Benzoic Acid Nitrile

Chemical Designations - Synonyms Benzoic Acid Nitrile, Cyanobenzene, Phenylcyanide Chemical Formula C HjCN. 

Chemical Name benzonitrile, benzoic acid nitrile... 

BENZOIC ACID NITRILE see BCQ250 BENZOIC ACID, PEROXIDE see BDSOOO BENZOIC ACID, o-(PHENYLHYDROXYARSINO)- see PFKOO... 

Benzonitrile Benzoic Acid Nitrile Cyanobenzene Phenylcyanide ... 

BENZOIC ACID NITRILE (100-47-0) Combustible liquid (flash point 158°F/70°C). Violent reaction with strong acids, forming hydrogen cyanide gas. Incompatible with oxidizers. Attacks some plastics, rubber, and coatings. 

AI3-241M Benzene, cyano- Benzenecarbonitrile Benzenenitrile Benzoic acid nitrile Benzonitrile CCRIS 3184 Cyanobenzene EINECS 202-855-7 Fenylkyanid HSDB 45 NSC 8039 Phenyl cyanide UN2224, Manufacture of benzoquanamine intermediate for rubber chemicals solvent for nitrile rubber, specialty lacquers, resins and polymers, anhydrous metallic salts. Liquid mp = -12.7° bp = 191.1" d s = 1.0093 Xm = 222, 230, 263, 277 nm (e = 10600,9100, 804, 932, MeOH) slightly soluble in H2O (1.0 g/100 ml), soluble in CCI4, very soluble in MezCO, CsH6, freely soluble in EtOH, EtzO LDso (mus orl) = 971 mg/kg, Renta Mfg PMC Spectrum Chem. Manufacturing. 

Benzoic acid, 4-(((ethylphenylamino) methylene) amino)-, ethyl ester. See N-(p-Ethoxycarbonylphenyl)-N-ethyl-N-phenylformamidine Benzoic acid, 2-hydroxy-, 4-(1,1-dimethylethyl) phenyl ester. See p-t-Butylphenyl salicylate Benzoic acid nitrile. See Benzonitrile Benzoic acid sodium salt. See Sodium benzoate Benzoic acid, tetraester with 2,2-bis (hydroxymethyl)-1,3-propanediol Benzoic acid, tetraester with pentaerythritol. See Pentaerythrityl tetrabenzoate... 

Synonynts Benzenenitrile Benzoic acid nitrile Cyanobenzene Phenyl cyanide... 

Benzoic acid nitrile. See Benzonitrile Benzoic acid, 2-nitro-. See o-Nitrobenzoic acid Benzoic acid, 4-nitro-. See p-Nitrobenzoic acid Benzoic acid, p-nitro-, ethyl ester. See Ethyl-p-nitrobenzoate... 

Chemical Designations — Synonyms Benzoic Acid Nitrile, Cyanobenzene, Phenylcyanide Chemical Formula C HsCN. Observable Characteristics — Physical State (as normally shipped) Liquid Color Colorless Odor Almond-like. Physical and Chemical Properties — Physical State at 15 C and 1 atm. Liquid Molecular Weight 103.12 Boiling Point at 1 atm. 376, 191, 464 Freezing Point 9.0, -12.8, 260.4 Critical Temperature 799.2, 426.2, 699.4 Critical Pressure 611, 41.6, 4.22 Specific Gravity 1.01 at25"C (liquid) Vapor (Gas) Density 3.6 Ratio of Specific Heats of Vapor (Gas) 1.091 Latent Heat of Vaporization 157.7, 87.6, 3.67 Heat of Combustion -15,100, -8,400, -351 Heat of Decomposition Not pertinent. Health Hazards Information — Recommended Personal Protective... 

Synonyms Benzoic Acid Nitrile, Cyanobenzene, Phenylcyanide Chemical Formula C H,CN (ii) Observable Characteristics — Physical State (as normally shipped) Liquid Color Colorless Odor Almond-like (iii) Physical and Chemical Properties — Physical State at 15 X and I atm. Liquid Molecular... 

Boil 5 ml. (5-1 g.) of benzonitrile and 75 ml. of 10% aqueous sodium hydroxide in a 200 ml. flask under a reflux water condenser until no more oily drops of unchanged nitrile run down from the condenser (usually about 40 minutes). Th detach the condenser and boil the solution in the open flask for a few minutes to remove free ammonia, Cool the liquid, and add concentrated hydrochloric acid cautiously until precipitation of benzoic acid is complete. Cool the mixture again thoroughly, filter off the benzoic acid at the pump, and wash well with cold water. Yield, 5 8 g. (almost theoretical). Confirm the identity of the benzoic acid by the tests given on p. 347. The benzoic acid obtained in this way should be pure and have m.p. 121 a portion may if desired be recrystallised from hot water. 

