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| Product Name: | Benzoyl chloride | | Synonyms: | alpha-Chlorobenzaldehyde;BENZOYL CHLORIDE, REAGENTPLUS, >=99%;BENZOYL CHLORIDE REAGENTPLUSTM >=99%;BENZOYL CHLORIDE, REAGENTPLUS, 99%;BENZOYL CHLORIDE, 99%, A.C.S. REAGENT;BENZOYL CHLORIDE REAGENTPLUS(TM) 99%;BENZOYL CHLORIDE, ACS;BenzoylChlorideGr | | CAS: | 98-88-4 | | MF: | C7H5ClO | | MW: | 140.57 | | EINECS: | 202-710-8 | | Product Categories: | Organics;Absolute Configuration Determination (Exciton Chirality CD Method);Amino Group Labeling Reagents for HPLC;Analytical Chemistry;Biochemistry;Enantiomer Excess & Absolute Configuration Determination;Exciton Chirality CD Method (for Hydroxyl Groups);HPLC Labeling Reagents;Hydroxyl Group Labeling Reagents for HPLC;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Reagents for Oligosaccharide Synthesis;UV Detection (HPLC Labeling Reagents);A-B, Puriss p.a. ACSOrganic Building Blocks;Pharmaceutical Intermediates;alkyl chloride;API Intermediate;organic chemical;Benzoyl chloride;Acid HalidesDerivatization Reagents;Analytical Reagents for General Use;Carbonyl Compounds;Derivatization Reagents HPLC;Puriss p.a. ACS;UV-VIS;ACS GradeProtection and Derivatization;Others;Protecting and Derivatizing Reagents;Essential Chemicals;Reagent Plus;Routine Reagents;Acid Halides;Organic Building Blocks;98-88-4;K00001 | | Mol File: | 98-88-4.mol |  |
| | Benzoyl chloride Chemical Properties |
| Melting point | -1 °C (lit.) | | Boiling point | 198 °C (lit.) | | density | 1.211 g/mL at 25 °C (lit.) | | vapor density | 4.88 (vs air) | | vapor pressure | 1 mm Hg ( 32 °C) | | refractive index | n20/D 1.553(lit.) | | Fp | 156 °F | | storage temp. | Store below +30°C. | | solubility | Acetonitrile (Slightly), Chloroform (Sparingly) | | form | Liquid | | color | Clear | | Odor | Pungent characteristic. | | PH Range | 2 at 1 g/l | | PH | 2 (1g/l, H2O, 20℃) | | explosive limit | 2.5-27%(V) | | Water Solubility | reacts | | FreezingPoint | -1℃ | | Sensitive | Moisture Sensitive | | Merck | 14,1112 | | BRN | 471389 | | Exposure limits | ACGIH: Ceiling 0.5 ppm | | Stability: | Stable. Combustible. Incompatible with strong oxidizing agents, water, alcohols, strong bases. Reacts violently with DMSO and vigorously with alkalies. | | InChIKey | PASDCCFISLVPSO-UHFFFAOYSA-N | | LogP | 1.44 at 21℃ and pH6 | | CAS DataBase Reference | 98-88-4(CAS DataBase Reference) | | IARC | 2A (Vol. 29, Sup 7, 71) 1999 | | NIST Chemistry Reference | Benzoyl chloride(98-88-4) | | EPA Substance Registry System | Benzoyl chloride (98-88-4) |
| Hazard Codes | C | | Risk Statements | 34-43-20/21/22 | | Safety Statements | 26-45-36/37/39 | | RIDADR | UN 1736 8/PG 2 | | WGK Germany | 1 | | RTECS | DM6600000 | | Autoignition Temperature | 600 °C | | Hazard Note | Corrosive | | TSCA | Yes | | HazardClass | 8 | | PackingGroup | II | | HS Code | 29310095 | | Hazardous Substances Data | 98-88-4(Hazardous Substances Data) | | Toxicity | LD50 orally in Rabbit: 2460 mg/kg LD50 dermal Rabbit 790 mg/kg |
| | Benzoyl chloride Usage And Synthesis |
