Basic information
- CAS
22445-41-6- Standard SMILES
Cc1cc(C)cc(I)c1- InChIKey
ZLMKEENUYIUKKC-UHFFFAOYSA-N- Molecular formula
- C8H9I
- Average molar mass
- 232.06 g/mol
- Monoisotopic mass
- 231.9749
Names & identifiers
- Preferred name
- 1-Iodo-3,5-dimethylbenzene
- IUPAC
- 1-iodo-3,5-dimethylbenzene
- English name
- 1-Iodo-3,5-dimethylbenzene
- Molecular formula
- C8H9I
- Molecular weight
- 232.06
Names & synonyms
1-Iodo-3,5-dimethylbenzeneRefChem:56249222445-41-65-Iodo-m-xylene1,3-dimethyl-5-iodobenzene3,5-DimethyliodobenzeneBenzene, 1-iodo-3,5-dimethyl-MFCD000606591-iodo-3,5-dimethyl-benzene1-Iodo-3,5-dimethylbenzene #STR09819AKOS005145655
Show more names
5-Iodo-m-xylene,99%1-Iodo-3,5-dimethyL3,5-Dinethyliodobenzene3,5-dimethylphenyl iodide5-Iodo-M-xylene, 99% 25ML3,5-diMethyl-1-iodobenzene
CS-W014173I0548EN300-349358AMY6055-Iodo-meta-xyleneFT-0620516A816213SCHEMBL79108
Database identifiers
- CAS
22445-41-6- PubChem CID
- 140924
- DTXSID
DTXSID90176985- EC Number
- 629-121-2
- Nikkaji
- J903.458G
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 80
Experimental & physicochemical properties
Kovats Retention Index1231.2
Physicochemical properties
- Melting point
- -2.9 °C · -2.9°C (estimate)
- Boiling point
- 92 · 92-94 °C3 mm Hg(lit.)
- Density
- 1.608 g/mL · 1.608 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.594(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Sparingly soluble (0.014 g/L) (25°C), Calc.
- form
- Liquid
- Specific Gravity
- 1.608 · 1.608
- color
- Clear light yellow
- Sensitive
- Light Sensitive
- BRN
- 2039353 · 2039353
- InChI
- 1S/C8H9I/c1-6-3-7(2)5-8(9)4-6/h3-5H,1-2H3
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (98%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (98%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (96%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (98%)；Eye Irrit. 2 (98%)；STOT SE 3 (96%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- hs_code
- 29039990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,C
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- Storage Class
- 10 - Combustible liquids
- target organs
- Respiratory system
Chemistry & industry
Applications
Usessuzuki reaction
Uses1-Iodo-3,5-dimethylbenzene (5-iodo-m-xylene) is suitable for use in the synthesis of N-(3,5-xylyl)-N-ethylaniline, an arylamine.It may be used in the following studies:α-Arylation of ketones.Copper-catalyzed N-arylation of imidazoles.Cyanation of 5-iodo-m-xylene to form 3,5-dimethylbenzonitrile.Synthesis of 1,3-Dimethyl-5-phenoxybenzene by nano-CuFe2O4 catalyzed C-O cross-coupling with phenol.CuBr-catalyzed amination of 1-iodo-3,5-dimethylbenzene to form N-Allyl-3,5-dimethylbenzenamine.Copper-catalyzed C-S bond-formation between 5-iodo-m-xylene and thiophenol.As a starting material in the synthesis of biphenyl-3,3′,5,5′-tetracarboxylic acid.Radical bromination of 5-iodo-m-xylene by N-bromosuccinimide to form 1,3-bis(bromomethyl)-5-iodobenzene.
Uses1-Iodo-3,5-dimethylbenzene (5-iodo-m-xylene) is suitable for use in the synthesis of N-(3,5-xylyl)-N-ethyl aniline, an aryl amine, It is also used in the following studies; α-Arylation of ketones, Copper-catalyzed N-arylation of imidazoles, Cyanation of 5-iodo-m-xylene to form 3,5-dimethylbenzonitrile, synthesis of 1,3-Dimethyl-5-phenoxybenzene by nano-CuFe2O4 catalyzed C-O cross-coupling with phenol, CuBr-catalyzed amination of 1-iodo-3,5-dimethylbenzene to form N-Allyl-3,5-dimethylbenzenamine, copper-catalyzed C-S bond-formation between 5-iodo-m-xylene and thiophenol. It is also employed as a starting material in the synthesis of biphenyl-3,3,5,5-tetracarboxylic acid, radical bromination of 5-iodo-m-xylene by N-bromosuccinimide to form 1,3-bis(bromomethyl)-5-iodobenzene.
General Description1-Iodo-3,5-dimethylbenzene (5-Iodo-m-xylene) is an aryl halide. It can be obtained from 5-bromo-m-xylene, via copper-catalyzed halogen exchange reaction, in the presence of NaI or KI in n-BuOH or DMF (solvents). It undergoes reaction with phenol in the presence of CuFe2O4 nano powder as a recyclable catalyst to afford 1,3-dimethyl-5-phenoxybenzene.
Upstream & downstream products
Upstream raw materials
Related reactions
212 records
Compound notes
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