1504-63-8

Basic information

• Product Name: 4-NITROCINNAMYL ALCOHOL
• Synonyms: 3-(4-nitrophenyl)-2-propen-1-o;P-NITROCINNAMYL ALCOHOL;3-(4-NITROPHENYL)-2-PROPEN-1-OL;3-(P-NITROPHENYL)-2-PROPEN-1-OL;4-Nitrociamyl alcohol;1-Hydroxy-3-(4-nitrophenyl)-2-propene;3-(4-Nitrophenyl)-2-propenol;3-(4-Nitrophenyl)prop-2-en-1-ol
• CAS NO: 1504-63-8
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.17
• Product Categories: Benzhydrols, Benzyl & Special Alcohols;Aromatics Compounds;Aromatics;Acyclic;Alkenes;Organic Building Blocks;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 1504-63-8.mol
• Article Data: 30

Chemical Properties

• Melting Point: 127-128 °C(lit.)
• Boiling Point: 311.69°C (rough estimate)
• Flash Point: 144 °C
• Appearance: Powder
• Density: 1.2822 (rough estimate)
• Vapor Pressure: 9.47E-05mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Solubility: Soluble in chloroform, dichloromethane and ethyl Acetate.
• PKA: 14.42±0.10(Predicted)
• BRN: 1948238
• CAS DataBase Reference: 4-NITROCINNAMYL ALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROCINNAMYL ALCOHOL(1504-63-8)
• EPA Substance Registry System: 4-NITROCINNAMYL ALCOHOL(1504-63-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1504-63-8(Hazardous Substances Data)

Usage

Description

4-Nitrocinnamyl alcohol, with the CAS number 1504-63-8, is a substituted benzyl alcohol characterized by its light yellow crystalline solid appearance. It is known for its reactivity in organic synthesis, particularly undergoing chlorination with tosyl chloride (TsCl) to produce 4-nitrocinnamyl chloride.

Uses

Used in Organic Synthesis:
4-Nitrocinnamyl alcohol is used as a synthetic intermediate for the production of various organic compounds. Its ability to undergo chlorination with tosyl chloride makes it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Nitrocinnamyl alcohol is used as a key component in the development of new drugs. Its unique chemical properties allow it to be incorporated into the molecular structures of potential therapeutic agents, contributing to their overall efficacy and safety.
Used in Agrochemical Industry:
4-Nitrocinnamyl alcohol also finds application in the agrochemical industry, where it is utilized in the synthesis of novel pesticides and other crop protection agents. Its versatility in organic synthesis enables the creation of new molecules with improved biological activity and selectivity.
Used in Specialty Chemicals:
In the specialty chemicals sector, 4-Nitrocinnamyl alcohol is employed as a raw material for the production of various high-value chemicals. Its unique reactivity and functional groups make it an attractive candidate for the development of new materials with specific properties, such as improved stability, reactivity, or selectivity.

InChI:InChI=1/C9H9NO3/c11-7-1-2-8-3-5-9(6-4-8)10(12)13/h1-6,11H,7H2/b2-1+

Upstream product

• 1734-79-8 3-(4-nitrophenyl)-2-propenal 
• 61921-33-3 p-nitrocinnamoyl chloride 
• 61266-32-8 3-(4-nitrophenyl)prop-2-yn-1-ol 
• 636-98-6 p-nitrobenzene iodide 
• 41234-97-3 2,2-dibutyl-2,5-dihydro-1,2-oxastannole 
• 619-89-6 p-nitrocinnamic acid 
• 24393-61-1 ethyl (E)-3-(4-nitrophenyl)-2-propenoate 
• 71269-07-3 3-(4-nitrophenyl)-2-propenyl chloride 
• 953-26-4 ethyl 4-nitrocinnamate 
• 637-57-0 methyl 4-nitrocinnamate 
• 555-16-8 4-nitrobenzaldehdye 
• 637-57-0 p-nitrocinnamic acid methyl ester 
• 882-06-4 4-nitro-trans-cinnamic acid 

