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65-85-0

Basic Information
CAS No.: 65-85-0
Name: Benzoic acid
Article Data: 6088
Cas Database
Molecular Structure:
Molecular Structure of 65-85-0 (Benzoic acid)
Formula: C7H6O2
Molecular Weight: 122.123
Synonyms: Carboxybenzene;Tenn-Plas;Salvo liquid;Unisept BZA;Benzoic acid, tech.;Benzeneformic acid;Salvo, liquid;Solvo, powder;Acide benzoique;Benzoic acid (JP14/USP);Retarder BA;Solvo powder;Benzoic acid tech.;Benzoic acid nat.;Benzoic Acid, Crystal, Reagent;Benzoic Acid, Reagent Special;2,40 DECADIENAL;Benzoic Acid [65-85-0];Benzoesaeure;Benzoic acid /Natural;Benzoic acid (MDS);Benzyl acid;Retardex;Benzenemethanoic acid;phenylformic acid;Benzenecarboxylic acid;HA 1 (acid);Benzoesaeure GV;E 210;582-25-2;Dracylic acid;Benzoic acid (7CI,8CI,9CI);Benzoesaeure GK;
EINECS: 200-618-2
Density: 1.197 g/cm3
Melting Point: 121-125 °C(lit.)
Boiling Point: 249.3 °C at 760 mmHg
Flash Point: 111.4 °C
Solubility: slightly soluble in water
Appearance: white crystals or powder
Hazard Symbols: HarmfulXn, ToxicT, IrritantXi
Risk Codes: 22-36-42/43-36/37/38-40-63-43-23/24/25-45
Safety: 26-45-37/39-24-22-36/37-24/25-23-53
Transport Information: UN 3077 9/PG 3
PSA: 37.30000
LogP: 1.38480
Synthetic route
100-52-7

benzaldehyde

65-85-0

benzoic acid

Conditions
ConditionsYield
With 2,2,2-trichloroethylperoxycarbonic acid; dihydrogen peroxide In dichloromethane Ambient temperature;100%
With potassium hydroxide; oxygen In 1,2-dimethoxyethane at 20℃; for 3.5h;100%
With [Cu2C6H4(CHNCH2CH2N(CH2C5H4N)2)2](2+)*2ClO4(1-)=C36H38Cu2N8(ClO4)2; oxygen In acetone at -90.16℃;100%
100-47-0

benzonitrile

65-85-0

benzoic acid

Conditions
ConditionsYield
With water at 45℃; pH=7.2; Microbiological reaction; aq. buffer;100%
With potassium tert-butylate; water In isopropyl alcohol at 25℃; Inert atmosphere;100%
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.25h; microwave irradiation;99%
100-51-6

benzyl alcohol

65-85-0

benzoic acid

Conditions
ConditionsYield
With barium permanganate In acetonitrile for 4h; Heating;100%
With iodosylbenzene In water at 20℃; for 30h; Oxidation;100%
With iodosylbenzene In water for 30h; sonication;100%
93-58-3

benzoic acid methyl ester

65-85-0

benzoic acid

Conditions
ConditionsYield
With sodium hydroxide at 166 - 168℃; under 5250.4 Torr; for 0.0166667h; Irradiation;100%
With potassium carbonate; thiophenol In 1-methyl-pyrrolidin-2-one at 190℃; for 0.166667h; Substitution;100%
With potassium hydroxide; Aliquat 336 at 200℃; for 0.0833333h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; microwave irradiation;98%
93-56-1

phenylethane 1,2-diol

65-85-0

benzoic acid

Conditions
ConditionsYield
With barium permanganate In acetonitrile for 0.5h; Heating;100%
With oxygen; sodium methylate; silver trifluoromethanesulfonate In tetrahydrofuran; methanol at 37℃; under 760.051 Torr; Sealed tube;98%
With sodium periodate; manganese(II) 5,10,15,20-tetrakis(N-ethylpyridinium-4-yl)porphyrin In water at 60℃; for 4h;96%
33868-50-7

