Basic information
- Standard SMILES
O=C(OO)c1cccc(Cl)c1- InChIKey
NHQDETIJWKXCTC-UHFFFAOYSA-N- Molecular formula
- C7H5ClO3
- Average molar mass
- 172.56 g/mol
- Monoisotopic mass
- 171.9927217
Overview
This solid peroxide is sensitive to heat. Storage of this material must be done so with stringent temperature control measures. Its explosion hazard is also mitigated by mixing the peroxide in a solvent slurry.
Names & identifiers
- Preferred name
- m-Chloroperbenzoic acid
- IUPAC
- 3-chlorobenzenecarboperoxoic acid
- English name
- 3-Chloroperoxybenzoic acid
- Molecular formula
- C7H5ClO3
- Molecular weight
- 172.57
Names & synonyms
3-Chloroperoxybenzoic acid937-14-43-Chloroperbenzoic acidM-Chloroperoxybenzoic acidM-Chloroperbenzoic acidMCPBA3-Chlorobenzenecarboperoxoic acidm-CPBABenzenecarboperoxoic acid, 3-chloro-m-Chlorobenzoyl hydroperoxidePerbenzoic acid, m-chloro-Peroxybenzoic acid, m-chloro-
Show more names
M-Chloroperoxybenzoic3-Chloroperoxybenzoic Acid (MCPBA)3-ChL3-CHLOROPEROXYBENZOIC ACID, 50-55%
G203D4H1RBNSC-97094DTXSID0061325CHEBI:52091RefChem:93524DTXCID7048879213-322-33-chlorobenzoperoxoic acid
Database identifiers
- CAS
937-14-4- PubChem CID
- 70297
- DTXSID
DTXSID0061325- ChEMBL
CHEMBL458855- ChEBI
CHEBI:52091- UNII
- G203D4H1RB
- EC Number
- 213-322-3
- Nikkaji
- J27.520D
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 149
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Other Organic Compounds
Physical Description
This solid peroxide is sensitive to heat. Storage of this material must be done so with stringent temperature control measures. Its explosion hazard is also mitigated by mixing the peroxide in a solvent slurry.
Solid; [CAMEO] White, wet crystalline aggregates; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 69 · 69-71 °C(lit.)
- Boiling point
- 244.67 °C · 244.67°C (rough estimate)
- Density
- 0.56 · 0.56
- vapor pressure
- 0.373 Pa · 0.373Pa at 25℃
- refractive index
- 1.458 · 1.4580 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- pka
- 7.57 · 7.57 (in water @ 25 °C)
- form
- Moist Powder
- color
- White
- PH
- 4.5 · 4.5@25 °C (saturated aq. sol)
- Odor
- slight pungent odor
- Water Solubility
- insoluble
- Decomposition
- 88 °C · >88 °C
- BRN
- 608317 · 608317
- Stability
- Strong oxidizing agent - contact with combustible material may cause fire. May be shock or heat sensitive. Incompatible with organic materials, strong reducing agents.
- InChI
- 1S/C7H5ClO3/c8-6-3-1-2-5(4-6)7(9)11-10/h1-4,10H
- InChIKey
- NHQDETIJWKXCTC-UHFFFAOYSA-N
- SMILES
- OOC(=O)c1cccc(Cl)c1
- LogP
- 1.03 at · 1.03 at 25℃
- CAS DataBase Reference
- 937 · 937-14-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 203 D4H1RB · G203D4H1RB
- NIST Chemistry Reference
- 3 · 3-Chloroperbenzoic acid(937-14-4)
- EPA Substance Registry System
- 3 · Benzenecarboperoxoic acid, 3-chloro- (937-14-4)
- UNSPSC Code
- 12352302 · 12352302
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 3 · GHS03,GHS07
- Signal word
- Danger
- Hazard statements
- 271 · H271-H315-H317-H319-H335
- Precautionary statements
- 264 · P264-P280-P261-P272-P271-P302+P352-P332+P313-P362+P364-P333+P313-P305+P351+P338-P337+P313-P304+P340-P312-P403+P233-P405-P501
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- O,Xi,C
- Risk Statements
- 5 · 5-8-36/37/38-43-7-34-22
- Safety Statements
- 17 · 17-26-36/37-45-36/37/39-3/7-14-27-7/9
- RIDADR
- 3106 · UN 3106 5.2
- WGK Germany
- 3 · 3
- RTECS
- 9470000 · SD9470000
- F
- 4.4 · 4.4
- TSCA
- TSCA listed
- HazardClass
- 5.2 · 5.2
- PackingGroup
- II
- HS Code
- 29163990 · 29163990
- Storage Class
- 5.2 · 5.2 - Organic peroxides and self-reacting hazardous materials
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Org. Perox. DSkin Corr. 1CSkin Sens. 1
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (60%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P220, P233, P234, P235, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P280, P283, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P306+P360, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P370+P378, P371+P380+P375, P403, P403+P233, P403+P235, P405, P410, P411, P420, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzenecarboperoxoic acid, 3-chloro-
Status: Active Update: 19-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/27379
Benzenecarboperoxoic acid, 3-chloro-: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelOrganic Peroxide
Fire HazardsExcerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:
Health HazardsExcerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:
Hazards Summary
A strong oxidizing agent that may ignite combustible materials; Explosion hazard by heat, shock, friction, or contamination; [CAMEO] Wetted with 57-86% water; An oxidizer that may cause fire on contact with combustible materials; May explode on heating; Causes irritation or burns; [Sigma-Aldrich MSDS]
Reactive GroupHalogenated Organic Compounds
Reactivity AlertsExplosive
Reactivity ProfileMay explode from heat, shock, friction or contamination. May ignite combustibles (wood, paper, oil, clothing, etc.). May be ignited by heat, sparks or flames.