Downstream Products

• 99361-40-7 p-Nitro-cinnamyl-thiocyanat 
• 1507-90-0 p-nitrocinnamyl chloride 
• 75059-04-0 1-(p-nitrophenyl)-3-bromopropene-1 
• 1885-06-9 [(2R,3S)-3-(4-Nitro-phenyl)-oxiranyl]-methanol 
• 143058-48-4 [(2S,3R)-3-(4-Nitro-phenyl)-oxiranyl]-methanol 
• 83101-11-5 γ-(4-Aminophenyl)propanol-hydrochlorid 
• 1734-79-8 3-(4-nitrophenyl)-2-propenal 
• 461461-89-2 (Z)-3-(4-Amino-phenyl)-prop-2-en-1-ol 
• 461461-89-2 4-aminocinnamyl alcohol 
• 14572-92-0 3-(4-aminophenyl)propan-1-ol 
• 83101-14-8 4-(3-bromo-propyl)-benzonitrile 
• 83101-12-6 4-(3-Hydroxypropyl)benzonitrile 
• 83101-16-0 γ-(4-Cyanphenyl)propylacetaminomalonsaeurediethylester 
• 83101-33-1 5-(4-Cyano-phenyl)-2-(toluene-4-sulfonylamino)-pentanoyl chloride 

Relevant articles and documents

Design, synthesis and antitumor activity evaluation of Chrysamide B derivatives

Marine natural products derived from special or extreme environment provide an important source for the development of anti-tumor drugs due to their special skeletons and functional groups. In this study, based on our previous work on the total synthesis and structure revision of the novel marine natural product Chrysamide B, a group of its derivatives were designed, synthesized, and subsequently of which the anti-cancer activity, structure-activity relationships and cellular mechanism were explored for the first time. Compared with Chrysamide B, better anti-cancer performance of some derivatives against five human cancer cell lines (SGC-7901, MGC-803, HepG2, HCT-116, MCF-7) was observed, especially for compound b-9 on MGC-803 and SGC-7901 cells with the IC 50 values of 7.88 ± 0.81 and 10.08 ± 1.08 μM, respectively. Subsequently, cellular mechanism study suggested that compound b-9 treatment could inhibit the cellular proliferation, reduce the migration and invasion ability of cells, and induce mitochondrial-dependent apoptosis in gastric cancer MGC-803 and SGC-7901 cells. Furthermore, the mitochondrial-dependent apoptosis induced by compound b-9 is related with the JAK2/STAT3/Bcl-2 signaling pathway. To conclude, our results offer a new structure for the discovery of anti-tumor lead compounds from marine natural products.

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.

Copper(i) pyrimidine-2-thiolate cluster-based polymers as bifunctional visible-light-photocatalysts for chemoselective transfer hydrogenation of α,β-unsaturated carbonyls

The photoinduced chemoselective transfer hydrogenation of unsaturated carbonyls to allylic alcohols has been accomplished using cluster-based MOFs as bifunctional visible photocatalysts. Assemblies of hexanuclear clusters [Cu6(dmpymt)6] (1, Hdmpymt = 4,6-dimethylpyrimidine-2-thione) as metalloligands with CuI or (Ph3P)CuI yielded cluster-based metal organic frameworks (MOFs) {[Cu6(dmpymt)6]2[Cu2(μ-I)2]4(CuI)2}n (2), {[Cu6(dmpymt)6]2[Cu2(μ-I)2]4}n (3), respectively. Nanoparticles (NPs) of 2 and 3 served both as photosensitizers and photocatalysts for the highly chemoselective reduction of unsaturated carbonyl compounds to unsaturated alcohols with high catalytic activity under blue LED irradiation. The photocatalytic system could be reused for several cycles without any obvious loss of efficiency.