13360-57-1

Basic information

• Product Name: Dimethylsulfamoyl chloride
• Synonyms: dimethylamidosulfonylchloride;dimethylaminosulfonylchloride;N,N-Dimethylaminosulfonyl chloride;Dimethylsulfamoyl chloride ,99%;Dimethylsulfamic acid chloride;Dimethylsulfamideoic chloride;N,N-Dimethylamidosulfuric acid chloride;Dimethylsulfamoyl chloride,97%
• CAS NO: 13360-57-1
• Molecular Formula: C₂H₆ClNO₂S
• Molecular Weight: 143.59
• EINECS: 236-412-4
• Product Categories: Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;Aliphatics, Impurities, Intermediates, Sulfur & Selenium Compounds
• Mol File: 13360-57-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: -13 °C
• Boiling Point: 114 °C75 mm Hg(lit.)
• Flash Point: 202 °F
• Appearance: clear colorless to slightly yellow liquid
• Density: 1.337 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.653mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: Store below +30°C.
• PKA: -8.25±0.70(Predicted)
• Water Solubility: DECOMPOSES
• BRN: 741979
• CAS DataBase Reference: Dimethylsulfamoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethylsulfamoyl chloride(13360-57-1)
• EPA Substance Registry System: Dimethylsulfamoyl chloride(13360-57-1)

Safety Data

• Hazard Codes: T+
• Statements: 45-21/22-26-34
• Safety Statements: 53-45
• RIDADR: UN 3390 6.1/PG 1
• WGK Germany: 3
• RTECS: WO7185500
• F: 10
• HazardClass: 6.1(a)
• PackingGroup: III
• Hazardous Substances Data: 13360-57-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

Dichlorofluanid is a degradation product of the pesticide Dichlorofluanid.

InChI:InChI=1/C2H6ClNO2S/c1-4(2)7(3,5)6/h1-2H3

Synthetic route

N,N-dimethylammonium chloride → dimethylamino sulfonyl chloride (13360-57-1)

dimethylchloroamine (1585-74-6) → dimethylamino sulfonyl chloride (13360-57-1)

Conditions	Yield
With sulfur dioxide In tetrachloromethane 1.) 0 deg C, 1.5 h, 2.) up to r.t., overnight;	70%

dimethyl amine (124-40-3) → dimethylamino sulfonyl chloride (13360-57-1)

Conditions	Yield
With sulfuryl dichloride
With sulfuryl dichloride; triethylamine In 1,4-dioxane; chloroform at 0 - 20℃;

N,N-Dimethylcarbamoyl chloride (79-44-7) → dimethylamino sulfonyl chloride (13360-57-1)

Conditions	Yield
With chlorosulphuric acid
With sulfur trioxide

Carbamidsaeure-methylester-N-sulfonsaeure-dimethylamid (89168-09-2) → dimethylamino sulfonyl chloride (13360-57-1)

Conditions	Yield
With phosphorus pentachloride

C5H15N2O2S(1+)*Cl(1-) (29777-18-2) → dimethylamino sulfonyl chloride (13360-57-1)

Conditions	Yield
at 60℃;

C2H6NO2S(1-)*Na(1+) → dimethylamino sulfonyl chloride (13360-57-1)

Conditions	Yield
With chlorine In tetrachloromethane

C2H6NO3S(1-)*Na(1+) (41955-27-5) → dimethylamino sulfonyl chloride (13360-57-1)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-ethane at 80℃; for 18h;

antimony (V) pentachloride + N,N-dimethylammonium chloride (506-59-2) → dimethylamino sulfonyl chloride (13360-57-1)

Conditions	Yield
With sulfuryl dichloride In acetonitrile	44.2 g (87%)
With sulfuryl dichloride In acetonitrile	44.2 g (87%)
With sulfuryl dichloride In acetonitrile	44.2 g (87%)

dipropylchloroborane (22086-53-9) + tetramethylsulfamide (3768-63-6) → (dimethylamino)di-n-propylborane (13113-78-5) + dimethylamino sulfonyl chloride (13360-57-1)

dibutylchloroborane (1730-69-4) + tetramethylsulfamide (3768-63-6) → dimethylamino sulfonyl chloride (13360-57-1)

