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1552-42-7

Basic Information
CAS No.: 1552-42-7
Name: Crystal violet lactone
Article Data: 8
Molecular Structure:
Molecular Structure of 1552-42-7 (Crystal violet lactone)
Formula: C26H29N3O2
Molecular Weight: 415.535
Synonyms: Phthalide,6-(dimethylamino)-3,3-bis[p-(dimethylamino)phenyl]- (6CI,7CI,8CI);3,3-Bis[4-(dimethylamino)phenyl]-6-(dimethylamino)-1,3-dihydroisobenzofuran-1-one;3,3-Bis[4-(dimethylamino)phenyl]-6-(dimethylamino)phthalide;3,3-Bis[p-(dimethylamino)phenyl]-6-(dimethylamino)phthalide;6-(Dimethylamino)-3,3-bis[4-(dimethylamino)phenyl]-1(3H)-isobenzofuranone;CVL;Color Former CVL;Copikem 1 Blue;Copikem I;NSC 32991;NSC 3562;Pergascript Blue I 2R;
EINECS: 216-293-5
Density: 1.198 g/cm
Melting Point: 180-183 °C
Boiling Point: 609.4 °C at 760 mmHg
Flash Point: 322.4 °C
Solubility: Insoluble in water
Appearance: Blue-green crystals or pale green powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
PSA: 36.02000
LogP: 4.34690
Synthetic route
1255-69-2

2-[4,4'-bis-(dimethylamino)-benzhydryl]-5-dimethylaminobenzoic acid

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water95.4%
76339-00-9

4,4-bis-(p-dimethylaminophenyl)-7-dimethylamino-3,4-dihydro-1(2H)-phthalazinone

A

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

B

76918-85-9

3,3-bis-(p-dimethylaminophenyl)-6-dimethylamino-N-aminophthalimidine

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;A 0.33 g
B 0.70 g
77-78-1

dimethyl sulfate

29199-07-3

6-amino-3,3-bis(4-dimethylaminophenyl)phthalide

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

5339-80-0

3,3-bis-p-dimethylaminophenylphthalide

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: nitric acid (d 1.45) / H2SO4
2: Fe / HCl
View Scheme
29199-08-4

6-nitro-3,3-bis(4-dimethylaminophenyl)phthalide

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Fe / HCl
View Scheme
77-09-8

phenolphthalein

A

1255-69-2

2-[4,4'-bis-(dimethylamino)-benzhydryl]-5-dimethylaminobenzoic acid

B

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

Conditions
ConditionsYield
With sodium hydroxide; acetic acid In water; toluene
623927-11-7

(4-dimethylamino-benzyliden)-urea

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

Conditions
ConditionsYield
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
100-10-7

4-dimethylamino-benzaldehyde

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

Conditions
ConditionsYield
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

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

A

926919-99-5

[(η6-crystal violet lactone)RuCp*]PF6

B

[(η6-crystal violet lactone)(RuCp*)2](PF6)2

Conditions
ConditionsYield
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%
88945-10-2

(η6-naphthalene)(η4-1,5-cyclooctadiene)ruthenium(0)

1552-42-7

3,3-Bis<-(dimethylamino)phenyl>-6-(dimethylamino)-1(3H)isobenzofuranone

926919-82-6

[(crystal violet lactone)Ru(η4-cod)]

Conditions
ConditionsYield
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%
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Chemistry

The Molecular Structure of 1(3H)-Isobenzofuranone, 6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-  (CAS NO.1552-42-7):

Empirical Formula: C26H29N3O2
Molecular Weight: 415.5274
Appearance: Blue-green crystals or pale green powder 
IUPAC: 6-(dimethylamino)-3,3-bis(4-dimethylaminophenyl)-2-benzofuran-1-one
Nominal Mass: 415 Da
Average Mass: 415.5274 Da
Monoisotopic Mass: 415.225977 Da 
Index of Refraction: 1.655
Molar Refractivity: 127.28 cm3
Molar Volume: 346.8 cm3 
Surface Tension: 53 dyne/cm
Density: 1.198 g/cm3
Flash Point: 322.4 °C
Enthalpy of Vaporization: 90.52 kJ/mol
Boiling Point: 609.4 °C at 760 mmHg
Vapour Pressure: 8.57E-15 mmHg at 25°C 
Water Solubility:  <0.1 g/100 mL at 22.5 ºC
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 
Smiles
O=C1OC(c2ccc(N(C)C)cc12)(c1ccc(N(C)C)cc1)c1ccc(N(C)C)cc1
Product Categories: Organics;Color Former;Color Former & Related Compounds;Functional Materials;C;Stains and Dyes;Stains&Dyes, A to 

Uses

 1(3H)-Isobenzofuranone, 6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-  (CAS NO.1552-42-7) is an important functional dye for the production of pressure sensitive materials.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S37/39:Wear suitable gloves and eye/face protection

Specification

 1(3H)-Isobenzofuranone, 6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-  (CAS NO.1552-42-7) is also called as Crystal violet lactone ; 3,3-Bis(4-dimethylaminophenyl)-6-dimethylaminophthalide ; 3,3-Bis(p-dimethylaminophenyl)-6-dimethylaminophthalate ; 3,3-Bis(p-dimethylaminophenyl)-6-dimethylaminophthalide ; 6-(Dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)phthalide ; AI3-17349 ; Crystal Violet lactone ; EINECS 216-293-5 ; NSC 32991 ; NSC 3562 ; Phthalide, 6-(dimethylamino)-3,3-bis(p-(dimethylamino)phenyl)- ; 1(3H)-Isobenzofuranone, 6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)- 6-Dimethylamino-3,3-bis(4-dimethylaminophenyl)phthalide ; Phthalide, 6-(dimethylamino)-3,3-bis(p-(dimethylamino)phenyl)- .