3375-50-6

Basic information

• Product Name: 2-Mercaptoethanesulfonic acid
• Synonyms: 2-mercaptoethanesulfonic acid sol. prot. seq.anal.;2-mercaptoethanesulphonic acid;2-MERCAPTOETHANESULFONIC ACID SOL. PROT. SEQ.ANAL., 10X1 ML;Mesna2-Mercaptoethanesulfonate;2-mercaptoethanesulfonic acid solution;2-sulfanylethanesulfonic acid;2-Mercaptoethane-1-sulfonic acid;Reduced coenzyme M
• CAS NO: 3375-50-6
• Molecular Formula: C₂H₆O₃S₂
• Molecular Weight: 142.2
• EINECS: 222-167-0
• Product Categories: Reagents for Protein SequencingAmino Acid Analysis;Protein Sequencing;Protein Structural Analysis;Reagents for amino acid derivatisation&detection;Regents for amino acid analysis
• Mol File: 3375-50-6.mol
• Article Data: 0

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.25 g/mL at 20 °C
• Refractive Index: 1.539
• PKA: pK1:;pK2:9.5(－1) (20°C)
• BRN: 1098878
• CAS DataBase Reference: 2-Mercaptoethanesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Mercaptoethanesulfonic acid(3375-50-6)
• EPA Substance Registry System: 2-Mercaptoethanesulfonic acid(3375-50-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 2
• F: 10-23
• Hazardous Substances Data: 3375-50-6(Hazardous Substances Data)

Usage

Definition

ChEBI: An organosulfonic acid consisting of sulfonic acid having a 2-mercaptoethyl group attached to sulfur.

Therapeutic Function

Mucolytic

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 6231, 1955 DOI: 10.1021/ja01628a052

InChI:InChI=1/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)

Synthetic route

thirane (420-12-2) + water (7732-18-5) + sodium hydrogensulfite → 2-Mercaptoethanesulfonic acid (3375-50-6)

ethylene sulphide (157-20-0) + sodium hydrogensulfite → 2-Mercaptoethanesulfonic acid (3375-50-6)

Conditions	Yield
In not given

2-Mercaptoethanesulfonic acid (3375-50-6) + 2-acetylamino-N-[2-(4-hydroxyphenyl)ethyl]acrylamide (646071-98-9) → 2-{2-acetylamino-2-[2-(4-hydroxyphenyl)ethylcarbamoyl]ethylsulfanyl}ethanesulfonic acid

Conditions	Yield
With triethylamine In water at 20℃; for 1h; Michael addition;	85%

2-Mercaptoethanesulfonic acid (3375-50-6) + C38H34F4N2O5 (1422728-56-0) + triethylamine (121-44-8) → C40H38F3N2O8S2(1-)*C6H15N

Conditions	Yield
Stage #1: 2-Mercaptoethanesulfonic acid; C38H34F4N2O5; triethylamine In water; N,N-dimethyl-formamide at 20℃; Schlenk technique; Inert atmosphere; Stage #2: With acetic acid In water; N,N-dimethyl-formamide Inert atmosphere; Schlenk technique;	76%

2-Mercaptoethanesulfonic acid (3375-50-6) + nocathiacin I → C63H66N14O21S7

Conditions	Yield
With triethylamine In water at -20℃; for 5.5h; Michael addition;	70%

2-Mercaptoethanesulfonic acid (3375-50-6) + C32H26F4N2O3 + triethylamine (121-44-8) → C34H31F3N2O6S2*2C6H15N

Conditions	Yield
In water; N,N-dimethyl-formamide at 0 - 20℃; regioselective reaction;	70%

2-Mercaptoethanesulfonic acid (3375-50-6) + C43H43F3N2O6S2 + triethylamine (121-44-8) → C45H48F2N2O9S4*C6H15N

Conditions	Yield
In water; N,N-dimethyl-formamide at 20℃;	65%

2-Mercaptoethanesulfonic acid (3375-50-6) + C41H39F4N2O3(1+) → C43H43F3N2O6S2

Conditions	Yield
With triethylamine regioselective reaction;	60%

2-Mercaptoethanesulfonic acid (3375-50-6) + acetyl chloride (75-36-5) → 2-(acetylthio)ethane-1-sulfonic acid (69536-71-6)

