Aromatic amineIn organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses anilines, but also many more complex aromatic rings and many amine substituents beyond NH2. Such compounds occur widely. Aromatic amines are widely used as precursor to pesticides, pharmaceuticals, and dyes.
AnilineNames Preferred IUPAC nameAnilineSystematic IUPAC nameBenzenamineOther names PhenylamineAminobenzeneBenzamineIdentifiers CAS Number62-53-3142-04-1 (HCl)3D model (JSmol)Interactive imageInteractive imageAbbreviations PhNH2H2NPh Beilstein Reference605631 ChEBICHEBI:17296ChEMBLChEMBL538ChemSpider5889DrugBankDB06728ECHA InfoCard100.000.491EC Number200-539-3Gmelin Reference2796 KEGGC00292PubChemCID61158870 (HCl)RTECS numberBW6650000UNIISIR7XX2F1K576R1193YL (HCl)UN number1547 CompTox Dashboard(EPA)DTXSID8020090InChIInChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2Key: PAYRUJLWNCNPSJ-UHFFFAOYSA-NInChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2Key: PAYRUJLWNCNPSJ-UHFFFAOYAPSMILESNc1ccccc1c1ccc(cc1)NProperties Chemical formulaC6H7NMolar mass93.129 g·mol Appearance Colorless liquid Density1.0297 g/mL Melting point−6.30 °C (20.66 °F; 266.85 K) Boiling point184.13 °C (363.43 °F; 457.28 K) Critical point (T, P) 698.8 K (425.7 °C), 4890 kPa Solubility in water3.6 g/(100 mL) at 20 °C Vapor pressure0.6 mmHg (20 °C) Acidity (pKa) 4.63 (conjugate acid; H2O)Magnetic susceptibility (χ)−62.95·10 cm/mol Refractive index (nD)1.58364 Viscosity3.71 cP (3.71 mPa·s at 25 °C) Thermochemistry Heat capacity(C)193.7 J/(mol K) Std molarentropy(S298)191 J/(mol K) Std enthalpy offormation(ΔfH298)31 kJ/mol Std enthalpy ofcombustion(ΔcH298)–3393 kJ/mol Enthalpy of fusion(ΔfHfus)10.54 kJ/mol Enthalpy of vaporization(ΔfHvap)55.83 kJ/mol at 25 °C Hazards Occupational safety and health (OHS/OSH): Main hazardspotential occupational carcinogen GHS labelling: PictogramsSignal wordDangerHazard statementsH301, H311, H317, H318, H331, H341, H351, H372, H400Precautionary statementsP201, P202, P260, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P314, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, P501NFPA 704 (fire diamond) 320Flash point70 °C (158 °F; 343 K) Autoignitiontemperature770 °C (1,420 °F; 1,040 K) Explosive limits1.3–11% Lethal dose or concentration (LD, LC): LDLo (lowest published)195 mg/kg (dog, oral)250 mg/kg (rat, oral)464 mg/kg (mouse, oral)440 mg/kg (rat, oral)400 mg/kg (guinea pig, oral) LC50 (median concentration)175 ppm (mouse, 7 h) LCLo (lowest published)250 ppm (rat, 4 h)180 ppm (cat, 8 h) NIOSH (US health exposure limits): PEL (Permissible)TWA 5 ppm (19 mg/m) [skin] REL (Recommended)Ca [potential occupational carcinogen] IDLH (Immediate danger)100 ppm Related compounds Related aromatic amines1-Naphthylamine2-NaphthylamineRelated compoundsPhenylhydrazineNitrosobenzeneNitrobenzeneSupplementary data page Aniline (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Nverify ( ?)Alkyl groupIn organic chemistry, an alkyl group is an alkane missing one hydrogen atom. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of −CnH2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula −CnH2n−1. Typically an alkyl is a part of a larger molecule.
