57960-19-7

Basic information

• Product Name: ACEQUINOCYL
• Synonyms: 1,4-Naphthoquinone, 3-dodecyl-2-hydroxy-, acetate;Acequincyl;Acequinocyl [iso];Ai3-29615;3-dodecyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate;3-Acetoxy-2-dodecyl-1,4-naphthoquinone;3-Acetyloxy-2-dodecyl-1,4-naphthoquinone;DPX 3792
• CAS NO: 57960-19-7
• Molecular Formula: C₂₄H₃₂O₄
• Molecular Weight: 384.51
• Mol File: 57960-19-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 59.6°
• Boiling Point: 504°Cat760mmHg
• Flash Point: 215.9°C
• Appearance: /
• Density: 1.08
• Vapor Pressure: 2.75E-10mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: 0-6°C
• BRN: 2016033
• CAS DataBase Reference: ACEQUINOCYL(CAS DataBase Reference)
• NIST Chemistry Reference: ACEQUINOCYL(57960-19-7)
• EPA Substance Registry System: ACEQUINOCYL(57960-19-7)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• RTECS: QJ5375500
• Hazardous Substances Data: 57960-19-7(Hazardous Substances Data)

Usage

Uses

Acaricide.

Definition

ChEBI: An acetate ester consisting of 1,4-naphthoquinone bearing acetoxy and dodecyl substituents at positions 2 and 3 respectively.

InChI:InChI=1/C24H32O4/c1-3-4-5-6-7-8-9-10-11-12-17-21-22(26)19-15-13-14-16-20(19)23(27)24(21)28-18(2)25/h13-16H,3-12,17H2,1-2H3

Synthetic route

2-(1-dodecyl)-3-hydroxy-1,4-naphthoquinone (57960-31-3) → 2-(1-methylaminododecyl)-3-hydroxy-1,4-naphthoquinone (125110-78-3) + acequinocyl (57960-19-7)

Conditions	Yield
With acetic anhydride; toluene-4-sulfonic acid In o-xylene; water

2-(1-dodecyl)-3-hydroxy-1,4-naphthoquinone (57960-31-3) → acequinocyl (57960-19-7)

Conditions	Yield
With acetic anhydride; toluene-4-sulfonic acid In o-xylene; water

2-(1-dodecyl)-3-hydroxy-1,4-naphthoquinone (57960-31-3) + acetyl chloride (75-36-5) → acequinocyl (57960-19-7)

Conditions	Yield
With triethylamine In dichloromethane
With triethylamine In dichloromethane

2-Acetoxy-2-n-dodecyl-1,4-naphthoquinone + 2-(1-dodecyl)-3-hydroxy-1,4-naphthoquinone (57960-31-3) + acetyl chloride (75-36-5) → acequinocyl (57960-19-7)

Conditions	Yield
With triethylamine In dichloromethane

3-chloro-2-n-dodecyl-1,4-naphthoquinone (64955-12-0) → acequinocyl (57960-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide 2: triethylamine / dichloromethane View Scheme

2-n-dodecyl-1-naphthol-4-sulfonic acid (64955-08-4) → acequinocyl (57960-19-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; chlorine; acetic acid / ethanol; hexane; water 2: sodium hydroxide 3: triethylamine / dichloromethane View Scheme

2-Dodecyl-[1]naphthol (64955-09-5) → acequinocyl (57960-19-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / dichloromethane 2: sulfuric acid; chlorine; acetic acid / ethanol; hexane; water 3: sodium hydroxide 4: triethylamine / dichloromethane View Scheme

Upstream product

• 64955-09-5 2-Dodecyl-[1]naphthol 
• 64955-08-4 2-n-dodecyl-1-naphthol-4-sulfonic acid 
• 64955-12-0 3-chloro-2-n-dodecyl-1,4-naphthoquinone 
• 57960-31-3 2-(1-dodecyl)-3-hydroxy-1,4-naphthoquinone 
• 75-36-5 acetyl chloride 

Relevant articles and documents

ACTIVE COMPOUND COMBINATIONS HAVING INSECTICIDAL AND ACARICIDAL PROPERTIES

The novel active compound combinations comprising a compound of the formula (I-1) or (I-2) and the active compounds (1) to (26) listed in the description have very good insecticidal and acaricidal properties.

2-Higher alkyl-3-hydroxy-1,4-naphthoquinone carboxylic acid esters

This invention relates to novel compounds useful for controlling mites which are represented by the following formula: STR1 wherein R1 is alkyl of 12-14 carbon atoms either branched, cyclic or straight chain; and R2 is alkyl of 1-17 carbon atoms either branched or straight chain, alkenyl of 2-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, alkoxy of 1-4 carbon atoms, --CH2 OCH3, --CH2 OCH2 CH3 or --CH=CH--CO2 H.

Miticidal and aphicidal method utilizing 2-higher alkyl-3-hydroxy-1,4-naphthoquinone carboxylic acid esters

This invention relates to a novel pesticidal, e.g., miticidal and aphicidal, method utilizing an active ingredient which is represented by the following formula: STR1 wherein R1 is alkyl of 8-14 carbon atoms either branched, cyclic or straight chain; and R2 is alkyl of 1-17 carbon atoms either branched or straight chain, alkenyl of 2-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, alkoxy of 1-4 carbon atoms, --CH2 OCH3, --CH2 OCH2 CH3 or --CH=CH--CO2 H.