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Name |
4-Chlorobenzyl chloride |
EINECS | 203-242-7 |
CAS No. | 104-83-6 | Density | 1.26 g/cm3 |
PSA | 0.00000 | LogP | 3.07880 |
Solubility | insoluble in water | Melting Point |
27-29 °C(lit.) |
Formula | C7H6Cl2 | Boiling Point | 223 °C at 760 mmHg |
Molecular Weight | 161.031 | Flash Point | 87.3 °C |
Transport Information | UN 3427 6.1/PG 3 | Appearance | colorless to light yellow liquid |
Safety | 26-36/37/39-45-29-61 | Risk Codes | 34-51/53-20/21/22 |
Molecular Structure | Hazard Symbols | C; N | |
Synonyms |
(4-Chlorophenyl)methyl chloride;alpha,4-Dichlorotoluene;p-Chlorobenzyl chloride;1-Chloro-4-(chloromethyl)benzene;Benzene, 1-chloro-4-(chloromethyl)-;p-Chlorobenzyl chloride, liquid or solid;alpha,p-Dichlorotoluene;α,4-dichlorotoluene;Chlorobenzyl Chloride;4-Chlorobenzyl chloride(PCBC);4-Chlorobenzylchloride;Toluene, p,alpha-dichloro-;p-Chlorophenylmethyl chloride;Benzene, 1-chloro-4- (chloromethyl)-; |
Article Data | 85 |
Conditions | Yield |
---|---|
With tetrachloromethane; cross-linked polymer (containing 2.50 mmol of phosphine/g) for 3h; Heating; | 100% |
With ziconium(IV) oxychloride octahydrate; lithium chloride In ethanol; water at 90℃; for 1.5h; | 95% |
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide at 20℃; for 0.25h; chemoselective reaction; | 94% |
Conditions | Yield |
---|---|
With hydrogenchloride; potassium chloride; tetrabutyl-ammonium chloride In water at 20℃; Irradiation; Green chemistry; | 94% |
With N-chloro-succinimide; N-hydroxyphthalimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 80℃; for 3h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere; | 93% |
With N-hydroxyphthalimide; carbon tetrabromide; trichloroisocyanuric acid; copper(II) acetate monohydrate In dichloromethane at 25℃; for 17h; | 73% |
Conditions | Yield |
---|---|
With dichloromethylsilane; iron(III) chloride In 1,2-dimethoxyethane for 3h; Heating; | 92% |
With chloro-trimethyl-silane; thionyl chloride; 1,1,3,3-Tetramethyldisiloxane; zinc(II) iodide at 70℃; for 0.75h; | 85% |
With indium(III) hydroxide; dimethylmonochlorosilane In chloroform at 20℃; for 2h; | 83% |
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 0 - 20 °C / Inert atmosphere 2: thionyl chloride / Reflux View Scheme |
4-chlorophenylacetic Acid
A
1-Chloro-4-(chloromethyl)benzene
B
4-chlorobenzyl bromide
Conditions | Yield |
---|---|
With tetra-N-butylammonium tribromide; 1,3-dichloro-[1,3,5]triazinane-2,4,6-trione In dichloromethane at 20℃; for 2h; Time; Reagent/catalyst; Concentration; Photolysis; | A 6% B 86% |
1-Chloro-4-(chloromethyl)benzene
Conditions | Yield |
---|---|
With indium(III) hydroxide In chloroform at 20℃; for 2h; | 83% |
Conditions | Yield |
---|---|
With tert-butylhypochlorite; Ag(Phen)2OTf In acetonitrile at 20℃; for 4h; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With triethylsilane; acetyl chloride; tin(ll) chloride In dichloromethane for 12h; Ambient temperature; | 79% |
(4-chlorobenzyl)(fluoromethyl)sulfane
A
monofluoromethylsulfonyl chloride
B
1-Chloro-4-(chloromethyl)benzene
Conditions | Yield |
---|---|
With water; chlorine In dichloromethane at -5℃; | A 69% B 74% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; pentane at 20 - 23℃; for 24h; | A 69% B 17% |
para-Chlorobenzyl alcohol
A
bis(4-chlorobenzyl) ether
B
1-Chloro-4-(chloromethyl)benzene
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In neat (no solvent) at 70 - 75℃; for 24h; Green chemistry; chemoselective reaction; | A 16 %Spectr. B 63% |
The CAS registry number of 4-Chlorobenzyl chloride is 104-83-6. Its EINECS registry number is 203-242-7. The IUPAC name is 1-chloro-4-(chloromethyl)benzene. In addition, the molecular formula is C7H6Cl2 and the molecular weight is 161.03. It is also called (4-chlorophenyl)methyl chloride. What's more, it is a kind of colorless to light yellow liquid and should be stored in a cool and dry place.
Physical properties about this chemical are: (1)ACD/LogP: 3.08; (2)ACD/LogD (pH 5.5): 3.08; (3)ACD/LogD (pH 7.4): 3.08; (4)ACD/BCF (pH 5.5): 129.51; (5)ACD/BCF (pH 7.4): 129.51; (6)ACD/KOC (pH 5.5): 1131.33; (7)ACD/KOC (pH 7.4): 1131.33; (8)#Freely Rotating Bonds: 1; (9)Polar Surface Area: 0 Å2; (10)Index of Refraction: 1.546; (11)Molar Refractivity: 40.91 cm3; (12)Molar Volume: 129 cm3; (13)Polarizability: 16.21 ×10-24cm3; (14)Surface Tension: 37 dyne/cm; (15)Density: 1.247 g/cm3; (16)Flash Point: 87.3 °C; (17)Enthalpy of Vaporization: 44.08 kJ/mol; (18)Boiling Point: 223 °C at 760 mmHg; (19)Vapour Pressure: 0.147 mmHg at 25°C.
Preparation of 4-Chlorobenzyl chloride: it can be prepared by (4-chloro-phenyl)-methanol. This reaction will need reagents CCl4 and 1 percent cross-linked polymer (containing 2.50 mmol of phosphine/g). The reaction time is 3 hours by heating. The yield is about 100%.
Uses of 4-Chlorobenzyl chloride: it can be used as organic synthesis intermediates, and used in pharmaceutical industry and dyestuff industry. In addition, it can react with 1,4-di-tert-butyl-benzene to get 2,5-di-tert-Butyl-4'-chlorodiphenylmethane. This reaction will need reagent TiCl4 and solvent CHCl3. The yield is about 80% at reaction temperature of 20-25 °C.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It can cause burns. And it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). In addition, you can not empty it into drains and release it to the environment. You can refer to special instructions safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: ClCc1ccc(Cl)cc1
(2)InChI: InChI=1/C7H6Cl2/c8-5-6-1-3-7(9)4-2-6/h1-4H,5H2
(3)InChIKey: JQZAEUFPPSRDOP-UHFFFAOYAV
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | unreported | 5625mg/kg (5625mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(5), Pg. 13, 1990. |
mouse | LD50 | unreported | 1156mg/kg (1156mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(5), Pg. 13, 1990. |
rat | LD50 | unreported | 1075mg/kg (1075mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(5), Pg. 13, 1990. |