5704-04-1

Basic information

• Product Name: Tricine
• Synonyms: LABOTEST-BB LT00454966;n-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-glycin;TRICINE;TRI(HYDROXYMETHYL) AMINO METHANE HYDROCHLORIDE;TRIMETHYLOLAMINOMETHANE HYDROCHLORIDE;TRIS-HCL;TRIS-HCL BUFFER;TRIS HYDROCHLORIDE
• CAS NO: 5704-04-1
• Molecular Formula: C₆H₁₃NO₅
• Molecular Weight: 179.17
• EINECS: 214-684-5
• Product Categories: Biochemistry;Good's Buffers;Buffer
• Mol File: 5704-04-1.mol

Chemical Properties

• Melting Point: 186-188 °C (dec.)
• Boiling Point: 311.69°C (rough estimate)
• Flash Point: 256.7 °C
• Appearance: clear colorless (40 % (w/w) in H2O) solution/crystalline
• Density: 1.05 g/mL at 20 °C
• Vapor Pressure: 3.92E-12mmHg at 25°C
• Refractive Index: 1.4240 (estimate)
• Storage Temp.: Store at RT.
• Solubility: H2O: 4 M at 20 °C, clear, colorless
• PKA: 8.1(at 25℃)
• Water Solubility: soluble
• Stability: Stable.
• Merck: 14,9651
• BRN: 1937804
• CAS DataBase Reference: Tricine(CAS DataBase Reference)
• NIST Chemistry Reference: Tricine(5704-04-1)
• EPA Substance Registry System: Tricine(5704-04-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 5704-04-1(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry:
Tricine is used as an electrophoresis buffer for the separation of low molecular weight proteins and peptides, operating in the pH range of 7.4-8.8.
Used in Radiation-induced membrane damage studies:
Tricine acts as an effective scavenger of hydroxyl radicals during the study of radiation-induced membrane damage.
Used in Cell Biology:
Tricine is used for the resuspension of cell pellets.
Used in Chromatography:
Tricine, as part of the Trizma Buffer substance, has been used as an eluent in asymmetrical flow field-flow fractionation (AFFFF).

Descriptioin

Tricine is a zwitterionic amino acid. It is a white crystalline powder. It was first prepared by Good to buffer chloroplast reaction.1 Tricine is a commonly used electrophoresis buffer and is also used in resuspension of cell pellets.1,2 Attributing to its higher negative charge than glycine, it can migrate faster. At the same time, its high ionic strength results in more ion movement and less protein movement. Therefore, it works as a buffer component for separation of low molecular weight peptides.3

Reference

S. R. Haider, B. L. Sharp, H. J. Reid, A comparison of Tris‐glycine and Tris‐tricine buffers for the electrophoretic separation of major serum proteins, Journal of Separation Science, 2011, vol. 34, pp. 2463-2467 H. Sch?gger, G. von Jagow, Tricine-sodium dodecyl sulfate-polyacrylamide gel electrophoresis for the separation of proteins in the range from 1 to 100 kDa, Analytical Biochemistry, 1987, vol. 166, pp. 368-379

Biological Activity

Electrophoresis buffer. Working pH range: 7.4 - 8.8. Commonly used in SDS-PAGE to seperate peptides. Also used in other electrophoresis methods, high performance liquid chromatography and ion exchange chromatopgraphy.

Purification Methods

Crystallise Tricine from EtOH and water. [Good et al. Methods Enzymol 24B 53 1968, McGothlin & Jordan Analyt Lett 9 245 1976, Beilstein 18 III/IV 3454.]

InChI:InChI=1/C6H13NO5/c8-2-6(3-9,4-10)7-1-5(11)12/h7-10H,1-4H2,(H,11,12)

Synthetic route

sodium [99Tc]pertechnetate + nitrilotriacetic acid (139-13-9) + N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) → (99m)Tc(HYNIC-Lys(OMe)-NIC)(tricine)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In water at 100℃; for 0.166667h; pH=5.0; Succinate buffer;	95%

1-(N-(6-(2-(2-sulfonatobenzaldehyde)hydrazono)nicotinyl))-6-(nicotinoyl) hexanediamine + sodium [99Tc]pertechnetate + N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) → (99m)Tc(HYNIC-HD-NIC)(tricine)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In ethanol; water at 100℃; for 0.166667h; pH=5.0;	95%

HYNIC-Lys(OMe)-His + sodium [99Tc]pertechnetate + N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) → (99m)Tc(HYNIC-Lys(OMe)-His)(tricine)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In water at 100℃; for 0.25h; pH=5.0; Succinate buffer;	95%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + octadecyldimethyl[3-(trimethoxysilyl)propyl]ammonium chloride (27668-52-6) → disodium 7-(2-((carboxymethyl)amino)-3-hydroxy-2-(hydroxymethyl)propoxy)-7-(3-(dimethyl(octadecyl)ammonio)propyl)-4,4,10,10-tetrakis(hydroxymethyl)-6,8-dioxa-3,11-diaza-7-silatridecanedioate chloride

