6424-77-7

Basic information

• Product Name: Pigment Red 190
• Synonyms: C.I.Vatred29;C.I.VatRed29(71140);IndanthrenScarletR;perylenered;VatscarletR;N,N'-Bis(4-methoxyphenyl)-3,4,9,10-perylenetetracarboxylic Diimide;N,N'-Bis(4-methoxyphenyl)-3,4,9,10-perylenetetracarboxylic Diimide;2,9-Bis(p-anisyl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone
• CAS NO: 6424-77-7
• Molecular Formula: C₃₈H₂₂N₂O₆
• Molecular Weight: 602.59
• EINECS: 229-187-9
• Product Categories: Organics;electronic
• Mol File: 6424-77-7.mol
• Article Data: 3

Chemical Properties

• Appearance: Amaranthine powder
• Density: 1.511 g/cm³
• Refractive Index: 1.831
• PKA: 3.48±0.20(Predicted)
• CAS DataBase Reference: Pigment Red 190(CAS DataBase Reference)
• NIST Chemistry Reference: Pigment Red 190(6424-77-7)
• EPA Substance Registry System: Pigment Red 190(6424-77-7)

Safety Data

• Hazardous Substances Data: 6424-77-7(Hazardous Substances Data)

Usage

Uses

N,N''-Bis(4-methoxyphenyl)-3,4,9,10-perylenetetracarboxylic diimide (CAS# 6424-77-7) is a redox-active perylenediimide dye, and has been proposed for use as a cathode for lithium ion batteries due to its affinity for Li+ uptake and release.

Properties and Applications

TEST ITEMS SPECIFICATION APPEARANCE RED POWDER SHADE YELLOWISH HEAT RESISTANCE 300 °C min LIGHT FASTNESS 7-8 ACID RESISTANCE 5 ALKALI RESISTANCE 5 FASTNESS TO BLEEDING 5 OIL ABSORPTION 35-50% SPECIFIC SURFACE 28m 2 /g DENSITY 1.60 g/cm 3 RESIDUE ON 80 MESH 5.0% max WATER SOLUBLE 1.0% max VOLATITE 105 °C 1.0% max TINTING STRENGTH 100-105 %

TEST ITEMS

SPECIFICATION

APPEARANCE

RED POWDER

SHADE

YELLOWISH

HEAT RESISTANCE

300 °C min

LIGHT FASTNESS

7-8

ACID RESISTANCE

5

ALKALI RESISTANCE

5

FASTNESS TO BLEEDING

5

DENSITY

1.60 g/cm 3

RESIDUE ON 80 MESH

5.0% max

WATER SOLUBLE

1.0% max

VOLATITE 105 °C

1.0% max

TINTING STRENGTH

100-105 %

InChI:InChI=1/C38H22N2O6/c1-45-21-7-3-19(4-8-21)39-35(41)27-15-11-23-25-13-17-29-34-30(38(44)40(37(29)43)20-5-9-22(46-2)10-6-20)18-14-26(32(25)34)24-12-16-28(36(39)42)33(27)31(23)24/h3-18H,1-2H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 128-69-8 perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride 
• 42340-32-9 2-(4-methoxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 

Relevant articles and documents

Greener Dye Synthesis: Continuous, Solvent-Free Synthesis of Commodity Perylene Diimides by Twin-Screw Extrusion

A continuous, scalable, and solvent-free method for the synthesis of various naphthalic imides and perylene diimides (PDIs) using twin-screw extrusion (TSE) is reported. Using TSE, naphthalic imides were obtained quantitatively without the need for excess amine reactant or product purification. With good functional-group tolerance, alkyl and benzyl amine derived PDIs (incl. commercial dyes) were obtained in 50–99 % yield. Use of K2CO3, enabled synthesis of more difficult aniline-derived PDIs. Furthermore, an automated continuous TSE process for Pigments Black 31 and 32 is demonstrated, with a throughput rate of about 1500 g day?1, corresponding to a space time yield of about 30×103 kg m?3 day?1, which is 1–2 orders of magnitude greater than for solvent-based batch methods. These methods provide substantial waste reductions and improved efficiency compared to conventional solvent-based methods.

A "green" route to perylene dyes: Direct coupling reactions of 1,8-naphthalimide and related compounds under mild conditions using a "new" base complex reagent, t-BuOK/DBN

The direct coupling reactions of 1,8-naphthalimide compounds efficiently occurred at 130 or 170 °C without the intervention of the leuco form dyes in the presence of base complex reagent, t-BuOK/1,5-diazabicyclo[4.3.0]non-5-ene (DBN), to give the corresponding perylene dyes in good yields with >95% purities. A possible mechanistic speculation for these oxidative coupling reactions is briefly discussed.