Record Information
Version2.0
Creation Date2009-06-22 16:08:38 UTC
Update Date2014-12-24 20:24:40 UTC
Accession NumberT3D1809
Identification
Common Namem-Xylyl bromide
ClassSmall Molecule
Descriptionm-Xylyl bromide, also known as methylbenzyl bromide or T-stoff, is a poisonous organic chemical compound, formerly used as a tear gas. Physically it is a colourless liquid (melting point 21 °C) with a pleasant aromatic odour. m-Xylyl bromide is highly toxic, irritant and lachrymatory, and has been incorporated in chemical weapons since the early months of World War I. The first extensive use of xylyl bromide was the firing by German forces of 18,000 "T-shells" at Russian positions in the Battle of Bolimów in January 1915. In the absence of clarification, the name "xylyl bromide" may refer to any one of 3 xylyl isomers (o-Xylyl, p-Xylyl, m-Xylyl) or a mixture of all three.
Compound Type
  • Aromatic Hydrocarbon
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
.alpha.-bromo-m-xylene
1-(Bromomethyl)-3-methylbenzene
3-(Bromomethyl)toluene
3-bromomethyl-1-methylbenzene
3-bromomethyltoluene
3-Methylbenzyl bromide
a-bromo-m-xylene
Alpha-bromo-m-xylene
M-(bromomethyl)toluene
M-methylbenzyl bromide
m-Xylene, alpha-bromo- (8CI)
M-XYLYL bromide
Chemical FormulaC8H9Br
Average Molecular Mass185.061 g/mol
Monoisotopic Mass183.989 g/mol
CAS Registry Number620-13-3
IUPAC Name1-(bromomethyl)-3-methylbenzene
Traditional Name1-(bromomethyl)-3-methylbenzene
SMILESCC1=CC=CC(CBr)=C1
InChI IdentifierInChI=1S/C8H9Br/c1-7-3-2-4-8(5-7)6-9/h2-5H,6H2,1H3
InChI KeyInChIKey=FWLWTILKTABGKQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzyl bromides. These are organic compounds containing a benzene skeleton substituted with a bromomethyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl halides
Direct ParentBenzyl bromides
Alternative Parents
Substituents
  • Benzyl bromide
  • Toluene
  • Hydrocarbon derivative
  • Organobromide
  • Organohalogen compound
  • Alkyl halide
  • Alkyl bromide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling Point212.5°C
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP3.46ALOGPS
logP3.26ChemAxon
logS-3.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability16.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-50afbcf7c2d69163ddb82016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-4d90d66096ffb1cd8a542016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-7900000000-3030ef487bc818c6bede2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-84dcb0548794810067262016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-84dcb0548794810067262016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-d43edb5531b18eb4c7ef2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-553e0ec999a7c06b539b2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityOrganobromide compounds such as m-Xylyl bromide are strong alkylating agents. Consequently they can readily modify free thiols (cysteines) and methionine residues of the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs.
MetabolismBromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (4)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (5)
Uses/SourcesOccupational exposure to xylyl bromide may occur through inhalation and dermal contact with this compound at workplaces where xylyl bromide is produced or used.
Minimum Risk LevelNot Available
Health EffectsStrong lachrymator. Strong irritant to eyes, skin and soft tissues. Highly toxic if inhaled, swallowed or absorbed through skin.
SymptomsCauses severe eye and skin burns. Irritating to eyes, skin, and respiratory system. Acute exposure (ingestion or inhalation) can lead to coma, nausea, vomiting, and metabolic acidosis may occur.
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID12099
ChEMBL IDNot Available
ChemSpider ID21168825
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDm-Xylyl bromide
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1809.pdf
General References
  1. Zielinski A: [First chemical mass attack in history of wars, Bolimow, January 31, 1915]. Przegl Epidemiol. 2010;64(3):449-53. [20976962 ]
  2. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  3. Wikipedia. Xylyl bromide. Last Updated 25 May 2009. [Link]
  4. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

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. Zielinski A: [First chemical mass attack in history of wars, Bolimow, January 31, 1915]. Przegl Epidemiol. 2010;64(3):449-53. [20976962 ]
  2. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
  3. Wikipedia. Xylyl bromide. Last Updated 25 May 2009. [Link]