Tris(hydroxymethyl)aminomethane (Tris base) - ≥99%(T) , CAS No.77-86-1

CAS: 77-86-1 Cat. No.: T434094 Formula: C₄H₁₁NO₃ Molecular Weight: 121.14 Beilstein Registry Number: 741883 EC Number: 201-064-4

GRADE & PURITY ≥99%(T)

Synonyms

Triladyl | Tris-hydroxymethyl-aminomethan [German] | Trometamole | NSC65434 | Trometamolum | TROMETHAMINE (II) | CAS-77-86-1 | (tris(hydroxymethyl)aminomethane) | THAM-E | tris-amine | 1,1,1-tris(hydroxymethyl)methanamine | 2-Amino-2-hydroxymethyl-1,3-pro

Storage

Room temperature

Overview

Tris is an established basimetric standard and buffer used in biochemistry and molecular biology. It may be used by itself as a buffer or as a component of mixed buffer formulations, such as Tris-EDTA (TE) buffer, Tris-acetate-EDTA (TAE) buffer, Tris-borate-EDTA (TBE) buffer, etc. It is pure, essentially stable, relatively non-hygroscopic and has a high equivalent weight.

Application

Trizma ® base was used as buffer for the following studies: Electrophoretic transfer for the specific identification of isozymes of starch debranching enzyme, α-amylase and 9-amylase. Electrophoretic separation of lipoproteins in polyacrylamide gels. Preparation of TRIS buffer having pH 8. It may be used to compose DN buffer for DNA nick-end labeling of tissue sections.

Other Notes

The pH values of all buffers are temperature- and concentration-dependent. For Tris buffers, pH increases about 0.03 unit per °C decrease in temperature, and decreases 0.03-0.05 unit per ten-fold dilution. For precise applications, use a carefully calibrated pH meter with a glass/calomel combination electrode.

Specifications

Synonyms

Triladyl | Tris-hydroxymethyl-aminomethan [German] | Trometamole | NSC65434 | Trometamolum | TROMETHAMINE (II) | CAS-77-86-1 | (tris(hydroxymethyl)aminomethane) | THAM-E | tris-amine | 1,1,1-tris(hydroxymethyl)methanamine | 2-Amino-2-hydroxymethyl-1,3-pro

Specifications & Purity

≥99%(T)

Storage

Room temperature

Purity

≥99%(T)

Names and Identifiers

Canonical Smiles

C(C(CO)(CO)N)O

IUPAC Name

2-amino-2-(hydroxymethyl)propane-1,3-diol

InChIKey

LENZDBCJOHFCAS-UHFFFAOYSA-N

INCHI

1S/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2

Isomeric SMILES

C(C(CO)(CO)N)O

WGK Germany

2

RTECS

TY2900000

Molecular Weight

121.14

Beilstein

741883

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines
        • Level5 Alkanolamines
          • Level6 1,2-aminoalcohols

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Alkanolamines
• Direct Parent: 1,2-aminoalcohols
• Alternative Parents: Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1,2-aminoalcohol - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Primary alcohol - Organooxygen compound - Primary aliphatic amine - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

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Sigmar1 Sigma opioid receptor (160 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: H2O: 1M at20°C, clear, colorless
• Boil Point(°C): 219-220 °C/10 mmHg (lit.)
• Melt Point(°C): 167-173 °C
• Molecular Weight: 121.140 g/mol
• XLogP3: -2.900
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 121.074 Da
• Monoisotopic Mass: 121.074 Da
• Topological Polar Surface Area: 86.700 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 54.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No item-specific, validated protocols are provided for this SKU. The following literature-style outlines are provided for guidance only and should be validated in your laboratory.

Example: 1 M Tris–HCl, pH 8.0 (literature)

• Dissolve 121.14 g Tris base in ~800 mL water.
• Adjust temperature to 25 °C; titrate with concentrated HCl to pH 8.0.
• Bring to 1 L with water; 0.22 µm filter if sterility is required; store at RT or 2–8 °C.

Example: 10× TBE buffer (literature)

• Dissolve appropriate amounts to give ~0.89 M Tris base, ~0.89 M boric acid, 20 mM EDTA; bring to volume with water.
• Mix until clear; dilute to 1× for use in DNA electrophoresis.

Example: Quenching an acylation (literature)

• After reaction completion, add an aqueous solution of Tris (1–2 eq relative to residual acylating agent) with stirring at 0–25 °C.
• Separate layers; wash organic phase with water; dry and concentrate.

For antibody-type application fields (WB, IHC, IF, FC): Not applicable to this product.

