4316-74-9

Basic information

• Product Name: N-METHYLTAURINE SODIUM SALT
• Synonyms: 2-METHYLAMINOETHANE-1-SULFONIC ACID SODIUM SALT;2-(methylamino)-ethanesulfonicacimonosodiumsalt;Ethanesulfonicacid,2-(methylamino)-,monosodiumsalt;N-METHYLTAURINE SODIUM SALT;SODIUM N-METHYLTAURINATE;N-Methyltaurine sodium salt anhydrous;SODIUM METHYLTAURATE;N-Methyltaurinesodiumsaltanhydrous,98%
• CAS NO: 4316-74-9
• Molecular Formula: C₃H₈NO₃S*Na
• Molecular Weight: 161.16
• EINECS: 224-339-0
• Mol File: 4316-74-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 493.73℃[at 101 325 Pa]
• Appearance: /
• Density: 1,21 g/cm3
• Vapor Pressure: 0Pa at 25℃
• PKA: 8.66[at 20 ℃]
• Water Solubility: 410g/L at 20℃
• Merck: 14,6124
• CAS DataBase Reference: N-METHYLTAURINE SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYLTAURINE SODIUM SALT(4316-74-9)
• EPA Substance Registry System: N-METHYLTAURINE SODIUM SALT(4316-74-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36
• Hazardous Substances Data: 4316-74-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4316-74-9 differently. You can refer to the following data:
1. N-Methyltaurine Sodium Salt is used in the analysis of the changing properties of anionic surfactants and the development of new skin cleansers or soaps. It is the salt of N-Methyltaurine, a compound used in sperm cryopreservation studies. N-Methyltaurine is also used in the studies relating to effects on oxidative damage to erythrocytes via phenylhydrazine.
2. Intermediate in the manufacture of surface-active agents.

InChI:InChI=1/C3H9NO3S.Na/c1-4-2-3-8(5,6)7;/h4H,2-3H2,1H3,(H,5,6,7);/q;+1/p-1

Synthetic route

formaldehyd (50-00-0) + sodium taurinate (7347-25-3) → 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9)

Conditions	Yield
Stage #1: formaldehyd; sodium taurinate With tetrakis(triphenylphosphine) palladium(0); scandium(III) chloride; cerium(III) chloride; (R,S)-(±)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline In water at 80℃; for 6h; Molecular sieve; Stage #2: With hydrogen In water under 5250.53 Torr; for 7h; Temperature; Reagent/catalyst;	482.3 g

tris(hydroxymethyl)phosphine (2767-80-8) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → tris(N-methyl-N-sodiumsulfonatoethylaminomethyl)phosphine

Conditions	Yield
In water at 20℃; for 1h; Condensation;	99%

2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → N-Methyltaurine (107-68-6)

Conditions	Yield
With acetic acid In methanol at 20 - 30℃; for 1h; Product distribution / selectivity;	97%
With propionic acid In methanol at 20 - 30℃; for 1h; Product distribution / selectivity;	95%

C32H49BrO3 + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → sodium 2-({2-[3-oxolup-20(29)-en-17β-carbonyloxy]ethyl}(methyl)amino)ethanesulfonate

Conditions	Yield
Stage #1: 2-methylamino-1-ethanesulphonic acid sodium salt With potassium carbonate In N,N-dimethyl-formamide for 0.25h; Stage #2: C32H49BrO3 In N,N-dimethyl-formamide at 95℃; for 50h;	74%

3-bromopropyl betulonate (1187656-58-1) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → sodium 2-({2-[3-oxolup-20(29)-en-17β-carbonyloxy]propyl}(methyl)amino)ethanesulfonate

Conditions	Yield
Stage #1: 2-methylamino-1-ethanesulphonic acid sodium salt With potassium carbonate In N,N-dimethyl-formamide for 0.25h; Stage #2: 3-bromopropyl betulonate In N,N-dimethyl-formamide at 95℃; for 50h;	69%

(S)-4-((1-(6-(2-((4-cyanophenethyl)carbamoyl)pyrrolidin-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)piperidin-4-yl)oxy)but-2-yn-1-yl methanesulfonate + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → (S)-2-((4-((1-(6-(2-((4-cyanophenethyl)carbamoyl)pyrrolidin-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)piperidin-4-yl)oxy)but-2-yn-1-yl)(methyl)amino)ethanesulfonic acid