AmmoniaNames IUPAC nameAmmoniaSystematic IUPAC nameAzaneOther names Hydrogen nitrideR-717R717 (refrigerant)AmidogenHydrogen amineNitrogen hydrideIdentifiers CAS Number7664-41-73D model (JSmol)Interactive imageBeilstein Reference3587154 ChEBICHEBI:16134ChEMBLChEMBL1160819ChemSpider217ECHA InfoCard100.028.760EC Number231-635-3Gmelin Reference79 KEGGD02916MeSHAmmoniaPubChemCID222RTECS numberBO0875000UNII5138Q19F1XUN number1005 CompTox Dashboard(EPA)DTXSID0023872InChIInChI=1S/H3N/h1H3Key: QGZKDVFQNNGYKY-UHFFFAOYSA-NInChI=1/H3N/h1H3Key: QGZKDVFQNNGYKY-UHFFFAOYAFSMILESNProperties Chemical formulaNH3Molar mass17.031 g·mol Appearance Colourless gas OdorStrong pungent odour Density0.86 kg/m (1.013 bar at boiling point)0.769 kg/m (STP)0.73 kg/m (1.013 bar at 15 °C)0.6819 g/cm at −33.3 °C (liquid) See also Ammonia (data page)0.817 g/cm at −80 °C (transparent solid)Melting point−77.73 °C (−107.91 °F; 195.42 K) (Triple point at 6.060 kPa, 195.4 K) Boiling point−33.34 °C (−28.01 °F; 239.81 K) Critical point (T, P) 132.4 °C (405.5 K), 111.3 atm (11,280 kPa) Solubility in water530 g/L (20 °C)320 g/L (25 °C)Solubilitysoluble in chloroform, ether, ethanol, methanolVapor pressure857.3 kPa Acidity (pKa) 32.5 (−33 °C), 9.24 (of ammonium) Basicity (pKb) 4.75 Conjugate acidAmmoniumConjugate baseAmideMagnetic susceptibility (χ)−18.0×10 cm/molRefractive index (nD)1.3327 Viscosity10.07 µPa·s (25 °C)0.276 mPa·s (−40 °C)Structure Point groupC3vMolecular shapeTrigonal pyramidDipole moment1.42 DThermochemistry Std molarentropy(S298)193 J/(mol·K) Std enthalpy offormation(ΔfH298)−46 kJ/mol Hazards GHS labelling: PictogramsSignal wordDangerHazard statementsH314, H331, H410Precautionary statementsP260, P273, P280, P303+P361+P353, P304+P340+P311, P305+P351+P338+P310NFPA 704 (fire diamond) 310CORAutoignitiontemperature651 °C (1,204 °F; 924 K) Explosive limits15.0–33.6% Lethal dose or concentration (LD, LC): LD50 (median dose)350 mg/kg (rat, oral) LC50 (median concentration)40,300 ppm (rat, 10 min)28,595 ppm (rat, 20 min)20,300 ppm (rat, 40 min)11,590 ppm (rat, 1 hr)7338 ppm (rat, 1 hr)4837 ppm (mouse, 1 hr)9859 ppm (rabbit, 1 hr)9859 ppm (cat, 1 hr)2000 ppm (rat, 4 hr)4230 ppm (mouse, 1 hr)LCLo (lowest published)5000 ppm (mammal, 5 min)5000 ppm (human, 5 min)NIOSH (US health exposure limits): PEL (Permissible)50 ppm (25 ppm ACGIH-TLV; 35 ppm STEL) REL (Recommended)TWA 25 ppm (18 mg/m) ST 35 ppm (27 mg/m) IDLH (Immediate danger)300 ppm Safety data sheet (SDS) ICSC 0414 (anhydrous) Related compounds Related nitrogen hydridesHydrazineHydrazoic acidRelated compoundsAmmonium hydroxidePhosphineArsineStibineBismuthineSupplementary data page Ammonia (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Yverify ( ?)
Organic compoundOrganic compounds are a subclass of chemical compounds of carbon. Little consensus exists among chemists on the exact definition of organic compound; the only universally accepted definition is the quasi-tautological "organic compounds are the subject matter of organic chemistry". Generally, any large chemical compound containing a carbon–hydrogen or carbon–carbon bond is accepted as an organic compound.
