CAS Number: 98-88-4
EC Number: 202-710-8
Preferred IUPAC name: Benzoyl chloride
Molecular formula: C7H5ClO
Molecular weight: 140.57 g•mol−1
DESCRIPTION:
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO.
Benzenecarbonyl chloride is a colourless, fuming liquid with an irritating odour.
Benzenecarbonyl chloride 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.
Benzoyl chloride appears as a colorless fuming liquid with a pungent odor.
Lachrymator, irritating to skin and eyes.
Benzoyl chloride is Corrosive to metals and tissue.
Benzoyl chloride is Used in medicine and in the manufacture of other chemicals.
Benzoyl chloride is an organochlorine useful for the production of peroxides.
Benzoyl chloride is an acyl chloride consisting of benzene in which a hydrogen is replaced by an acyl chloride group.
Benzoyl chloride is an important chemical intermediate for the manufacture of other chemicals, dyes, perfumes, herbicides and pharmaceuticals.
Benzoyl chloride has a role as a carcinogenic agent.
Benzoyl chloride is an acyl chloride and a member of benzenes.
Benzoyl chloride derives from a benzoic acid.
Preparation of Benzenecarbonyl chloride:
Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:
C6H5CCl3 + H2O → C6H5COCl + 2 HCl
C6H5CCl3 + C6H5CO2H → 2 C6H5COCl + HCl
As with other acyl chlorides, Benzenecarbonyl chloride can be generated from the parent acid and standard chlorinating agents such as phosphorus pentachloride, thionyl chloride, and oxalyl chloride.
Benzenecarbonyl chloride was first prepared by treatment of benzaldehyde with chlorine.
An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.
Reactions of Benzenecarbonyl chloride:
Benzenecarbonyl chloride reacts with water to produce hydrochloric acid and benzoic acid:
C6H5COCl + H2O → C6H5COOH + HCl
Benzoyl chloride is a typical acyl chloride.
Benzenecarbonyl chloride reacts with alcohols to give the corresponding esters.
Similarly, Benzenecarbonyl chloride reacts with amines to give the amide.
Benzenecarbonyl chloride undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives.
With carbanions, Benzenecarbonyl chloride serves again as a source of the benzoyl cation synthon, C6H5CO+.
Benzoyl peroxide, a common reagent in polymer chemistry, is produced industrially by treating benzoyl chloride with hydrogen peroxide and sodium hydroxide:
2 C6H5COCl + H2O2 + 2 NaOH → (C6H5CO)2O2 + 2 NaCl + 2 H2O
Information available in 1995 indicated that benzoyl chloride was produced in 11 countries.
Benzoyl chloride is used in the manufacture of benzoyl peroxide and dye intermediates, for acylation (introduction of the benzoyl group into alcohols, phenols and amines), and as an analytical reagent
Properties of Benzenecarbonyl chloride:
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
Molecular Weight: 140.56
XLogP3: 2.9
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 1
Exact Mass: 140.0028925
Monoisotopic Mass: 140.0028925
Topological Polar Surface Area:17.1 Ų
Heavy Atom Count: 9
Formal Charge: 0
Complexity: 106
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Color/Form: Liquid
Odor: Penetrating odor
Vapor Pressure : 0.4 mm Hg at 68 °F ; 1 mm Hg at 89.8° F
Vapor Density: 4.88
Henry's Law constant = 1.32X10-4 atm-cu m/mol at 25 °C
Stability/Shelf Life:
Stable under recommended storage conditions
Autoignition Temperature: 197.2 °C
Decomposition:
Hazardous decomposition products formed under fire conditions: Carbon oxides, hydrogen chloride gas.
Corrosivity: Slow corrosion of metals
Heat of Combustion:
-10,030 Btu/lb = -5570 Cal/g = -233.2X10+5 J/kg
Heat of Vaporization: 11,438.0 gcal/gmol
Surface Tension:
36.3 dynes/cm = 0.0363 N/m at 20 °C
Refractive Index:
Index of refraction: 1.5537 at 20 °C/D
Application of Benzoyl chloride:
Benzoyl chloride may be used in the synthesis of the following organic building blocks:
N,N-diethylbenzamide via condensation with diethylamine
N-2-bromophenylbenzamide by reacting with 2-bromoaniline via N-benzoylation
propargyl benzoate via O-benzoylation of propargyl alcohol
The most important application of benzoyl chloride is the production of benzoyl peroxide, that is commonly used for skin treatment, as an initiator in the polymer industry and to bleach wheat and rice.
