3541-42-2

Basic information

• Product Name: 2-HYDROXYCINNAMALDEHYDE
• Synonyms: AKOS BC-1812;2-HYDROXYCINNAMALDEHYDE;3-(2-HYDROXYPHENYL)-2-PROPENAL;2-hydroxycinnamicaldehyde;3-(2-hydroxyphenyl)-2-propena;o-hydroxy-cinnamaldehyd;o-hydroxycinnamaldehyde;Hydroxycinnamaldehyde
• CAS NO: 3541-42-2
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16
• Mol File: 3541-42-2.mol

Chemical Properties

• Melting Point: 126 °C
• Boiling Point: 311.3 °C at 760 mmHg
• Flash Point: 131.8 °C
• Appearance: /
• Density: 1.174 g/cm³
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 8.99±0.35(Predicted)
• CAS DataBase Reference: 2-HYDROXYCINNAMALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYCINNAMALDEHYDE(3541-42-2)
• EPA Substance Registry System: 2-HYDROXYCINNAMALDEHYDE(3541-42-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37
• RTECS: GD6565000
• Hazardous Substances Data: 3541-42-2(Hazardous Substances Data)

Upstream product

• 91-64-5 coumarin 
• 1481-93-2 4-hydroxychroman 
• 254-04-6 2H-chromene 
• 14864-24-5 (Z)-2-(3-hydroxyprop-1-en-1-yl)phenol 
• 90-02-8 salicylaldehyde 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 20883-98-1 methyl 2-coumarate 
• 495-79-4 2-hydroxycinnamic acid 
• 51764-86-4 2-hydroxycinnamyl alcohol 
• 33538-94-2 3-(2'-O-acetylphenyl)-2-propenal 

Downstream Products

• 107826-22-2 C₁₀H₁₁NO₂ 
• 107898-00-0 C₁₆H₁₅NO₂ 
• 91-64-5 coumarin 
• 119-84-6 C₆H₄(CH₂CH₂C(O)O) 
• 107853-78-1 C₁₅H₁₃NO₂ 

Relevant articles and documents

Method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and diphosphine ligand used in method

The invention discloses a method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and a diphosphine ligand used in the method. According to the invention, indole-substituted phosphoramidite diphosphine ligand which is stable in air and insensitive to light is synthesized by utilizing a continuous one-pot method, and the indole-substituted phosphoramidite diphosphine ligand and a rhodium catalyst are used for jointly catalyzing to successfully achieve a hydroformylation reaction of aromatic terminal alkyne and terminal conjugated eneyne under the condition of synthesis gas for the first time, so that an olefine aldehyde structure compound can be rapidly and massively prepared, and particularly, a polyolefine aldehyde structure compound which is more difficult to synthesize in the prior art can be easily prepared and synthesized, and a novel method is provided for synthesis and modification of drug molecules, intermediates and chemical products.

Kinetic Resolution and Dynamic Kinetic Resolution of Chromene by Rhodium-Catalyzed Asymmetric Hydroarylation

A highly efficient kinetic resolution and dynamic kinetic resolution of chromene is reported for the first time and they procced by a rhodium-catalyzed asymmetric hydroarylation pathway. This new approach offers versatile access to various chiral 2,3-diaryl-chromanes containing vicinal stereogenic centers, as well as the recovered chiral flavenes, in high yields with excellent ee values (s factor up to 532). Particularly noteworthy is that this strategy can be further extended to the establishment of a dynamic version of the kinetic resolution of chromene acetals and allows complete access to chiral isoflavanes and α-aryl hydrocoumarins.

Organocatalytic asymmetric Michael/hemiacetalization/acyl transfer reaction of α-nitroketones with o-hydroxycinnamaldehydes: Synthesis of 2,4-disubstituted chromans

An organocatalytic asymmetric cascade Michael/hemiketalization/acyl transfer reaction between o-hydroxycinnamaldehydes and α-nitroketones is developed. Prolinol TMS ether catalyst in combination with benzoic acid was found to be the most effective for this reaction which proceeds through an equilibrium of lactols to provide a single diastereomer of enantiopure 2,4-disubstituted chromans.