4,4-ethylenedioxy-piperidine (177-11-7) + dimethylamino sulfonyl chloride (13360-57-1) → N,N-dimethyl-1,4-dioxa-8-azaspiro[4.5]decane-8-sulfonamide (877796-41-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1h;	100%

dimethylamino sulfonyl chloride (13360-57-1) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → (S)-6'-chloro-N-((R)-hept-6-en-3-ylsulfonyl)-5-((2-((S)-1-hydroxyallyl)-2-methylcyclobutyl)methyl)-3',4,4',5-tetrahydro-2H,2’H-spiro[benzo[b][1,4]oxazepine-3,1’-naphthalene]-7-carboxamide (253176-45-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	100%
With triethylamine In dichloromethane at 20℃; for 12h;	92%
With triethylamine at 0 - 20℃; for 4h; Inert atmosphere;	89%

dimethylamino sulfonyl chloride (13360-57-1) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → piperazine-1-sulfonic acid dimethylamide (98961-97-8)

Conditions	Yield
Stage #1: dimethylamino sulfonyl chloride; 1-t-Butoxycarbonylpiperazine With triethylamine In tetrahydrofuran at 0℃; for 1h; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 48h; Stage #3: With sodium hydroxide In dichloromethane; water	100%

N,N-diethyl-4-[7-hydroxy-6-methoxy-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]benzamide (857252-49-4) + dimethylamino sulfonyl chloride (13360-57-1) → 1-{4-[(diethylamino)carbonyl]phenyl}-6-methoxy-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinolin-7-yl dimethylsulfamate (857252-50-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 22h;	100%

dimethylamino sulfonyl chloride (13360-57-1) + (2S,4S)-2-aminomethyl-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine (148016-92-6) → (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-N,N-dimethylsulfamoylaminomethyl-4-tritylthiopyrrolidine

Conditions	Yield
With triethylamine In dichloromethane	100%

2-fluorophenol (367-12-4) + dimethylamino sulfonyl chloride (13360-57-1) → C8H10FNO3S (1201594-21-9)

Conditions	Yield
Stage #1: 2-fluorophenol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 23℃; for 0.166667h; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane at 23℃; for 11h;	100%

salicylonitrile (611-20-1) + dimethylamino sulfonyl chloride (13360-57-1) → C9H10N2O3S (1263387-24-1)

Conditions	Yield
Stage #1: salicylonitrile With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0℃; for 0.166667h; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 11h;	100%

4-(3-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole (1288963-67-6) + dimethylamino sulfonyl chloride (13360-57-1) → 2-(3,5-dimethylisoxazol-4-yl)-3-(4-methoxyphenyl)-N,N-dimethyl-1H-indole-1-sulfonamide (1288963-72-3)

Conditions	Yield
Stage #1: 4-(3-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole With sodium hydride In n-heptane; N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: dimethylamino sulfonyl chloride In n-heptane; N,N-dimethyl-formamide at 0 - 20℃; for 2h;	100%
Stage #1: 4-(3-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: dimethylamino sulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #3: With water In N,N-dimethyl-formamide	100%

2-(3-amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (1343453-37-1) + dimethylamino sulfonyl chloride (13360-57-1) → ethyl 2-(3-(N,N-dimethylsulfamoylamino)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (1343454-35-2)

Conditions	Yield
With pyridine In dichloromethane at 0 - 25℃; for 16h;	100%
With pyridine In dichloromethane at 0 - 25℃; for 16h;

3-methoxy-4-hydroxybenzonitrile (4421-08-3) + dimethylamino sulfonyl chloride (13360-57-1) → 4-cyano-2-methoxyphenyl N,N-dimethylsulfamate (1432739-31-5)

Conditions	Yield
Stage #1: 3-methoxy-4-hydroxybenzonitrile With dmap; triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: dimethylamino sulfonyl chloride In dichloromethane at 20℃; for 16h;	100%

4-chloro-phenol (106-48-9) + dimethylamino sulfonyl chloride (13360-57-1) → 4-chlorophenyl N,N-dimethylsulfamate (1135-05-3)

Conditions	Yield
Stage #1: 4-chloro-phenol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 0.166667h; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 16h;	100%
Stage #1: 4-chloro-phenol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 10h; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃;	83%

2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine hydrochloride + dimethylamino sulfonyl chloride (13360-57-1) → 2,4-dichloro-N,N-dimethyl-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-sulfonamide

Conditions	Yield
Stage #1: 2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine hydrochloride With triethylamine In dichloromethane Stage #2: dimethylamino sulfonyl chloride In dichloromethane	100%