Biological Roles

Tris is not a natural metabolite but is widely used as a buffering agent in biological research due to its amine functionality and suitable pKa near physiological pH.

General biochemical characteristics (literature):

• Protonation behavior: Tris accepts a proton to form its conjugate acid (Tris·H+), providing buffering capacity in the ~7–9 pH window.
• Minimal UV absorbance: Compatible with nucleic acid and protein quantification at 260/280 nm with low background.
• Metal interactions: Exhibits weak coordination to some metal ions; typically less chelating than amine-polycarboxylates. In presence of borate, forms borate esters (basis of TBE buffers).
• Enzyme compatibility: Often suitable for enzymes operating near neutral pH, but the primary amine can interact with active sites or cofactors; assay validation is recommended.
• Biomolecular interactions: The amine can react with activated esters (e.g., NHS esters), potentially quenching labeling reactions; avoid Tris in such steps.

Use considerations:

• Temperature sensitivity: Buffer pH shifts with temperature; prepare and calibrate at the intended working temperature.
• CO2 exposure: Although less sensitive than bicarbonate buffers, open containers can undergo slight pH drift over time; seal and minimize prolonged air exposure to maintain pH accuracy.

Buffer Applications

Primary use-case: Tris is a cornerstone buffer component across molecular biology and protein chemistry.

Key buffering characteristics (literature):

• pKa (25 °C): ~8.06; effective range ~pH 7.2–9.0.
• Temperature coefficient: ΔpKa/ΔT ≈ −0.028/°C; always adjust pH at the working temperature.

Common formulations (literature examples):

• 1.0 M Tris–HCl, pH 8.0: Dissolve Tris base in ~80% of final volume of water (e.g., 121.14 g per 1 L for 1 M), cool/heat to working temperature, adjust to pH 8.0 with concentrated HCl, bring to volume, and filter-sterilize (0.22 µm) if sterility is required.
• TAE (50× stock): 2 M Tris base, 1 M acetic acid, 50 mM EDTA (disodium), dilute to 1× for agarose electrophoresis.
• TBE (10× stock): ~0.89 M Tris, ~0.89 M boric acid, 20 mM EDTA; dilute to 1× for nucleic acid electrophoresis.
• Tris–glycine buffers: Standard SDS-PAGE running buffer and Western transfer buffer formulations use Tris with glycine (and SDS for running buffer; methanol often for transfer).

Practical tips:

• Use high-purity, nuclease-free Tris for DNA/RNA applications.
• Calibrate pH meter at the buffer’s working temperature; pH can shift by ~0.3 units between 4 °C and 37 °C for Tris solutions.
• Avoid Tris during amine-reactive labeling (e.g., NHS-ester conjugations); substitute phosphate/HEPES during coupling, then exchange back to Tris if desired.

Green Alternatives

Environmental and safety profile (general):

• Tris base is nonflammable, has low volatility, and is typically of low acute toxicity—attributes favorable from a green chemistry and EHS perspective.
• Main considerations are aquatic release of high-ionic-strength buffers and energy associated with temperature control due to Tris’s temperature-dependent pKa.

Alternatives and trade-offs (literature/general):

• HEPES/MOPS/MES (Good’s buffers): Offer low metal binding and minimal temperature/pCO2 sensitivity. Trade-offs include higher cost and, in some cases, more complex synthesis with larger environmental footprints.
• Phosphate buffers: Abundant and inexpensive with excellent biodegradability, but can precipitate with Ca2+/Mg2+ and may inhibit phosphoryl-transfer enzymes.
• Bicarbonate/CO2 systems: Renewable and biocompatible but require CO2 atmosphere control; pH drifts in open systems.

Comparison snapshot (general):

• Tris: pKa ~8.06 at 25 °C; strong temperature dependence; very low UV absorbance; economical.
• HEPES: pKa ~7.5; very low temperature coefficient; higher cost; minimal UV.
• Phosphate: Multiple pKa values; minimal temperature effect; potential precipitation with divalent cations.

Greener use tips:

• Prepare only the volume needed; avoid unnecessary disposal of high-salt buffers.
• Reuse/recirculate electrophoresis buffers where method allows, monitoring conductivity and pH.
• Use room temperature protocols when possible to reduce active temperature control demands.

