Basic Info

Common NameBromoacetone(F04344)
2D Structure
Description

Bromoacetone is an organobromide compound. It is a lachrymatory agent and was used in World War I as a chemical weapon (called BA by British and B-Stoff by Germans) and later as a riot control agent. Today it is considered obsolete (due to its toxicity) and is no longer in use for riot control purposes, but is a useful reagent in organic synthesis. Bromoacetone is prepared by combining bromine and acetone with a catalytic acid such as sulfuric acid. Bromoacetone has been shown to be a by-product of drinking water treatment using chlorine dioxide and chloramines in water high in bromide concentrations. Bromoacetone is found in the essential oil of a seaweed species (Asparagopsis taxiformis) that grows in the ocean around the Hawaiian Islands. Bromoacetone is structurally similar to chloroacetone. Both chemicals are irritants however, data suggest that bromoacetone is more toxic than chloroacetone. As a chemical warfare or riot control agent, bromoacetone is/was considered to be a rapid acting casualty producing agent capable of causing casualties within minutes of dissemination. Eye exposure to as little as 1 mg can cause pain and irritation. Inhalation of as little as 2-5 mg can cause coughing, nose and throat irritation and congestion. Inhalation of higher concentrations may lead to severe sore throat, nasal congestion and serious discomfort. Skin contact with as little as 2-30 mg can produce irritation, itching, swelling and general discomfort. Skin exposure to 50-100mg may lead to blisters.

FRCD IDF04344
CAS Number598-31-2
PubChem CID11715
FormulaC3H5BrO
IUPAC Name

1-bromopropan-2-one

InChI Key

VQFAIAKCILWQPZ-UHFFFAOYSA-N

InChI

InChI=1S/C3H5BrO/c1-3(5)2-4/h2H2,1H3

Canonical SMILES

CC(=O)CBr

Isomeric SMILES

CC(=O)CBr

Synonyms
        
            BROMOACETONE
        
            Bromo-2-propanone
        
            1-Bromo-2-propanone
        
            598-31-2
        
            Monobromoacetone
        
            Acetonyl bromide
        
            Martonite
        
            1-bromopropan-2-one
        
            2-Propanone, 1-bromo-
        
            1-Bromoacetone
        
Classifies
                

                  
                    Plant Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbonyl compounds
Intermediate Tree NodesKetones
Direct ParentAlpha-haloketones
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsAlpha-haloketone - Organic oxide - Hydrocarbon derivative - Organobromide - Organohalogen compound - Alkyl halide - Alkyl bromide - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as alpha-haloketones. These are organic compounds contaning a halogen atom attached to the alpha carbon atom relative to C=O group.

Properties

Property NameProperty Value
Molecular Weight136.976
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Complexity42.2
Monoisotopic Mass135.952
Exact Mass135.952
XLogP0.7
Formal Charge0
Heavy Atom Count5
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9894
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7386
P-glycoprotein SubstrateNon-substrate0.8263
P-glycoprotein InhibitorNon-inhibitor0.9197
Non-inhibitor0.9286
Renal Organic Cation TransporterNon-inhibitor0.8718
Distribution
Subcellular localizationMitochondria0.6569
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8099
CYP450 2D6 SubstrateNon-substrate0.8509
CYP450 3A4 SubstrateNon-substrate0.6921
CYP450 1A2 InhibitorInhibitor0.5120
CYP450 2C9 InhibitorNon-inhibitor0.9295
CYP450 2D6 InhibitorNon-inhibitor0.9407
CYP450 2C19 InhibitorNon-inhibitor0.8610
CYP450 3A4 InhibitorNon-inhibitor0.9407
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9126
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9296
Non-inhibitor0.9436
AMES ToxicityAMES toxic0.7915
CarcinogensCarcinogens 0.7698
Fish ToxicityLow FHMT0.7591
Tetrahymena Pyriformis ToxicityHigh TPT0.9402
Honey Bee ToxicityHigh HBT0.7670
BiodegradationReady biodegradable0.5859
Acute Oral ToxicityII0.5434
Carcinogenicity (Three-class)Non-required0.5529

Model Value Unit
Absorption
Aqueous solubility-0.1006LogS
Caco-2 Permeability1.4854LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.1016LD50, mol/kg
Fish Toxicity1.3890pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8772pIGC50, ug/L

Targets

General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Garner CE, Sumner SC, Davis JG, Burgess JP, Yueh Y, Demeter J, Zhan Q, Valentine J, Jeffcoat AR, Burka LT, Mathews JM: Metabolism and disposition of 1-bromopropane in rats and mice following inhalation or intravenous administration. Toxicol Appl Pharmacol. 2006 Aug 15;215(1):23-36. Epub 2006 Mar 2. [16513153 ]