1552-42-7

Basic information

• Product Name: Crystal violet lactone
• Synonyms: 3,3-bis(p-Dimethylaminophenyl)-6-dimethylaminophthalate;6-(dimethylamino)-3,3-bis[4-(dimethylamino)phenyl]-1(3h)-isobenzofuranon;6-(Dimethylamino)-3,3-bis[4-(dimethylamino)phenyl]phthalide;Pergascript Blue I 2R;6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-1(3h)-isobenzofuranone;6-(DIMETHYLAMINO)-3,3-BIS[P-(DIMETHYLAMINO)PHENYL]PHTHALIDE;3,3-BIS(P-DIMETHYLAMINOPHENYL)-6-DIMETHYLAMINOPHTHALIDE;3,3-BIS-4-DIMETHYLAMINOPHENYL-6-DIMETHYLAMINOPHTHALIDE
• CAS NO: 1552-42-7
• Molecular Formula: C₂₆H₂₉N₃O₂
• Molecular Weight: 415.53
• EINECS: 216-293-5
• Product Categories: Organics;Color Former;Color Former & Related Compounds;Functional Materials;C;Stains and Dyes;Stains&Dyes, A to;Pharmaceutical intermediates
• Mol File: 1552-42-7.mol

Chemical Properties

• Melting Point: 180-183°C
• Boiling Point: 534.12°C (rough estimate)
• Flash Point: 322.4 °C
• Appearance: Blue-green crystals or pale green powder
• Density: 1.1424 (rough estimate)
• Vapor Pressure: 8.57E-15mmHg at 25°C
• Refractive Index: 1.7120 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.73±0.24(Predicted)
• Water Solubility: <0.1 g/100 mL at 22.5℃
• CAS DataBase Reference: Crystal violet lactone(CAS DataBase Reference)
• NIST Chemistry Reference: Crystal violet lactone(1552-42-7)
• EPA Substance Registry System: Crystal violet lactone(1552-42-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1552-42-7(Hazardous Substances Data)

Usage

Uses

Used in Pressure Sensitive Materials Industry:
Crystal violet lactone is used as a functional dye for the production of pressure-sensitive materials, such as carbonless copy paper and pressure-sensitive adhesives. Its unique properties allow it to create a visible mark upon application of pressure, making it an essential component in these materials.
Used in Thermal/Carbonless Paper Industry:
In the thermal/carbonless paper industry, crystal violet lactone is used as a chemical intermediate to facilitate the color-forming reaction when pressure is applied. This reaction is crucial for the creation of duplicate copies without the need for carbon paper, streamlining the process of document duplication.
Used in Medicine and Biochemical Research:
Crystal violet lactone is utilized in the medical and biochemical research fields as a valuable intermediate compound. Its properties make it suitable for various applications, such as staining and visualization of biological samples, as well as serving as a starting material for the synthesis of other pharmaceutical compounds.
Used as a Leuco Dye:
As a leuco dye, crystal violet lactone is employed in various applications where its color-changing properties are advantageous. This includes its use in the development of color indicators, sensors, and other technologies that rely on color changes as a means of detection or measurement.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Crystal violet lactone may be sensitive to excessive light and heat.

Health Hazard

SYMPTOMS: Symptoms of exposure to Crystal violet lactone may include irritation.

Fire Hazard

Flash point data for Crystal violet lactone are not available; however, Crystal violet lactone is probably combustible.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C26H29N3O2/c1-27(2)20-11-7-18(8-12-20)26(19-9-13-21(14-10-19)28(3)4)24-16-15-22(29(5)6)17-23(24)25(30)31-26/h7-17H,1-6H3

Synthetic route

2-[4,4'-bis-(dimethylamino)-benzhydryl]-5-dimethylaminobenzoic acid (1255-69-2) → 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water	95.4%

4,4-bis-(p-dimethylaminophenyl)-7-dimethylamino-3,4-dihydro-1(2H)-phthalazinone (76339-00-9) → 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7) + 3,3-bis-(p-dimethylaminophenyl)-6-dimethylamino-N-aminophthalimidine (76918-85-9)

Conditions	Yield
With hydrogenchloride for 2h; Heating;	A 0.33 g B 0.70 g

dimethyl sulfate (77-78-1) + 6-amino-3,3-bis(4-dimethylaminophenyl)phthalide (29199-07-3) → 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7)