Conditions	Yield
Stage #1: N-[tris(hydroxymethyl)methyl]glycine; octadecyldimethyl[3-(trimethoxysilyl)propyl]ammonium chloride In N,N-dimethyl-formamide at 145℃; Stage #2: With sodium methylate In N,N-dimethyl-formamide	89%

[Re(carbonyl)3(water)3]Br + N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + water (7732-18-5) + triethylamine (121-44-8) → [HNEt3][Re(CO)3(κ3-NH2,O,CO2-tricine)][Re(CO)3(κ3-NH2,OH,CO2-tricine)]*2H2O

Conditions	Yield
In water Re(CO)3(H2O)3Br (0.371 mmol), tricine (0.0445 mmol), NEt3 (1.12 mmol) inH2O refluxed (0.5 h); solvent removed; washed with acetone; elem. anal.;	88%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + 3H3N*3H(1+)*[CrMo6O18(OH)6](3-) → 3H3N*3H(1+)*[HOOCCH2NHC(CH2O)3]CrMo6O18(OH)3(3-)

Conditions	Yield
In water at 130℃; for 12h;	88%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + cobalt(II) nitrate + 2-sulfanyl-1,3-benzoxazole (2382-96-9) → [Co[(HOCH2)3CNCH2COO][C7H4NO(S)]2](2-)*2H(1+)=H2[Co[(HOCH2)3CNCH2COO][C7H4NO(S)]2]

Conditions	Yield
With KOH In ethanol Co-salt in H2O added slowly to tricine in EtOH with stirring, mercapto-comp. in EtOH added dropwise with stirring, pH ajusted to 8 with 0.1 M KOH, refluxed for 5 h; evapd., cooled, filtered, washed with H2O and EtOH, dried in vac. over P4H10, elem. anal.;	55%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + water (7732-18-5) + 2-Mercaptobenzothiazole (149-30-4) + nickel(II) nitrate → [Ni[(HOCH2)3CNCH2COO][C7H4NS(S)]2(H2O)2](2-)*2H(1+)=H2[Ni[(HOCH2)3CNCH2COO][C7H4NS(S)]2(H2O)2]

Conditions	Yield
With KOH In ethanol Ni-salt in H2O added slowly to tricine in EtOH with stirring, mercapto-comp. in EtOH added dropwise with stirring, pH ajusted to 8 with 0.1 M KOH, refluxed for 5 h; evapd., cooled, filtered, washed with H2O and EtOH, dried in vac. over P4H10, elem. anal.;	53%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + copper(II) nitrate + Benzimidazol-2-thiol (134469-07-1) → [Cu[(HOCH2)3CNCH2COO][C7H5N2(S)]2](2-)*2H(1+)=H2[Cu[(HOCH2)3CNCH2COO][C7H5N2(S)]2]

Conditions	Yield
With KOH In ethanol Cu-salt in H2O added slowly to tricine in EtOH with stirring, mercapto-comp. in EtOH added dropwise with stirring, pH ajusted to 8 with 0.1 M KOH, refluxed for 5 h; evapd., cooled, filtered, washed with H2O and EtOH, dried in vac. over P4H10, elem. anal.;	52%

8-quinolinol (148-24-3) + nickel(II) nitrate hexahydrate + N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + water (7732-18-5) → H(1+)*Ni((HOCH2)3CNCH2CO2)(C5H3NC4H3O)(H2O)2(1-)*H2O=H[Ni((HOCH2)3CNCH2CO2)(C5H3NC4H3O)(H2O)2]H2O

Conditions	Yield
With KOH In ethanol; water soln. of nitrate salt in water added slowly to soln. of tricine in C2H5OH with stirring, soln. of hydroxyquinoline in C2H5OH added dropwise withstirring, adjusting pH to 8 by aq. KOH, mixt. refluxed for 5 h; mixt. evapd., cooled, ternary complex filtered off, washed (H2O, C2H5OH), dried (vac., P4O10); elem. anal.;	51%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + water (7732-18-5) + Benzimidazol-2-thiol (134469-07-1) + nickel(II) nitrate → [Ni[(HOCH2)3CNCH2COO][C7H5N2(S)]2(H2O)2](2-)*2H(1+)=H2[Ni[(HOCH2)3CNCH2COO][C7H5N2(S)]2(H2O)2]

Conditions	Yield
With KOH In ethanol Ni-salt in H2O added slowly to tricine in EtOH with stirring, mercapto-comp. in EtOH added dropwise with stirring, pH ajusted to 8 with 0.1 M KOH, refluxed for 5 h; evapd., cooled, filtered, washed with H2O and EtOH, dried in vac. over P4H10, elem. anal.;	51%

N-ε-(picolinyl)-N-α-(6-(2-(2-sulfonatobenzaldehyde)hydrazono)nicotinyl)lysine methyl ester + sodium [99Tc]pertechnetate + N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) → (99m)Tc(HYNIC-Lys(OMe)-Pic)(tricine)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In water at 100℃; for 0.166667h; pH=5.0;	50%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + ammonium pertechnetate + C51H61BrClN8O14P + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C75H84BrClN9O28P2S3(99)Tc

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 0.166667h; Microwave irradiation;	47%