Pharmaceutical Uses

No therapeutic claims are made. The following are general excipient and manufacturing roles for tromethamine (Tris) in pharmaceutical contexts (literature/general):

• Buffering agent: Maintains pH in the mildly alkaline range for small-molecule and biologic formulations where stability requires pH ~7–9.
• Process buffer: Widely used in upstream and downstream bioprocessing (chromatography equilibration/wash, viral inactivation quench, UF/DF diafiltration buffers), subject to grade and documentation.
• Excipient status: Tromethamine/Tris appears in major pharmacopeias (e.g., USP–NF, Ph. Eur.) as a compendial excipient; specific monograph tests and limits apply per pharmacopeia (consult the current compendium and CoA).
• Compatibility notes: The primary amine can react with activated esters and aldehydes; assess interactions with actives and packaging (e.g., epoxy-lined closures) during development.
• Analytical considerations: Low UV absorbance facilitates UV-based release assays; ionic strength and pH should be controlled to meet method system-suitability criteria.

Item-specific compliance or grade claims are not provided for this SKU; refer to the CoA/Spec Sheet and regulatory documentation requirements for your intended use.

Physical Properties

Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.

Typical physical constants (literature/general):

• Appearance: White crystalline solid (literature)
• Molecular weight: 121.14 g/mol (literature)
• Melting point: ~168–172 °C (literature; may discolor/decompose on prolonged heating)
• Boiling point: Not applicable (decomposes before boiling, literature)
• Density (solid): Not well-defined; bulk density varies with granulation (literature)
• Solubility: Highly soluble in water (e.g., >500 g/L at 25 °C, literature); soluble in methanol and ethanol; practically insoluble in nonpolar solvents (literature)
• LogP (oct/water): Strongly negative (very hydrophilic; XlogP3 ≈ −2 to −3, literature)
• pKa (Tris·H+/Tris): ~8.06 at 25 °C; temperature coefficient ΔpKa/ΔT ≈ −0.028 per °C (literature)
• pH of solutions (for guidance): 1.0 M Tris base in water typically ~10.4–10.6 before acid adjustment (literature)
• UV cut-off: Tris is weakly UV-absorbing; usable at 260/280 nm with minimal background compared to many organic buffers (literature)

Practical notes (general):

• Hygroscopicity: Low-to-moderate; keep container tightly closed to prevent moisture uptake and caking (general practice).
• Heat sensitivity: Extended heating can cause Maillard-type browning in presence of sugars or carbonyls; prepare fresh when purity of buffer is critical (general).

Quality & Grades

Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Context for common Tris grades (general information to aid selection):

• Reagent grade/AR: Suitable for routine buffer preparation where trace organics/UV background are not critical.
• Molecular biology/bioultra grade: Low nuclease (RNase/DNase) and protease activity; low UV-absorbing impurities; intended for nucleic acid/protein electrophoresis and enzymology.
• BioPerformance/HPLC grade: Tight control of particulates and UV absorbance at 210–280 nm; recommended when UV detection is used or when background must be minimal.
• Endotoxin-tested/cGMP-supporting grades: For bioprocess buffers; documentation packages (BSE/TSE, residual solvents, elemental impurities) typically available from suppliers.

Stabilizers/antioxidants: Tris base is typically offered neat without stabilizers; if any stabilizer is used, it will be declared on the CoA/Spec (not specified for this item).

What to check on the CoA/Spec Sheet:

• Assay (typically by acidimetric titration), loss on drying, UV absorbance (230/260/280 nm), heavy metals/elemental impurities, residue on ignition/ash, chloride/nitrate/sulfate tests, bioburden/endotoxin and nuclease testing for bio grades.

Traceability and lot consistency:

• For sensitive biological workflows (e.g., long electrophoresis runs, enzyme assays), prefer a grade with certified low UV background and nuclease-free status.

Reaction & Applications

This product is most commonly used as a buffer component in biochemical and molecular biology workflows. It can also participate in organic reactions due to its primary amine and triol functionalities.

Biochemical applications (literature/general):

• Electrophoresis buffers: TAE (Tris–acetate–EDTA), TBE (Tris–borate–EDTA), Tris–glycine (SDS-PAGE running/transfer buffers), and Tris–glycine–HCl (Laemmli).
• Nucleic acid workflows: pH-stable environments for ligation, PCR setup, and storage when nuclease-free quality is ensured.
• Protein biochemistry: Lysis buffers, chromatography equilibration/wash buffers, enzyme assay media (after confirming compatibility), dialysis and sample storage.

Synthetic/analytical applications (literature):

• Base/nucleophile: Catalyzes acylation/esterification in protic media, promotes epoxide ring-opening, and can quench acylating/sulfonylating reagents.
• Scavenger: Captures acid and electrophiles in workups; forms salts with strong acids for facilitated separation.
• Complexation: Forms weak complexes/borate esters (basis of Tris–borate buffers), and transient imine/Schiff-base adducts with reactive carbonyls.

