36451-09-9

Basic information

• Product Name: 2-Diazo-1-naphthol-4-sulfonyl chloride
• Synonyms: 3-DIAZO-4-OXO-3,4-DIHYDRO-NAPHTHALENE-1-SULFONYL CHLORIDE;3-DIAZO-3,4-DIHYDRO-4-OXO-1-NAPHTHALENESULFONYL CHLORIDE;2-diazo-1-naphthol-4-sulfonyl chloride;2-DIAZO-1-NAPHTHOL-4-SULPHOCHLORIDE;1,2-NAPHTHOQUINONE-2-DIAZIDO-4-SULFONYL CHLORIDE;3-diazo-3,4-dihydro-4-oxo-1-naphthalenesulfonylchlorid;3-diazo-3,4-dihydro-4-oxonaphthalene-1-sulphonyl chloride;1,2-NAPHTHOQUINONE-2-DIAZIDO-4-SULFONYL CHLORIDE 98+%
• CAS NO: 36451-09-9
• Molecular Formula: C₁₀H₅ClN₂O₃S
• Molecular Weight: 268.68
• EINECS: 253-042-9
• Mol File: 36451-09-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Diazo-1-naphthol-4-sulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Diazo-1-naphthol-4-sulfonyl chloride(36451-09-9)
• EPA Substance Registry System: 2-Diazo-1-naphthol-4-sulfonyl chloride(36451-09-9)

Safety Data

• RIDADR: 3222
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 36451-09-9(Hazardous Substances Data)

Usage

Form

Light yellow to Brown to Dark green powder to crystal

Uses

2-Diazo-1-naphthol-4-sulfonyl chloride is a useful research chemical.

Flammability and Explosibility

Flammable

Synthetic route

1,2-Naphthochinondiazid-(2)-4-sulfonsaeure Natriumsalz (64173-96-2) → 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9)

Conditions	Yield
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) → 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9)

Conditions	Yield
With chlorosulfonic acid

2-diazo-1,2-naphthoquinone (879-15-2) → 2-Diazo-1-oxo-1,2-dihydronaphthalen-5-sulfonsaeure (94386-30-8) + 1,2-Naphthoquinone diazide-(2)-4-sulfonic acid (887-77-4) + 2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride (1001756-09-7, 3770-97-6) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9)

Conditions	Yield
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) → 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9)

Conditions	Yield
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) → 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9)

Conditions	Yield
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) → 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9)

Conditions	Yield
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) → 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9)

Conditions	Yield
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) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 3-Diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonic acid ethyl ester

Conditions	Yield
With triethylamine In 1,4-dioxane for 1h; Ambient temperature;	90%

4,4',4''-methylidynetrisphenol (603-44-1) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → C49H28N6O12S3

Conditions	Yield
With triethylamine In acetone at 20℃; for 3h;	89.5%

α,α,α',α'-tetrakis(3-methyl-4-hydroxyphenyl)-4,4'-dimethyldiphenyl ether + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → C82H54N8O17S4

Conditions	Yield
With triethylamine In acetone at 20℃; for 3h;	89.1%

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) + phenol (108-95-2) → phenyl naphthoquinone-1,2-(diazide-2)-4-sulfonate (110673-14-8)

Conditions	Yield
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) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 4-(3-Diazo-4-oxo-3,4-dihydro-naphthalene-1-sulfonyloxy)-benzoic acid propyl ester

Conditions	Yield
With triethylamine In 1,4-dioxane for 1h; Ambient temperature;	82%

p-cresol (106-44-5) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 1-oxo-2-diazo-1,2-dihydronaphthalenesulfonic acid p-tolyl ester (120410-45-9)

Conditions	Yield
With triethylamine In 1,4-dioxane for 1h; Ambient temperature;	81%

(1,1,3,3-tetramethyldisiloxane-1,3-diyl)dimethanol (5833-59-0) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → bis[2,1-(diazonaphthalenone-4-sulfoxido)methyldimethyl]siloxane

Conditions	Yield
In pyridine at 20℃; for 2h;	67.6%

BPA (80-05-7) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 2,2-bis<4-(2,1-diazonaphthalenone-4-sulfonyloxy)phenyl>propane

Conditions	Yield
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) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → bis[(2,1-diazonaphthalenone-4-sulfonamido)dimethylpropyl]siloxane

Conditions	Yield
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) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → C30H34N4O9S2Si2

Conditions	Yield
In pyridine Ambient temperature;	55.3%

2,4-dihydroxybenzophenone (131-56-6) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → C33H18N4O9S2

Conditions	Yield
With sodium carbonate In acetone at 35 - 40℃; for 0.666667h;	40.6%

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) + 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (83558-87-6) → C35H20F6N6O8S2

Conditions	Yield
With sodium carbonate In acetone at 35 - 40℃; for 40h;	37.6%

methanol (67-56-1) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 1-hydroxy-4-methoxysulfonyl-naphthalene-2-diazonium-betaine

2',4'-dihydroxy-4-acetophenone (89-84-9) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 4-(4-acetyl-3-hydroxy-phenoxysulfonyl)-1-hydroxy-naphthalene-2-diazonium-betaine

