(chlorodiphenylmethyl)benzene

• ChemBase ID: 78377
• Molecular Formular: C19H15Cl
• Molecular Mass: 278.7754
• Monoisotopic Mass: 278.08622816
• SMILES: ClC(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: ClC(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C19H15Cl/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
• InChIKey: JBWKIWSBJXDJDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (chlorodiphenylmethyl)benzene
• IUPAC Traditional name: triphenylmethyl chloride
• Synonyms: Triphenylmethyl chloride; Trityl chloride; Chlorotriphenylmethane; (Chloromethanetriyl)tribenzene; 1,1',1''-(Chloromethylidyne)tris[benzene]; NSC 435; Chlorotriphenylmethane; 1,1',1''-(Chloromethanetriyl)tribenzene; Trityl chloride; Trityl chloride; Triphenylchloromethane; TRIPHENYLMETHYL CHLORIDE; TRIPHENYLCHLOROMETHANE; 三苯基甲基氯; 氯三苯甲烷; 氯代三苯甲烷; 三苯基氯甲烷

Database IDs

• CAS Number: 76-83-5
• EC Number: 200-986-4
• MDL Number: MFCD00000813
• Beilstein Number: 397363
• PubChem SID: 162043146; 24889652; 24900525
• PubChem CID: 6456
• Chemspider ID: 17344583
• Wikipedia Title: Triphenylmethyl_chloride

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.99297
• LogD (pH = 7.4): 5.99297
• Log P: 5.99297
• Molar Refractivity: 86.3625 cm^3
• Polarizability: 33.236782 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; chloroform 0.1g/ml; chloroform: soluble0.1 g/mL, clear
• Apperance: Off-White Solid; white to yellow solid
• Melting Point: 109-112 °C(lit.); 109-112°C; 109-113 °C; 110°C; 110-114°C; 111-113°C; 112-114°C
• Boiling Point: 230°C; 230°C (at 20mmHg) and 374.3°C (at 760mmHg); 230-235 °C/20 mmHg(lit.); 230-235°C/20mm; 230-235°C/20mm
• Flash Point: 177.9°C
• Density: 1.141g/cm^3

Safety Information

• Storage Condition: 2-8°C, Store Under Nitrogen; Refrigerator
• Storage Warning: Corrosive/Lachrymatory/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS: PA6450000
• European Hazard Symbols: Corrosive (C); Nature polluting (N)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; II
• Risk Statements: 34; 34-50/53; R:34
• Safety Statements: 26-36/37/39-45; 26-36/37/39-45-60-61; S:26-27/28-36/37/39-46-64
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318-H400-H410
• GHS Precautionary statements: P280-P273-P305+P351+P338-P309-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 3

Product Information

• Purity: ≥98%; ≥97.0% (AT); ≥97.0% (HPLC); 97%; 98%
• Grade: purum
• Ignition Residue: ≤0.2% (as SO4)
• Linear Formula: (C6H5)3CCl

DETAILS

MP Biomedicals - 02152175

Crystalline
Purity: 98+%
N-protecting reagent.

MP Biomedicals - 05207858

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T83801

Application
Protecting reagent for amines, alcohols, and thiols.1,2
Packaging
25, 100, 500 g in poly bottle

Sigma Aldrich - 93000

Other Notes
Reagent for tritylations;; Efficient method of tritylation of sensitive compounds and their subsequent detritylation1,2

Toronto Research Chemicals - T887260

Trityl Chloride is an alkyl halide commonly used in organic synthesis to introduce the trityl protecting group. Trityl Chloride is used in the preparation of S-trityl-L-cysteine (STLC), a tight-binding inhibitor of Eg5 that prevents mitotic progression.

REFERENCES

• DeBonis, S. et al.: J. Med. Chem., 51, 1115 (2008)
• Chadwick, D.J. et al.: J. Chem. Soc. Perk. Trans. Org. Bio-Org. Chem., 1, 102 (2008)
• Reagent for protection of N, S and particularly O functions as trityl (Trt) derivatives, stable to a wide range of conditions, but readily cleaved by mild acid.
• For an improved method for O-tritylation in triethylamine in the presence of catalytic amounts of DMAP, see: Tetrahedron Lett., 95 (1979).
• Progressively more acid-labile protecting groups contain one, two or three p-methoxy-groups: 4-Methoxytrityl chloride, A10545, 4,4'-Dimethoxytrityl chloride, A11626, and 4,4',4''-Trimethoxytrityl chloride, L00629, respectively.
• For a one-pot procedure for the high yield, racemization-free N-tritylation of amino acids, by means of prior in situ O-silylation, see: J. Org. Chem., 47, 1324 (1982). N-Trt- derivatives of amino acids have also been converted to Leuchs' anhydrides by treatment with phosgene or triphosgene, and the products coupled with amino acid esters to give dipeptides in good yields without racemization: J. Org. Chem., 64, 2532 (1999). See also 9-Bromo-9-phenylfluorene, L14225.