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{{chembox
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 464201153
| verifiedrevid = 464201153
| Name = Phenylhydrazine
| Name = Phenylhydrazine
| Reference =<ref name="Merck">''Merck Index'', 11th Edition, '''7264'''.</ref><ref>[http://www.cheric.org/kdb/kdb/hcprop/showprop.php?cmpid=1470 Pure component properties]</ref>
| Reference =<ref name="Merck">''Merck Index'', 11th Edition, '''7264'''.</ref><ref>[https://web.archive.org/web/20020802222945/http://www.cheric.org/kdb/kdb/hcprop/showprop.php Pure component properties]</ref>
| ImageFile = phenylhydrazine.png
| ImageFile = phenylhydrazine.png
| ImageSize = 100px
| ImageSize = 100px
| ImageName = Phenylhydrazine
| ImageName = Phenylhydrazine
| ImageFileL1 = Phenylhydrazine-3D-balls.png
| ImageFileL1 = Phenylhydrazine-from-xtal-3D-bs-17.png
| ImageNameL1 = Ball-and-stick model of phenylhydrazine
| ImageNameL1 = Ball-and-stick model of phenylhydrazine
| ImageFileR1 = Phenylhydrazine-3D-vdW.png
| ImageFileR1 = Phenylhydrazine-from-xtal-3D-sf.png
| ImageNameR1 = Space-filling model of phenylhydrazine
| ImageNameR1 = Space-filling model of phenylhydrazine
| IUPACName = Phenylhydrazine
| PIN = Phenylhydrazine
| OtherNames = Hydrazinobenzene
| OtherNames = Hydrazinobenzene
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
Line 29: Line 30:
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 100-63-0
| CASNo = 100-63-0

| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 064F424C9K

| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27924
| ChEBI = 27924
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}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>8</sub>N<sub>2</sub>
| Formula = {{chem2|C6H5NHNH2}}
| C=6|H=8|N=2
| MolarMass = 108.14 g/mol
| Density = 1.0978 g/cm<sup>3</sup>
| Density = 1.0978 g/cm<sup>3</sup>
| MeltingPtC = 19.5
| MeltingPtC = 19.5
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| Appearance = Colorless to pale-yellow liquid or solid<ref name=PGCH/>
| Appearance = Colorless to pale-yellow liquid or solid<ref name=PGCH/>
| Odor = faint, aromatic<ref name=PGCH/>
| Odor = faint, aromatic<ref name=PGCH/>
| VaporPressure = 0.04 mmHg (25°C)<Ref name=PGCH/>
| VaporPressure = 0.04 mmHg (25°C)<ref name=PGCH/>
| MagSus = -67.82·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
}}
|Section7={{Chembox Hazards
|Section7={{Chembox Hazards
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| NFPA-R = 3
| NFPA-R = 3
| IDLH = Ca [15 ppm]<ref name=PGCH>{{PGCH|0499}}</ref>
| IDLH = Ca [15 ppm]<ref name=PGCH>{{PGCH|0499}}</ref>
| LD50 = 188 mg/kg (rat, oral)<br/>175 mg/kg (mouse, oral)<br/>80 mg/kg (rabbit, oral)<br/>80 mg/kg (guinea pig, oral)<br/>200-250 mg/kg (dog, oral)<ref>{{IDLH|100630|Phenylhydrazine}}</ref>
| LD50 = {{ubl|188 mg/kg (rat, oral)|175 mg/kg (mouse, oral)|80 mg/kg (rabbit, oral)|80 mg/kg (guinea pig, oral)|200-250 mg/kg (dog, oral)}}<ref>{{IDLH|100630|Phenylhydrazine}}</ref>
| REL = Ca C 0.14 ppm (0.6 mg/m<sup>3</sup>) [2-hr] [skin]<ref name=PGCH/>
| REL = Ca C 0.14 ppm (0.6 mg/m<sup>3</sup>) [2-hr] [skin]<ref name=PGCH/>
| PEL = TWA 5 ppm (22 mg/m<sup>3</sup>) [skin]<ref name=PGCH/>
| PEL = TWA 5 ppm (22 mg/m<sup>3</sup>) [skin]<ref name=PGCH/>
| FlashPtF = 190
| FlashPtF = 190
| FlashPt_notes = <ref name=PGCH/>
| FlashPt_ref = <ref name=PGCH/>
}}
}}
}}
}}