NH-pyrazole (288-13-1) + dimethylamino sulfonyl chloride (13360-57-1) → N,N-dimethyl-1H-pyrazole-1-sulfonamide (133228-21-4)

Conditions	Yield
Stage #1: NH-pyrazole With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: dimethylamino sulfonyl chloride In tetrahydrofuran for 1.5h;	99%
Stage #1: NH-pyrazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: dimethylamino sulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;	99%
With sodium hydride In tetrahydrofuran; mineral oil for 1.33333h; Inert atmosphere;	91%

methoxybenzene (100-66-3) + dimethylamino sulfonyl chloride (13360-57-1) → N,N-dimethyl-4-methoxybenzenesulfonamide (59907-37-8)

Conditions	Yield
indium(III) triflate In 1,2-dichloro-ethane at 100℃; for 24h;	99%

4-hydroxy-benzaldehyde (123-08-0) + dimethylamino sulfonyl chloride (13360-57-1) → 4-formylphenyl N,N-dimethylsulfamate

Conditions	Yield
With N,N-dimethyl-cyclohexanamine at 90 - 95℃; for 3h;	99%
With N-ethyl-N,N-diisopropylamine at 90℃; for 2.5h;

4-Fluorophenol + dimethylamino sulfonyl chloride (13360-57-1) → 4-fluorophenyl N,N-dimethylsulfamate (1259092-05-1)

Conditions	Yield
Stage #1: 4-Fluorophenol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 0.166667h; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 16h;	99%
Stage #1: 4-Fluorophenol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; Inert atmosphere;	91%
With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 11h; Inert atmosphere;
Stage #1: 4-Fluorophenol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 0.166667h; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 12h;

4-ethoxycarbonylpyrazole (37622-90-5) + dimethylamino sulfonyl chloride (13360-57-1) → ethyl 1-(N,N-dimethylsulfamoyl)-1H-pyrazole-4-carboxylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile for 1h; Inert atmosphere;	99%
Stage #1: 4-ethoxycarbonylpyrazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: dimethylamino sulfonyl chloride In tetrahydrofuran; mineral oil at 25℃; for 22h; Inert atmosphere;	91%

methyl 3-(acetylamino)-1H-pyrazole-5-carboxylate (1202657-29-1) + dimethylamino sulfonyl chloride (13360-57-1) → C9H14N4O5S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 0 - 20℃; for 18h;	99%

C17H19NO4 + dimethylamino sulfonyl chloride (13360-57-1) → C23H34N4O10S3

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 10h;	98.2%

methylamine (74-89-5) + dimethylamino sulfonyl chloride (13360-57-1) → N,N,N′-trimethylsulfamide (76820-42-3)

Conditions	Yield
In tetrahydrofuran	98%
With potassium carbonate In tetrahydrofuran; dichloromethane at 0 - 25℃; for 2h;	97%
In water; benzene at 50℃; for 5h;	87%
With toluene

dimethylamino sulfonyl chloride (13360-57-1) → N,N-dimethylsulfamide (3984-14-3)

Conditions	Yield
With ammonia In methanol at 60℃; for 16h; Sealed tube;	98%
With ammonium hydroxide at 0℃; for 3h;	94%
With ammonium hydroxide at 0℃; ice-bath;	76%

1H-imidazole (288-32-4) + dimethylamino sulfonyl chloride (13360-57-1) → N,N-dimethyl-1H-imidazole-1-sulfonamide (78162-58-0)

Conditions	Yield
With triethylamine In toluene at 20℃; for 8h;	98%
With triethylamine In benzene for 16h; Ambient temperature;	95%
With triethylamine In diethyl ether at 20℃; for 16h;	94.75%

1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose (17073-95-9) + dimethylamino sulfonyl chloride (13360-57-1) → 1,6-anhydro-2-O-(N,N-dimethylsulfamoyl)-3,4-O-isopropylidene-β-D-talopyranose (98815-77-1)

Conditions	Yield
With 1H-imidazole; sodium hydride In tetrahydrofuran for 2h; Heating;	98%

α-naphthol (90-15-3) + dimethylamino sulfonyl chloride (13360-57-1) → naphthalen-1-yl N,N-dimethylsulfamate (1144-13-4)

Conditions	Yield
With sodium hydride In 1,2-dimethoxyethane at 23℃; for 17h; Inert atmosphere;	98%
Stage #1: α-naphthol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 23℃; for 0.166667h; Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 23℃; for 11h;	95%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In benzene at 50℃; for 6h;	94%

