2-sulfanylethan-1-ol

• ChemBase ID: 3033
• Molecular Formular: C2H6OS
• Molecular Mass: 78.13344
• Monoisotopic Mass: 78.01393581
• SMILES: OCCS
• Canonical SMILES: OCCS
• InChI: InChI=1S/C2H6OS/c3-1-2-4/h3-4H,1-2H2
• InChIKey: DGVVWUTYPXICAM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-sulfanylethan-1-ol
• IUPAC Traditional name: β-mercaptoethanol
• Synonyms: 2-Sulfhydryl-Ethanol; β-Mercaptoethanol; Thioglycol; Thioethylene glycol; BME; 2-Mercaptoethanol; β-Mercaptoethanol; 2-Hydroxyethylmercaptan; 2-MERCAPTOETHANOL; 2-Thioethanol; 2-Hydroxyethyl Mercaptan; 2-Hydroxy-1-Ethanethiol; 2ME; β-巯基乙醇; 2-羟基乙硫醇; 硫代乙二醇; 2-巯基乙醇

Database IDs

• CAS Number: 60-24-2
• EC Number: 200-464-6
• MDL Number: MFCD00004890
• Beilstein Number: 773648
• Merck Index: 145869
• PubChem SID: 24897085; 160966480; 46506852; 24897143; 24896800; 24897168; 24882813
• PubChem CID: 1567
• CHEBI ID: 41218
• CHEMBL: 254951
• Chemspider ID: 1512
• DrugBank ID: DB03345
• Gmelin ID: 1368
• KEGG ID: C00928
• MeSH Name: Mercaptoethanol
• Wikipedia Title: 2-Mercaptoethanol

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.969782
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): -0.11323081
• LogD (pH = 7.4): -0.114300944
• Log P: -0.113217145
• Molar Refractivity: 20.7362 cm^3
• Polarizability: 8.098647 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.11
• LOG S: -0.43
• Solubility (Water): 2.92e+01 g/l

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.5 M at 20 °C, clear, colorless; H2O: soluble1 mL/mL
• Apperance: liquid
• Melting Point: < -50 °C; <-50°C; -100°C; -100°C
• Boiling Point: 154 - 161 °C; 154°C; 156.85°C (430K); 156-158°C; 157 °C(lit.)
• Flash Point: 154.4 °F; 68 °C; 70.5 °C (DIN 51758); 73°C(163°F)
• Auto Ignition Point: 295 °C
• Density: 1.114; 1.114 g cm^-3; 1.114 g/mL at 25 °C(lit.); 1.115 g/mL at 20 °C; 1.12 g/cm^3 at 20 °C; 1.12 g/ml
• Refractive Index: 1.4996; 1.500; n20/D 1.500(lit.); n20/D 1.501
• Vapor Pressure: .76 hPa at 20 °C; 1 mmHg ( 20 °C); 100 Pa (at 20 °C)
• Vapor Density: 2.69 (air = 1); 2.69 (vs air)
• Partition Coefficient: -0.23
• Absorption Wavelength: λ: 260 nm Amax: 1.5; λ: 280 nm Amax: 0.3
• pKa: 9.643
• pKb: 4.354

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Air Sensitive & Hygroscopic
• RTECS: KL5600000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2966; UN2966
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 22-24-37/38-41-43-50/53; 23/24/25-38-41-43-48/22-50/53; 23/24/25-38-41-43-50/53; R:22-27; R20/22, R24, R34, R51/53
• Safety Statements: 20-23-26-27-36/37/39-45-57; 26-36/37/39-45-60-61; S:28-29-36/37/39-45; S26, S36/37/39, S45, S61
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS corrosion; GHS environment; GHS skull and crossbones; GHS05; GHS06; GHS08; GHS09
• GHS Signal Word: DANGER; Danger
• Explode Limits: 18 %; 18%
• GHS Hazard statements: 301, 310, 315, 317, 318, 330, 410; H301 + H331-H310-H315-H317-H318-H373-H410; H301-H310 + H330-H315-H317-H318-H410; H301-H310-H315-H317-H335-H318-H400-H410-H227
• GHS Precautionary statements: 260, 273, 280, 284, 301+310, 302+350; P210-P301+P310-P305+P351+P338-P361-P405-P501A; P260-P273-P280-P284-P301 + P310-P302 + P350; P261-P273-P280-P301 + P310-P302 + P350-P305 + P351 + P338
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2966 6.1/PG 2
• Storage Temperature: 2-8°C; room temp