'''Phenylhydrazine''' is the [[chemical compound]] with the formula {{chem2|C6H5NHNH2}}. It is often abbreviated as '''{{chem2|PhNHNH2}}'''. It is also found in [[Edible mushroom|edible mushrooms]].<ref>{{cite book | url=https://orbit.dtu.dk/en/publications/phenylhydrazines-in-the-cultivated-mushroom-agaricus-bisporus | isbn=9789289301978 | title=Phenylhydrazines in the cultivated mushroom (Agaricus bisporus) | year=2004 | last1=Andersson | first1=H. C. | last2=Gry | first2=Jørn | publisher=Nordic Council of Ministers }}</ref>
'''Phenylhydrazine''' is the [[chemical compound]] with the formula C<sub>6</sub>H<sub>5</sub>NHNH<sub>2</sub>. Organic chemists abbreviate the compound as PhNHNH<sub>2</sub>.


== Chemical properties ==
== Properties ==
⚫
Phenylhydrazine forms [[Monoclinic crystal system|monoclinic]] prisms that melt to an oil around room temperature which may turn yellow to dark red upon exposure to air.<ref name="Merck"/> Phenylhydrazine is miscible with [[ethanol]], [[diethyl ether]], [[chloroform]] and [[benzene]]. It is sparingly soluble in water.

⚫
Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow to dark red upon exposure to air.<ref name="Merck"/> Phenylhydrazine is miscible with [[ethanol]], [[diethyl ether]], [[chloroform]], and [[benzene]]. It is sparingly soluble in water.


== Preparation ==
== Preparation ==
⚫
Phenylhydrazine is prepared by reacting [[aniline]] with [[sodium nitrite]] in the presence of [[hydrogen chloride]] to form the [[diazonium salt]], which is subsequently reduced using [[sodium sulfite]] in the presence of [[sodium hydroxide]] to form the final product.<ref name="merck">''Merck Index of Chemicals and Drugs, 9th ed.'' monograph 7098</ref>

⚫
Phenylhydrazine is prepared by reducing [[aniline]] with [[sodium nitrite]] in the presence of [[hydrogen chloride]] to form the [[diazonium salt]], which is subsequently reduced using [[sodium sulfite]] in the presence of [[sodium hydroxide]] to form the final product.<ref name="merck">''Merck Index of Chemicals and Drugs, 9th ed.'' monograph 7098</ref>


== History ==
== History ==
⚫
Phenylhydrazine was the first [[hydrazine]] derivative characterized, reported by [[Hermann Emil Fischer]] in 1875.<ref>Nobel Committee [https://www.nobelprize.org/nobel_prizes/chemistry/laureates/1902/fischer-bio.html Emil Fischer - Biographical]</ref><ref>Fischer, E. (1875) [http://gallica.bnf.fr/ark:/12148/bpt6k90680z/f589.zoom.langEN "Ueber aromatische Hydrazinverbindungen,"] ''Berichte der deutschen chemischen Gesellschaft'', '''8''': 589-594.</ref> He prepared it by [[organic reduction|reduction]] of a phenyl diazonium salt using [[sulfite]] salts. Fischer used phenylhydrazine to characterize [[sugar]]s via formation of [[hydrazone]]s known as [[osazone]]s with the sugar [[aldehyde]]. He also demonstrated in this first paper many of the key properties recognized for hydrazines.