Conditions	Yield
With trifluoroacetic acid at 0 - 25℃; for 4h;	59%

2-Mercaptoethanesulfonic acid (3375-50-6) + C34H31F3N2O6S2 → C36H35F2N2O9S4(1-)

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide at 40℃;	53%

2-Mercaptoethanesulfonic acid (3375-50-6) + N-acetyl-S-phenylsulphonyl-L-cysteine (102837-27-4) → S-(2-Sulphonylethylthio)-N-acetyl-L-cysteine (128505-54-4)

Conditions	Yield
In methanol; water for 2h;	20%

2-Mercaptoethanesulfonic acid (3375-50-6) + S-Phenylsulphonylglutathione (97512-84-0) → S-(2-Sulfoethylthio)glutathione (69536-72-7)

Conditions	Yield
In formic acid for 2.5h;	11%

2-Mercaptoethanesulfonic acid (3375-50-6) + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ile-OH (71989-23-6) + Fmoc-Arg(Pbf)-OHFmoc-His(Trt)-OH → {(S)-2-[(2S,3S)-2-({(S)-1-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-3-methyl-pentanoylamino]-5-guanidino-pentanoylamino}-thioacetic acid S-(2-sulfo-ethyl) ester

Conditions	Yield
Multistep reaction;	8.2%

2-Mercaptoethanesulfonic acid (3375-50-6) + Fmoc-Leu-OH (35661-60-0) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ile-OH (71989-23-6) + Fmoc-Arg(Pbf)-OHFmoc-His(Trt)-OH → (S)-2-{(S)-2-[(2S,3S)-2-({(S)-1-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-3-methyl-pentanoylamino]-5-guanidino-pentanoylamino}-4-methyl-pentanethioic acid S-(2-sulfo-ethyl) ester

Conditions	Yield
Multistep reaction;	5.2%

2-Mercaptoethanesulfonic acid (3375-50-6) → 2,2’-dithio-bis-ethane sulfonate (45127-11-5)

Conditions	Yield
(i) I2, (ii) aq. NaOH; Multistep reaction;

2-Mercaptoethanesulfonic acid (3375-50-6) + rifamycin S (62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2) → C39H51NO15S2

2-Mercaptoethanesulfonic acid (3375-50-6) + C2H5NO4S2 → 2,2’-dithio-bis-ethane sulfonate (45127-11-5)

Conditions	Yield
In water at 25℃; Rate constant;

2-Mercaptoethanesulfonic acid (3375-50-6) + per-2-O-allyl-γ-cyclodextrin → per-2-O-[3-(2-sulfoethylthio)propyl]-γ-cyclodextrin

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 110℃;

2-Mercaptoethanesulfonic acid (3375-50-6) + heptakis(6-deoxy-6-iodo)cyclomaltoheptaose (30754-23-5) → C56H98O49S14

Conditions	Yield
With triethylamine In dimethyl sulfoxide

2-Mercaptoethanesulfonic acid (3375-50-6) + thiostrepton → C74H91N19O21S7

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide at 4℃; Michael condensation; Inert atmosphere;

2-Mercaptoethanesulfonic acid (3375-50-6) + C45H71N13O14S → H-Met-Glu-Glu-Leu-Tyr-Lys-Ser-His-SCH2CH2SO3H (1224852-91-8)

Conditions	Yield
Stage #1: C45H71N13O14S With sodium nitrite at -10℃; for 0.333333h; pH=4; Stage #2: 2-Mercaptoethanesulfonic acid for 2h; pH=4;

2-Mercaptoethanesulfonic acid (3375-50-6) + para-hydroxymercuribenzoic acid (1214321-39-7) → C2H5O3S2(1-)*C7H5HgO2(1+)

Conditions	Yield
Stage #1: 2-Mercaptoethanesulfonic acid With tris(2-carboxyethyl)phosphine at 20℃; for 0.25h; Stage #2: para-hydroxymercuribenzoic acid In water for 0.0833333h; Acidic conditions;

2-Mercaptoethanesulfonic acid (3375-50-6) + ubiquitin-(1-75)-azide → ubiquitin-(1-75)-Mesna thioester

Conditions	Yield
pH=5;

Upstream product

• 157-20-0 ethylene sulphide 
• 420-12-2 thirane 
• 7732-18-5 water 

Downstream Products

• 69536-71-6 2-(acetylthio)ethane-1-sulfonic acid 
• 45127-11-5 2,2’-dithio-bis-ethane sulfonate