Pharmacology Properties

• Target Organ: Heart, Liver

Product Information

• Purity: ≥98%; ≥99.0%; ≥99.0% (GC); 98%; 98+%; 99%; 99% (GC/titration)
• Concentration: 14.3 M (pure liquid)
• Grade: for electrophoresis; for molecular biology; purum; SAJ special grade
• Suitability: suitable for cell culture
• Ignition Residue: ≤0.01%
• Impurities: DNases, none detected; insoluble matter, passes filter test; phosphatases, none detected; proteases, none detected; RNases, none detected
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: <1 ppm; Cu: ≤0.02 mg/kg; Fe: <1 ppm; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤1 mg/kg; Ni: ≤0.05 mg/kg; Pb: <5 ppm; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: <1 ppm; Zn: ≤0.1 mg/kg
• Foreign Activity: DNase, RNase, protease, none detected
• λ: 0.5 M in H2O
• Product Line: BioUltra
• Linear Formula: HSCH2CH2OH

DETAILS

MP Biomedicals - 02194834

Molecular Biology Reagent
Purity: 98+%
Specially purified for molecular biology applications.

MP Biomedicals - 04806444

Purity: >98%
Specially purified for use in solubilizing proteins for gel electrophoresis.

MP Biomedicals - 04806445

Purity: >98%
Specially purified for use in solubilizing proteins for gel electrophoresis.

MP Biomedicals - 02194705

Cell Culture Reagent
Used to reduce disulfide linkages in solubilizing proteins for gel electrophoresis. Also reduces excess oxidative polymerization of catalysts.
Density = 1.12 g/ml

MP Biomedicals - 04806443

Purity: >98%
Specially purified for use in solubilizing proteins for gel electrophoresis.

MP Biomedicals - 02190242

Used to reduce disulfide linkages in solubilizing proteins for gel electrophoresis. Also reduces excess oxidative polymerization of catalysts.
1 ml = approx. 1.12 g

Sigma Aldrich - M7154

Application
BME 用于在聚丙烯酰胺凝胶电泳前还原蛋白质二硫键，通常以 5% 的浓度包含在用于 SDS-PAGE 的样本缓冲液中。裂解分子间（亚基之间）的二硫键，从而使蛋白质亚基在 SDS-PAGE 上各自分开。裂解分子内（亚基内）的二硫键从而使亚基完全变性，以便每个肽按照其链长迁移而不受二级结构的影响。
包装
25, 100 mL in glass bottle

Sigma Aldrich - 63700

Application
BME is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE at a concentration of 5%. Cleaving intermolecular (between subunits) disulfide bonds allows the subunits of a protein to separate independently on SDS-PAGE. Cleaving intramolecular (within subunit) disulfide bonds allows the subunits to become completely denatured so that each peptide migrates according to its chain length with no influence due to secondary structure.

Sigma Aldrich - 19-1335

Application
BME is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE at a concentration of 5%. Cleaving intermolecular (between subunits) disulfide bonds allows the subunits of a protein to separate independently on SDS-PAGE. Cleaving intramolecular (within subunit) disulfide bonds allows the subunits to become completely denatured so that each peptide migrates according to its chain length with no influence due to secondary structure.
Suitability
for biological purposes

Sigma Aldrich - 568678

Application
BME is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE at a concentration of 5%. Cleaving intermolecular (between subunits) disulfide bonds allows the subunits of a protein to separate independently on SDS-PAGE. Cleaving intramolecular (within subunit) disulfide bonds allows the subunits to become completely denatured so that each peptide migrates according to its chain length with no influence due to secondary structure.
Legal Information
Product of Arkema Inc.

Sigma Aldrich - M7522

Application
BME 用于在聚丙烯酰胺凝胶电泳前还原蛋白质二硫键，通常以 5% 的浓度包含在用于 SDS-PAGE 的样本缓冲液中。裂解分子间（亚基之间）的二硫键，从而使蛋白质亚基在 SDS-PAGE 上各自分开。裂解分子内（亚基内）的二硫键从而使亚基完全变性，以便每个肽按照其链长迁移而不受二级结构的影响。
包装
100, 250, 500 mL in glass bottle

Sigma Aldrich - 19-1330

Application
BME is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE at a concentration of 5%. Cleaving intermolecular (between subunits) disulfide bonds allows the subunits of a protein to separate independently on SDS-PAGE. Cleaving intramolecular (within subunit) disulfide bonds allows the subunits to become completely denatured so that each peptide migrates according to its chain length with no influence due to secondary structure.