Conditions	Yield
In water; acetonitrile at 75℃;	43%

2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) + 1-Benzyl-4-(3-chloro-propoxy)-benzene (148258-35-9) → 2-{[3-(4-benzyl-phenoxy)-propyl]-methyl-amino}-ethanesulfonic acid (452897-33-5)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 40℃; for 60h;	37%

3-(3-(4-chloro-5-fluoropyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazol-5-yl)isoxazole (1446358-48-0) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → C20H18F2N6O4S

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 65℃; for 24h;	33%

ω-phenyl undecanoic acid (3343-24-6) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → N-Methyl-N-(11-phenyl-undecanoyl)-taurin

Conditions	Yield
(i) SOCl2, (ii) /BRN= 6012642/; Multistep reaction;

13-phenyl-tridecanoic acid (20913-07-9) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → N-Methyl-N-(13-phenyl-tridecanoyl)-taurin (101524-00-9)

Conditions	Yield
(i) SOCl2, (ii) /BRN= 6012642/; Multistep reaction;

11-Phenoxyundecanoic acid (7170-44-7) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → 2-[Methyl-(11-phenoxy-undecanoyl)-amino]-ethanesulfonic acid

Conditions	Yield
(i) SOCl2, (ii) /BRN= 6012642/; Multistep reaction;

9-phenoxy-nonanoic acid (7170-43-6) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → 2-[Methyl-(9-phenoxy-nonanoyl)-amino]-ethanesulfonic acid

Conditions	Yield
(i) SOCl2, (ii) /BRN= 6012642/; Multistep reaction;

9-phenylnonanoic acid (16269-06-0) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → N-Methyl-N-(9-phenyl-nonanoyl)-taurin

Conditions	Yield
(i) SOCl2, (ii) /BRN= 6012642/; Multistep reaction;

9-[1]naphthyl-nonanoic acid (96766-58-4) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → N-Methyl-N-<9-(1-naphthyl)-nonanoyl>-taurin

Conditions	Yield
(i) SOCl2, (ii) /BRN= 6012642/; Multistep reaction;

9-(4-methylphenyl)-8-nonanoic acid (101271-63-0) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → N-Methyl-N-(9-p-tolyl-nonanoyl)-taurin

Conditions	Yield
(i) SOCl2, (ii) /BRN= 6012642/; Multistep reaction;

11-(4-methylphenyl)undecanoic acid (108240-91-1) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → N-Methyl-N-(11-p-tolyl-undecanoyl)-taurin

Conditions	Yield
(i) SOCl2, (ii) /BRN= 6012642/; Multistep reaction;

methyl bromide (74-83-9) + 2,6-bis(bromomethyl)naphthalene (4542-77-2) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → C20H30N2O6S2

Conditions	Yield
With sodium carbonate 1.) ethanol, 3 days, 2.) H2O-methanol, room temp., 3 days; Yield given. Multistep reaction;

methyl bromide (74-83-9) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) + 1-Chloromethylnaphthalene (86-52-2) → C15H19NO3S

Conditions	Yield
With sodium carbonate 1.) ethanol, 3 days, 2.) H2O-methanol, room temp., 3 days; Yield given. Multistep reaction;

benzyl chloroformate (501-53-1) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → 2-[[(benzyloxy)carbonyl](methyl)amino]-ethane-1-sulfonic acid, sodium salt (1146526-01-3)

Conditions	Yield
In aq. sodium hydroxide

3-(31,41 -dichloro-61 -methyl)-phenyl-Δ2 -pyrazoline-1-p-phenylsulphinic acid sodium salt + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) + 2-chloropropionyl chloride (625-36-5) → 4,5-dihydro-1H-pyrazole (109-98-8)

Conditions	Yield
With sodium hydroxide; sodium chloride; sodium carbonate In 2-ethoxy-ethanol; water; acetic acid

3-(3',4'-dichloro-6'-methyl)-phenyl-4-methyl-Δ2 -pyrazoline-1-(p-phenylsulphinic acid) sodium salt + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) + 2-chloropropionyl chloride (625-36-5) → 4,5-dihydro-1H-pyrazole (109-98-8)

Conditions	Yield
With sodium hydroxide; sodium chloride; sodium carbonate In 2-ethoxy-ethanol; water

C20H9BrCl2O3 (1140967-03-8) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) + triethylamine (121-44-8) → 2C6H16N(1+)*C26H23BrN2O9S2(2-)

Conditions	Yield
Stage #1: C20H9BrCl2O3; 2-methylamino-1-ethanesulphonic acid sodium salt With tributyl-amine; zinc(II) chloride In 1-methyl-pyrrolidin-2-one at 160℃; for 9h; Stage #2: triethylamine In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane

