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Benzoyl chloride-Wikipedia

Benzoyl chloride

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Benzoyl chloride

Benzoyl Chloride

Benzoyl-chloride-from-xtal-3D-bs-17.png

Benzoyl-chloride-from-xtal-3D-sf.png

Names

Preferred IUPAC name

Benzoyl chloride
Identifiers

CAS Number

  • 98-88-4

     checkY

3D model (

JSmol

)

  • Interactive image

  • Interactive image

ChEBI

  • CHEBI:82275

ChEMBL

  • ChEMBL2260719

ChemSpider

  • 7134

     checkY

ECHA InfoCard

100.002.464

Edit this at Wikidata

EC Number

  • 202-710-8

KEGG

  • C19168

     checkY

PubChem

CID

  • 7412

RTECS number

  • DM6600000

UNII

  • VTY8706W36

UN number

1736

CompTox Dashboard

(EPA)

  • DTXSID9026631

    Edit this at Wikidata

InChI

  • InChI=1S/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H checkY
    Key: PASDCCFISLVPSO-UHFFFAOYSA-N checkY
  • InChI=1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H
    Key: PASDCCFISLVPSO-UHFFFAOYAL

SMILES

  • ClC(=O)c1ccccc1
  • c1ccc(cc1)C(=O)Cl
Properties

Chemical formula

C7H5ClO

Molar mass

140.57 g·mol−1
Appearance colorless liquid

Odor

Benzaldehyde like but more pungent

Density

1.21 g/mL, liquid

Melting point

−1 °C (30 °F; 272 K)

Boiling point

197.2 °C (387.0 °F; 470.3 K)

Solubility in water

reacts

Magnetic susceptibility

(χ)

-75.8·10−6 cm3/mol
Hazards

Safety data sheet

Fisher Scientific MSDS

GHS pictograms

GHS05: Corrosive

GHS07: Harmful

GHS Signal word

Danger

GHS hazard statements

H302, H312, H314, H317, H332

GHS precautionary statements

P260, P261, P264, P270, P271, P272, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P310, P312, P321, P322, P330, P333+313, P363, P405, P501

NFPA 704

(fire diamond)

3

2

0

W

Flash point

72 °C (162 °F; 345 K)
Related compounds
Related compounds

benzoic acid

,

benzoic anhydride

,

benzaldehyde

Except where otherwise noted, data are given for materials in their

standard state

(at 25 °C [77 °F], 100 kPa).

checkY 

verify

 (

what is

 checkY☒N ?)

Infobox references

Chemical compound

Benzoyl chloride, also known as benzenecarbonyl chloride, is an

organochlorine compound

with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of

peroxides

but is generally useful in other areas such as in the preparation of

dyes

,

perfumes

,

pharmaceuticals

, and

resins

.

Xem thêm: Bột huỳnh quang là gì, khác gì bột phản quang ?-Daxinco Việt Nam

Preparation[

edit

]

Benzoyl chloride is produced from

benzotrichloride

using either water or benzoic acid:

[1]

C6H5CCl3 + H2O → C6H5COCl + 2 HCl
C6H5CCl3 + C6H5CO2H → 2 C6H5COCl + HCl

As with other

acyl chlorides

, it can be generated from the parent acid and standard chlorinating agents such as

phosphorus pentachloride

,

thionyl chloride

, and

oxalyl chloride

. It was first prepared by treatment of

benzaldehyde

with chlorine.

[2]

An early method for production of benzoyl chloride involved

chlorination

of

benzyl alcohol

.

[3]

Xem thêm: Cách sử dụng some, many, much, any, a lot of, lots of, few, a few, little and a little

Reactions[

edit

]

It reacts with water to produce

hydrochloric acid

and

benzoic acid

:

C6H5COCl + H2O → C6H5CO2H + HCl

Benzoyl chloride is a typical

acyl chloride

. It reacts with

alcohols

to give the corresponding

esters

. Similarly, it reacts with amines to give the

amide

.

[4]

[5]

It undergoes the

Friedel-Crafts acylation

with

aromatic compounds

to give the corresponding

benzophenones

and related derivatives.

[6]

With carbanions, it serves again as a source of “PhCO+“.

[7]

Benzoyl peroxide

, a common reagent in

polymer chemistry

, is produced industrially by treating benzoyl chloride with

hydrogen peroxide

and

sodium hydroxide

:

[8]

2 C6H5COCl + H2O2 + 2 NaOH → (C6H5CO)2O2 + 2 NaCl + 2 H2O

Xem thêm: [C++] Viết chương trình tìm UCLN, BCNN của 2 số a, b-Kiến Thức 24h

References[

edit

]

  1. ^

    Maki, Takao; Takeda, Kazuo (2000). “Benzoic Acid and Derivatives”.

    Ullmann’s Encyclopedia of Industrial Chemistry

    . Weinheim: Wiley-VCH.

    doi

    :

    10.1002/14356007.a03_555

    .

  2. ^

    Friedrich Wöhler

    ,

    Justus von Liebig

    (1832). “Untersuchungen über das Radikal der Benzoesäure”.

    Annalen der Pharmacie

    . 3 (3): 262–266.

    doi

    :

    10.1002/jlac.18320030302

    .

    hdl

    :

    2027/hvd.hxdg3f

    .

  3. ^

    US1851832

    , 29 March 1932

  4. ^

    Marvel, C. S.; Lazier, W. A. (1929). “Benzoyl Piperidine”. Organic Syntheses. 9: 16.

    doi

    :

    10.15227/orgsyn.009.0016

    .

  5. ^

    Prasenjit Saha, Md Ashif Ali, and Tharmalingam Punniyamurthy “Ligand-free Copper(ii) Oxide Nanoparticles Catalyzed Synthesis Of Substituted Benzoxazoles” Org. Synth. 2011, volume 88, pp. 398.

    doi

    :

    10.15227/orgsyn.088.0398

    . (an illustrative reaction of an amine with benzoyl chloride).

  6. ^

    Minnis, Wesley (1932). “Phenyl Thienyl Ketone”. Organic Syntheses. 12: 62.

    doi

    :

    10.15227/orgsyn.012.0062

    .

  7. ^

    Fujita, M.; Hiyama, T. (1990). “Directed Reduction of a beta-keto Amide: Erythro-1-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine”. Organic Syntheses. 69: 44.

    doi

    :

    10.15227/orgsyn.069.0044

    .

  8. ^

    El-Samragy, Yehia (2004). “Chemical and Technical Assessment”.

    Benzoyl Peroxide

    (PDF). 61st JECFA (Technical report). Joint FAO/WHO Expert Committee on Food Additives. p. 1. Retrieved 31 October 2013.

External links[

edit

]

  • International Chemical Safety Card 1015

Retrieved from “

https://en.wikipedia.org/w/index.php?title=Benzoyl_chloride&oldid=1024616748

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