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) + aniline (62-53-3) → 1-hydroxy-4-phenylsulfamoyl-naphthalene-2-diazonium-betaine

2-Hydroxybenzophenone (117-99-7) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 2-diazonaphthalenone 4-sulfonyl ester of o-hydroxybenzophenone

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether

2-Hydroxybenzophenone (117-99-7) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → C33H18N4O9S2

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether

3-hydroxybenzophenone (13020-57-0) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 2-diazonaphthalenone 4-sulfonyl ester of m-hydroxybenzophenone

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) + 4-Hydroxybenzophenone (1137-42-4) → 2-diazonaphthalenone 4-sulfonyl ester of p-hydroxybenzophenone

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether

1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) + 4-Hydroxybenzophenone (1137-42-4) → C33H18N4O9S2 (118429-49-5)

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether

4,4'-Dihydroxybenzophenone (611-99-4) + 2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride (1001756-09-7, 3770-97-6) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 4,4'-di(1,2-naphthoquinone-2-diazide-5-sulfonyl-oxy)-benzophenone (106301-90-0) + C33H18N4O9S2 (118429-49-5) + C33H18N4O9S2

4,4'-Dihydroxybenzophenone (611-99-4) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 4,4'-di(1,2-naphthoquinone-2-diazide-5-sulfonyl-oxy)-benzophenone (106301-90-0) + C33H18N4O9S2 (118429-49-5) + C33H18N4O9S2

Conditions	Yield
With 1,2-naphthoquinone-2-diazide-5-sulfochloride

Propyl gallate (121-79-9) + 2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride (1001756-09-7, 3770-97-6) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 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 + 3,4,5-Tris-(6-diazo-5-oxo-5,6-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	Yield
With TEA In 1,4-dioxane

Propyl gallate (121-79-9) + 2-diazo-1-oxo-1,2-dihydronaphthalene-4-sulfonyl chloride (1001756-09-7, 3770-97-6) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 3,4,5-Tris-(6-diazo-5-oxo-5,6-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 + 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	Yield
With TEA In 1,4-dioxane

Propyl gallate (121-79-9) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → 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 + 3,4,5-Tris-(6-diazo-5-oxo-5,6-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	Yield
With 1,2-naphthoquinone-2-diazide-5-sulfochloride; TEA In 1,4-dioxane

Upstream product

• 887-77-4 1-hydroxy-4-sulfo-naphthalene-2-diazonium-betaine 
• 64173-96-2 1,2-Naphthochinondiazid-⁽²⁾-4-sulfonsaeure Natriumsalz 
• 130-13-2 sodium 4-amino-1-naphthalenesulfonate 
• 567-13-5 2-amino-1-naphthol-4-sulfonic acid 
• 879-15-2 2-diazo-1,2-naphthoquinone 
• 1787-54-8 2-Nitroso-1-naphthol-4-sulfonsaeure Natriumsalz 
• 6099-57-6 sodium 1-naphthol-4-sulfonate 

Downstream Products

• 110673-14-8 phenyl naphthoquinone-1,2-(diazide-2)-4-sulfonate 
• 124-18-5 decane 
• 910883-20-4 C₃₀H₂₂N₂O₅S 
• 796857-56-2 C₃₀H₂₂N₂O₅S 
• 910883-12-4 C₄₀H₂₆N₄O₈S₂ 
• 910883-38-4 C₄₀H₂₆N₄O₈S₂ 
• 136830-35-8 C₄₀H₂₆N₄O₈S₂ 
• 120410-45-9 1-oxo-2-diazo-1,2-dihydronaphthalenesulfonic acid p-tolyl ester 

Relevant articles and documents

Single Pot Process For The Preparation Of Diazonaphthoquinonesulfonyl Ester

The present invention provides a single pot process for the preparation of diazonaphthoquinonesulfonyl ester, a useful organic material for micro electronic and dye industry. This study pertains to the one pot preparation of diazonaphthoquinonesulfonyl esters using the corresponding diazonaphthoquinine sulfonic acid or its sodium salt, diphosgene or triphosgene, variety of hydroxy compounds and tertiary organic base in an organic solvent medium.

A process for the preparation of diazonaphthoquinonesulfonylchlorides using diphosgene and triphosgene

The invention relates to a a process for the preparation of diazonaphthoquinonesulfonylchlorides using diphosgene and triphosgene of the formula 1a, 1b, 1c using diphosgene or triphosgene.

Sulfochlorination of 1,2-Naphthoquinone-(2)-diazide by Chlorosulfonic acid

The sulfochlorination of 1,2-naphthoquinone diazide-(2) (1) by chlorosulfonic acid was investigated.The yields of the formed products (1,2-naphthoquinone diazide-(2)-4-sulfonic acid (4), 1,2-naphthoquinone diazide-(2)-5-sulfonic acid (5), 1,2-naphthoquinone diazide-(2)-4-sulfochloride (2) and 1,2-naphthoquinone diazide-(2)-5-sulfochloride (3)) depend on the temperature and on the time of reaction.The highest yields of the favoured 1,2-naphthoquinone diazide-(2)-4-sulfochloride (2) are obtained at 63 deg C and after a reaction time of 80 minutes (50percent).