phenacyl benzoate

65-85-0

benzoic acid

Conditions
ConditionsYield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2h; Irradiation;100%
With sodium hydrogen telluride In N,N-dimethyl-formamide for 0.333333h; Product distribution; Ambient temperature;1.11 g
With tetrabutyl ammonium fluoride; phenylmethanethiol In tetrahydrofuran Product distribution; various concentrations, other solvent, other thiols; other educts; selective removal of phenacyl ester group in the presence of benzyl and 4-nitrobenzyl ester groups;
774-65-2

benzoic acid tert-butyl ester

A

65-85-0

benzoic acid

B

75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
With aluminum oxide; potassium hydroxide In diethyl ether for 21h; Product distribution; Ambient temperature; other solvent;A 100%
B 80%
583-04-0

vinyl benzoate

65-85-0

benzoic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In benzene at 65 - 70℃; for 3h;100%
With Fe3O4@SiO2-[(4-(5-O3Si-pentylcarbamoyl)-2-pyridinecarboxylato)CpRu(η3-C3H5)]PF6 In methanol at 30℃; for 1h; Inert atmosphere; chemoselective reaction;99%
[(cyclopentadienyl)bis(acetonitrile)(triphenylphosphine)ruthenium(II)] hexafluorophosphate In methanol at 25℃; for 6h; Product distribution; Further Variations:; Solvents; Temperatures;98%
120-51-4

benzoic acid benzyl ester

65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogen In methanol at 25℃; for 24h; Reagent/catalyst; Solvent; Temperature; chemoselective reaction;100%
With hydrogen; palladium diacetate; pyrographite In tetrahydrofuran; methanol at 25℃; under 760.051 Torr; for 12h;99%
With hydrogen; palladium diacetate; pyrographite In isopropyl alcohol at 25℃; under 760.051 Torr; for 14h;99%
119-53-9

2-hydroxy-2-phenylacetophenone

65-85-0

benzoic acid

Conditions
ConditionsYield
With NH-pyrazole; air; sodium hydride In tetrahydrofuran for 5h; Ambient temperature;100%
With iodopentafluorobenzene bis(trifluoroacetate) In water; benzene Mechanism;94%
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 Torr; for 48h;94%
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    Chinese Name: benzoic acid (also called benzoic acid), benzene carboxylic acid;benzoic acid English Name: Benzoic Acid Molecular formula: C7H6O2 Molecular weight: 122.12 CAS NO.:65-85-0 Use: Industrial grade: mainly used for dye interme

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History

 Benzoic acid (CAS NO.65-85-0) was discovered in the 16th century. The dry distillation of gum benzoin first described by Nostradamus in 1556, and subsequently by Alexius Pedemontanus (1560) and Blaise de Vigenère (1596). Justus von Liebig and Friedrich Wöhler determined the structure in 1832.They also investigated how hippuric acid is related to it. In 1875, Salkowski discovered the antifungal abilities of Benzoic acid, which was used for a long time in the preservation of benzoate-containing cloudberry fruits.

Specification

1. Introduction of Benzoic acid
Benzoic acid , its cas register number is 65-85-0. It also can be called Benzenecarboxylic acid; Benzeneformic acid; Benzenemethonic acid; Carboxybenzene; Oracylic acid; phenyl carboxylic acid; Phenylformic acid. It is a white crystals or powder and slightly soluble in water. At high temperature it can react with oxidizing reagents.Dust may be irritating to nose and eyes. At elevated temperatures, fumes may cause irritation of eyes, respiratory system, and skin.

