creation of a wide range of organic compounds for different applications, including pharmaceuticals, agrochemicals, and specialty chemicals.

Air & Water Reactions

Sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

3-METHOXY-4-METHYLANILINE neutralizes acids in weakly exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. Reacts with oxidizing agents .

Fire Hazard

3-METHOXY-4-METHYLANILINE is probably combustible.

InChI:InChI=1/C8H11NO/c1-6-3-4-7(9)5-8(6)10-2/h3-5H,9H2,1-2H3

Upstream product

• 13120-77-9 2-methyl-5-nitroanisole 
• 52200-69-8 1-bromo-2-methoxy-3-methylbenzene 
• 7664-41-7 ammonia 
• 5428-54-6 2-methyl-5-nitrophenol 
• 13319-71-6 2-bromo-6-methylphenol 

Downstream Products

• 51307-87-0 acetic acid-(3-methoxy-4-methyl-anilide) 
• 111663-90-2 4-methoxy-5-methyl-2,3-diphenyl-indole 
• 105973-39-5 2-Methyl-5-piperidino-phenol 
• 4274-06-0 2-(2-chloro-4-nitro-phenylazo)-5-methoxy-4-methyl-aniline 
• 103230-79-1 2-(4-chloro-2-nitro-phenylazo)-5-methoxy-4-methyl-aniline 
• 107624-19-1 2-methyl-5-(phenylamino)phenol 
• 56140-36-4 3-Methoxy-4-methyl-N,N-dimethylanilin 
• 97581-31-2 7-methoxy-6-methylquinoline 
• 72685-18-8 (-)-1-Deoxy-1-<(3-methoxy-4-methylphenyl)-amino>-D-ribitol 
• 114474-35-0 5-Methoxy-4-methyl-2-[4-(1-phenyl-1H-pyrazol-4-yl)-phenylazo]-phenylamine 
• 24973-22-6 3-methoxy-4-methylbenzaldehyde 
• 112949-95-8 4-(5-methoxy-6-methyl-benzotriazol-2-yl)-stilbene-2-sulfonyl chloride 
• 24224-28-0 2-methoxy-3-methyl-9H-carbazole 
• 36013-67-9 N-Acetyl-3,5-diiod-L-tyrosinaethylester-4'-methyl-3'-methoxyphenylaeter 

Relevant articles and documents

Preparation method of 6-tert-butyl-3 ', 3', 3-trimethyl pyran [3, 2-a] carbazole

The invention provides a preparation method of 6-tert-butyl-3 ', 3', 3-trimethyl pyran [3, 2-a] carbazole, and belongs to the technical field of medicines. The method comprises the following steps: S1) carrying out hydrogenation reduction reaction under palladium-carbon catalysis to obtain an intermediate 1; S2) carrying out diazotization reduction reaction on the intermediate 1 to obtain an intermediate 2; S3) performing cyclization reaction on the intermediate 2 and 4-tert-butyl cyclohexanone in an acidic solvent to obtain an intermediate 3; S4) dehydrogenating and aromatizing the intermediate 3 under palladium-carbon catalysis to obtain to obtain an intermediate 4; S5) performing boron tribromide demethylation on the intermediate 4 to obtain an intermediate 5, S6) performing cyclizationreaction on the intermediate 5 and 3-methylcrotonaldehyde under the catalysis of tetraisopropyl titanate to obtain an end product crude product, and S7) recrystallizing the crude product with ethanolto obtain 6-tert-butyl-3 ', 3', 3-trimethyl pyran [3, 2-a] carbazole with purity of 99% or above.

Development of 2-thioxoquinazoline-4-one derivatives as dual and selective inhibitors of dynamin-related protein 1 (Drp1) and puromycin-sensitive aminopeptidase (PSA)

An established inhibitor ot dynamin-related protein 1 (Drp1), 3-(2,4-dichloro-5-methoxyphenyl)- 2- thioxoquinazoline-4-one (mdivi-1), was recently reported also to show potent puromycin-sensitive aminopeptidase (PSA)-inhibitory activity. Herein, we report structural development of mdivi-1 derivatives and structure-activity relationship (SAR) analysis of the synthesized compounds, as well as the structurally related PSA-specific inhibitor 3-(2,6-diethylphenyl)quinazoline-2,4-dione (PAQ-22), with the aim of identifying key structural features for inhibitory activity in order to develop selective inhibitors of Drpl, which is a potential target for treatment of Huntington's disease. Among the synthesized compounds, 3-(4-chloro3methoxyphenyl)-2-thioxoquinazoline-4-one 10g) exhibited more potent Drpl-inhibitory activity than mdivi-1 with high selectivity for Drpl over PSA.