SAFETY INFORMATION ABOUT BENZOYL CHLORIDE:
Hazard Statement(s)
H302 + H312: Harmful if swallowed or in contact with skin.
H314: Causes severe skin burns and eye damage.
H317: May cause an allergic skin reaction.
H331: Toxic if inhaled.
Precautionary Statement(s)
P261: Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P280: Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection.
P301 + P312: IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell.
P303 + P361 + P353: IF ON SKIN (or hair): Take off immediately all contaminated clothing.
Rinse skin with water.
P304 + P340 + P310: IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338: IF IN EYES: Rinse cautiously with water for several minutes.
Remove contact lenses, if present and easy to do.
Continue rinsing.
Signal Word: Danger
Storage class: 6.1C Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK: WGK 1 slightly hazardous to water
Disposal: 11
Organic acid halides, anhydrides and isocyanates can be added dropwise to an excess of methanol (Cat. No. 822283) to convert them into the corresponding methyl esters or methyl carbamates.
If necessary, neutralize with sodium hydroxide solution (Cat. No. 105587).
Fill into container A.
Safety Information:
Categories of danger: harmful, corrosive, sensitizing
Storage and Shipping Information:
Storage Store below +30°C.
Reactivity Alerts:
BENZOYL CHLORIDE is Water-Reactive
BENZOYL CHLORIDE is Air-Reactive
Air & Water Reactions:
Fumes in air.
Decomposes exothermically and rapidly in water to form insoluble benzoic acid and hydrochloric acid (HCl) .
This is not supported by Argonne experiments which have not observed any gas generation upon mixing with water.
Experimental work at Argonne National Laboratory has determined that there is no HCl formation; the substance was quite unreactive in water.
This does not prevent HCl formation by a catalytic mechanism, but under normal conditions benzoyl chloride is quite unreactive.
Fire Hazard:
Special Hazards of Combustion Products: Highly poisonous phosgene gas may be formed in fires.
Behavior in Fire: At fire temperatures the compound may react violently with water or steam.
Health Hazard:
INHALATION: may irritate eyes, nose and throat.
INGESTION: causes acute discomfort.
SKIN: causes irritation and burning.
Reactivity Profile:
BENZOYL CHLORIDE reacts violently with protic solvents such as alcohols, with amines and amides (for example dimethylformamide ) and with inorganic bases.
Causes the violent decomposition of dimethyl sulfoxide.
May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts.
Friedel-Crafts acylation of naphthalene using benzoyl chloride, catalyzed by AlCl3, must be conducted above the melting point of the mixture, or the reaction may be violent
Synonyms:
benzoyl chloride
98-88-4
Benzoylchloride
Benzenecarbonyl chloride
Benzoic acid, chloride
alpha-Chlorobenzaldehyde
benzoic acid chloride
UNII-VTY8706W36
Benzaldehyde, .alpha.-chloro-
CHEBI:82275
VTY8706W36
benzoylchlorid
Benzaldehyde, alpha-chloro-
CCRIS 802
Benzoyl chloride, ReagentPlus(R), >=99%
HSDB 383
EINECS 202-710-8
UN1736
BRN 0471389
benzoyl chlorid
benzoyl choride
bezoyl chloride
benzoic chloride
BzCl
benzoyl chloride-
PhCOCl
Bz-Cl
MFCD00000653
Benzoyl chloride [UN1736] [Corrosive]
.alpha.-Chlorobenzaldehyde
Benzaldehyde, |A-chloro-
DSSTox_CID_6631
EC 202-710-8
SCHEMBL1241
BENZOIC ACID,CHLORIDE
DSSTox_RID_78168
DSSTox_GSID_26631
4-09-00-00721 (Beilstein Handbook Reference)
Benzoyl Chloride, ACS reagent
Benzoylchloride, ACS Reagent,
CHEMBL2260719
DTXSID9026631
Benzoyl chloride, AR, >=99%
Benzoyl chloride, LR, >=99%
OTAVA-BB 1051706
LABOTEST-BB LTBB000456
CS-B1785
ZINC2041164
Tox21_200431
STL264120
Benzoyl chloride, ACS reagent, 99%
AKOS000121308
AS00010
MCULE-3627399529
UN 1736
CAS-98-88-4
Benzoyl chloride, purum, >=99% (GC)
Benzoyl chloride, ReagentPlus(R), 99%
NCGC00248610-01
NCGC00257985-01
Benzoyl chloride, p.a., 98-100.5%
PS-10801
DB-002645
DB-051009
B0105
FT-0622741
FT-0639824
Benzoyl chloride, SAJ first grade, >=98.0%
C19168
A845919
Q412825