Aryl groupIn organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as a placeholder for the aryl group in chemical structure diagrams, analogous to “R” used for any organic substituent. “Ar” is not to be confused with the elemental symbol for argon.
Carbon–nitrogen bondA carbon–nitrogen bond is a covalent bond between carbon and nitrogen and is one of the most abundant bonds in organic chemistry and biochemistry. Nitrogen has five valence electrons and in simple amines it is trivalent, with the two remaining electrons forming a lone pair. Through that pair, nitrogen can form an additional bond to hydrogen making it tetravalent and with a positive charge in ammonium salts.
Heterocyclic compoundA heterocyclic compound or ring structure is a hydrocarbon-based cyclic compound that contains at least one heteroatom as member(s) of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes.
Electron pairIn chemistry, an electron pair or Lewis pair consists of two electrons that occupy the same atomic or molecular orbital but have opposite spins. Gilbert N. Lewis introduced the concepts of both the electron pair and the covalent bond in a landmark paper he published in 1916. Because electrons are fermions, the Pauli exclusion principle forbids these particles from having all the same quantum numbers.
ChemistryScientific study of matter's behavior and propertiesImages relating to the six main branches of chemistry, clockwise from the upper left : a BeF₂ glass network (inorganic chemistry), a caffeine molecule (organic chemistry), a reaction coordinate diagram (physical chemistry), a proton NMR spectrum (analytical chemistry), the RGS4 protein (biochemistry), and a glowstick using chemiluminescence (applied chemistry).Chemistry is the scientific study of the properties and behavior of matter.
Hydrogen atomA hydrogen atom is an atom of the chemical elementhydrogen. The electrically neutral hydrogen atom contains a single positively charged proton in the nucleus, and a single negatively charged electron bound to the nucleus by the Coulomb force. Atomic hydrogen constitutes about 74% of the baryonic mass of the universe. In everyday life on Earth, isolated hydrogen atoms (called "atomic hydrogen") are extremely rare.
BenzeneBenzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. As it contains only carbon and hydrogen atoms, benzene is a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals.
AnilineNames Preferred IUPAC nameAnilineSystematic IUPAC nameBenzenamineOther names PhenylamineAminobenzeneBenzamineIdentifiers CAS Number62-53-3142-04-1 (HCl)3D model (JSmol)Interactive imageInteractive imageAbbreviations PhNH2H2NPh Beilstein Reference605631 ChEBICHEBI:17296ChEMBLChEMBL538ChemSpider5889DrugBankDB06728ECHA InfoCard100.000.491EC Number200-539-3Gmelin Reference2796 KEGGC00292PubChemCID61158870 (HCl)RTECS numberBW6650000UNIISIR7XX2F1K576R1193YL (HCl)UN number1547 CompTox Dashboard(EPA)DTXSID8020090InChIInChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2Key: PAYRUJLWNCNPSJ-UHFFFAOYSA-NInChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2Key: PAYRUJLWNCNPSJ-UHFFFAOYAPSMILESNc1ccccc1c1ccc(cc1)NProperties Chemical formulaC6H7NMolar mass93.129 g·mol Appearance Colorless liquid Density1.0297 g/mL Melting point−6.30 °C (20.66 °F; 266.85 K) Boiling point184.13 °C (363.43 °F; 457.28 K) Critical point (T, P) 698.8 K (425.7 °C), 4890 kPa Solubility in water3.6 g/(100 mL) at 20 °C Vapor pressure0.6 mmHg (20 °C) Acidity (pKa) 4.63 (conjugate acid; H2O)Magnetic susceptibility (χ)−62.95·10 cm/mol Refractive index (nD)1.58364 Viscosity3.71 cP (3.71 mPa·s at 25 °C) Thermochemistry Heat