4316-73-8

Basic information

• Product Name: Sodium sarcosinate
• Synonyms: Glycine,N-methyl-,monosodiumsalt;n-methyl-glycinmonosodiumsalt;SodiumN-methylaminoacetate;N-METHYLAMINOACETIC ACID SODIUM SALT;n-methylglycine monosodium salt;N-METHYLGLYCINE SODIUM SALT;SODIUM SARCOSINATE;SODIUM SARCOSINATE 405
• CAS NO: 4316-73-8
• Molecular Formula: C₃H₆NO₂*Na
• Molecular Weight: 111.08
• EINECS: 224-338-5
• Mol File: 4316-73-8.mol

Chemical Properties

• Boiling Point: 108℃
• Flash Point: 71.8 °C
• Appearance: /
• Density: 1,2 g/cm3
• Vapor Pressure: 0.184mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: Sodium sarcosinate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium sarcosinate(4316-73-8)
• EPA Substance Registry System: Sodium sarcosinate(4316-73-8)

Safety Data

• Hazardous Substances Data: 4316-73-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4316-73-8 differently. You can refer to the following data:
1. Intermediate, stabilizer for diazonium salts, chelating agent.
2. Sarcosine Sodium Salt is a salt of Sarcosine (S140500) which has been found in starfish and sea urchins. It is used as intermediate in the synthesis of antienzyme agents for toothpaste. Found to be a marker for prostate cancer bioagression.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C3H7NO2.Na/c1-4-2-3(5)6;/h4H,2H2,1H3,(H,5,6);/q;+1/p-1

Synthetic route

(2-hydroxyethyl)(methyl)amine (109-83-1) → sodium sarcosinate (4316-73-8)

Conditions	Yield
With sodium hydroxide; Cu/Ni Raney catalyst In water at 160℃; under 7500.75 Torr; for 4h;	97.2%
With (6-di-tert-butylphosphinomethyl-2,2’-bipyridyl)Ru(CO)HCl; water; sodium hydroxide In 1,4-dioxane for 24h; Schlenk technique; Inert atmosphere; Glovebox; Reflux;	> 99 %Spectr.

sarcosine (107-97-1) → sodium sarcosinate (4316-73-8)

Conditions	Yield
With ammonia; sodium

(methylamino)acetonitrile (5616-32-0) → sodium sarcosinate (4316-73-8)

Conditions	Yield
With sodium hydroxide at 75℃; for 4h; Temperature; Large scale;

sodium monochloroacetic acid (3926-62-3) + methylamine (74-89-5) → sodium sarcosinate (4316-73-8)

Conditions	Yield
at 10 - 200℃; under 836.056 - 228015 Torr; Flow reactor;

tris(hydroxymethyl)phosphine (2767-80-8) + sodium sarcosinate (4316-73-8) → tris(N-methyl-N-sodiumcarboxylatomethylaminomethyl)phosphine

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

sodium sarcosinate (4316-73-8) + chloroacetic acid (79-11-8) → sodium methyliminodiacetate (71160-37-7)

Conditions	Yield
Stage #1: sodium sarcosinate; chloroacetic acid With sodium iodide In water at 20℃; for 1h; Large scale; Stage #2: With sodium hydroxide In water at 55 - 90℃; for 4.5h; pH=8.5 - 9; Large scale;	98%

sodium sarcosinate (4316-73-8) + oleic acid chloride → N-oleoylsarcosine (110-25-8)

Conditions	Yield
With water; sodium hydroxide In toluene at 30℃; for 1h; Solvent;	97.8%

2M-NaOH + sarcosine (107-97-1) + di-o-tolyl carbonate (617-09-4) + sodium sarcosinate (4316-73-8) → N-methoxycarbonyl-N-methyl-glycine (116714-27-3)

Conditions	Yield
With hydrogenchloride	90.5%

calcium cyanamide (156-62-7) + sodium sarcosinate (4316-73-8) → Creatinine (57-00-1)

Conditions	Yield
With phosphoric acid; sulfuric acid	86%
phosphoric acid	75%
sulfuric acid

2,6-bis-(bromomethyl)pyridine (7703-74-4) + sodium sarcosinate (4316-73-8) → N,N'-<(pyridine-2,6-diyl)bis(methylene)>bis (146448-83-1)

Conditions	Yield
With sodium hydroxide In methanol for 13h; Heating;	85%

bis(trichloromethyl) carbonate (32315-10-9) + sodium sarcosinate (4316-73-8) → sarcosine-N-carboxyanhydride (5840-76-6)

Conditions	Yield
With 4-methyl-morpholine In water; acetonitrile at 20℃; Flow reactor;	81%

sodium sarcosinate (4316-73-8) + 4-[(3-bromophenyl)-amino]-6-fluoropyrido[3,4-d]pyrimidine (171179-03-6) → {[4-(3-Bromo-phenylamino)-pyrido[3,4-d]pyrimidin-6-yl]-methyl-amino}-acetic acid