4(5)-(4-tolyl)-1H-imidazole (670-91-7) + dimethylamino sulfonyl chloride (13360-57-1) → 1-(dimethylsulfamoyl)-5-p-tolylimidazole

Conditions	Yield
With potassium carbonate In ethyl acetate at 77℃; for 6h; Temperature;	98%

C17H20N6 + dimethylamino sulfonyl chloride (13360-57-1) → C21H30N8O4S2

Conditions	Yield
Stage #1: C17H20N6 With sodium hydroxide In N,N-dimethyl-formamide for 0.5h; Cooling; Stage #2: dimethylamino sulfonyl chloride In N,N-dimethyl-formamide at 220℃; for 4h; Autoclave;	97.6%

4-iodoimidazole (71759-89-2) + dimethylamino sulfonyl chloride (13360-57-1) → 4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide (135773-25-0)

Conditions	Yield
Stage #1: 4-iodoimidazole; dimethylamino sulfonyl chloride With sodium hydroxide In tetrahydrofuran at 8 - 20℃; Stage #2: In n-heptane at 70℃; for 4h;	97.3%
With triethylamine In acetonitrile at 20℃; for 2h;	80%
With triethylamine In dichloromethane for 60h; Heating;	60%
With triethylamine In dichloromethane at 20℃; for 26h; Inert atmosphere;	58%

2-methyl-propan-1-ol (78-83-1) + dimethylamino sulfonyl chloride (13360-57-1) → isobutyl N,N-dimethylsulfamate (66950-72-9)

Conditions	Yield
With sodium hydride In 1,2-dimethoxyethane	97%

(+/-)-(1S*,6S*,8R*,9R*,10S*,11S*)-2,2-Dimethoxy-10,11-epoxy-6-methyl-12-oxatricyclo<6.3.1.01,6>dodecan-9-ol + dimethylamino sulfonyl chloride (13360-57-1) → C16H27NO7S

Conditions	Yield
With sodium hydride In tetrahydrofuran 1.) r.t., 5 min, 2.) r.t., 1 h;	97%

dimethylamino sulfonyl chloride (13360-57-1) + 3,4-bis(trimethylsilyl)-1H-pyrrole (195820-65-6) → N-N-dimethyl 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide (278167-17-2)

Conditions	Yield
Stage #1: 3,4-bis(trimethylsilyl)-1H-pyrrole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h; Metallation; Stage #2: dimethylamino sulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Substitution; Further stages.;	97%

Upstream product

• 506-59-2 N,N-dimethylammonium chloride 
• 1730-69-4 dibutylchloroborane 
• 3768-63-6 tetramethylsulfamide 
• 22086-53-9 dipropylchloroborane 
• 41955-27-5 C₂H₆NO₃S^(1-)*Na⁽¹⁺⁾ 
• 1585-74-6 dimethylchloroamine 
• 29777-18-2 C₅H₁₅N₂O₂S⁽¹⁺⁾*Cl^(1-) 
• 89168-09-2 Carbamidsaeure-methylester-N-sulfonsaeure-dimethylamid 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 124-40-3 dimethyl amine 

Downstream Products

• 5433-60-3 3,4-dihydro-2H-quinoline-1-sulfonic acid dimethylamide 
• 5433-61-4 N'-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-N,N-dimethyl-sulfamide 
• 104037-14-1 N-dimethylsulfamoyl-sulfanilic acid thiazol-2-ylamide 
• 66840-71-9 N,N-dimethyl-N'-(4-methylphenyl)-sulfamide 
• 10290-40-1 N'-(4-chloro-phenyl)-N,N-dimethyl-sulfamide 
• 82936-47-8 N'-(4-methoxy-phenyl)-N,N-dimethyl-sulfamide 
• 3768-63-6 tetramethylsulfamide 
• 7463-22-1 N,N-Dimethyl-p-chlorobenzenesulfonamide 
• 90810-07-4 N,N-dimethyl-N'-m-tolyl-sulfamide 
• 349573-61-1 N,N-dimethyl-N'-(2,4-dimethyl-phenyl)-sulfamide 
• 5433-58-9 2-methyl-piperidine-1-sulfonic acid dimethylamide 
• 71270-65-0 C₁₀H₁₆N₂O₂S 
• 54838-86-7 Dimethyl-sulfamic acid 2,4-dinitro-phenyl ester 
• 1142-27-4 p-nitrophenyl N,N-dimethylsulphamate 

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