capacity(C)193.7 J/(mol K) Std molarentropy(S298)191 J/(mol K) Std enthalpy offormation(ΔfH298)31 kJ/mol Std enthalpy ofcombustion(ΔcH298)–3393 kJ/mol Enthalpy of fusion(ΔfHfus)10.54 kJ/mol Enthalpy of vaporization(ΔfHvap)55.83 kJ/mol at 25 °C Hazards Occupational safety and health (OHS/OSH): Main hazardspotential occupational carcinogen GHS labelling: PictogramsSignal wordDangerHazard statementsH301, H311, H317, H318, H331, H341, H351, H372, H400Precautionary statementsP201, P202, P260, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P314, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, P501NFPA 704 (fire diamond) 320Flash point70 °C (158 °F; 343 K) Autoignitiontemperature770 °C (1,420 °F; 1,040 K) Explosive limits1.3–11% Lethal dose or concentration (LD, LC): LDLo (lowest published)195 mg/kg (dog, oral)250 mg/kg (rat, oral)464 mg/kg (mouse, oral)440 mg/kg (rat, oral)400 mg/kg (guinea pig, oral) LC50 (median concentration)175 ppm (mouse, 7 h) LCLo (lowest published)250 ppm (rat, 4 h)180 ppm (cat, 8 h) NIOSH (US health exposure limits): PEL (Permissible)TWA 5 ppm (19 mg/m) [skin] REL (Recommended)Ca [potential occupational carcinogen] IDLH (Immediate danger)100 ppm Related compounds Related aromatic amines1-Naphthylamine2-NaphthylamineRelated compoundsPhenylhydrazineNitrosobenzeneNitrobenzeneSupplementary data page Aniline (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Nverify ( ?)Alkyl groupIn organic chemistry, an alkyl group is an alkane missing one hydrogen atom. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of −CnH2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula −CnH2n−1. Typically an alkyl is a part of a larger molecule.AmmoniaNames IUPAC nameAmmoniaSystematic IUPAC nameAzaneOther names Hydrogen nitrideR-717R717 (refrigerant)AmidogenHydrogen amineNitrogen hydrideIdentifiers CAS Number7664-41-73D model (JSmol)Interactive imageBeilstein Reference3587154 ChEBICHEBI:16134ChEMBLChEMBL1160819ChemSpider217ECHA InfoCard100.028.760EC Number231-635-3Gmelin Reference79 KEGGD02916MeSHAmmoniaPubChemCID222RTECS numberBO0875000UNII5138Q19F1XUN number1005 CompTox Dashboard(EPA)DTXSID0023872InChIInChI=1S/H3N/h1H3Key: QGZKDVFQNNGYKY-UHFFFAOYSA-NInChI=1/H3N/h1H3Key: QGZKDVFQNNGYKY-UHFFFAOYAFSMILESNProperties Chemical formulaNH3Molar mass17.031 g·mol Appearance Colourless gas OdorStrong pungent odour Density0.86 kg/m (1.013 bar at boiling point)0.769 kg/m (STP)0.73 kg/m (1.013 bar at 15 °C)0.6819 g/cm at −33.3 °C (liquid) See also Ammonia (data page)0.817 g/cm at −80 °C (transparent solid)Melting point−77.73 °C (−107.91 °F; 195.42 K) (Triple point at 6.060 kPa, 195.4 K) Boiling point−33.34 °C (−28.01 °F; 239.81 K) Critical point (T, P) 132.4 °C (405.5 K), 111.3 atm (11,280 kPa) Solubility in water530 g/L (20 °C)320 g/L (25 °C)Solubilitysoluble in chloroform, ether, ethanol, methanolVapor pressure857.3 kPa Acidity (pKa) 32.5 (−33 °C), 9.24 (of ammonium) Basicity (pKb) 4.75 Conjugate acidAmmoniumConjugate baseAmideMagnetic susceptibility (χ)−18.0×10 cm/molRefractive index (nD)1.3327 Viscosity10.07 µPa·s (25 °C)0.276 mPa·s (−40 °C)Structure Point groupC3vMolecular shapeTrigonal pyramidDipole moment1.42 DThermochemistry Std molarentropy(S298)193 J/(mol·K) Std enthalpy offormation(ΔfH298)−46 kJ/mol Hazards GHS labelling: PictogramsSignal wordDangerHazard statementsH314, H331, H410Precautionary statementsP260, P273, P280, P303+P361+P353, P304+P340+P311, P305+P351+P338+P310NFPA 704 (fire diamond) 310CORAutoignitiontemperature651 °C (1,204 °F; 924 K) Explosive limits15.0–33.6% Lethal dose or concentration (LD, LC): LD50 (median dose)350 mg/kg (rat, oral) LC50 (median concentration)40,300 