Practical tips:

• Buffer prep: Adjust pH with HCl (for Tris–HCl) at the working temperature; Tris pH drifts with temperature (−0.028 pKa/°C, literature).
• Electrophoresis: Use high-purity Tris to reduce background conductivity and Joule heating; verify ionic strength for long runs.
• Enzymology: Verify enzyme compatibility; some enzymes exhibit activity shifts in Tris due to amine interactions or metal coordination.

Reaction Conditions

Guidance below summarizes common, literature-based conditions for typical uses of Tris base; adapt to your system and consult primary references.

Buffer preparation (literature):

• Solvent: Water (Type 1 recommended for analytical/biological work).
• Concentration: 10–1000 mM depending on application (e.g., 25–50 mM for enzyme assays; 0.89 M stocks for electrophoresis buffers).
• Temperature: Adjust pH at working temperature due to ΔpKa/ΔT ≈ −0.028/°C. Example: a solution at pH 8.0 at 25 °C may read ~pH 7.7 at 4 °C.
• Sterilization: Filter through 0.22 µm; avoid autoclaving with carbonyl-containing components (risk of reactions/browning).

As base/nucleophile in synthesis (literature/general):

• Solvents: Water, MeOH, EtOH; for less polar substrates consider DMSO/DMF co-solvents.
• Temperatures: Ambient to 60 °C commonly sufficient for neutralizations and epoxide openings; higher temperatures may lead to side reactions.
• Catalysis/quenching: Use 1–3 equivalents relative to electrophile for scavenging; monitor by TLC/LC.
• Metal complexation: Typically weak; if metal catalysis is involved, verify that Tris does not inhibit the catalyst.

Electrophoresis buffers (literature):

• TAE/TBE working concentrations: 1×; reuse possible with monitoring of conductivity and pH.
• SDS-PAGE running buffer: Tris–glycine–SDS at pH ~8.3; maintain temperature to limit Joule heating.

Expected performance:

• Tris buffers provide stable pH within their effective range under moderate ionic strengths; verify by pH-meter calibration and ionic strength adjustments.

Safety & Handling

Item-specific hazard data: Not specified for this item; refer to SDS.

General GHS guidance (literature/typical):

• Classification: Often not classified as hazardous or may be Eye Irrit. 2A; check the specific SDS for this SKU.
• Signal word and H/P statements: Not specified for this item; refer to SDS.

Safe handling and PPE (best practice):

• Wear appropriate PPE: laboratory coat, safety glasses/goggles, and nitrile gloves.
• Avoid creating or breathing dust; use local exhaust ventilation when weighing.
• Wash thoroughly after handling; avoid contact with eyes and prolonged skin contact.

Storage and incompatibilities (general):

• Storage temperature: Room temperature (per Product Data); keep tightly sealed in a dry place.
• Incompatible materials: Strong acids (will form Tris salts and heat may evolve upon neutralization), acylating agents, sulfonyl chlorides, isocyanates, strong oxidizers, aldehydes (may undergo Schiff base or other reactions), and reactive carbonyl compounds.
• Container advice: Use clean, dry utensils; reseal promptly to minimize moisture uptake and contamination.

First aid overview (general):

• Inhalation: Move to fresh air; if symptoms persist, seek medical attention.
• Skin contact: Wash with soap and water; remove contaminated clothing.
• Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists.
• Ingestion: Rinse mouth; seek medical advice if unwell.

Always consult the SDS for authoritative, product-specific safety information.

Solvent Selection

Applicability: Tris base is a solid buffer component rather than a solvent. However, proper solvent choice is essential for dissolving and using Tris effectively.

Solubility/miscibility profile (literature):

• Highly soluble in water; readily forms clear solutions over a wide concentration range.
• Soluble in lower alcohols (methanol, ethanol); limited or negligible solubility in aprotic nonpolar solvents (e.g., hexanes, toluene) and limited in chlorinated solvents.

Polarity and dielectric considerations (general):

• Tris is strongly hydrophilic and ionizable; aqueous systems are preferred. For organic syntheses requiring Tris as a base/nucleophile, polar protic (MeOH, EtOH) or highly polar aprotics (DMSO, DMF) can be used to improve dissolution.

When to choose Tris-based buffers vs alternatives:

• Choose Tris when pH 7.2–9.0 is desired, with low UV absorbance and minimal metal chelation.
• Consider HEPES/MOPS/MES for reduced temperature dependence of pH or where CO2 absorption and pH drift must be minimized in open systems.
• Consider phosphate when buffering near pH 6.5–7.5 and compatibility with enzymes/life science assays is validated; avoid phosphate with calcium/magnesium precipitation risks.