2. Properties of Benzoic acid
H-Bond Donor: 1
H-Bond Acceptor: 2
Melting Point: 121-125 °C(lit.)
Water Solubility: Slightly soluble. 0.34 g/100 mL
Refractive index: 1.504
Stability: Stable. Combustible. Incompatible with strong bases, strong oxidizing agents, alkalies.
Surface Tension: 48.7 dyne/cm
Flash Point: 111.4 °C
Enthalpy of Vaporization: 51.4 kJ/mol
Boiling Point: 249.3 °C at 760 mmHg
Vapour Pressure: 0.0122 mmHg at 25°C

3. Toxicity of Benzoic acid

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo subcutaneous 100mg/kg (100mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 23, 1959.
guinea pig LDLo intraperitoneal 1400mg/kg (1400mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 23, 1959.
guinea pig LDLo oral 2gm/kg (2000mg/kg)   Muenchener Medicinische Wochenschrift. Vol. 77, Pg. 13, 1930.
human TDLo skin 6mg/kg (6mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
Journal of Allergy. Vol. 16, Pg. 195, 1945.
man LDLo oral 500mg/kg (500mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 715, 1979.
mouse LD50 intraperitoneal 1460mg/kg (1460mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 160, Pg. 1097, 1966.
mouse LD50 oral 1940mg/kg (1940mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: OTHER CHANGES
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 15, Pg. 359, 1984.
rabbit LD50 skin > 10gm/kg (10000mg/kg)   BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 28-4/1973,
rabbit LDLo oral 2gm/kg (2000mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 23, 1959.
rabbit LDLo subcutaneous 2gm/kg (2000mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 23, 1959.
rat LC50 inhalation > 26mg/m3/1H (26mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 28-4/1973,
rat LD50 intraperitoneal 1600mg/kg (1600mg/kg)   Bollettino Chimico Farmaceutico. Vol. 112, Pg. 53, 1973.
rat LD50 intravenous 1700mg/kg (1700mg/kg)   Acta Physiologica Polonica. Vol. 12, Pg. 173, 1961.
rat LD50 oral 1700mg/kg (1700mg/kg)   International Polymer Science and Technology. Vol. 3, Pg. 93, 1976.


4. Safety Information of Benzoic acid
Hazard Codes: Xn,T
Risk Statements: 22-36-42/43-36/37/38-40-63-43-23/24/25-45
22: Harmful if swallowed
36: Irritating to the eyes
42/43: May cause sensitization by inhalation and skin contact
36/37/38: Irritating to eyes, respiratory system and skin
40: Limited evidence of a carcinogenic effect
63: In case of accident by inhalation, remove casualty to fresh air and keep at rest
43: In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water)
23/24/25: Toxic by inhalation, in contact with skin and if swallowed
45: May cause cancer
41: Risk of serious damage to eyes
37/38: Irritating to respiratory system and skin
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 26-45-37/39-24-22-36/37-24/25-23-53
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
37/39: Wear suitable gloves and eye/face protection
24: Avoid contact with skin
22: Do not breathe dust
36/37: Wear suitable protective clothing and gloves
24/25: Avoid contact with skin and eyes
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
53: Avoid exposure - obtain special instruction before use
36: Wear suitable protective clothing
RIDADR: UN 3077 9/PG 3
WGK Germany: 1
RTECS: DG0875000
F: 21
Hazard Note: Harmful

5. Use of Benzoic acid
The usage of the Benzoic acid as following:
1.Feedstock: It is an important precursor for the synthesis of many other organic substances.
2.Food preservative: It and its salts are used as a food preservative.
3.Medicinal
4.Biology and health effects

6. Preparation of Benzoic acid
 Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value.
For all syntheses, it can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water. The avoidance of organic solvents for the recrystallization makes this experiment particularly safe. Other possible recrystallization solvents include acetic acid (anhydrous or aqueous), benzene, petroleum ether, and a mixture of ethanol and water.
It can be manufactured by the liquid-phase oxidation of toluene by air in a continuous oxidation reactor operated at moderate pressure and temperature:
2C6H5CH3 + 3O2 → 2C6H5COOH + 4H2O
It also can be obtained as a by-product of the manufacture of benzaldehyde from benzal chloride or benzyl chloride.
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