| Physical and Chemical Properties | Its pure product is a colorless and transparent flammable liquid, which is smoking exposed to air in the air. In Industry, it is slightly pale yellow, with a strong pungent odor. Its steam has a strong stimulating effect for eye mucous membranes, skin and respiratory tract, by stimulating the mucous membranes and eyes tear. Benzoyl chloride Melting point is-1.0 ℃, boiling point is 197.2 ℃, and the relative density is 1.212 (20 ℃), while a flash point is 72 ℃, and refractive index (n20) is 1.554. It is soluble in the ether, chloroform, benzene and carbon disulfide. It can gradually decomposed in water or ethanol, ammonia, which generates benzoic acid, generating benzamide, ethyl benzoate and hydrogen chloride. In the laboratory, it can be obtained by distillation of benzoic acid and phosphorus pentachloride under anhydrous conditions. Industrial production process can be obtained by the use of thionyl chloride benzaldehyde. Benzoyl chloride is an important intermediate for preparing dyes, perfumes, organic peroxides, resins and drugs. It is also used in photography and artificial tannin production, which was formerly used as an irritant gas in chemical warfare. | | Application | Benzoyl chloride is used for organic synthesis, dye and pharmaceutical raw material, manufacturing initiator benzoyl peroxide, t-butyl peroxybenzoate, pesticides and herbicides. In pesticides, it is a new insecticide, which is inducible isoxazole parathion (Isoxathion, Karphos) intermediate. Benzoyl chloride is an important benzoyl and benzyl reagent. Most of benzoyl chloride is used in the production of benzoyl peroxide, and secondly for the production of benzophenone, benzyl benzoate, benzyl cellulose. Benzoyl peroxide catalyzes polymerization initiator for the monomer plastic, polyester, epoxy, acrylic resin production, self-curing agent, which is a glass fiber material, fluorine rubber, silicone crosslinking agents, oil refined, bleached flour, fiber decolorizing. | | Chemical Properties | Benzoyl chloride is a colorless to slight brown liquid with a strong, penetrating odor; vapor causes tears. Soluble in ether and carbon disulfide; decomposes in water. Combustible. It is a liquid acyl chloride used as a benzoylating agent. | | Uses | Benzoyl Chloride is used in the manufacturing of dye intermediates. | | Uses | For acylation, i.e., introduction of the benzoyl group into alcohols, phenols, and amines (Schotten-Baumann reaction); in the manufacture of benzoyl peroxide and of dye intermediates. In organic analysis for making benzoyl derivatives for identification purposes. | | Uses | Benzoyl chloride is widely utilized for the synthesis of peroxides. It is employed in the production of dyes and perfumes. It also serves in the manufacturing of pharmaceuticals and resins. | | Definition | ChEBI: Benzoyl chloride is an acyl chloride consisting of benzene in which a hydrogen is replaced by an acyl chloride group. It is an important chemical intermediate for the manufacture of other chemicals, dyes, perfumes, herbicides and pharmaceuticals. It has a role as a carcinogenic agent. It is an acyl chloride and a member of benzenes. It is functionally related to a benzoic acid.? | | Production Methods | Benzoyl chloride can be prepared from benzoic acid by reaction with PCl5 or SOCl2, from benzaldehyde by treatment with POCl3 or SO2 Cl2, from benzotrichloride by partial hydrolysis in the presence of H2SO4 or FeCl3, from benzal chloride by treatment with oxygen in a radical source, and from several other miscellaneous reactions. Benzoyl chloride can be reduced to benzaldehyde, oxidized to benzoyl peroxide, chlorinated to chlorobenzoyl chloride and sulfonated to m-sulfobenzoic acid. It will undergo various reactions with organic reagents. For example, it will add across an unsaturated (alkene or alkyne) bond in the presence of a catalyst to give the phenylchloroketone:
 | | Synthesis Reference(s) | Journal of the American Chemical Society, 73, p. 702, 1951 DOI: 10.1021/ja01146a061