Conditions	Yield
In ethanol at 95℃; for 48h;	79%

CYANAMID (420-04-2) + sodium sarcosinate (4316-73-8) → Creatinine (57-00-1)

Conditions	Yield
Stage #1: sodium sarcosinate With hydrogenchloride In water pH=9.6; Cooling; Stage #2: CYANAMID In water at 75 - 80℃; for 3.5h;	76.2%
In 2-Methyl-1,2-propanediol	75%
With carbon dioxide In water at 75℃; for 6h; pH=9 - 10;	75%
With formic acid In tert-butyl methyl ether at 50℃; for 1h; pH=9.8;	70%
With ammonium chloride	68%

2,4,6-trinitrochlorobenzene (88-88-0) + sodium sarcosinate (4316-73-8) → N-methyl-N-(2,4,6-trinitrophenyl)glycine (124052-31-9)

Conditions	Yield
In methanol; water for 0.333333h;	70%

Boc-Ser(Bn)-OH + sodium sarcosinate (4316-73-8) → Boc-L-Ser(O-Bn)-Sar-OH

Conditions	Yield
Stage #1: Boc-Ser(Bn)-OH With 4-methyl-morpholine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate In acetonitrile at 20℃; for 0.00138889h; Flow reactor; Stage #2: sodium sarcosinate In water; acetonitrile at 20℃; for 0.00277778h; Flow reactor;	67%

sodium sarcosinate (4316-73-8) + 2-chloro-1,3,2-dioxaphospholan (822-39-9) → 9-methyl-1,4,6-trioxa-9-aza-5λ5-phospha-spiro[4.4]nonan-7-one (63972-72-5)

sodium sarcosinate (4316-73-8) + methyloxirane (75-56-9, 16033-71-9) → 2-oxo-4,6-dimethyl-morpholine (18484-89-4)

Conditions	Yield
In water

n-dodecanoyl chloride (112-16-3) + sodium sarcosinate (4316-73-8) → N-acyl sarcosinate (97-78-9)

Conditions	Yield
In water at 40 - 50℃; for 1h; pH 9.5-10.5;
With hydrogenchloride In hexane; water at 5 - 15℃; for 6h; pH=11 - 11.5; Temperature; pH-value;	586 g

undecanoyl chloride (17746-05-3) + sodium sarcosinate (4316-73-8) → N-methyl-N-undecanoyl-glycine (36461-64-0)

Conditions	Yield
In water at 40 - 50℃; for 1h; pH 9.5-10.5;

n-tridecanoyl chloride (17746-06-4) + sodium sarcosinate (4316-73-8) → N-methyl-N-tridecanoyl-glycine (83871-14-1)

Conditions	Yield
In water at 40 - 50℃; for 1h; pH 9.5-10.5;

heptadecanoyl chloride (40480-10-2) + sodium sarcosinate (4316-73-8) → N-heptadecanoyl-N-methyl-glycine (83871-15-2)

Conditions	Yield
In water at 40 - 50℃; for 1h; pH 9.5-10.5;

sodium sarcosinate (4316-73-8) + n-decanoyl chloride (112-13-0) → N-decanoyl sarcosine (2671-91-2)

Conditions	Yield
In water at 40 - 50℃; for 1h; pH 9.5-10.5;

sodium sarcosinate (4316-73-8) + tetradecanoyl chloride (112-64-1) → N-tetradecanoylsarcosine (52558-73-3, 2421-31-0)

Conditions	Yield
In water at 40 - 50℃; for 1h; pH 9.5-10.5;

sodium sarcosinate (4316-73-8) + Stearoyl chloride (112-76-5) → N-stearoyl sarcosine (142-48-3)

Conditions	Yield
In water at 40 - 50℃; for 1h; pH 9.5-10.5;

sodium sarcosinate (4316-73-8) + n-hexadecanoyl chloride (112-67-4) → N-hexadecanoylsarcosine (2421-33-2)

Conditions	Yield
In water at 40 - 50℃; for 1h; pH 9.5-10.5;
With sodium hydroxide at 45℃; for 1h;

undec-10-enoyl chloride (38460-95-6) + sodium sarcosinate (4316-73-8) → N-undecylenoyl sarcosine

Conditions	Yield
With hydrogenchloride; sodium hydroxide for 0.5h; Ambient temperature;

sodium allyloxide (20907-32-8) + sodium sarcosinate (4316-73-8) → N-methyl-N-<3-hydroxy-propyl>-glycine methyl ester

Conditions	Yield
at 108℃; und Veresterung des Reaktionsprodukts mit methanol.HCl;

sarcosine (107-97-1) + cis-Octadecenoic acid (112-80-1) + sodium sarcosinate (4316-73-8) → N-oleoylsarcosine (110-25-8)

Conditions	Yield
In water; isopropyl alcohol

Decyl-oxiran (2855-19-8) + sodium sarcosinate (4316-73-8) + isopropyl alcohol (67-63-0) → C15H32O2 + C15H30NO3(1-)*Na(1+) + dodecane-1,2-diol (1119-87-5)

