Product Name

  • Name

    2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)prop-1-enyl]-1,3,3-trimethyl-3H-indolium chloride

  • EINECS 228-668-0
  • CAS No. 6320-14-5
  • Density 1.06[at 20℃]
  • Solubility 26.53mg/L at 25℃
  • Melting Point
  • Formula C25H29ClN2
  • Boiling Point 608.73℃[at 101 325 Pa]
  • Molecular Weight 392.972
  • Flash Point
  • Transport Information
  • Appearance gray powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 6320-14-5 (2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)prop-1-enyl]-1,3,3-trimethyl-3H-indolium chloride)
  • Hazard Symbols
  • Synonyms 1,3,3-Trimethyl-2-[3-(1,3,3-trimethyl-2-indolinylidene)propenyl]-3H-indoliumchloride (6CI,7CI);3H-Indolium,1,3,3-trimethyl-2-[3-(1,3,3-trimethyl-2-indolinylidene)propenyl]-, chloride(8CI);3H-Indolium,2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl]-1,3,3-trimethyl-,chloride (9CI);1,3,3,1',3',3'-Hexamethylindocarbocyanine chloride;1,3,3-Trimethyl-2-[3-(1,3,3-trimethyl-1,3-dihydroindol-2-ylidene)propenyl]-3H-indoliumchloride;Acronol Phloxine FF;Aizen Astra Phloxine FF;Aizen Astra Phloxine FFConc.;Astra Phloxine;Astra Phloxine F;Astra Phloxine FF;Astra Phloxine G;Astra Phloxine G extra;Astrafloxin;Astrafloxin F;Astraphloxin;AstraphloxinG;Atlantic Paper Red P;Basic Red 12;Brilliant Pink AS;C.I. 48070;C.I.Basic Red 12;Cosmophloxine F;Tokyo Aniline Astraphloxine FF;Verona Paper Red;
  • PSA 6.25000
  • LogP 2.58810

Synthetic route

formic acid
64-18-6

formic acid

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride
6320-14-5

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

Conditions
ConditionsYield
With acetic anhydride Behandeln des Reaktionsprodukts mit wss. HCl;
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1,3,3-trimethyl-2-formylmethyleneindoline
84-83-3

1,3,3-trimethyl-2-formylmethyleneindoline

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride
6320-14-5

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

Conditions
ConditionsYield
With trichlorophosphate; benzene
With trichlorophosphate; benzene
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

ethyl formimidate hydrochloride
16694-46-5

ethyl formimidate hydrochloride

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride
6320-14-5

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

Conditions
ConditionsYield
With acetic anhydride Behandeln des Reaktionsgemisches mit wss. HCl;
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

N,N'-diphenylformamidine
864131-95-3

N,N'-diphenylformamidine

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride
6320-14-5

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

Conditions
ConditionsYield
With acetic anhydride Behandeln des Reaktionsprodukts mit wss. HCl;
1,3-bis-<1,3,3-trimethyl-indolin-2-ylidene>-propane

1,3-bis-<1,3,3-trimethyl-indolin-2-ylidene>-propane

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride
6320-14-5

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

Conditions
ConditionsYield
With lead dioxide; acetic acid; calcium chloride Behandeln des Reaktionsgemisches mit wss. HCl;
With acetic acid; p-benzoquinone; benzene aufeinanderfolgendes Behandeln des Reaktionsprodukts mit wss. NaOH und wss. HCl;
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride
6320-14-5

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,2-dichloro-benzene; phosphoryl chloride / anschliessendes Hydrolysieren
2: POCl3; benzene
View Scheme
1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride
6320-14-5

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

ethyl ester of p-toluenesulfonic acid
80-40-0

ethyl ester of p-toluenesulfonic acid

1,3,3-Trimethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)propenyl>-3H-indolium tosylate
119020-55-2

1,3,3-Trimethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)propenyl>-3H-indolium tosylate

Conditions
ConditionsYield
at 90 - 95℃; for 0.5h;93%
1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride
6320-14-5

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

1,3,3-Trimethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)propenyl>-3H-indolium methanesulfonate
88519-83-9

1,3,3-Trimethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)propenyl>-3H-indolium methanesulfonate

Conditions
ConditionsYield
at 90 - 95℃; for 0.5h;92%
1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride
6320-14-5

1,1′,3,3,3′,3′-hexamethylindocarbocyanine chloride

1,3,3-Trimethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)propenyl>-3H-indolium Fluoride
126565-16-0

1,3,3-Trimethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)propenyl>-3H-indolium Fluoride

Conditions
ConditionsYield
With silver fluoride In water; acetonitrile68%

2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)prop-1-enyl]-1,3,3-trimethyl-3H-indolium chloride Consensus Reports

Reported in EPA TSCA Inventory.

2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)prop-1-enyl]-1,3,3-trimethyl-3H-indolium chloride Specification

The IUPAC name of C.I. Basic Red 12 is (2Z)-1,3,3-trimethyl-2-[(E)-3-(1,3,3-trimethylindol-1-ium-2-yl)prop-2-enylidene]indole chloride. With the CAS registry number 6320-14-5, it is also named as Acronol Phloxine FF; 2-(3-(1,3-Dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)prop-1-enyl)-1,3,3-trimethyl-3H-indolium chloride. The product's categories are dyes and pigments; organics. It exists as gray powder which is soluble in water, ethanol and ethylene glycol ether. This chemical appears yellow pink in concentrated sulfuric acid and blu-ray pink in the diluted solution. The color of C.I. Basic Red 12 in concentrated nitric acid is apricot. When heated to decomposition it emits toxic vapors of NOx and Cl-. 

The other characteristics of this product can be summarized as: (1)#H bond acceptors: 2; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 2; (4)Rotatable Bond Count: 2; (5)Exact Mass: 392.201927; (6)MonoIsotopic Mass: 392.201927; (7)Topological Polar Surface Area: 6.2; (8)Heavy Atom Count: 28; (9)Complexity: 623; (10)Defined Bond StereoCenter Count: 2; (11)Covalently-Bonded Unit Count: 2.

Preparation of C.I. Basic Red 12: Using ω-aldehyde as raw material which condensates with sodium formate in acetic anhydride at the presence of magnesium oxide to get the product. The product is dumped into the water to precipitate dye. After filtration, drying and grinding, we can get the crude product.

Uses of C.I. Basic Red 12: It is mainly used in dyeing silk, cotton, acetate fibers, nylon and acrylic. And it is also used in coloring leather and paper. In addition, it is used in the preparation of 1,3,3-Trimethyl-2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)propenyl]-3H-indolium Fluoride. This reaction needs reagent silver fluoride and solvent acetonitrile and H2O. The yield is 68 %.

People can use the following data to convert to the molecule structure. 
1. SMILES: [Cl-].c1cccc4c1C(C(=C/C=C/C3=[N+](/c2ccccc2C3(C)C)C)\N4C)(C)C;
2. InChI: InChI=1/C25H29N2.ClH/c1-24(2)18-12-7-9-14-20(18)26(5)22(24)16-11-17-23-25(3,4)19-13-8-10-15-21(19)27(23)6;/h7-17H,1-6H3;1H/q+1;/p-1.

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 18mg/kg (18mg/kg)   United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-1285-0581,

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