Product Name

  • Name

    2-Diazo-1-naphthol-4-sulfonyl chloride

  • EINECS 253-042-9
  • CAS No. 36451-09-9
  • Article Data6
  • CAS DataBase
  • Density 1.107?g/mL?at 25?°C(lit.)
  • Solubility
  • Melting Point 28-31°C
  • Formula C10H5ClN2O3S
  • Boiling Point 215-217?°C30?mm Hg(lit.)
  • Molecular Weight 268.68
  • Flash Point >230?°F
  • Transport Information UN 3222
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 36451-09-9 (2-Diazo-1-naphthol-4-sulfonyl chloride)
  • Hazard Symbols
  • Synonyms 1,2-Naphthoquinone-2-diazide-4-sulfonylchloride;1,2-Naphthoquinonediazide-4-sulfonic acid chloride;1,2-Naphthoquinonediazide-4-sulfonyl chloride;2-Diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyl chloride;3-Diazo-3,4-dihydro-4-oxo-1-naphthalenesulfonyl chloride;
  • PSA 96.98000
  • LogP 2.62506

Synthetic route

1,2-Naphthochinondiazid-(2)-4-sulfonsaeure Natriumsalz
64173-96-2

1,2-Naphthochinondiazid-(2)-4-sulfonsaeure Natriumsalz

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

Conditions
ConditionsYield
With triethylamine; trichloromethyl chloroformate In dichloromethane at -50℃; for 1.33333 - 1.5h; Product distribution / selectivity;80%
With bis(trichloromethyl) carbonate; triethylamine In dichloromethane at -50℃; for 1.33333h; Product distribution / selectivity;80%
With chlorosulfonic acid 1) 65 deg, 5h, 2) overnight;30%
1-hydroxy-4-sulfo-naphthalene-2-diazonium-betaine
887-77-4

1-hydroxy-4-sulfo-naphthalene-2-diazonium-betaine

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid
2-diazo-1,2-naphthoquinone
879-15-2

2-diazo-1,2-naphthoquinone

A

2-Diazo-1-oxo-1,2-dihydronaphthalen-5-sulfonsaeure
94386-30-8

2-Diazo-1-oxo-1,2-dihydronaphthalen-5-sulfonsaeure

B

1,2-Naphthoquinone diazide-(2)-4-sulfonic acid
887-77-4

1,2-Naphthoquinone diazide-(2)-4-sulfonic acid

C

2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride
1001756-09-7, 3770-97-6

2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride

D

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

Conditions
ConditionsYield
In water at 65℃; for 1.25h; Mechanism; variation of time and temperature;
In water at 65℃; for 1.25h;
2-amino-1-naphthol-4-sulfonic acid
567-13-5

2-amino-1-naphthol-4-sulfonic acid

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / CuSO4, NaNO2 / H2O / 0.17 h
2: 30 percent / chlorosulfonic acid / 1) 65 deg, 5h, 2) overnight
View Scheme
sodium 1-naphthol-4-sulfonate
6099-57-6

sodium 1-naphthol-4-sulfonate

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 60 percent / NaNO2, conc. HCl / H2O / 0.83 h
2: 34 percent / sodium dithionite / aq. NaOH / 0.08 h
3: 60 percent / CuSO4, NaNO2 / H2O / 0.17 h
4: 30 percent / chlorosulfonic acid / 1) 65 deg, 5h, 2) overnight
View Scheme
sodium 4-amino-1-naphthalenesulfonate
130-13-2

sodium 4-amino-1-naphthalenesulfonate

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / sodium hydrogensulfite / H2O / 24 h / Heating
2: 60 percent / NaNO2, conc. HCl / H2O / 0.83 h
3: 34 percent / sodium dithionite / aq. NaOH / 0.08 h
4: 60 percent / CuSO4, NaNO2 / H2O / 0.17 h
5: 30 percent / chlorosulfonic acid / 1) 65 deg, 5h, 2) overnight
View Scheme
2-Nitroso-1-naphthol-4-sulfonsaeure Natriumsalz
1787-54-8

2-Nitroso-1-naphthol-4-sulfonsaeure Natriumsalz

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 34 percent / sodium dithionite / aq. NaOH / 0.08 h
2: 60 percent / CuSO4, NaNO2 / H2O / 0.17 h
3: 30 percent / chlorosulfonic acid / 1) 65 deg, 5h, 2) overnight
View Scheme
ethanol
64-17-5

ethanol

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

3-Diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonic acid ethyl ester

3-Diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane for 1h; Ambient temperature;90%
4,4',4''-methylidynetrisphenol
603-44-1

4,4',4''-methylidynetrisphenol

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

C49H28N6O12S3

C49H28N6O12S3

Conditions
ConditionsYield
With triethylamine In acetone at 20℃; for 3h;89.5%
α,α,α',α'-tetrakis(3-methyl-4-hydroxyphenyl)-4,4'-dimethyldiphenyl ether