Synthesis, p. 306, 1983 DOI: 10.1055/s-1983-30314 | | General Description | Benzoyl chloride appears as a colorless fuming liquid with a pungent odor. Flash point 162 °F. Lachrymator, irritating to skin and eyes. Corrosive to metals and tissue. Density 10.2 lb / gal. Used in medicine and in the manufacture of other chemicals. | | Reactivity Profile | Benzoyl chloride reacts violently with protic solvents such as alcohols, with amines and amides (for example dimethylformamide [Bretherick 1979 p. 6] ) and with inorganic bases. Causes the violent decomposition of dimethyl sulfoxide [Chem. Eng. News 35(9): 87 1957]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. 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 [Clar, E. et al., Tetrahedron, 1974, 30, 3296]. | | Hazard | Highly toxic. Strong irritant to skin, eyes,
and mucous membranes, and via ingestion, inhala-
tion. Upper respiratory tract irritant. Probable car-
cinogen.
| | Health Hazard | INHALATION: may irritate eyes, nose and throat. INGESTION: causes acute discomfort. SKIN: causes irritation and burning. | | Chemical Reactivity | Reactivity with Water Slow reaction with water to produce hydrochloric acid fumes. The reaction is more rapid with steam; Reactivity with Common Materials: Slow corrosion of metals but no immediate danger; Stability During Transport: Not pertinent; Neutralizing Agents for Acids and Caustics: Soda ash and water, lime; Polymerization: Does not occur; Inhibitor of Polymerization: Not pertinent. | | Safety Profile | Confirmed carcinogen withexperimental tumorigenic data by skin contact. Humansystemic effects by inhalation: unspecified effects onolfaction and respiratory systems. Corrosive effects on theskin, eyes, and mucous membranes by inhalation.Flammable whe | | Potential Exposure | Benzoyl chloride is used as a chemical
intermediate; in organic synthesis; to produce other chemicals,
dyes, perfumes, herbicides, and medicines. | | Shipping | UN 1736 Benzoylchloride, Hazard class: 8;
Labels: 8—Corrosive material. | | Purification Methods | A solution of benzoyl chloride (300mL) in *C6H6 (200mL) is washed with two 100mL portions of cold 5% NaHCO3 solution, separated, dried with CaCl2 and distilled [Oakwood & Weisgerber Org Synth III 113 1955]. Repeated fractional distillation at 4mm Hg through a glass helices-packed column (avoiding porous porcelain or silicon-carbide boiling chips, and hydrocarbon or silicon greases on the ground joints) gave benzoyl chloride that did not darken on addition of AlCl3. Further purification is achieved by adding 3 mole% each of AlCl3 and toluene, standing overnight, and distilling off the benzoyl chloride at 1-2mm [Brown & Jenzen J Am Chem Soc 80 2291 1958]. Refluxing for 2hours with an equal weight of thionyl chloride before distillation has also been used. [Beilstein 9 IV 721.] Strong IRRITANT. Use in a fume cupboard. | | Incompatibilities | May form explosive mixture with air.
Contact with heat, hot surfaces, and flames causes decomposition,
forming phosgene and hydrogen chloride. Water
contact may be violent; forms hydrochloric acid. Reactions
with amines, alcohols, alkali metals, dimethyl sulfoxide,
strong oxidizers, and metal salts may be violent, causing
fire and explosions. Attacks metals in the presence of
moisture, forming explosive hydrogen gas. Attacks some
plastics, rubber or coatings. | | Waste Disposal | Pour into sodium bicarbonate
solution and flush to sewer. |
| | Benzoyl chloride Preparation Products And Raw materials |
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