Patai S., Rappoport Z. 1996 The chemistry of functional groups. The chemistry of amino, nitroso, nitro and related groups. Part 2 / 1169 1214

Sudan IV

Guiba Black D

(C.I. Direct Black 17)

Methyl Red

Methyl Orange

N,N-Dimethyl-4- aminoazobenzene

N-Methyl-4- aminoazobenzene

4-Aminoazobenzene

2-Methyl-N,N dimethyl-4- aminoazobenzene

	CH3		CH3 OH
	N N		N N
			OH
		OCH2		NH3
H2 N	N N		N N
	H3 C		NaO3 S
	HO
	O		CH3
	N N
			N
			CH3
	N2 O2 S	N N	N(OH2 )2
	N N		CH3
			H
			CH3
	N	N	NHCH3
	N N		NH3
		H3 C
	N	N	N(CH3 )2

C

š

C

C

C

C

C

C

1199

(continued overleaf )

TABLE 8. (continued)

Common		Chemical
name		structure
		CH3		CH3
O-Aminoazotoluene		N	N	NH3
				OCH2
3-Methoxy-4-		N N		NH2
aminoazobenzene
N-Hydroxy-4-		N	N	N(CH)
aminoazobenzene				N
				CH3
N-Acetoxy-N-methyl-		N N		N
4-aminoazobenzene				OCOCH2
				CH3
N-Benzoyloxy-		N N		N O
				O C
N-methyl-4-
aminoazobenzene
40 -Methoxycarbonyl-N-		O
	CH3	O C	N N		H	OH
hydroxy					CH3
N-methyl-4-
aminoazobenzene
40 -Methoxycarbonyl-N-		O			CH3
	CH3 O	C	N N	H	O
methoxycarbonyl				O	C	CH3
N-methyl-4-

aminoazobenzene

Metabolic activationa

C

C

C

š

š

1200

40 -Methoxycarbonyl-N- benzoyloxy- N-methyl-4- aminoazobenzene

N-Hydroxyl-N-methyl- 4-aminoazobenzene

N-Methyl-N-hydroxy- 4-aminoazobenzene

30 -Methyl-N,N dimethyl-4- aminoazobenzene

30 -Methyl-N-methyl-4- aminoazobenzene

30 -Methyl-4- aminoazobenzene

O

CH3 O C

H3 C

H3 C

H3 C

CH3

			CH3
	N N		H O
			O C
N	N	H	CH3
		OH
N	N	H	CH3
		OH
	N N	N(CH3 )2

N N	H	CH3
	H
N N	NH2

š

š

š

C

C

C

30 -Methyl-N-	N N	C
methyl-N-acetyl-4-		NCH3
		COCH3
aminoazobenzene
		(continued overleaf )

1201

TABLE 8. (continued)

	Common	Chemical
	name	structure
	30 -Methyl-N-acetyl-4-	CH2
		N N	NHCOCH3
	aminoazobenzene

HOH2 C

30 -Hydroxylmethyl-

N,N-dimethyl-4- N N N(CH3 )2 aminoazobenzene

HOH2 C

30 -Hydroxylmethyl- N-methyl-4- aminoazobenzene

30 -Hydroxylmethyl-4- aminoazobenzene

30 -Formyl-N,N- dimethyl-4- aminoazobenzene

30 -Carboxylic N,N-dimethyl-4- aminoazobenzene

N N	N CH3
	H
HOH2 C
N N	NH2
O
HC
N N	N(CH3 )2

O

HOC

N N

N(CH3 )2

1202

Metabolic activationa

C

C

C

C

C

C

30 -Carboxylic- N-methyl-4- aminoazobenzene

30 -Methyl-40 -hydroxyl- N,N-dimethyl-4 -aminoazobenzene

3,30 -Bischloromethyl-4- aminoazobenzene

O
HOC			C
	N	N	HHCH3
CH2			C
HO	N	N	N(CH3 )2
CH2 Cl			CNCH3
		N N	NH2
CH2 OAc

30 -Acetoxymethane- N,N-dimethyl-4- aminoazobenzene

20 -Methyl-N,N- dimethyl-4- aminoazobenzene

20 ,3-Hydroxylmethyl- N,N-dimethyl-4- aminoazobenzene

40 -Methyl-N,N- dimethyl-4- aminoazobenzene

	N	N	N(CH3 )2	C
	CH3			C
	N	N	N(CH3 )2
	CH2 OH		CH2 OH	C
	N	N	N(CH3 )2
	H3 C	N N	N(CH3 )2	C

(continued overleaf )

1203

TABLE 8.	(continued)
Common	Chemical
name	structure

40 -Hydroxymethyl- N,N-dimethyl-4- aminoazobenzene

6-Dimethylaminophenyl- azobenzthiazole (6BT)

