25646-77-9

Basic information

• Product Name: 4-(N-Ethyl-N-2-hydroxyethyl)-2-methylphenylenediamine sulfate
• Synonyms: N4-ETHYL-N4-(2-HYDROXYETHYL)-2-METHYL-1,4-PHENYLENEDIAMINE SULFATE;N4-ETHYL-N4-(2-HYDROXYETHYL)-2-METHYL-1,4-PHENYLENE-DIAMINE SULFATE SALT;2-(4-AMINO-N1-ETHYL-M-TOLUIDINO)-ETHANOL SULFATE HYDRATE;2-[(4-AMINO-3-METHYLPHENYL)ETHYLAMINO]ETHANOL SULFATE;4-(N-ETHYL-N-2-HYDROXYETHYL)-2-METHYLPHENYLENEDIAMINE SULFATE;4-[N-ETHYL-N-2-HYDROXYETHYL]-2-METHYLPHENYLENEDIAMINE SULPHATE;4-(N-ETHYL-N-HYDROXYETHYL)-2-METHYLPHENYLENE DIAMINE SULFATE MONOHYDRATE;CD4 DEVELOPER
• CAS NO: 25646-77-9
• Molecular Formula: C₁₁H₁₈N₂O*H₂O₄S
• Molecular Weight: 292.35
• EINECS: 247-162-0
• Product Categories: Amino Alcohols;Organic Building Blocks;Oxygen Compounds;monoclonal antibody
• Mol File: 25646-77-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 155 °C
• Boiling Point: 364.3 °C at 760 mmHg
• Flash Point: 174.1 °C
• Appearance: Beige/Fine Crystalline Powder
• Density: 1.1g/cm3
• Storage Temp.: -20°C
• Water Solubility: Soluble in water
• CAS DataBase Reference: 4-(N-Ethyl-N-2-hydroxyethyl)-2-methylphenylenediamine sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(N-Ethyl-N-2-hydroxyethyl)-2-methylphenylenediamine sulfate(25646-77-9)
• EPA Substance Registry System: 4-(N-Ethyl-N-2-hydroxyethyl)-2-methylphenylenediamine sulfate(25646-77-9)

Safety Data

• Hazard Codes: T,N,Xi
• Statements: 25-43-48/22-50/53-36/37/38
• Safety Statements: 24-37-45-60-61-36-26
• RIDADR: 2811
• WGK Germany: 3
• RTECS: KJ6477000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 25646-77-9(Hazardous Substances Data)

Usage

Description

CD4 is a color-film developer, and both an allergen and an irritant in photographers. Cross reactivity is possible with Disperse Blue 124, Disperse Blue 106, and Disperse red 17.

Chemical Properties

beige fine crystalline powder

Uses

4-(N-Ethyl-N-2-hydroxyethyl)-2-methylphenylenediamine sulfate is used as a color developer for Kodacolor II film, identicaI to Flexicolor or C-41 process; color developer for use in color microautoradiography for color development of immunogold-labeled antibodies.

Contact allergens

Color film developer. It is both an allergen and an irritant in photographers. Cross-reactivity is possible with Disperse Blue 124, Disperse Blue 106, and Disperse Red 17.

InChI:InChI=1/C11H18N2O.H2O4S/c1-3-13(6-7-14)10-4-5-11(12)9(2)8-10;1-5(2,3)4/h4-5,8,14H,3,6-7,12H2,1-2H3;(H2,1,2,3,4)

Synthetic route

i-propyl nitrite (541-42-4) + N-ethyl-N-(2-hydroxyethyl)-3-methylaniline (91-88-3) → 2-[(4-amino-3-methylphenyl)(ethyl)amino]ethanol sulfate (25646-77-9)

Conditions	Yield
With sulfuric acid; palladium-carbon In ethanol; isopropyl alcohol	100%

2-[(4-amino-3-methylphenyl)(ethyl)amino]ethanol sulfate (25646-77-9) + edaravone (89-25-8) → 4-<-4- (104525-76-0)

Conditions	Yield
With potassium ferrocyanide In water Ambient temperature;	52%

2-(naphthalen-1-yl)malononitrile (5518-09-2) + 2-[(4-amino-3-methylphenyl)(ethyl)amino]ethanol sulfate (25646-77-9) → 4-<4'--2-methylphenylimino>-1,4-dihydronaphthylidenemalononitrile (116429-27-7)

Conditions	Yield
With sodium hydroxide; sodium hypochlorite In water for 0.166667h; Ambient temperature;	29%