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
Hazard Classes and CategoriesFlam. Liq. 3 (60%)
CSL Reaction Information
CSL00076
3-CHLOROPEROXYBENZOIC ACID + 2-BROMO-6-METHYLPYRIDINE
exploded on the rotovap after work up
Explosive
User-Reported
7/8/18
Safety & protection
Fire FightingExcerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:
First AidExcerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:
Nonfire Spill ResponseExcerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:
Isolation and EvacuationExcerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:
Protective Action Criteria (PAC)
5.4 [mg/m3]
60 [mg/m3]
360 [mg/m3]
Personal Protective Equipment (PPE)Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 4.4
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SD9470000
- ridadr
- UN 3106 5.2
- hs_code
- 29163990
- risk_code
- 5-8-36/37/38-43-7-34-22
- Signal word
- Danger
- Symbol(GHS)
- GHS03,GHS07
- hazard_code
- O,Xi,C
- safety_code
- 17-26-36/37-45-36/37/39-3/7-14-27-7/9
- hazard_class
- 5.2
- Storage Class
- 5.2 - Organic peroxides and self-reacting hazardous materials
- packing_group
- II
- Hazard statements
- H271-H315-H317-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Org. Perox. DSkin Corr. 1CSkin Sens. 1
- Precautionary statements
- P264-P280-P261-P272-P271-P302+P352-P332+P313-P362+P364-P333+P313-P305+P351+P338-P337+P313-P304+P340-P312-P403+P233-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Electron-accepting molecules in chemical reactions in which electrons are transferred from one molecule to another (OXIDATION-REDUCTION).
Uses & manufacturing
UsesAn oxidizing agent; [ChemIDplus]
General Manufacturing InformationBenzenecarboperoxoic acid, 3-chloro-: ACTIVE
Applications
Uses3-Chloroperoxybenzoic acid is commonly used in double bond epoxidation, nitridation, cyclization, Baeyer-Villiger oxidation, and N-oxidation. It can also be used as an oxidant for fine chemicals such as synthetic medicine and pesticides. It is also sometimes used as a bleaching agent [1-6]. • Used in cyclization reaction, Baeyer-Villiger reaction, N-oxidation reaction and S-oxidation reaction. • Used as an oxidant for fine chemical products such as synthetic medicine and pesticides. • Used as oxidant and bleach. • As a good electrophilic reagent, it can react with many functional groups and can oxidize olefins, enol silyl ethers, furans, sulfides, selenides and amino compounds.
Uses3-Chloroperoxybenzoic acid is a strong oxidizing agent used in the oxidation reactions such as aldehydes and ketones to esters (Bayer-Villiger-Oxidation), olefines to epoxides, sulfides to sulfoxides and sulfones, and amines to nitroalkanes, N-oxides.
UsesEffective oxidant for epoxidizing di-, tri-, and tetra-substituted olefins.
General Description3-Chloroperoxybenzoic acid is sensitive to heat. Storage of 3-Chloroperoxybenzoic acid must be done so with stringent temperature control measures. It's explosion hazard is also mitigated by mixing the peroxide in a solvent slurry.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 3-chloroperbenzoic acid is a peroxy acid and a member of monochlorobenzenes.
Related reactions
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Linked notes
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