3,3-bis-p-dimethylaminophenylphthalide (5339-80-0) → 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid (d 1.45) / H2SO4 2: Fe / HCl View Scheme

6-nitro-3,3-bis(4-dimethylaminophenyl)phthalide (29199-08-4) → 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Fe / HCl View Scheme

phenolphthalein (77-09-8) → 2-[4,4'-bis-(dimethylamino)-benzhydryl]-5-dimethylaminobenzoic acid (1255-69-2) + 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7)

Conditions	Yield
With sodium hydroxide; acetic acid In water; toluene

(4-dimethylamino-benzyliden)-urea (623927-11-7) → 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 2 h / 80 °C 2.1: water / 2 h / 90 °C 2.2: 50 - 70 °C 3.1: dihydrogen peroxide / water / 2 h View Scheme

4-dimethylamino-benzaldehyde (100-10-7) → 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sulfuric acid / water / 2 h / 50 °C 2.1: 2 h / 80 °C 3.1: water / 2 h / 90 °C 3.2: 50 - 70 °C 4.1: dihydrogen peroxide / water / 2 h View Scheme

tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate + 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7) → [(η6-crystal violet lactone)RuCp*]PF6 (926919-99-5) + [(η6-crystal violet lactone)(RuCp*)2](PF6)2

Conditions	Yield
In dichloromethane (inert conditions); stirring mixture of ruthenium compd. and crystal violet lactone in CH2Cl2 at room temp. for 2 h; evapn., chromy. (alumina, CH2Cl2-CH3CN (8:1)) to elute mononuclear complex, eluting with CH3CN to give dinuclear complex, elem. anal.;	A 72% B 8%

(η6-naphthalene)(η4-1,5-cyclooctadiene)ruthenium(0) (88945-10-2) + 3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7) → [(crystal violet lactone)Ru(η4-cod)] (926919-82-6)

Conditions	Yield
With CH3CN In tetrahydrofuran (inert conditions); stirring mixture of ruthenium compd., crystal violetlactone and acetonitrile in THF at room temp. for 2 d; concn., filtration through alumina, evapn., chromy. (alumina, toluene, then toluene-THF (25:1)), evapn., (1)H NMR;	47%

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7) + methylhydrazine (60-34-4) → 2-methyl-4,4-bis-(p-dimethylaminophenyl)-7-dimethylamino-3,4-dihydro-1(2H)-phthalazinone (76347-53-0)

Conditions	Yield
In ethanol for 10h; Heating;	34%

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7) → 4,4-bis-(p-dimethylaminophenyl)-7-dimethylamino-3,4-dihydro-1(2H)-phthalazinone (76339-00-9)

Conditions	Yield
With hydrazine hydrate In ethanol at 70℃; for 2h; Rate constant;	3.7 g
With hydrazine hydrate In ethanol for 2h; Heating;	3.7 g

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7) + nitrobenzene (98-95-3) → C44H44N6O8

Conditions	Yield
Mechanism;

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone (1552-42-7) → C26H27N3O2

Conditions	Yield
With aluminium trichloride; urea at 135 - 140℃; for 22h;	1.20 g

Upstream product

• 1255-69-2 2-[4,4'-bis-(dimethylamino)-benzhydryl]-5-dimethylaminobenzoic acid 
• 77-78-1 dimethyl sulfate 
• 29199-07-3 6-amino-3,3-bis(4-dimethylaminophenyl)phthalide 
• 77-09-8 phenolphthalein 
• 623927-11-7 (4-dimethylamino-benzyliden)-urea 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 29199-08-4 6-nitro-3,3-bis(4-dimethylaminophenyl)phthalide 
• 5339-80-0 3,3-bis-p-dimethylaminophenylphthalide  
• 76339-00-9 4,4-bis-(p-dimethylaminophenyl)-7-dimethylamino-3,4-dihydro-1(2H)-phthalazinone 

Downstream Products

• 76347-53-0 2-methyl-4,4-bis-(p-dimethylaminophenyl)-7-dimethylamino-3,4-dihydro-1(2H)-phthalazinone 
• 76339-00-9 4,4-bis-(p-dimethylaminophenyl)-7-dimethylamino-3,4-dihydro-1(2H)-phthalazinone 
• 926919-99-5 [(η6-crystal violet lactone)RuCp*]PF6 
• 926919-82-6 [(crystal violet lactone)Ru(η4-cod)] 

Relevant articles and documents

Crystal violet lactone synthesis method (by machine translation)