Bi(OTf)3-catalyzed addition of isocyanides to 2: H -chromene acetals: An efficient pathway for accessing 2-carboxamide-2 H -chromenes

Bismuth triflate (Bi(OTf)3) is identified as an efficient catalyst for the direct addition of isocyanides to 2H-chromene acetals. The large scope of isocyanides and chromene acetals makes them suitable substrates in this catalytic system. By this synthetic strategy, a polyfunctional molecular scaffold, 2-carboxamide-2H-chromenes could be prepared efficiently in one step up to 95% yield. In addition, this efficient and practical protocol proceeded smoothly in the gram scale even when the catalytic loading was reduced to 2 mol%.

SELECTIVE NAV1.7 INHIBITORS FOR THE TREATMENT OF DIABETES

Provided herein are methods for treating or preventing prediabetes or diabetes, or maintaining or lowering blood or plasma glucose or maintaining or lowering blood or plasma glycated hemoglobin comprising administering to a subject in need thereof a therapeutically effective amount of a compound selectively inhibiting NaVl.7. In particular, provided herein are processes for the preparation of and intermediates used in the preparation of compounds selectively inhibiting NaV1.7, such as the compounds of Formula (I) or compounds of Formula (I').

SODIUM CHANNEL MODULATORS FOR THE TREATMENT OF PAIN AND DIABETES

Provided herein are sodium channel modulating Compounds, in particular NaV1.7 modulating compounds of Formula I or compounds of Formula I′: In particular, provided herein are processes for the preparation of, intermediates used in the preparation of, pharmaceutical compositions comprising, and therapeutic methods comprising administering such compounds. In particular, provided herein are compounds for the treatment of pain and diabetes.

Trimethylsilyl iodide mediated one-pot synthesis of 2-allyl-2H-chromenes

A new and efficient metal-free trimethylsilyl iodide (TMSI) catalyzed one-pot synthesis of 2-allyl-2H-chromenes has been developed that takes place under mild conditions. The synthesis proceeds through a Wittig reaction by using (triphenylphosphoranylidene)acetaldehyde to form an ohydroxycinnamaldehyde derivative followed by a tandem isomerization and C-O and C-C bond-forming reactions. The procedure was carried out at room temperature in the presence of 20 mol-% of TMSI and allyltrimethylsilane in tetrahydrofuran (THF) and provided the 2-allyl-2H-chromenes in good to excellent yields.

Synthesis and biological activity of cinnamaldehydes as angiogenesis inhibitors

A series of 2-hydroxycinnamaldehyde derivatives was synthesized for examing a structure-activity relationship for inhibition of angiogenesis. The anti-angiogenic effects of 2'-substituted cinnamaldehydes and related analogs were determined in a chick embryo chorioallantoic membrane assay system.

Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1)

Procaryotic (bacterial) dioxygenase-catalysed asymmetric dihydroxylation of chromene and 2,2-dimethylchromene to yield the (4S)-enantiomers of the corresponding cis-diols exclusively is reported. The epoxide, and derived cis- and trans-diol products from the previously reported eucaryotic (mammalian) metabolism of precocene-1 (7-methoxy-2,2-dimethylchromene), and the corresponding epoxide and diol derivatives of chromene and 2,2-dimethylchromene, have now been obtained in enantiopure form by chemical resolution of the corresponding bromohydrins using methoxy-(trifluoromethyl)phenylacetic acid (MTPA) or camphanate esters. The absolute configurations of the epoxides, cis- and trans-diols have been determined by chemical synthesis from, and stereochemical correlation with, the corresponding camphanate and MTPA esters. X-Ray crystal structure analysis has provided an unequivocal method for assignment of the absolute stereochemistry in each case.