Conditions	Yield
at 70 - 82℃; for 5.5h;

CYANAMID (420-04-2) + sodium sarcosinate (4316-73-8) → creatine monohydrate powder (6020-87-7)

Conditions	Yield
In water
With water at 20 - 80℃; for 1h; Temperature; Large scale;

erucic acid chloride (59044-32-5, 7459-29-2) + sodium sarcosinate (4316-73-8) → C25H47NO3 (133152-18-8)

Conditions	Yield
With sodium hydroxide In water at 30 - 35℃; for 1h; pH=9 - 11;

n-dodecanoyl chloride (112-16-3) + sodium sarcosinate (4316-73-8) → sodium N-lauroylsarcosinate (137-16-6)

Conditions	Yield
In water at 10 - 30℃; for 5h; pH=10.3 - 10.6; Schotten-Baumann Reaction; Inert atmosphere;
With sodium hydroxide In water at 10 - 30℃; for 5h; pH=10.3 - 10.6; Inert atmosphere;

Upstream product

• 107-97-1 sarcosine 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 5616-32-0 (methylamino)acetonitrile 
• 3926-62-3 sodium monochloroacetic acid 
• 74-89-5 methylamine 

Downstream Products

• 97-78-9 N-acyl sarcosinate 
• 124052-31-9 N-methyl-N-(2,4,6-trinitrophenyl)glycine 
• 36461-64-0 N-methyl-N-undecanoyl-glycine 
• 2671-91-2 N-decanoyl sarcosine 
• 52558-73-3 N-tetradecanoylsarcosine 
• 142-48-3 N-stearoyl sarcosine 
• 2421-33-2 N-hexadecanoylsarcosine 
• 110-25-8 N-oleoylsarcosine 
• 57-00-1 Creatinine 
• 1119-87-5 dodecane-1,2-diol 
• 6020-87-7 creatine monohydrate powder 
• 137-16-6 sodium N-lauroylsarcosinate 
• 5840-76-6 sarcosine-N-carboxyanhydride 
• 71160-37-7 sodium methyliminodiacetate 

Relevant articles and documents

SYSTEM FOR CONTINUOUS MANUFACTURING OF SODIUM SARCOSINATE

The invention relates to a system for continuous manufacturing of sodium sarcosinate. The system for continuous manufacturing of sodium sarcosinate in high pressure apparatus includes steps of : (a) mixing sodium chloroacetate solution with methylamine solution. (b)amination of mixed solution of sodium chloroacetate and methylamine under high pressure to obtain product of amination.(c)separating product of amination to obtain sodium sarcosinate. System for continuous manufacturing of sodium sarcosinate comprises: amination of mixed solution of sodium chloroacetate and methylamine under high pressure with continuous module to simplify process and improve reaction efficiency.

General Synthesis of Amino Acid Salts from Amino Alcohols and Basic Water Liberating H2

An atom-economical and environmentally friendly method to transform amino alcohols to amino acid salts using just basic water, without the need of pre-protection or added oxidant, catalyzed by a ruthenium pincer complex, is developed. Water is the solvent, the source of the oxygen atom of the carboxylic acid group, and the actual oxidant, with liberation of dihydrogen. Many important and useful natural and unnatural amino acid salts can be produced in excellent yields by applying this new method.

Process for the preparation of creatine water (by machine translation)

The invention discloses a preparation method of creatine monohydrate, and provides the preparation method of the creatine monohydrate. The method comprises the following steps: step 1, carrying out a nucleophilic substitution reaction on a glycolonitrile aqueous solution and a methylamine aqueous solution for 1 to 6 hours at a temperature of 10 DEG C to 40 DEG C so as to generate methylamino acetonitrile; step 2, carrying out a hydrolysis reaction on the methylamino acetonitrile reaction liquid obtained in the step 1 for 2 to 6 hours at the temperature of 60 DEG C to 80 DEG C and in the presence of sodium hydroxide so as to obtain a sodium sarcosinate aqueous solution; step 3, regulating pH to 9 to 12 and carrying out a condensation reaction on the sodium sarcosinate aqueous solution and the cyanamide for 1 to 6 hours at the temperature of 50 DEG C to 90 DEG C so as to obtain the creatine monohydrate. The method is moderate in reaction condition, less in byproduct, high in yield and suitable for industrial production. The structure of the creatine monohydrate is as shown in the specification.

Process for Preparing Creatine, Creatine Monohydrate or Guanidinoacetic Acid

A process for producing creatine, creatine monohydrate or guanidinoacetic acid is proposed, wherein firstly N-methylethanolamine or ethanolamine is catalytically dehydrogenated in each case in alkaline solution and the sarcosinate or glycinate solutions that are obtained in this manner are finally reacted under acidic conditions with a guanylating agent such as for example O-alkylisourea or cyanamide. In this manner products are obtained in high yields and very good purity where in contrast to the prior art no traces whatsoever of hydrocyanic acid, formaldehyde, chloroacetic acid or ammonia are present. The formation of the toxicologically critical dihydrotriazine is also avoided.