Efficient construction of pyrano [3, 2-a]carbazoles: Application to a biomimetic total synthesis of cyclized monoterpenoid pyrano [3, 2-a]carbazole Alkaloids

We have developed a highly efficient route to 2-hydroxy-3-methyl-carbazole (1) via a palladium-catalyzed construction of the carbazole skeleton. Using 1 as relay compound, different methods for annulations of pyran rings by reaction with terpenoid building blocks have been tested. The Lewis acid promoted reaction of 1 with prenal (21) opened up an efficient route to girinimbine (3) and the corresponding reaction with citral (25) afforded mahanimbine (5). Oxidation of compounds 3 and 5 provided murraya-cine (4) and murrayacinine (6). Following the biogenetic proposal, mahanim-bine (5) has been exploited for efficient biomimetic syntheses of the cyclized monoterpenoid pyrano[3, 2-a]carbazole alkaloids cyclomahanimbine (7), maha-nimbidine (8) and bicyclomahanimbine (9). The interconversions of 5, 7, 8 and 9 are described and mechanistic implications are discussed. Structural assignments are unambiguously verified by X-ray crystal structure determinations. Moreover, cyclomahanimbine (7) was transformed into murrayazolinine (10) and exozoline (11).

Iron-mediated total synthesis of 2,7-dioxygenated carbazole alkaloids

We describe the efficient iron-mediated total synthesis of clausine O, clausine H (clauszoline-C) and anti-HIV active 7-methoxy-O-methylmukonal and clausine K (clauszoline-J). Consecutive C-C and C-N bond formations between 3-methoxy-4-methylaniline and a cyclohexadienyliumiron complex salt afforded 2,7-dimethoxy-3-methylcarbazole, which served as common intermediate en route to the four alkaloids. Four 2,7-dioxygenated carbazole alkaloids, clausine O, clausine H (clauszoline-C), and the anti-HIV active 7-methoxy-O-methylmukonal and clausine K (clauszoline-J), have been synthesized by using an iron-mediated approach for the construction of the carbazole framework. Copyright

HYDANTOIN DERIVATIVES USEFUL AS KV3 INHIBITORS

The invention provides compounds of formula (I): Said compounds being inhibitors of Kv3 channels and of use in the prophylaxis or treatment of related disorders.

HYDANTOIN DERIVATIVES USEFUL AS KV3 INHIBITORS

The invention provides compounds of formula (I): Said compounds being inhibitors of Kv3 channels and of use in the prophylaxis or treatment of related disorders.

IMIDAZOLIDINEDIONE DERIVATIVES

The invention provides a compound of formula (Ia), and pharmaceutically acceptable salts thereof. The invention also provides use of the compounds or salts as modulators of Kv3.1 and/or Kv3.2, and in the treatment of diseases or disorders where a modulator of Kv3.1 and/or Kv3.2 is required, such as depression and mood disorders, hearing disorders, schizopherenea, substance abuse disorders, sleep disorders or epilepsy.

Optimization of 1,2,3,4-tetrahydroacridin-9(10 H)-ones as antimalarials utilizing structure-activity and structure-property relationships

Antimalarial activity of 1,2,3,4-tetrahydroacridin-9(10H)-ones (THAs) has been known since the 1940s and has garnered more attention with the development of the acridinedione floxacrine (1) in the 1970s and analogues thereof such as WR 243251 (2a) in the 1990s. These compounds failed just prior to clinical development because of suboptimal activity, poor solubility, and rapid induction of parasite resistance. Moreover, detailed structure-activity relationship (SAR) studies of the THA core scaffold were lacking and SPR studies were nonexistent. To improve upon initial findings, several series of 1,2,3,4-tetrahydroacridin-9(10H)-ones were synthesized and tested in a systematic fashion, examining each compound for antimalarial activity, solubility, and permeability. Furthermore, a select set of compounds was chosen for microsomal stability testing to identify physicochemical liabilities of the THA scaffold. Several potent compounds (EC50 100 nM) were identified to be active against the clinically relevant isolates W2 and TM90-C2B while possessing good physicochemical properties and little to no cross-resistance.

HETEROCYCLIC COMPOUNDS AND THEIR USES

Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjoegren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity, The present invention also enables methods for treating cancers that are mediated, dependent on or associated with p110 activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo-dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia ( T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.

Acid-free synthesis of carbazoles and carbazolequinones by intramolecular Pd-catalyzed, microwave-assisted oxidative biaryl coupling reactions efficient syntheses of murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine

A mild and. efficient methodology for the synthesis of oxygenated. carbazoles from diarylamines under non-acidic conditions was developed, based on a palladium-catalyzed, microwave-assisted double C-H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine. The scope of the reaction was also expanded, to include the synthesis of benzo fused carbazolequinones. Wiley-VCH Verlag GmbH & Co. KGaA.