Quick comparison (general):

• Tris: pKa ~8.06 (25 °C), ΔpKa/ΔT ≈ −0.028/°C; excellent conductivity for electrophoresis; minimal UV background.
• HEPES: pKa ~7.5, very low temperature coefficient; zwitterionic Good’s buffer; higher cost.
• Phosphate: Multiple pKa values; may interact with metal-dependent enzymes; UV-transparent.

Storage & Reconstitution

Item-specific storage condition:

• Storage Conditions: Room temperature (per Product Data).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General storage guidance (solid):

• Keep tightly closed in a clean, dry container; protect from moisture and reactive vapors (acids, carbonyls).
• Store away from strong oxidizers and acids.

Reconstitution/preparation (literature/general):

• Dissolution: Add Tris base to water with stirring; it dissolves readily. For sterile applications, use sterile water and 0.22 µm filter-sterilize the final solution.
• pH adjustment: For Tris–HCl, adjust with HCl at the intended working temperature due to temperature-dependent pKa.
• Typical stock solutions: 0.5–2.0 M (depending on downstream dilution); label with concentration, pH, and preparation temperature.

Solution stability (literature/general):

• Room temperature: Clear, unsterilized Tris solutions are typically stable for days to weeks; for critical assays, prepare fresh or store at 2–8 °C.
• Refrigerated (2–8 °C): Weeks to months when sterile and in clean containers; minimize headspace and seal to reduce pH drift.
• Freezing: Generally not necessary; if frozen, allow to thaw completely and mix before use.

Research Use Only: For research use only (per Product Data).

Structure & Identity

Overview: Tris(hydroxymethyl)aminomethane (Tris base) is a small, highly polar, primary alkanolamine widely used as a biological buffer component.

Item-specific (from Product Data):

• SKU: T434094
• Product name: Tris(hydroxymethyl)aminomethane (Tris base)
• CAS: 77-86-1
• PubChem CID: 6503
• InChIKey: 197534 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature identity (for reference):

• Synonyms: Tris base; THAM; Tromethamine; 2-amino-2-(hydroxymethyl)-1,3-propanediol
• Molecular formula: C4H11NO3 (literature)
• Molecular weight: 121.14 g/mol (literature)
• SMILES (one representation): N(CO)(CO)C(O)CO (literature)
• InChIKey: KQNIJPIBGCXZOO-UHFFFAOYSA-N (literature)

Structural features (general description):

• Core scaffold: A quaternary carbon (C-2) bearing one primary amino group (–NH2) and three hydroxymethyl substituents (–CH2OH).
• Functional groups: One primary amine and three primary alcohols (triol). No rings, no stereocenters (achiral).
• 2D description: Central carbon connected to –NH2 and three –CH2OH groups, producing a highly hydrogen-bonding, polyfunctional molecule.
• Acid/base character: A weak base (conjugate acid pKa ~8.06 at 25 °C, literature), enabling buffering around neutral to slightly basic pH when protonated (as Tris·H+).

Synthetic Utility

Although best known as a buffer, Tris base is a versatile multifunctional reagent owing to its primary amine and triol functionality.

Functional-group reactivity (literature/general):

• As a base/nucleophile: Neutralizes acids; participates in nucleophilic acyl substitution (forms amides/carbamates with activated carboxylic derivatives and isocyanates) and promotes epoxide ring-opening in protic/polar media.
• Triol reactivity: Forms borate esters with boric acid (reversible), enabling borate-complexation chemistry; can form carbonate/carbamate derivatives under activating conditions.
• Scavenging: Efficiently traps acid chlorides/sulfonyl chlorides and activated esters during workup, improving product purity.
• Ligand behavior: The amine and hydroxyls can chelate metals weakly; Tris-derived ligands (e.g., TREN variants) illustrate the scaffold’s utility in coordination chemistry.

Retrosynthetic value and practical use:

• Protecting/derivatization: The amine can transiently protect/react with electrophilic handles, assisting in purification or analysis.
• Phase-transfer aid: In water-rich biphasic systems, protonated Tris can enhance partitioning of acidic species into the aqueous phase.
• Green aspect: Nonvolatile, low-toxicity base alternative in place of volatile amines for some neutralizations.

Caveats:

• Limited solubility in many nonpolar organics; choose solvent systems accordingly (water/MeOH/EtOH, DMSO, DMF).
• Competing hydrogen bonding may slow some reactions; catalysts or activation may be required.

Target Specificity

Not applicable to this product type. This item is a small-molecule buffer component and not a biological targeting reagent (e.g., antibody, ligand, or probe). No antigen/epitope specificity data are associated with this SKU.