Hydrolysis of />-Tolunitrile. As in the case of benzonitrile, alkaline h> drolysis is preferable to hydrolysis by 70% sulphuric acid. Boil a mixture of 5 g. of p-tolunitrile, 75 ml. of 10% aqueous sodium hydroxide solution and 15 ml. of ethanol under a reflux water-condenser. The ethanol is added partly to increase the speed of the hydrolysis, but in particular to prevent the nitrile (which volatilises in the steam) from actually crystallising in the condenser. The solution becomes clear after about i hour s heating, but the boiling should be continued for a total period of 1-5 hours to ensure complete hydrolysis. Then precipitate and isolate the p-toluic acid, CH3CgH4COOH, in precisely the same way as the benzoic acid in the above hydrolysis of benzonitrile. Yield 5 5 g. (almost theoretical). The p-toluic acid has m.p. 178°, and may be recrystallised from a mixture of equal volumes of water and rectified spirit. 

Because cyano groups may be hydrolyzed to carboxylic acids (Section 20 19) the Sand meyer preparation of aryl nitriles is a key step m the conversion of arylammes to sub stituted benzoic acids In the example just cited the o methylbenzomtnle that was formed was subsequently subiected to acid catalyzed hydrolysis and gave o methylbenzoic acid in 80-89% yield... 

By introducing reasonable values (about 2 for nitrogen, 4 for oxygen) for the electron affinity parameter relative to carbon, 8, and for the induced electron affinity for adjacent atoms (32/8i = Vio), we have shown that the calculated permanent charge distributions for pyridine, toluene, phenyltrimethylammonium ion, nitrobenzene, benzoic acid, benzaldehyde, acetophenone, benzo-nitrile, furan, thiophene, pyrrole, aniline, and phenol can be satisfactorily correlated qualitatively with the observed positions and rates of substitution. For naphthalene and the halogen benzenes this calculation does not lead to results... 

Free carboxylic acids such as benzoic acid, phenylacetic acid, or 4-hydroxyben-zoic acid 297 are converted on heating with HMDS 2 or OMCTS 52, via their N,0-bis(silylated) amides such as 22a, into nitriles such as 298 [99, 100] (Scheme 4.38). 

The side products of the reaction between benzoylnitromethane 279 and dipolarophiles (norbornene, styrene, and phenylacetylene) in the presence of l,4-diazabicyclo[2.2.2]octane (DABCO) were identified as furazan derivatives (Scheme 72). The evidence reported indicates that benzoylnitromethane gives the dibenzoylfuroxan as a key intermediate, which is the dimerization product of the nitrile oxide. The furoxan then undergoes addition to the dipolarophile, hydrolysis, and ring rearrangement to the final products (furazans and benzoic acid) <2006EJ03016>. 

There are a few data in the literature to suggest that the hydrolysis of aliphatic nitriles occurs in mammals, but only as a minor or even undetectable pathway in competition with oxidative denitrilation. For example, benzyl cyanide (11.80, Fig. 11.12) undergoes cytochrome P450 catalyzed hydroxy-lation to mandelonitrile (11.81), from which cyanide and benzaldehyde are produced, the latter being oxidized to benzoic acid (11.83) [118]. However, a careful metabolic study of mandelonitrile has shown that, in the rat, this pathway accounts for ca. 90% and not 100% of the dose [122], Only ca. 10% of orally administered benzyl cyanide was converted to mandelic acid (11.82, Fig. 11.12) by hydrolysis of the CN group. 

The cyclocondensation of l,3-amino alcohols with carboxylic acid derivatives is a method often applied for the synthesis of 5,6-dihydro-4/7-l,3-oxazines <1996CHEC-II(6)301 >. Ebsorb-4, a weakly acidic zeolite-type adsorbent with 4 A pore size, proved an efficient catalyst of the cyclization of benzoic acid and 3-aminopropanol <2002TL3985>. In the presence of zinc chloride as a catalyst, the expulsion of ammonia drove the reactions of 3-aminopropanol with nitriles to completion, affording 2-substituted 5,6-dihydro-47f-l,3-oxazines in good yields... 

The action of benzoyl chloride on the nitrile-oxide gives the chloro-oxadiazole XXXVII. In this reaction no hydrochloric but benzoic acid is formed (71, 78). 

Carboxylic acids show most of the standard reactions of benzoic acid. Amides, esters, hydrazides, azides and nitriles can be prepared by standard methods. Thiophenes form stable acid chlorides, furans unstable ones, and A-unsubstituted pyrroles do not form them. 

C-Acylations of C,H-acidic compounds have also been realized on insoluble supports. The few examples that have been reported include the C-acylation of support-bound ester enolates with acyl halides [9], Claisen condensations of polystyrene-bound ketones with benzoic acid esters, the C-acylation of nitriles with acyl nitriles or anhydrides, and the C-acylation of phosphonates with acyl halides (Entries 5-9, Table... 

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