Sigma Aldrich - M6250

Application
BME 用于在聚丙烯酰胺凝胶电泳前还原蛋白质二硫键，通常以 5% 的浓度包含在用于 SDS-PAGE 的样本缓冲液中。裂解分子间（亚基之间）的二硫键，从而使蛋白质亚基在 SDS-PAGE 上各自分开。裂解分子内（亚基内）的二硫键从而使亚基完全变性，以便每个肽按照其链长迁移而不受二级结构的影响。
广泛用于延缓溶液中生物化合物的氧化。
包装
1, 2.5 L in glass bottle
10, 100, 250, 500 mL in glass bottle

Sigma Aldrich - M3701

Application
BME is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE at a concentration of 5%. Cleaving intermolecular (between subunits) disulfide bonds allows the subunits of a protein to separate independently on SDS-PAGE. Cleaving intramolecular (within subunit) disulfide bonds allows the subunits to become completely denatured so that each peptide migrates according to its chain length with no influence due to secondary structure.
Charge transfer agent for the preparation of polyvinyl chloride. Synthon for the preparation of 1,3-oxathiolanes.

Sigma Aldrich - M3148

Application
BME 用于在聚丙烯酰胺凝胶电泳前还原蛋白质二硫键，通常以 5% 的浓度包含在用于 SDS-PAGE 的样本缓冲液中。裂解分子间（亚基之间）的二硫键，从而使蛋白质亚基在 SDS-PAGE 上各自分开。裂解分子内（亚基内）的二硫键从而使亚基完全变性，以便每个肽按照其链长迁移而不受二级结构的影响。
还原剂
包装
25, 100, 250, 500 mL in glass bottle

Sigma Aldrich - 516732

Application
BME is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE at a concentration of 5%. Cleaving intermolecular (between subunits) disulfide bonds allows the subunits of a protein to separate independently on SDS-PAGE. Cleaving intramolecular (within subunit) disulfide bonds allows the subunits to become completely denatured so that each peptide migrates according to its chain length with no influence due to secondary structure.
Legal Information
Product of Arkema

Sigma Aldrich - 63689

Application
BME is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE at a concentration of 5%. Cleaving intermolecular (between subunits) disulfide bonds allows the subunits of a protein to separate independently on SDS-PAGE. Cleaving intramolecular (within subunit) disulfide bonds allows the subunits to become completely denatured so that each peptide migrates according to its chain length with no influence due to secondary structure.
Other Notes
Isolation of RNA using guanidinium salts. Inclusion of a reductant enhances denaturation by breaking intramolecular protein disulfide bonds1

Sigma Aldrich - 63690

Application
BME is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE at a concentration of 5%. Cleaving intermolecular (between subunits) disulfide bonds allows the subunits of a protein to separate independently on SDS-PAGE. Cleaving intramolecular (within subunit) disulfide bonds allows the subunits to become completely denatured so that each peptide migrates according to its chain length with no influence due to secondary structure.
Other Notes
A reducing agent in fluorescent reaction of o-phthaldialdehyde and amino acids in alkaline medium1,2,3; For the dissociation of proteins4,5

DrugBank - DB03345

Drug information: experimental

REFERENCES

• In the presence of BF₃ etherate, reacts with carbonyl compounds to give monothioacetals (1,3-oxathiolanes): J. Org. Chem., 33, 2133 (1968). Amberlyst 15 is also effective: Synthesis, 1826 (2001), as is In(OTf)₃: Synlett, 1535 (2002). 1,3-Oxathiolanes can be prepared from acid-sensitive aldehydes with LiBH₄ as catalyst in acetonitrile: Synlett, 238 (2001). Cleavage can be effected, e.g. with chloramine-T: Tetrahedron Lett., 3445 (1971), isoamyl nitrite: Tetrahedron. Lett., 3561 (1978), or periodic acid: Tetrahedron Lett., 37, 4331 (1996). Selective cleavage of oxathiolanes in the presence of dithiolanes has been achieved with triphenylcarbenium tetrafluoroborate: J. Chem. Soc., Perkin 1, 542 (1972), or 4-nitrobenzaldehyde catalyzed by TMS-OTf: J. Chem. Soc. Chem. Commun., 1937 (1994). Compare 1,2-Ethanedithiol, L12865.
• 2-Mercaptoethanol is a reagent for the specific cleavage of the N-dithiasuccinimide protecting group from amines. See Chlorocarbonylsulfenyl chloride, L06432.
• Protective agent for preventing oxidation of thiol groups in proteins: Enzyme Assays, R. Eisenthal and M. J. Danson, Eds., OUP, Oxford (1992), p 265.