α,α,α',α'-tetrakis(3-methyl-4-hydroxyphenyl)-4,4'-dimethyldiphenyl ether

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

C82H54N8O17S4

C82H54N8O17S4

Conditions
ConditionsYield
With triethylamine In acetone at 20℃; for 3h;89.1%
1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

phenol
108-95-2

phenol

phenyl naphthoquinone-1,2-(diazide-2)-4-sulfonate
110673-14-8

phenyl naphthoquinone-1,2-(diazide-2)-4-sulfonate

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane for 1h; Ambient temperature;84%
With potassium hydroxide; 18-crown-6 ether
With triethylamine In dichloromethane at 0℃; for 1h; Product distribution / selectivity;
nipasol
94-13-3

nipasol

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

4-(3-Diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

4-(3-Diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane for 1h; Ambient temperature;82%
p-cresol
106-44-5

p-cresol

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

1-oxo-2-diazo-1,2-dihydronaphthalenesulfonic acid p-tolyl ester
120410-45-9

1-oxo-2-diazo-1,2-dihydronaphthalenesulfonic acid p-tolyl ester

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane for 1h; Ambient temperature;81%
(1,1,3,3-tetramethyldisiloxane-1,3-diyl)dimethanol
5833-59-0

(1,1,3,3-tetramethyldisiloxane-1,3-diyl)dimethanol

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

bis[2,1-(diazonaphthalenone-4-sulfoxido)methyldimethyl]siloxane

bis[2,1-(diazonaphthalenone-4-sulfoxido)methyldimethyl]siloxane

Conditions
ConditionsYield
In pyridine at 20℃; for 2h;67.6%
1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

2,2-bis<4-(2,1-diazonaphthalenone-4-sulfonyloxy)phenyl>propane

2,2-bis<4-(2,1-diazonaphthalenone-4-sulfonyloxy)phenyl>propane

Conditions
ConditionsYield
With sodium carbonate In acetone at 35 - 40℃; for 0.666667h;67.5%
1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane
2469-55-8

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

bis[(2,1-diazonaphthalenone-4-sulfonamido)dimethylpropyl]siloxane

bis[(2,1-diazonaphthalenone-4-sulfonamido)dimethylpropyl]siloxane

Conditions
ConditionsYield
With pyridine at 30 - 35℃; for 0.666667h;63.9%
4,4,6,6-tetramethyl-5-oxa-4,6-disila-nonane-1,9-diol
18001-97-3

4,4,6,6-tetramethyl-5-oxa-4,6-disila-nonane-1,9-diol

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

C30H34N4O9S2Si2

C30H34N4O9S2Si2

Conditions
ConditionsYield
In pyridine Ambient temperature;55.3%
2,4-dihydroxybenzophenone
131-56-6

2,4-dihydroxybenzophenone

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

C33H18N4O9S2

C33H18N4O9S2

Conditions
ConditionsYield
With sodium carbonate In acetone at 35 - 40℃; for 0.666667h;40.6%
1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane
83558-87-6

2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane

C35H20F6N6O8S2

C35H20F6N6O8S2

Conditions
ConditionsYield
With sodium carbonate In acetone at 35 - 40℃; for 40h;37.6%
methanol
67-56-1

methanol

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

1-hydroxy-4-methoxysulfonyl-naphthalene-2-diazonium-betaine

1-hydroxy-4-methoxysulfonyl-naphthalene-2-diazonium-betaine

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

4-(4-acetyl-3-hydroxy-phenoxysulfonyl)-1-hydroxy-naphthalene-2-diazonium-betaine

4-(4-acetyl-3-hydroxy-phenoxysulfonyl)-1-hydroxy-naphthalene-2-diazonium-betaine

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

aniline
62-53-3

aniline

1-hydroxy-4-phenylsulfamoyl-naphthalene-2-diazonium-betaine

1-hydroxy-4-phenylsulfamoyl-naphthalene-2-diazonium-betaine

2-Hydroxybenzophenone
117-99-7

2-Hydroxybenzophenone

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

2-diazonaphthalenone 4-sulfonyl ester of o-hydroxybenzophenone

2-diazonaphthalenone 4-sulfonyl ester of o-hydroxybenzophenone

Conditions
ConditionsYield
With potassium hydroxide; 18-crown-6 ether
2-Hydroxybenzophenone
117-99-7

2-Hydroxybenzophenone

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

C33H18N4O9S2

C33H18N4O9S2

Conditions
ConditionsYield
With potassium hydroxide; 18-crown-6 ether
3-hydroxybenzophenone
13020-57-0

3-hydroxybenzophenone

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

2-diazonaphthalenone 4-sulfonyl ester of m-hydroxybenzophenone

2-diazonaphthalenone 4-sulfonyl ester of m-hydroxybenzophenone

Conditions
ConditionsYield
With potassium hydroxide; 18-crown-6 ether
1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