(E)-10-pentafluorosulfanyldec-9-enecarbonyl chloride + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → C13H23F5NO4S2(1-)*Na(1+)

Conditions	Yield
Stage #1: (E)-10-pentafluorosulfanyldec-9-enecarbonyl chloride; 2-methylamino-1-ethanesulphonic acid sodium salt With triethylamine In tetrahydrofuran Stage #2: With sodium hydroxide In ethanol; water

n-dodecanoyl chloride (112-16-3) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → sodium N-lauroyl N-methyl taurate (4337-75-1)

Conditions	Yield
With sodium hydroxide In water at 10 - 30℃; for 7h; pH=10.3 - 10.6; Schotten-Baumann Reaction; Inert atmosphere;
With sodium hydroxide In water at 10 - 30℃; for 7h; pH=10.3 - 10.6; Inert atmosphere;

lauric acid (143-07-7) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → sodium N-lauroyl N-methyl taurate (4337-75-1)

Conditions	Yield
Stage #1: lauric acid With magnesium oxide; acetic acid In paraffin oil at 100℃; for 0.0833333h; Stage #2: 2-methylamino-1-ethanesulphonic acid sodium salt In water; paraffin oil at 220℃; for 4h; Temperature;

3-[2-(tridecafluorohexyl)ethoxy]-1,2-epoxypropane (122193-68-4) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → C14H17F13NO5S(1-)*Na(1+)

Conditions	Yield
at 80℃; for 5h;

octanol (111-87-5) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → N-octanoyl-N-methyl taurine sodium

Conditions	Yield
With manganese(II) acetate at 200℃; for 9h;

1-dodecyl alcohol (112-53-8) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → sodium N-lauroyl N-methyl taurate (4337-75-1)

Conditions	Yield
With manganese(II) acetate at 210℃; for 6h;

acetic anhydride (108-24-7) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) + 1-hexadecylcarboxylic acid (57-10-3) → sodium myristoyl methyl taurate (3737-55-1)

Conditions	Yield
Stage #1: acetic anhydride; 1-hexadecylcarboxylic acid at 150℃; for 8h; Stage #2: 2-methylamino-1-ethanesulphonic acid sodium salt In water at 90 - 260℃; for 5h;

lauric acid (143-07-7) + acetic anhydride (108-24-7) + 2-methylamino-1-ethanesulphonic acid sodium salt (4316-74-9) → sodium N-lauroyl N-methyl taurate (4337-75-1)

Conditions	Yield
Stage #1: lauric acid; acetic anhydride at 140℃; Stage #2: 2-methylamino-1-ethanesulphonic acid sodium salt In water at 45 - 90℃; for 6h;

Upstream product

• 50-00-0 formaldehyd 
• 7347-25-3 sodium taurinate 

Downstream Products

• 452897-33-5 2-{[3-(4-benzyl-phenoxy)-propyl]-methyl-amino}-ethanesulfonic acid 
• 1146526-01-3 2-[[(benzyloxy)carbonyl](methyl)amino]-ethane-1-sulfonic acid, sodium salt 
• 4337-75-1 sodium N-lauroyl N-methyl taurate 
• 3737-55-1 sodium myristoyl methyl taurate 
• 109-98-8 4,5-dihydro-1H-pyrazole 
• 107-68-6 N-Methyltaurine 
• 101524-00-9 N-Methyl-N-(13-phenyl-tridecanoyl)-taurin 

Relevant articles and documents

Preparation method of sodium methyl taurate

The invention discloses a method for preparing sodium methyl taurate by using a sodium taurate one-pot two-step method. The method comprises the following steps: reacting sodium taurate with formaldehyde under the action of a novel supported composite metal organic catalyst to obtain a sodium methyl taurate water solution, crystallizing, separating, and drying to finally obtain sodium methyl taurate. Wherein the catalyst is represented as Pd-Ce-Z-X/Y, wherein Z is a cocatalyst and is selected from one or more of Re, Sn, In, Sc and Al; X is one or more of 2-(2-diphenylphosphine) phenylpyridine,2-(diphenylphosphine) methyl pyrrole, N-methyl-2-(diphenylphosphine) methyl pyrrole and 1-(2-diphenylphosphine-1-naphthalene) isoquinoline; Y is a carrier and is selected from one or more of orderedmesoporous carbon, a molecular sieve, silicon dioxide and neutral aluminum oxide. The method is simple in process, the raw material conversion rate is greater than 90%, and the product selectivity isgreater than 95%.