ppm (rat, 10 min)28,595 ppm (rat, 20 min)20,300 ppm (rat, 40 min)11,590 ppm (rat, 1 hr)7338 ppm (rat, 1 hr)4837 ppm (mouse, 1 hr)9859 ppm (rabbit, 1 hr)9859 ppm (cat, 1 hr)2000 ppm (rat, 4 hr)4230 ppm (mouse, 1 hr)LCLo (lowest published)5000 ppm (mammal, 5 min)5000 ppm (human, 5 min)NIOSH (US health exposure limits): PEL (Permissible)50 ppm (25 ppm ACGIH-TLV; 35 ppm STEL) REL (Recommended)TWA 25 ppm (18 mg/m) ST 35 ppm (27 mg/m) IDLH (Immediate danger)300 ppm Safety data sheet (SDS) ICSC 0414 (anhydrous) Related compounds Related nitrogen hydridesHydrazineHydrazoic acidRelated compoundsAmmonium hydroxidePhosphineArsineStibineBismuthineSupplementary data page Ammonia (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Yverify ( ?)Organic compoundOrganic compounds are a subclass of chemical compounds of carbon. Little consensus exists among chemists on the exact definition of organic compound; the only universally accepted definition is the quasi-tautological "organic compounds are the subject matter of organic chemistry". Generally, any large chemical compound containing a carbon–hydrogen or carbon–carbon bond is accepted as an organic compound.Aryl groupIn organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as a placeholder for the aryl group in chemical structure diagrams, analogous to “R” used for any organic substituent. “Ar” is not to be confused with the elemental symbol for argon.Carbon–nitrogen bondA carbon–nitrogen bond is a covalent bond between carbon and nitrogen and is one of the most abundant bonds in organic chemistry and biochemistry. Nitrogen has five valence electrons and in simple amines it is trivalent, with the two remaining electrons forming a lone pair. Through that pair, nitrogen can form an additional bond to hydrogen making it tetravalent and with a positive charge in ammonium salts.Heterocyclic compoundA heterocyclic compound or ring structure is a hydrocarbon-based cyclic compound that contains at least one heteroatom as member(s) of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes.Electron pairIn chemistry, an electron pair or Lewis pair consists of two electrons that occupy the same atomic or molecular orbital but have opposite spins. Gilbert N. Lewis introduced the concepts of both the electron pair and the covalent bond in a landmark paper he published in 1916. Because electrons are fermions, the Pauli exclusion principle forbids these particles from having all the same quantum numbers.ChemistryScientific study of matter's behavior and propertiesImages relating to the six main branches of chemistry, clockwise from the upper left : a BeF₂ glass network (inorganic chemistry), a caffeine molecule (organic chemistry), a reaction coordinate diagram (physical chemistry), a proton NMR spectrum (analytical chemistry), the RGS4 protein (biochemistry), and a glowstick using chemiluminescence (applied chemistry).Chemistry is the scientific study of the properties and behavior of matter.Hydrogen atomA hydrogen atom is an atom of the chemical elementhydrogen. The electrically neutral hydrogen atom contains a single positively charged proton in the nucleus, and a single negatively charged electron bound to the nucleus by the Coulomb force. Atomic hydrogen constitutes about 74% of the baryonic mass of the universe. In everyday life on Earth, isolated hydrogen atoms (called "atomic hydrogen") are extremely rare.BenzeneBenzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. As it contains only carbon and hydrogen atoms, benzene is a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals.*As an Amazon Associate I earn from qualifying purchases.