69922-28-7

Basic information

• Product Name: 3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE
• Synonyms: 3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE, 9 8%;1,3-Benzodioxole,5-isocyanato-(9CI);3,4-(Methylenedioxy)phenyl isocyanate ,97%;5-Isocyanato-1,3-benzodioxole;3,4-(Methylenedioxy)phenyl isocyanate;5-isocyanato-1,3-benzodioxole(SALTDATA: FREE);1,3-Benzodioxol-5-yl isocyanate;5-Isocyanato-1,3-benzodioxole, 3,4-(Methylenedioxy)phenyl isocyanate
• CAS NO: 69922-28-7
• Molecular Formula: C₈H₅NO₃
• Molecular Weight: 163.1302
• Product Categories: ISOCYANATE;Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 69922-28-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 48-51 °C(lit.)
• Boiling Point: 265.6 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 0.0091mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE(69922-28-7)
• EPA Substance Registry System: 3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE(69922-28-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36
• RIDADR: UN 3335
• WGK Germany: 3
• HazardClass: IRRITANT, TOXIC
• Hazardous Substances Data: 69922-28-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-white solid

General Description

3,4-(Methylenedioxy)phenyl isocyanate, an aryl isocyanate, is also known as 5-isocyanato-1,3-benzodioxole.

InChI:InChI=1/C8H5NO3/c10-4-9-6-1-2-7-8(3-6)12-5-11-7/h1-3H,5H2

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 75-44-5 phosgene 
• 94-53-1 Piperonylic acid 
• 503-38-8 trichloromethyl chloroformate 
• 70156-94-4 benzo[1,3]dioxole-5-carboxylic acid hydroxyamide 
• 54022-34-3 benzo[d][1,3]dioxole-5-carbonyl azide 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 

Downstream Products

• 121809-71-0 2-[4-(3-Benzo[1,3]dioxol-5-yl-ureido)-phenoxy]-2-methyl-propionic acid 
• 141473-75-8 4-(3-Chlorophenyl)-1-[3-(3,4-methylenedioxyphenylcarbamoyloxy)propyl]piperazine, hydrochloride 
• 1061377-19-2 1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(3-morpholinopropoxy)phenyl)urea 
• 958244-71-8 1-benzo[1,3]dioxol-5-yl-3-[3-fluoro-4-(1H-imidazol-1-yl)phenyl]urea 
• 698984-83-7 N-(benzo[d][1,3]dioxol-5-yl)morpholine-4-carboxamide 
• 1220691-98-4 C₂₈H₂₉N₃O₄ 
• 1252606-96-4 N-({1-[4-(3-Benzo[1,3]dioxol-5-yl-ureido)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide 
• 1374006-37-7 C₁₇H₁₇N₃O₄ 
• 1374006-49-1 C₂₂H₁₉N₃O₄ 
• 1347008-61-0 1-(benzo[d][1,3]dioxol-5-yl)-3-(4-(2-(5-(trifluoromethyl)-1H-imidazol-2-yl)pyridin-4-yloxy)phenyl)urea 
• 1467739-14-5 1-(3-(2-amino-6-oxo-1,6-dihydropyrimidin-4-ylamino)-4-methylphenyl)-3-(benzo[1,3]dioxol-5-yl)urea 
• 387358-85-2 N-(benzo[d][1,3]dioxol-5-yl)-3-phenylpropanamide 

Relevant articles and documents

Discovery of novel VEGFR-2 inhibitors. Part 5: Exploration of diverse hinge-binding fragments via core-refining approach

Pathological angiogenesis plays a critical role in numerous diseases including malignancy. VEGFR-2 is the central regulators in angiogenesis and has become a promising target for anticancer drug design. We have identified a novel biphenyl-aryl urea incorporated with salicyladoxime (BPS-7) as potent VEGFR-2 inhibitor. As a continuation to our previous research, various aromatic-heterocyclic were introduced as hinge-binding fragment via a core-refining approach. Interestingly, many compounds exhibited comparable VEGFR-2 inhibition to Sorafenib. In particular, 12e and 12o displayed excellent VEGFR-2 inhibitory activity with IC50 values of 0.50 nM and 0.79 nM, respectively. Several title compounds showed considerable antiproliferative activity against A549 and SMMC-7721 cells. In addition, molecular docking was performed to rationalize the efficiency of the better compounds. These results will be instructive for further inhibitor design and optimization.

Synthesis of N-methylphenanthridinone derivatives fused with a silacyclohexane ring by radical reaction using tributyltin hydride

Radical reaction of (N-methyl-7-bromo-2,2-dimethyl-2-silatetralin-6-ylamino)veratramide (8a) and -piperonamides (8b) in boiling benzene using tributyltin hydride and AIBN gave two kinds of N-methylphenanthridinone derivatives (15 and 16), which were cyclized at 6- and 2-positions of aroylic acid moiety. On the other hand, similar reaction of N-methyl-N-(2-bromoveratryl and 2-bromopiperonyl)-2,2-dimethyl-2-silatetralin-6-carboxamides (14) produced N-methylphenanthridinone deivatives (17) as each sole product, in which cyclization occurred at 5-position of 2-silatetralin moiety.

Synthesis of new substituted 6-ureidopurines and 6-ureido-9-(2,3,5-triacetyl ribofuranosyl)purines having cytokinin (plant growth promoting) activity

Substituted 6-ureidopurines 6a-j and 6-ureido-9-(2,3,5-triacetylribofuranosyl) purines 7a-j have been synthesized by condensing substituted phenyl isocyanates with adenine 3 and 2,3,5-triacetyladenosine 5 respectively in pyridine. Substituted phenyl isocyanates 2a-j are prepared from substituted anilines 1a-j in the presence of triphosgene and triethylamine in dry benzene. Compounds 6a-j and 7a-j have been evaluated for cytokinin activity on seeds of Raphanus sativus, family Brassicaceae (common name white radish) at 5 different concentrations in distilled water ranging from 0.001 to 10 mg litre-1. Compounds 6a, 7a, 7b and 7i having substitutents at 3 position of phenyl ring are found to show higher cytokinin activity than benzyladenine at all concentrations (Table II).