⚫
Phenylhydrazine was the first [[hydrazine]] derivative characterized, reported by [[Hermann Emil Fischer|Emil Fischer]] in 1875.<ref>Nobel Committee [http://www.nobelprize.org/nobel_prizes/chemistry/laureates/1902/fischer-bio.html Emil Fischer - Biographical]</ref><ref>Fischer, E. (1875) [http://gallica.bnf.fr/ark:/12148/bpt6k90680z/f589.zoom.langEN "Ueber aromatische Hydrazinverbindungen,"] ''Berichte der deutschen chemischen Gesellschaft'', '''8''': 589-594.</ref> He prepared it by [[organic reduction|reduction]] of a phenyl [[diazonium]] salt using [[sulfite]] salts. Fischer used phenylhydrazine to characterize [[sugar]]s via formation of [[hydrazone]]s with the sugar [[aldehyde]]. He also demonstrated in this first paper many of the key properties recognized for hydrazines.


== Uses ==
== Uses ==
⚫
Phenylhydrazine is used to prepare [[indole]]s by the [[Fischer indole synthesis]], which are intermediates in the synthesis of various dyes and pharmaceuticals.


⚫
Phenylhydrazine is used to form [[phenylhydrazone]]s of natural mixtures of simple [[sugar]]s in order to render the differing sugars easily separable from each other.<ref>{{cite book|author1=Andrew Streitwieser|author-link=Andrew Streitwieser|author2=Clayton Heathcock|author2-link=Clayton Heathcock|title=Introduction to Organic Chemistry|url=https://archive.org/details/introductiontoor00stre |url-access=registration |publisher=Macmillan|year=1976|isbn=0-02-418010-6}}</ref>
⚫
Phenylhydrazine is used to prepare [[indole]]s via the [[Fischer_indole_synthesis|Fischer Indole Synthesis]], which are intermediates in the synthesis of various dyes and pharmaceuticals.

⚫
Phenylhydrazine is used to form [[phenylhydrazone]]s of natural mixtures of simple [[sugar]]s in order to render the differing sugars easily separable from each other.<ref>{{cite book|author=[[Andrew Streitwieser|Streitweiser, Andrew Jr.]]; [[Clayton Heathcock|Heathcock, Clayton H.]]|title=Introduction to Organic Chemistry|publisher=Macmillan|year=1976|isbn=0-02-418010-6}}</ref>


The compound is also used to induce acute hemolytic anemia in studies examining the hematopoietic system.
This molecule is also used to induce acute [[hemolytic anemia]] in animal models.


== Safety ==
== Safety ==
⚫
Exposure to phenylhydrazine may cause [[contact dermatitis]], [[hemolytic anemia]], and [[liver damage]].<ref name="Merck"/>

⚫
Exposure to phenylhydrazine may cause [[contact dermatitis]], [[hemolytic anemia]], and liver and kidney injury.<ref name="Merck"/>

== See also ==
* [[Fischer indole synthesis]]


== References ==
== References ==
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== External links ==
== External links ==
* {{MeshName|Phenylhydrazines}}
* {{MeshName|Phenylhydrazines}}
* [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7516 PubChem]
* [https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7516 PubChem]
* [http://www.chemicalland21.com/lifescience/agro/PHENYL%20HYDRAZINE.htm Additional chemical properties of phenylhydrazine]
* [http://www.chemicalland21.com/lifescience/agro/PHENYL%20HYDRAZINE.htm Additional chemical properties of phenylhydrazine]
* [http://www.cdc.gov/niosh/npg/npgd0499.html CDC - NIOSH Pocket Guide to Chemical Hazards]
* [https://www.cdc.gov/niosh/npg/npgd0499.html CDC - NIOSH Pocket Guide to Chemical Hazards]


{{Hydrazines}}
{{Hydrazines}}


{{Authority control}}
{{Authority control}}

⚫
[[Category:Aromatic compounds]]
[[Category:Hydrazines]]
[[Category:Hydrazines]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Emil Fischer]]
⚫
[[Category:Phenyl compounds]]

