(chloromethyl)benzene

• ChemBase ID: 77921
• Molecular Formular: C7H7Cl
• Molecular Mass: 126.58348
• Monoisotopic Mass: 126.0236279
• SMILES: ClCc1ccccc1
• Canonical SMILES: ClCc1ccccc1
• InChI: InChI=1S/C7H7Cl/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
• InChIKey: KCXMKQUNVWSEMD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (chloromethyl)benzene
• IUPAC Traditional name: benzyl chloride
• Synonyms: 6-(Chloromethyl)benzene; 1-Chloromethylbenzene; Benzyl Chloride; Chlorophenylmethane; NSC 8043; Phenylmethyl Chloride; Tolyl Chloride; ω-Chlorotoluene; (Chloromethyl)benzene; Benzyl chloride 99%; Benzyl chloride; α-Chlorotoluene; Benzyl chloride; alpha-Chlorotoluene; (Chloromethyl)benzene; α-氯甲苯; 苄氯; 苄基 氯

Database IDs

• CAS Number: 100-44-7
• EC Number: 202-853-6
• MDL Number: MFCD00000889
• Beilstein Number: 471308
• Merck Index: 141129
• PubChem SID: 162042762; 24851148
• PubChem CID: 7503
• CHEBI ID: 615597
• CHEMBL: 498878
• Chemspider ID: 13840690
• KEGG ID: C19167
• Unique Ingredient Identifier: 83H19HW7K6
• Wikipedia Title: Benzyl_chloride

CALCULATED PROPERTIES

• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.560488
• LogD (pH = 7.4): 2.560488
• Log P: 2.560488
• Molar Refractivity: 35.9249 cm^3
• Polarizability: 13.9815035 Å^3
• Polar Surface Area: 0.0 Å^2

PROPERTIES

Physical Property

• Solubility: Miscible with alcohol, ether. Insoluble in water
• Melting Point: -39 °C; -39.2°C; -43 °C(lit.); -43°C
• Boiling Point: 177-181 °C(lit.); 177-181°C; 178-180°C; 179 °C
• Flash Point: 140 °F; 60 °C; 73°C(163°F); 74°C
• Auto Ignition Point: 1085 °F
• Density: 1.099; 1.1; 1.1 g/mL at 25 °C(lit.); 1.100 g/cm^3
• Refractive Index: 1.5380; n20/D 1.538(lit.); n20/D 1.539
• Vapor Pressure: 10.3 mmHg ( 60 °C); 7 mmHg ( 55 °C)
• Vapor Density: 4.36 (vs air)

Safety Information

• Storage Warning: Toxic/Lachrymatory/Light Sensitive/Moisture Sensitive
• RTECS: XS8925000
• European Hazard Symbols: Toxic (T)
• UN Number: 1738; UN1738
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 45-22-23-37/38-41-48/22; 45-46-22-23-37/38-41-48/22
• Safety Statements: 53-26-39-45; 53-45
• TSCA Listed: 是
• EU Index: 602-037-00-3
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• Explode Limits: 14 %
• GHS Hazard statements: H226-H302-H315-H318-H330-H335-H340-H350-H373; H302-H315-H318-H331-H335-H350-H373; H331-H302-H315-H335-H350-H373-H318-H227
• GHS Precautionary statements: P201-P260-P280-P284-P305 + P351 + P338-P310; P201-P261-P280-P305 + P351 + P338-P311; P210-P260-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1738 6.1/PG 2

Product Information

• Purity: ≥99.0% (GC); ≥99.5% (GC); 95+%; 97%; 99%; 99%, stab.
• Grade: puriss.; purum; reagent grade; ReagentPlus®
• Contains: ≤1% propylene oxide as stabilizer; 0.25% propylene oxide as inhibitor
• Linear Formula: C6H5CH2Cl

DETAILS

Apollo Scientific Ltd - OR16493

Stabilised

Sigma Aldrich - 185558

Packaging
1, 2, 4 kg in glass bottle
50, 250 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - B233675

An intermediate in the preparation of phenylacetic acid (precursor to phamaceuticals). Also a precursor molecule to benzyl esters which are used as plasticizer, flavorants, and perfumes.

REFERENCES

• Qiu, Z.: J Nat. Gas Chem., 14, 40 (2005)
• Abdelhalim, M.M. at al.: Steroids, 72, 459 (2005)
• Elmegeed, Get al.: Eur. J. Med. Chem., 40, 1283 (2005)
• Benzyllithium and substituted analogues have proved difficult to generate in a pure state owing to competing Wurtz coupling. Conditions have been described for efficient generation of benzyllithiums from the chlorides using Li naphthalenide in a mixed diethyl ether - THF - petroleum ether solvent system at -95^o: J. Chem. Soc., Perkin 1, 185 (1995).
• Amidocarbonylation with acetamide and a CO/H₂ mixture under pressure, in the presence of Co₂(CO)₈ catalyst, provides a novel route to N-acetyl-DL-phenylalanine: J. Org. Chem., 61, 1842 (1996).