605-69-6

Basic information

• Product Name: Martius Yellow
• Synonyms: 1-Naphthol, 2,4-dinitro-;2,4-Dinitro-1-naftol;2,4-dinitro-1-naphthaleno;2,4-dinitro-1-Naphthalenol;2,4-dinitro-1-naphtho;2,4-Dinitro-1-naphthol,CI 10315;2-4 Dinitro-alpha-naphtol;2-4dinitro-alpha-naphtol
• CAS NO: 605-69-6
• Molecular Formula: C₁₀H₆N₂O₅
• Molecular Weight: 234.17
• EINECS: 210-093-1
• Product Categories: Nitro
• Mol File: 605-69-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 130-133 °C(lit.)
• Boiling Point: 376.48°C (rough estimate)
• Flash Point: 179.8 °C
• Appearance: Yellow orange/powder
• Density: 1.4886 (rough estimate)
• Vapor Pressure: 3.08E-07mmHg at 25°C
• Refractive Index: 1.7040 (estimate)
• Solubility: Solubility Very slightly soluble in water, ethanol
• PKA: 2.12(at 25℃)
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 2057462
• CAS DataBase Reference: Martius Yellow(CAS DataBase Reference)
• NIST Chemistry Reference: Martius Yellow(605-69-6)
• EPA Substance Registry System: Martius Yellow(605-69-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• RIDADR: 2811
• WGK Germany: 3
• RTECS: QL3850000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 605-69-6(Hazardous Substances Data)

Usage

Chemical Properties

solid

Definition

ChEBI: A naphthol in which the hydroxy substituent is at C-1 with nitro groups at C-2 and -4.

Safety Profile

Poison by subcutaneous, intramuscular, intravenous, and intraperitoneal routes. Human reproductive effects by skin contact: skin toxicity. Mutation data reported. For fire, disaster, and explosion hazards, see NITRATES.

Purification Methods

Crystallise the naphthol from *benzene or aqueous EtOH. [Beilstein 6 IV 4240.]

InChI:InChI=1/C10H6N2O5/c13-10-7-4-2-1-3-6(7)8(11(14)15)5-9(10)12(16)17/h1-5,13H/p-1

Upstream product

• 830-81-9 1-naphthyl acetate 
• 90-15-3 α-naphthol 
• 4965-30-4 [1,4]naphthoquinone monooxime 
• 605-62-9 4-nitro-1-naphthol 
• 607-24-9 2-nitro-1-naphthol 
• 13029-24-8 2,4-dinitro-1-naphthalenamine 
• 2401-85-6 1-chloro-2,4-dinitronaphthalene 
• 6373-60-0 1,2-naphthoquinone-2-oxime 
• 1857-16-5 4-hydroxy-naphthalene-1,3-disulfonic acid 
• 91494-26-7 N-(2,4-dinitronaphthalen-1-yl)acetamide 
• 108-24-7 acetic anhydride 
• 134-32-7 1-amino-naphthalene 
• 612-52-2 2-naphthylamine hydrochloride 
• 2216-69-5 1-Methoxynaphthalene 

Downstream Products

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 13243-65-7 2,3-Dibromo-1,4-naphthoquinone 
• 92859-08-0 N-phenyl-2,4-dinitronaphthylamine 
• 20513-06-8 2-amino-[1,4]naphthoquinone-4-imine 
• 6532-66-7 2.4-diamino-1-oxy-naphthalene 
• 319918-83-7 4-amino-2-nitronaphthalen-1-ol 
• 124855-07-8 1-(4-Methylanilino)-2,4-dinitronaphthalene 
• 2401-85-6 1-chloro-2,4-dinitronaphthalene 
• 144-62-7 oxalic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 46967-18-4 N¹-phenyl-naphthalene-1,2,4-triyltriamine 
• 126911-42-0 benzyl-(2,4-dinitro-[1]naphthyl)-amine 
• 15252-69-4 2-chloro-1,4-dihydro-3-methylamino-1,4-dioxonaphthalene 

Relevant articles and documents

Ultrasonic and microwave-assisted synthesis of β-nitro styrenes and nitro phenols with tertiary butyl nitrite under acid-free conditions

Tertiary butyl nitrite (TBN) is an acid-free and safe nitrating agent that provides preferentially β-nitrostyrenes with cinnamic acids and corresponding nitro derivatives with phenols in good yields under classical conditions. However, ultrasonic and microwave-assisted reactions reduced the reaction times substantially and enhanced the yields from good to excellent. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Nitrophenol derivatives oxidized by cerium(IV) ammonium nitrate (CAN) and their cytotoxicity

Oxidation of a series of phenols with cerium(IV) ammonium nitrate (CAN) in acetonitrile undermild conditions yields the mixture of corresponding nitrophenols. In the cases of methylphenols and hydroxy-carboxylic acids, the steric effect may reduce the nitration reaction. Compounds 3 a and 4b showed selective activities to Hep 3B and Hep G2 cancer cell lines, respectively. Compound 2c showed selective activities to Hep G2 and MDA-MB-231 cancer cell lines. Further more, com pound 10b showed selective activities to Hep G2, Hep 3B, MCF-7 and MDA-MB-231 cancer cell lines.