4727-41-7

Basic information

• Product Name: Sulfobetaine
• Synonyms: dimethylsulfonioacetate;SULPHOBETAINE;SULFOBETAINE;2-dimethylsulfonioethanoate;Sulfonium, (carboxymethyl)dimethyl-, inner salt;S,S-Dimethylthetin/DMT/Sulfobetaine;Thiobetaine
• CAS NO: 4727-41-7
• Molecular Formula: C₄H₈O₂S
• Molecular Weight: 120.17
• Product Categories: fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis
• Mol File: 4727-41-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 241-242 °C(Solv: ethanol (64-17-5))
• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: Sulfobetaine(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfobetaine(4727-41-7)
• EPA Substance Registry System: Sulfobetaine(4727-41-7)

Safety Data

• Hazardous Substances Data: 4727-41-7(Hazardous Substances Data)

Usage

General Description

Sulfobetaine is a type of zwitterionic chemical compound that contains both positively and negatively charged chemical groups within the same molecule. These unique properties make sulfobetaine useful in a variety of applications, including as a surfactant in personal care products and in the biomedical and pharmaceutical industries. Sulfobetaine is known for its ability to reduce surface tension, improve the solubility and stability of formulations, and enhance the biocompatibility of materials. Additionally, sulfobetaine is often used as a biological buffer due to its ability to maintain a stable pH, making it a valuable tool in cell culture and biochemistry. Overall, sulfobetaine is a versatile and valuable chemical that offers a wide range of practical applications.

InChI:InChI=1/C5H11NO5S/c1-6(2,3)4(5(7)8)12(9,10)11/h4H,1-3H3,(H-,7,8,9,10,11)

Synthetic route

dimethylsulfide (75-18-3) + bromoacetic acid (79-08-3) → dimethylsulfonioacetate (4727-41-7)

Conditions	Yield
at 55℃; for 0.0333333h;	61%

carboxymethyl-dimethyl sulfonium ; hydroxide (625-63-8, 19643-24-4) → dimethylsulfonioacetate (4727-41-7)

Conditions	Yield
bei 8-taegigem Stehen im Vakuum ueber Schwefelsaeure;

methylsulfanyl-acetic acid (2444-37-3) + dimethyl sulfate (77-78-1) → dimethylsulfonioacetate (4727-41-7)

Conditions	Yield
With water in neutraler, schwach saurer oder schwach alkal.Loesung;

ethyl (dimethylsulfuranylidene)acetate (7380-81-6) → dimethylsulfonioacetate (4727-41-7)

Conditions	Yield
In water Heating;

(ethoxycarbonylmethyl)dimethylsulfonium bromide (5187-82-6) → dimethylsulfonioacetate (4727-41-7)

Conditions	Yield
With silver(l) oxide

(Dimethylsulfuranyliden)essigsaeure-methylester (103548-67-0) → dimethylsulfonioacetate (4727-41-7)

Conditions	Yield
In tetrahydrofuran

methylsulfanyl-acetic acid (2444-37-3) + water (7732-18-5) + dimethyl sulfate (77-78-1) → dimethylsulfonioacetate (4727-41-7)

Conditions	Yield
in neutraler, schwach saurer oder schwach alkal. Loesung;

L-homocysteine (6027-13-0) → dimethylsulfonioacetate (4727-41-7) + betaine (107-43-7) + 3-dimethylsulfonio-proionoic acid betaine

Conditions	Yield
ueber die Methylierung in Gegenwart von Transmethylase-Praeparaten aus Leber und Niere unter anaeroben Bedingungen;

dimethylthetin-base → dimethylsulfonioacetate (4727-41-7)

Conditions	Yield
bei 8-taegigem Stehen im Vakuum uebeer Schwefelsaeure;

dimethylsulfonioacetate (4727-41-7) + trichloroacetic acid anhydride (4124-31-6) → Dimethylsulfonium-di-trichloracetyl-methylid

Conditions	Yield
at 0 - 40℃; for 2h;	71.4%

dimethylsulfonioacetate (4727-41-7) + trifluoroacetic anhydride (407-25-0) → Dimethylsulfonium-di-trifluoracetyl-methylid (104917-89-7)

Conditions	Yield
at 0 - 23℃; for 5h;	65%

dimethylsulfonioacetate (4727-41-7) + 4-nitrobenzenediazonium tetrafluoroborate (456-27-9) → 1,5-Bis-(4-nitrophenyl)-3-dimethylsulfonium-formazan-tetrafluorborat

Conditions	Yield
In acetic acid at 20℃; for 40h;	30%

dimethylsulfonioacetate (4727-41-7) + Chloroacetic anhydride (541-88-8) → Dimethylsulfonium-di-chloracetyl-methylid

Conditions	Yield
at 40℃; for 0.833333h;	27%

dimethylsulfonioacetate (4727-41-7) + Trichloroacetyl chloride (76-02-8) → Dimethylsulfonium-trichloracetyl-methylid-hydrochlorid-hydrat

Conditions	Yield
at 20 - 42℃; for 4h;	11.6%

2-amino-4-mercaptobutyric acid (454-29-5) + dimethylsulfonioacetate (4727-41-7) → DL-methionine (59-51-8)

Conditions	Yield
at 38℃; Kinetics; Geschwindigkeit in Gegenwart verschiedener Leberfermentpraeparate unter anaeroben Bedingungen; Einfluss des pH;

dimethylsulfonioacetate (4727-41-7) + p-toluidine (106-49-0) → methyl p-tolylcarbamate (5602-96-0) + N-methyl-p-toluidine (623-08-5) + 1,3-di-p-tolylurea (621-00-1)