4-butoxybenzene-1,3-diamine dihydrochloride + 2-[(4-amino-3-methylphenyl)(ethyl)amino]ethanol sulfate (25646-77-9) → 2-{[4-(2-amino-5-butoxy-4-iminocyclohexa-2,5-dienylideneamino)-3-methylphenyl]ethylamino}ethanol (1442579-55-6)

Conditions	Yield
With ammonia; dihydrogen peroxide In ethanol; water for 12h; pH=9.5;	2.81 g

3-hydroxy-N-phenylaniline (101-18-8) + 2-[(4-amino-3-methylphenyl)(ethyl)amino]ethanol sulfate (25646-77-9) → 2-{4-[ethyl-(2-hydroxyethyl)amino]2-methylphenylamino}-4-{4-[ethyl-(2-hydroxyethyl)amino]-2-methyl phenylimino}-5-phenylaminocyclohexa-2,5-dienone (1442650-45-4)

Conditions	Yield
With ammonia; dihydrogen peroxide In ethanol; water for 24h; pH=9.5;	802 mg

orcinol (504-15-4) + 2-[(4-amino-3-methylphenyl)(ethyl)amino]ethanol sulfate (25646-77-9) → 2-{4-[ethyl(2-hydroxyethyl)-amino]-2-methylphenylamino}-4-{4-[ethyl(2-hydroxyethyl)amino]-2-methylphenylimino}-5-hydroxy-3-methylcyclohexa-2,5-dienone (1443206-53-8)

Conditions	Yield
With ammonium peroxydisulfate; ammonia In ethanol; water at 30℃; pH=9.5;	108 mg

Upstream product

• 541-42-4 i-propyl nitrite 
• 91-88-3 N-ethyl-N-(2-hydroxyethyl)-3-methylaniline 

Downstream Products

• 1443206-53-8 2-{4-[ethyl(2-hydroxyethyl)-amino]-2-methylphenylamino}-4-{4-[ethyl(2-hydroxyethyl)amino]-2-methylphenylimino}-5-hydroxy-3-methylcyclohexa-2,5-dienone 
• 1442650-45-4 2-{4-[ethyl-(2-hydroxyethyl)amino]2-methylphenylamino}-4-{4-[ethyl-(2-hydroxyethyl)amino]-2-methyl phenylimino}-5-phenylaminocyclohexa-2,5-dienone 
• 1442579-55-6 2-{[4-(2-amino-5-butoxy-4-iminocyclohexa-2,5-dienylideneamino)-3-methylphenyl]ethylamino}ethanol 
• 104525-76-0 4-<-4--2-methylphenylimino>-3-methyl-1-phenyl-2-pyrazolin-5-on 
• 116429-27-7 4-<4'--2-methylphenylimino>-1,4-dihydronaphthylidenemalononitrile 

Relevant articles and documents

Aggregated dyes for radiation-sensitive elements

A dispersion comprising an aqueous medium having dispersed therein an aggregated dye of the Formula (I): wherein X is oxygen or sulfur; R1-R4each independently represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group or an unsubstituted or substituted heteroaryl group; L1, L2and L3each independently represent substituted or unsubstituted methine groups; M+represents a proton or an inorganic or organic cation; and n is 0, 1, 2 or 3 and wherein the aggregated dye in the dispersion has an absorption halfbandwidth of less than 55 nm.

Process for preparing 4-amino-3-methyl-N-substituted or unsubstituted alkylanilines

A process for the preparation of 4-amino-3-methyl-N-substituted or unsubstituted alkylanilines comprising acylating and/or sulfonylating 4-amino-3-methyl-nitro-benzene having the formula (I) STR1 with an acylation or sulfonylation agent to obtain a compound having the general formula (II) STR2 wherein R1 represents a hydrogen atom or an acyl group, R2 represents an acyl group or a sulfonyl group, or R1 and R2 can combine as a difunctional acyl group; reducing the nitro group of the compound having the general formula (II) with hydrogen in the presence of a metal hydrogenation catalyst to obtain a compound having the general formula (III) STR3 wherein R1 and R2 are as above defined; alkylating the amino group of the compound having the general formula (III) with an alkylation agent selected from the group consisting of an alkyl halide, a substituted alkyl halide and an alkylene oxide to obtain a compound having the general formula (IV) STR4 wherein R1 and R2 are as above defined, R3 represents an alkyl group or a substituted alkyl group and R4 represents a hydrogen atom, an alkyl group or a substituted alkyl group; and hydrolyzing the compound having the general formula (IV) to obtain a compound having the general formula (V) STR5 wherein R3 and R4 are as above defined.