Latest revision as of 19:42, 12 April 2024

Phenylhydrazine[1][2]
Phenylhydrazine
Ball-and-stick model of phenylhydrazine
Ball-and-stick model of phenylhydrazine
Space-filling model of phenylhydrazine
Space-filling model of phenylhydrazine
Names
Preferred IUPAC name
Phenylhydrazine
Other names
Hydrazinobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.612 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2 checkY
    Key: HKOOXMFOFWEVGF-UHFFFAOYSA-N checkY
  • InChI=1/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2
    Key: HKOOXMFOFWEVGF-UHFFFAOYAN
  • NNc1ccccc1
Properties
C6H5NHNH2
Molar mass 108.144 g·mol−1
Appearance Colorless to pale-yellow liquid or solid[3]
Odor faint, aromatic[3]
Density 1.0978 g/cm3
Melting point 19.5 °C (67.1 °F; 292.6 K) (24 °C for hemihydrate)
Boiling point 243.5 °C (470.3 °F; 516.6 K) (decomposition)
Vapor pressure 0.04 mmHg (25°C)[3]
-67.82·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
3
2
3
Flash point 88 °C; 190 °F; 361 K[3]
Lethal dose or concentration (LD, LC):
  • 188 mg/kg (rat, oral)
  • 175 mg/kg (mouse, oral)
  • 80 mg/kg (rabbit, oral)
  • 80 mg/kg (guinea pig, oral)
  • 200-250 mg/kg (dog, oral)
[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 5 ppm (22 mg/m3) [skin][3]
REL (Recommended)
 Ca C 0.14 ppm (0.6 mg/m3) [2-hr] [skin][3]
IDLH (Immediate danger)
 Ca [15 ppm][3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Phenylhydrazine is the chemical compound with the formula C6H5NHNH2. It is often abbreviated as PhNHNH2. It is also found in edible mushrooms.[5]

Properties

[edit]

Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow to dark red upon exposure to air.[1] Phenylhydrazine is miscible with ethanol, diethyl ether, chloroform and benzene. It is sparingly soluble in water.

Preparation

[edit]

Phenylhydrazine is prepared by reacting aniline with sodium nitrite in the presence of hydrogen chloride to form the diazonium salt, which is subsequently reduced using sodium sulfite in the presence of sodium hydroxide to form the final product.[6]

History

[edit]

Phenylhydrazine was the first hydrazine derivative characterized, reported by Hermann Emil Fischer in 1875.[7][8] He prepared it by reduction of a phenyl diazonium salt using sulfite salts. Fischer used phenylhydrazine to characterize sugars via formation of hydrazones known as osazones with the sugar aldehyde. He also demonstrated in this first paper many of the key properties recognized for hydrazines.

Uses

[edit]

Phenylhydrazine is used to prepare indoles by the Fischer indole synthesis, which are intermediates in the synthesis of various dyes and pharmaceuticals.

Phenylhydrazine is used to form phenylhydrazones of natural mixtures of simple sugars in order to render the differing sugars easily separable from each other.[9]

This molecule is also used to induce acute hemolytic anemia in animal models.

Safety

[edit]

Exposure to phenylhydrazine may cause contact dermatitis, hemolytic anemia, and liver damage.[1]

References

[edit]
  1. ^ a b c Merck Index, 11th Edition, 7264.
  2. ^ Pure component properties
  3. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0499". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "Phenylhydrazine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ Andersson, H. C.; Gry, Jørn (2004). Phenylhydrazines in the cultivated mushroom (Agaricus bisporus). Nordic Council of Ministers. ISBN 9789289301978.
  6. ^ Merck Index of Chemicals and Drugs, 9th ed. monograph 7098
  7. ^ Nobel Committee Emil Fischer - Biographical
  8. ^ Fischer, E. (1875) "Ueber aromatische Hydrazinverbindungen," Berichte der deutschen chemischen Gesellschaft, 8: 589-594.
  9. ^ Andrew Streitwieser; Clayton Heathcock (1976). Introduction to Organic Chemistry. Macmillan. ISBN 0-02-418010-6.
[edit]
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