5-[(Z)-2-nitroethenyl]-1,3-benzodioxole

Base Information

• Chemical Name: 5-[(Z)-2-nitroethenyl]-1,3-benzodioxole
• CAS No.: 1485-00-3
• Molecular Formula: C9H7NO4
• Molecular Weight: 193.159
• Hs Code.: 29329990
• NSC Number: 170724,149598,105303,10120
• ChEMBL ID: CHEMBL4291121
• Mol file: 1485-00-3.mol

Synonyms:5-[(Z)-2-nitroethenyl]-1,3-benzodioxole;1, 5-nitrovinyl-;1, 5-(2-nitroethenyl)-;WLN: T56 BO DO CHJ G1U1NW;Styrene,4-methylenedioxy-.beta.-nitro-;5-(2-nitroethenyl)-2H-1,3-benzodioxole;CHEMBL4291121;SCHEMBL16211885;3,4-Methylenedioxy-b-nitrostyrene;NSC10120;NSC-10120;NSC105303;NSC149598;NSC170724;STK397212;AKOS005434103;NSC-105303;NSC-149598;NSC-170724;NCGC00342054-01;5-[(Z)-2-nitroethenyl]-1,3-dioxaindane;AB01334069-02;AB01334069-03;EN300-27127243;1577213-04-7

Chemical Property of 5-[(Z)-2-nitroethenyl]-1,3-benzodioxole

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 0.000242mmHg at 25°C
• Melting Point: 159-163 °C
• Refractive Index: 1.64
• Boiling Point: 334.862 °C at 760 mmHg
• Flash Point: 168.837 °C
• PSA: 64.28000
• Density: 1.401 g/cm³
• LogP: 2.18590
• Storage Temp.: Store at +4°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in DMSO (up to 50 mg/ml).
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 193.03750770
• Heavy Atom Count: 14
• Complexity: 248

Purity/Quality:

MDBN ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R22:; R36/37/38:
• Hazard Codes: Xn,Xi,T
• Statements: 36/37/38-22-25
• Safety Statements: 36/37/39-26-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C=C[N+](=O)[O-]
• Isomeric SMILES: C1OC2=C(O1)C=C(C=C2)/C=C\[N+](=O)[O-]
• Description: MDBN (1485-00-3) is an irreversible inhibitor of p97 (IC50 < 10 μM). Cell permeable.
• Uses: MDBN is a Src and Syk kinase inhibitor that prevents phosphorylation and cytoskeletal association of GPIIb/IIIa and talin.

Technology Process of 5-[(Z)-2-nitroethenyl]-1,3-benzodioxole

There total 47 articles about 5-[(Z)-2-nitroethenyl]-1,3-benzodioxole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

piperonal (120-57-0,30024-74-9) + nitromethane (75-52-5) → 5-((E)-2-nitroethenyl)-1,3-benzodioxole (1485-00-3,22568-48-5)

Guidance literature:

With ammonium acetate; acetic acid; at 22 ℃; for 3h; ultrasound;

DOI:10.1016/S0040-4039(98)01789-4

Reference yield: 95.0%

5-vinyl-1,3-benzodioxole (7315-32-4) → 5-((E)-2-nitroethenyl)-1,3-benzodioxole (1485-00-3,22568-48-5)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In 1,4-dioxane; at 80 ℃; for 1h; stereoselective reaction; Green chemistry;

DOI:10.1055/s-0034-1378513

Reference yield: 91.0%

piperonal (120-57-0,30024-74-9) + nitromethane (75-52-5) → 5-(2-nitrovinyl)benzo[1,3]dioxole (1485-00-3)

Guidance literature:

With sodium acetate; methylamine; In methanol; ethanol; for 2h;

upstream raw materials:

piperonal

nitromethane

3,4-methylenedioxy-trans-cinnamic acid

1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethanol

Downstream raw materials:

trans-4-(3,4-methylenedioxyphenyl)-5-nitrocyclohexene

(3R,4S)-3-Benzo[1,3]dioxol-5-yl-1-benzyl-4-nitro-pyrrolidine

(R)-((R)-1-Benzo[1,3]dioxol-5-yl-2-nitro-ethyl)-phenyl-phosphinic acid ethyl ester

(R)-((S)-1-Benzo[1,3]dioxol-5-yl-2-nitro-ethyl)-phenyl-phosphinic acid ethyl ester

Refernces

• 1、 Kamlet. "-". . p. 4896. Retrieved 1955.
• 2、 Puerto Galvis, Carlos E.,Kouznetsov, Vladimir V.. "Regio- and stereoselective synthesis of spirooxindole 1′-nitro pyrrolizidines with five concurrent stereocenters under aqueous medium and their bioprospection using the zebrafish (Danio rerio) embryo model". . p. 7372 - 7386. Retrieved 2013.
• 3、 Milhazes, Nuno,Calheiros, Rita,Marques, M. Paula M.,Garrido, Jorge,Cordeiro, M. Natália D.S.,Rodrigues, Cátia,Quinteira, Sandra,Novais, Carla,Peixe, Luísa,Borges, Fernanda. "β-Nitrostyrene derivatives as potential antibacterial agents: A structure-property-activity relationship study". . p. 4078 - 4088. Retrieved 2006.
• 4、 Fan, Tian-Yun,Yang, Yu-Xin,Zeng, Qing-Xuan,Wang, Xue-Lei,Wei, Wei,Guo, Xi-Xi,Zhao, Li-Ping,Song, Dan-Qing,Wang, Yan-Xiang,Wang, Li,Hong, Bin. "Structure–activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents". . . Retrieved 2021/06/01.
• 5、 -. "A synthetic preparation method for small carbags hydrochloric acid". Paragraph 0197-0199. . Retrieved 2021/12/08.