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
• Article Data: 8

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

Chemical Properties

Light yellow solid

Uses

Crystal Violet lactone is an important functional dye for the production of pressure sensitive materials. It is a chemical intermediate , intermediates for thermal/carbonless Paper, used in medicine and biochemical research, a leuco dye..

General Description

Blue-green crystals or pale green powder.

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

Downstream Products

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

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)

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.

STRUCTURE OF THE PRODUCT FROM NITRATION OF MALACHITE GREEN LACTONE

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