5-Dimethylamino- phenylazoindoline (5I)

Chrysoidin Y

(C.I. Index 11325)

Bismark Brown Y

(C.I. Index 21000)

Bismark Brown R

(C.I. Index 21010)

HOH2 C	N N
HN	N	N
S
HN	N	N
N
	CH	N2 H
	3
	N N
	NH2
H2 N	N N
	NH2
H2 N	N N

	N(CH3 )2
	CH3
	N
	CH3
	CH2
	N
	CH2
	NH2
	CH3
	H2 N
N	N	NH2
	H2 N
N	N	NH2

CH3		CH3	CH3
4,40 -Diaminoazobenzene	H2 N	N N	NH2

Metabolic activationa

C

C

C

C

C

C

C

1204

4,40 -(B-Hydroxyethyl- amino)Azobenzine

Direct Black 19

Direct Black 38

(Direct Deep Black EX)

Direct Black GB NB

		HOH2 CH2 CHN	N	N	NHCH2 CH2 OH	C
		NH2	NH2	OH	N2 H
						C
	N2 H	N N	N N	N N	N N
						NH2
		NO2 S		SO2 N
		NH2		NH2 OH
						C
	H1N	N N		N N	N N
				NaO2 S	SO2 Na
		OH			NH2 OH
	H1N	N N	C NH	N N	N N	C
			O	HO2 S	SO2 H

		NH2	NH	OH		H2 N
			2					C
Direct Black 19	H1N	N N	N N		N N	N N	NH2
Analogue	HO	S	HO S		SO H		SO2 H
	2		2		2
		OH	NH2	OH		HO		C
Direct Black 19	OH	N N	N N		N N	N N	OH
Analogue			HO2 S		SO2 H	OH
	HO

(continued overleaf )

1205

TABLE 8. (continued)

Common				Chemical					Metabolic
name				structure					activationa
	HO	OH		NH2	OH		OH		C
Direct Black 19		N N		N N	N N		N N	OH
Analogue				HO2 S	SO2 H
	HO	OH					OH
	HOOC			OH OH			COOH
Direct Black 19	HO	N N		N N	N N		N N	HO	C
Analogue
				SO2 H
Azo Dyes Containing the Benzidine Group
			O			H2 N SO2 Na
		H3 C	S O	N N		N N			š
Brown 5 R			O
(C.I. Acid Orange 45)
							SO2 Na
		NaO2 S		SO2 Na	NaO2 S		SO2 Na
Trypan Blue				N N	N N				C
(Direct Blue 14)		NH2	OH	H C	CH	OH	NH2
				3	3
		NH2	OH			OH	NH2
		NaO2 S		N N	N N		SO3 Na		C
Evan’s Blue
		NaO2 S		H3 C	CH3		SO3 Na

1206

Congo Red

Benzopurpurin 4 B (Deltapurpurin)

Direct Blue I

Pentacyl Sky

Blue 4 B X

	NH2
		N N	N N
	SO3 Na
	NH	H3 C	CH3
	2
		N N	N N
	SO3 Na
NH	OH	H3 CO	OCH3
2
NaO3 S		N N	N N
SO3 Na
NH	OH	H3 CO	OCH3
2
		N N	N N
NaO2 S		SO2 Na	NaO3 S

NH2

SO3 Na

NH2

SO3 Na

OH NH2

SO3 Na

SO3 Na

OH NH2

SO2 Na

C

C

C

C

			O	O	O
	NaOOC				C
Direct Brown 95	HO	N N	N N	N N
			HO		SO2 Na
	NH2	OH		OH	NH2
Direct Blue 6		N N	N N		C
	NaO2 S	SO3 Na	NaO3 S		SO3 Na

(continued overleaf )

1207

TABLE 8. (continued)

Common						Chemical
name						structure
	NaOOC						NH2
Direct Brown 1:2	HO	N	N			N N	N N	SO2 Na
						N2 H
							OH2
NaOOC				NH2		HO
Direct Brown 31 HO	N N		N N		N	N	N N	SO2 Na
			N2 H	NaO2 S			SO2 Na
				OH2				HO
		O
	H3 C	S O			N	N	N	N
Acid Red 85		O					NaO2 S
								SO2 Na
			NH2	H3 C		OH2	NH2
Direct Red 2				N N		N N
			SO2 Na				SO2 Na
	NaO2 S	NH2	OH	H3 C		OH2	OH	OH
								SO	Na
Direct Blue 53				N N		N N		2
	NaO2 S							SO2 Na

Metabolic activationa

C

C

C

C

C

1208