Conditions	Yield
at 140℃;

dimethylsulfonioacetate (4727-41-7) + aniline (62-53-3) → N-phenylglycine anilide (2567-62-6) + N-methylaniline (100-61-8) + bis(diphenyl)urea (102-07-8)

Conditions	Yield
at 140℃;

dimethylsulfonioacetate (4727-41-7) + phenol (108-95-2) → dimethylsulfide (75-18-3) + methylsulfanyl-acetic acid (2444-37-3) + methoxybenzene (100-66-3) + 2-phenoxyacetic acid (122-59-8)

Conditions	Yield
at 140℃;

diazomethane (186581-53-3, 908094-01-9) + dimethylsulfonioacetate (4727-41-7) + (3E)-1,4-diphenylbut-3-en-1-one (17572-77-9, 32363-55-6, 3420-52-8) → (+/-)-2c-phenyl-3t-benzoyl-cyclopropane-carboxylic acid-(1r)-methyl ester (23511-08-2, 23511-09-3, 120201-78-7) + 2c-benzoyl-3t-phenyl-cyclopropane-r-carboxylic acid methyl ester (23511-08-2, 23511-09-3, 120201-78-7)

Conditions	Yield
(i) NaH, DMSO, (ii) /BRN= 102415/; Multistep reaction;

3-methylbutyric acid (503-74-2) + dimethylsulfonioacetate (4727-41-7) → methyl 3-methylbutanoate (556-24-1)

2.6-dimethylphenol (576-26-1) + dimethylsulfonioacetate (4727-41-7) → 2-methoxy-1,3-dimethylbenzene (1004-66-6)

Mesitol (527-60-6) + dimethylsulfonioacetate (4727-41-7) → 2,4,6-trimethylanisole (4028-66-4)

4,6-dichloro-2-methylphenol (1570-65-6) + dimethylsulfonioacetate (4727-41-7) → 2,4-dichloro-6-methyl-anisole (13334-73-1)

dimethylsulfonioacetate (4727-41-7) + 3,5-Dimethylphenol (108-68-9) → 3,5-dimethylmethoxybenzene (874-63-5)

dimethylsulfonioacetate (4727-41-7) + malonic acid dimethyl ester (108-59-8) → methyl-malonic acid dimethylester (609-02-9)

dimethylsulfonioacetate (4727-41-7) + 2,4,6-Trichlorophenol (88-06-2) → 2,4,6-trichloroanisole (87-40-1)

dimethylsulfonioacetate (4727-41-7) → C4H8O2S(1-) (4727-41-7, 55284-63-4)

Conditions	Yield
With e1-aq Rate constant; Ambient temperature;

dimethylsulfonioacetate (4727-41-7) + water (7732-18-5) → methylsulfanyl-acetic acid (2444-37-3)

dimethylsulfonioacetate (4727-41-7) + aqueous NaOH-solution → glycolic Acid (79-14-1) + methylsulfanyl-acetic acid (2444-37-3)

Upstream product

• 2444-37-3 methylsulfanyl-acetic acid 
• 77-78-1 dimethyl sulfate 
• 6027-13-0 L-homocysteine 
• 75-18-3 dimethylsulfide 
• 79-08-3 bromoacetic acid 
• 103548-67-0 (Dimethylsulfuranyliden)essigsaeure-methylester 
• 5187-82-6 (ethoxycarbonylmethyl)dimethylsulfonium bromide 
• 7380-81-6 ethyl (dimethylsulfuranylidene)acetate 
• 7732-18-5 water 
• 625-63-8 carboxymethyl-dimethyl sulfonium ; hydroxide 

Downstream Products

• 59-51-8 DL-methionine 
• 5602-96-0 methyl p-tolylcarbamate 
• 623-08-5 N-methyl-p-toluidine 
• 621-00-1 1,3-di-p-tolylurea 
• 556-24-1 methyl 3-methylbutanoate 
• 1004-66-6 2-methoxy-1,3-dimethylbenzene 
• 87-40-1 2,4,6-trichloroanisole 
• 4727-41-7 C₄H₈O₂S^(1-) 
• 2444-37-3 methylsulfanyl-acetic acid 
• 79-14-1 glycolic Acid 
• 75-18-3 dimethylsulfide 
• 123-93-3 thiodiacetic acid 
• 3086-29-1 trimethylsulfonium chloride 
• 609-02-9 methyl-malonic acid dimethylester 

Relevant articles and documents

One-electron Reduction of Sulphonium Salts in Aqueous Solution: a Pulse Radiolysis Study

Absolute rate constants have been measured for the reduction of 1-alkylthiolanium (1a-c), 1-alkylthianium (2a-e), 1-(n-carboxyalkyl)thiolanium (3a,b) and 1-(n-carboxyalkyl)thianium (4a,b) salts, and ω-dimethylsulphonioalkanoic acids (5a,b), including biologically active S-methylmethionine (6) and dimethyl-β-propiothetin (5b), by hydrated electrons in aqueous solutions using the pulse radiolysis method.This reaction was found to occur very rapidly (k in the range 109-1010 dm3mol-1s-1), the individual rate constants being dependent on the electron inductive power of the substituents on the positive sulphur centre.The sulphuranyl radical R3S., a possible reaction intermediate, could not be detected within the 0.1 μs time resolution of the applied technique.No reaction was observed between S-methylmethionine and CO2.- or Me2C.OH under experimental conditions.The one-electron reduction potential of this sulphonium salt has been estimated to be -aq. were characterized by using p-benzoquinone as a radical scavenger.It was found that ring opening is the predominant process rather than the cleavage of methyl or methyl radicals.