8-quinolinol (148-24-3) + cobalt(II) nitrate hexahydrate + N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + water (7732-18-5) → H(1+)*Co((HOCH2)3CNCH2CO2)(C5H3NC4H3O)(H2O)2(1-)*H2O=H[Co((HOCH2)3CNCH2CO2)(C5H3NC4H3O)(H2O)2]H2O

Conditions	Yield
With KOH In ethanol; water soln. of nitrate salt in water added slowly to soln. of tricine in C2H5OH with stirring, soln. of hydroxyquinoline in C2H5OH added dropwise withstirring, adjusting pH to 8 by aq. KOH, mixt. refluxed for 5 h; mixt. evapd., cooled, ternary complex filtered off, washed (H2O, C2H5OH), dried (vac., P4O10); elem. anal.;	46%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + cobalt(II) nitrate + Benzimidazol-2-thiol (134469-07-1) → [Co[(HOCH2)3CNCH2COO][C7H5N2(S)]2](2-)*2H(1+)=H2[Co[(HOCH2)3CNCH2COO][C7H5N2(S)]2]

Conditions	Yield
With KOH In ethanol Co-salt in H2O added slowly to tricine in EtOH with stirring, mercapto-comp. in EtOH added dropwise with stirring, pH ajusted to 8 with 0.1 M KOH, refluxed for 5 h; evapd., cooled, filtered, washed with H2O and EtOH, dried in vac. over P4H10, elem. anal.;	46%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + benzaldehyde (100-52-7) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → C72H19NO3

Conditions	Yield
In N,N-dimethyl-formamide; toluene for 168000h; Heating;	45.8%

formaldehyd (50-00-0) + N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) → C14H29N2O12P

Conditions	Yield
Stage #1: N-[tris(hydroxymethyl)methyl]glycine With hydrogenchloride; hypophosphorous acid In water at 20℃; for 1h; Stage #2: formaldehyd In water at 20℃; for 24h;	40%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + [Fe3O(2-phenoxybenzoato)6(methanol)3][NO3]*3(methanol) + diethylamine (109-89-7) + acetonitrile (75-05-8) → [Et2NH2][[Fe9O4(OH)2(N-(2-hydroxy-1,1-bis(hydroxymethyl)ethyl)glycine(-3H))2(2-phenoxybenzoato)12]*7(acetonitrile)*H2O

Conditions	Yield
In acetonitrile ligand added to a soln. of Fe complex, (C2H5)2NH added, stirred overnight; filtered, crystd. upon vapor diffusion of Et2O; elem. anal.;	11%

N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) + 2,3,4,5-tetrahydro-2-oxo-1,5-ethanolbenzazepine (102586-88-9) → (N,N-dimethylamino)ethyl 1,2,3,4-tetrahydroquinoline-4-propanoate (104876-18-8)

Conditions	Yield
In water at 25℃; Rate constant;

N-ε-(2-(diphenylphosphino)benzoyl)-N-α-(6-(2-(2-sulfonatobenzaldehyde)hydrazono)nicotinyl)-lysine methyl ester + 99mtechnetium pertechnetate + N-[tris(hydroxymethyl)methyl]glycine (5704-04-1) → 99mTc(HYNIC-Lys(OMe)-2-TPP)(tricine)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In Saline; ethanol; water at 95 - 100℃; for 0.166667 - 0.25h; pH=5.0; succinate buffer;

Upstream product

• 1068-52-6 sodium 2-bromoacetate 
• 77-86-1 2-amino-2-hydroxymethyl-1,3-propanediol 
• 105-39-5 chloroacetic acid ethyl ester 
• 773837-37-9 sodium cyanide 
• 50-00-0 formaldehyd 
• 107-07-3 2-chloro-ethanol 
• 598-42-5 glycolamide 
• 590-17-0 cyanomethyl bromide 
• 764-41-0 1,4-dichloro-2-butene 

Downstream Products

• 216527-01-4 ⁽⁹⁹⁾Tc(NC₅H₄N₂)(P(C₆H₅)3)(O₂CCH₂NHC(CH₂OH)2CH₂O) 
• 190974-77-7 ⁽⁹⁹⁾Tc(NC₅H₄N₂)(P(C₆H₅)3)2Cl₂ 

Relevant articles and documents

Preparation method of tris (hydroxymethyl) methylglycine

The invention relates to the technical field of biological buffering agents, and discloses a preparation method of tris (hydroxymethyl) methylglycine, which comprises the following preparation steps: reacting a compound I with a compound A to obtain a compound II; the compound II is subjected to at least one of a hydrolysis reaction, an oxidation reaction and an acid-base treatment reaction to obtain a tri(hydroxymethyl)methylglycine crude product, and the tri(hydroxymethyl)methylglycine crude product is purified to obtain a tri(hydroxymethyl)methylglycine refined product. The raw materials used in the preparation method are low in cost, operation is easy, the obtained product is high in purity, the yield of the product is increased, the application cost of the product is reduced, the obtained product meets the requirements for the purity, the impurity content, the cost and the like of the product in the field of biological buffering agents, and the method is suitable for industrial production, and the method is suitable for application in the field of biological buffers.

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