4-Hydroxybenzophenone
1137-42-4

4-Hydroxybenzophenone

2-diazonaphthalenone 4-sulfonyl ester of p-hydroxybenzophenone

2-diazonaphthalenone 4-sulfonyl ester of p-hydroxybenzophenone

Conditions
ConditionsYield
With potassium hydroxide; 18-crown-6 ether
1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

4-Hydroxybenzophenone
1137-42-4

4-Hydroxybenzophenone

C33H18N4O9S2
118429-49-5

C33H18N4O9S2

Conditions
ConditionsYield
With potassium hydroxide; 18-crown-6 ether
4,4'-Dihydroxybenzophenone
611-99-4

4,4'-Dihydroxybenzophenone

2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride
1001756-09-7, 3770-97-6

2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

A

4,4'-di(1,2-naphthoquinone-2-diazide-5-sulfonyl-oxy)-benzophenone
106301-90-0

4,4'-di(1,2-naphthoquinone-2-diazide-5-sulfonyl-oxy)-benzophenone

B

C33H18N4O9S2
118429-49-5

C33H18N4O9S2

C

C33H18N4O9S2

C33H18N4O9S2

4,4'-Dihydroxybenzophenone
611-99-4

4,4'-Dihydroxybenzophenone

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

A

4,4'-di(1,2-naphthoquinone-2-diazide-5-sulfonyl-oxy)-benzophenone
106301-90-0

4,4'-di(1,2-naphthoquinone-2-diazide-5-sulfonyl-oxy)-benzophenone

B

C33H18N4O9S2
118429-49-5

C33H18N4O9S2

C

C33H18N4O9S2

C33H18N4O9S2

Conditions
ConditionsYield
With 1,2-naphthoquinone-2-diazide-5-sulfochloride
Propyl gallate
121-79-9

Propyl gallate

2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride
1001756-09-7, 3770-97-6

2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

A

3,5-Bis-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-4-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

3,5-Bis-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-4-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

B

3,4,5-Tris-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

3,4,5-Tris-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

C

3,4,5-Tris-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

3,4,5-Tris-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

Conditions
ConditionsYield
With TEA In 1,4-dioxane
Propyl gallate
121-79-9

Propyl gallate

2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride
1001756-09-7, 3770-97-6

2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

A

3,4,5-Tris-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

3,4,5-Tris-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

B

3,4,5-Tris-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

3,4,5-Tris-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

C

3,5-Bis-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-4-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

3,5-Bis-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-4-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

Conditions
ConditionsYield
With TEA In 1,4-dioxane
Propyl gallate
121-79-9

Propyl gallate

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride
36451-09-9

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride

A

3,5-Bis-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-4-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

3,5-Bis-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-4-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

B

3,4,5-Tris-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

3,4,5-Tris-(6-diazo-5-oxo-5,6-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

C

3,4,5-Tris-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

3,4,5-Tris-(3-diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

Conditions
ConditionsYield
With 1,2-naphthoquinone-2-diazide-5-sulfochloride; TEA In 1,4-dioxane

2-Diazo-1-naphthol-4-sulfonyl chloride Chemical Properties


IUPAC Name: 4-Chlorosulfonyl-2-diazonionaphthalen-1-olate
Molecular Formula: C10H5ClN2O3S
Molecular Weight: 270.69 g/mol
Canonical SMILES: O=C1c2c(C(S(=O)(=O)Cl)=CC1=N#N)cccc2
InChI: InChI=1/C10H5ClN2O3S/c11-17(15,16)9-5-8(13-12)10(14)7-4-2-1-3-6(7)9/h1-5H
Mol File: 36451-09-9.mol
EINECS: 253-042-9
XLogP3-AA: 4.1
H-Bond Acceptor: 4
Rotatable Bond Count: 1
Exact Mass: 267.97094
Topological Polar Surface Area: 85.4
Heavy Atom Count: 17
Complexity of 2-Diazo-1-naphthol-4-sulfonyl chloride (CAS NO.36451-09-9): 438

2-Diazo-1-naphthol-4-sulfonyl chloride Safety Profile

HazardClass: 4.1
PackingGroup of 2-Diazo-1-naphthol-4-sulfonyl chloride (CAS NO.36451-09-9): III

2-Diazo-1-naphthol-4-sulfonyl chloride Specification

 2-Diazo-1-naphthol-4-sulfonyl chloride (CAS NO.36451-09-9), its Synonyms are 1-Naphthalenesulfonyl chloride, 3-diazo-3,4-dihydro-4-oxo- ; 3-Diazo-3,4-dihydro-4-oxonaphthalene-2-sulphonyl chloride ; 3-Diazo-3,4-dihydro-4-oxo-1-naphthalenesulfonylchlorid ; 1,2-naphthoquinone-2-diazido-4-sulfonyl chloride 98+% .

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