Basic information
- Standard SMILES
S=c1[nH]c2ccccc2[nH]1- InChIKey
YHMYGUUIMTVXNW-UHFFFAOYSA-N- Molecular formula
- C7H6N2S
- Average molar mass
- 150.2 g/mol
- Monoisotopic mass
- 150.02516919
Overview
2-mercaptobenzimidazole appears as white to yellow crystals or cream colored powder. Slight odor. (NTP, 1992)
Names & identifiers
- Preferred name
- 2-Mercaptobenzimidazole
- IUPAC
- 1,3-dihydrobenzimidazole-2-thione
- English name
- 2-Mercaptobenzimidazole
- Molecular formula
- C7H6N2S
- Molecular weight
- 150.2
Names & synonyms
Show more names
Database identifiers
- CAS
583-39-1- PubChem CID
- 707035
- DTXSID
DTXSID9025536- ChEMBL
CHEMBL70141- ChEBI
CHEBI:228724- UNII
- 619CVM6HOK
- EC Number
- 209-502-6
- Nikkaji
- J1.632B、J3.800.039J
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 56.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 142
Experimental & physicochemical properties
Solubility
less than 1 mg/mL at 74.3 °F (NTP, 1992)
>22.5 [ug/mL] (The mean of the results at pH 7.4)
Vapor Pressure
30.2 mmHg at 142 °F (NTP, 1992)
0.00000466 [mmHg]
Physical Description
2-mercaptobenzimidazole appears as white to yellow crystals or cream colored powder. Slight odor. (NTP, 1992)
CBI
Glistening solid; [Merck Index] White to yellow or cream solid with a mild odor; [CAMEO] Beige crystalline solid; [Sigma-Aldrich MSDS]
Ionization Efficiency
Positive
1.49
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Physicochemical properties
- Melting point
- 300 · 300-304 °C (lit.)
- Boiling point
- 270.6 · 270.6±23.0 °C(Predicted)
- Density
- 1.42 · 1.42
- vapor pressure
- 0 · 0-0.001Pa at 25℃
- refractive index
- 1.55 · 1.5500 (estimate)
- Flash point
- 250 °C · >250°C
- storage temp.
- 2 · 2-8°C
- solubility
- 0.3 g/l · 0.3g/l
- form
- Powder
- pka
- 10.24 · 10.24±0.10(Predicted)
- color
- White to beige
- Water Solubility
- 0.1 g/100 · <0.1 g/100 mL at 23.5 ºC
- Merck
- 14 · 14,1082
- BRN
- 119867 · 119867
- Stability
- Stable. Incompatible with strong oxidizing agents.
- InChI
- 1S/C7H6N2S/c10-7-8-5-3-1-2-4-6(5)9-7/h1-4H,(H2,8,9,10)
- InChIKey
- YHMYGUUIMTVXNW-UHFFFAOYSA-N
- SMILES
- S=C1Nc2ccccc2N1
- LogP
- 0.88 · 0.88-1.66 at 20-25℃
- CAS DataBase Reference
- 583 · 583-39-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 619 CVM6HOK · 619CVM6HOK
- NIST Chemistry Reference
- 2 · 2-Mercaptobenzimidazole(583-39-1)
- EPA Substance Registry System
- 2 · 2-Mercaptobenzimidazole (583-39-1)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 6 · GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 301 · H301-H317-H373-H412
- Precautionary statements
- 260 · P260-P273-P280-P301+P310-P302+P352-P314
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 20 · 20/21/22-36/37/38-22
- Safety Statements
- 26 · 26-36-24/25
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 2 · 2
- RTECS
- 1050000 · DE1050000
- Autoignition Temperature
- 480 °C · 480 °C
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29339910 · 29339910
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 OralAquatic · Acute Tox. 3 OralAquatic Chronic 3Skin Sens. 1ASTOT RE 2
- Toxicity
- 50 orally · LD50 orally in Rabbit: 300 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (80.3%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 279 reports by companies from 30 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2H-Benzimidazole-2-thione, 1,3-dihydro-
2H-Benzimidazole-2-thione, 1,3-dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-Benzimidazole-2-thione, 1,3-dihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 01-06-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/10415
2-Mercaptobenzimidazole: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
A mild skin and eye irritant; Causes somnolence, ataxia, coma, changes in liver weight, and evidence of thyroid hypofunction in acute oral studies of rats; Causes changes in thymus and thyroid weights and changes in erythrocyte count in 13-week intermittent inhalation studies of rats; [RTECS] A skin and strong eye irritant; Toxic by ingestion; Harmful by inhalation and skin absorption; [Sigma-Aldrich MSDS] See Benzimidazole.
Reactivity Profile
An organosulfide and an amine. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- DE1050000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29339910
- Toxicity
- LD50 orally in Rabbit: 300 mg/kg
- risk_code
- 20/21/22-36/37/38-22
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- Xn
- safety_code
- 26-36-24/25
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301-H317-H373-H412
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 OralAquatic Chronic 3Skin Sens. 1ASTOT RE 2
- Autoignition Temperature
- 480 °C
- Precautionary statements
- P260-P273-P280-P301+P310-P302+P352-P314
Chemistry & industry
Uses & manufacturing
Uses
Purine synthesis antimetabolite. [ChemIDplus] Used as an intermediate, in rubber product manufacturing, and electroplating, [ExPub: ECHA REACH Registrations]
Electroplating [Category: Plate]
General Manufacturing Information
Plastics Product Manufacturing
2H-Benzimidazole-2-thione, 1,3-dihydro-: ACTIVE
Applications
Description2-Mercaptobenzimidazole is a very useful corrosion inhibitor and cleaner. It can be used to remove the mercury (II) from aqueous solutions and chlor-alkali industry wastewater1. It can be added to the surface film to inhibit the corrosion of metals like copper2-3 and mild steel4. It can also be used as the carrier for the coated-wire mercury (II)-selective electrodes5. 2-Mercaptobenzimidazole is also used as an anti-degradant. It is utilized for protecting rubber from oxidation. It is also employed as an intermediate in the preparation of rabeprazole. Further, it finds application in anti-leprosy drugs in medicine6.
UsesAn antidegradant, protecting rubber from oxidation. An intermediate in the synthesis of Rabeprazole (R070500)
Uses2-Mercaptobenzimidazole is used as an antidegradant. It is utilized for protecting rubber from oxidation. It is also employed as an intermediate in the preparation of rabeprazole. Further, it finds application in anti-leprosy drugs in medicine. In addition to this, it is used as a copper plating brightener.
General DescriptionWhite to yellow crystals or cream colored powder. Slight odor.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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