Crystal violet lactone synthesis method, relates to a method for synthesizing the thermo-compression is sensitive dye, in order to urea, dimethyl aniline, inter-a aminobenzoic acid, P-dimethyl amino formaldehyde and other material as the raw material for synthesis, through the Schiff base stage, urea intermediate stage, colorless crystalviolet stage and the last stage of the oxidation reaction, synthetic crystal violet lactone. Synthetic method comprises the stage of: (1) Schiff base stage: to di-methyl amino formaldehyde and urea reaction generating Schiff base; (2) urea intermediate stage: a stage on the production of products and dimethyl aniline reaction to obtain the urea intermediate; (3) colorless crystal violet lactone stage: urea intermediate and inter-dimethylamino benzoic acid as a raw material reacts to produce a colourless crystalviolet; (4) oxidation reaction stage: colorless crystalline purple after hydrogen peroxide generating crystal violet lactone catalytic oxidation. The method to avoid impurity generated synthetic method, thereby improving the yield of the product, at the same time reduces the discharge of solid wastes. (by machine translation)

Thermochromic microencapsulated pigments

Disclosed is a thermochromic microencapsulated pigment which comprises as four essential components (a) an electron-donating chromatic organic compound, (b) an electron-accepting compound, (c) a reaction medium determining the temperatures at which the color reactions of component (a) with component (b) take place, and (d) a color change temperature regulator, the color change temperature regulator (d) comprising one or more compounds selected from the group consisting of esters, alcohols, ketones, acid amides, hydrocarbons, and fatty acids and having a melting point Y (° C.) satisfying the relationship (X+30)° C.≦Y≦200° C., wherein X (° C.) is the melting point of component (c), and the four essential components being microencapsulated.

Preparation process of phthalide compound

A process for preparing a phthalide compound represented by the formula (1): STR1 wherein R1, R2, R3, R4, R5 and R6 are individually an alkyl group, and R1 and R2, R3 and R4, and R5 and R6 can respectively bond to each other to form a heterocyclic ring together with a nitrogen atom, comprising oxidizing a triphenylmethane compound represented by the formula (2) STR2 wherein R1, R2, R3, R4, R5 and R6 are the same as above, is oxidized in the presence of activated carbon in an aqueous solvent by an oxidizing agent. The process can provide a fast reaction that produces a high purity product with high yield.

3-(substituted phenyl)phthalides

Process comprises the combination of the three steps of condensing 3-N(R)2 -4-X-benzoic acid with an aromatic or heterocyclic aldehyde, Y-CHO, under acidic conditions to produce 3-Y-5-X-6-N(R)2 phthalide (II), condensing said phthalide with a compound of the formula Z-H under alkaline or acid conditions to produce 2-(α-Y-α-Z)methyl-4-X-5-N(R)2 benzoic acid (III), and oxidizing said benzoic acid to produce 3-Y-3-Z-5-X-6-N(R)2 phthalide (I) where: R is hydrogen, non-tertiary alkyl of one to four carbon atoms, benzyl or substituted benzyl; X is hydrogen or halo; Y is 4-R1 -3-R2 -2-R1 -phenyl, 1-R5 -2-R6 -5/6-R4 -3-indolyl, 9-R7 -3-carbazolyl, 9-julolidinyl, 3,4-dioxymethylenephenyl, 2-thienyl, 1-R8 -2-pyrrolyl, or 4-pyridinyl; and Z is 4-R1 -3-R2 -2-R1 -phenyl, 1-R5 -2-R6 -5/6-R4 -3-indolyl or 1-R8 -2-pyrrolyl which are useful as colorless precursor color formers in carbonless duplicating and in thermal marking systems. The intermediates, 3-Y-5-X-6-N(R)2 phthalides (II) and 2-(α-Y-α-Z)methyl-4-X-5-N(R)2 benzoic acids (III) also have utility as colorless precursor color formers in carbonless duplicating and thermal marking systems.

Process for producing 3,3-bis-(4-dimethylaminophenyl)-6-dimethylaminophthalide

3,3-Bis-(4-dimethylaminophenyl)-6-dimethylaminophthalide is produced by oxidizing an alkali metal salt of 2-[4,4'-bis-(dimethylamino)-benzhydryl]-5-dimethylaminobenzoic acid in an aqueous solution of pH of 8 to 14 with hydrogen peroxide, oxygen or air in the presence of a catalyst selected from the group consisting of cobalt compounds and copper compounds.