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Sigma-Aldrich

1-Phenylbiguanide

98%

Synonym(s):

1-(Diaminomethylidene)-2-phenylguanidine, 1-Carbamimidamido-N-phenylmethanimidamide, N-Phenyl-N′-guanylguanidine, N-Phenylbiguanide, N-Phenylimidodicarbonimidic diamide, N1-Phenylbiguanide, PBG

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About This Item

Linear Formula:
C6H5NHC(=NH)NHC(=NH)NH2
CAS Number:
102-02-3
Molecular Weight:
177.21
EC Number:
202-998-5
MDL number:
MFCD00179077
UNSPSC Code:
12352100
PubChem Substance ID:
24850064
NACRES:
NA.22

Assay

98%

form

solid

mp

135-142 °C (lit.)

solubility

alcohol: freely soluble
water: freely soluble

SMILES string

NC(=N)\N=C(/N)Nc1ccccc1

InChI

1S/C8H11N5/c9-7(10)13-8(11)12-6-4-2-1-3-5-6/h1-5H,(H6,9,10,11,12,13)

InChI key

CUQCMXFWIMOWRP-UHFFFAOYSA-N

Gene Information

mouse ... Htr3a(15561)

General description

1-Phenylbiguanide is a 5-hydroxytryptamine receptor agonist and increases extracellular dopamine release in rat nucleus accumbens in vivo. It serves as building block for synthesis of heterocyclic compounds.

Application

1-Phenylbiguanide was used in one pot synthesis of :
  • 4-chloro-2,5-dihydro-2,5-dioxonaphtho[1,2-d]imidazole-3-carboxylic acid phenyl amide
  • 6-chloro-8-phenylamino-9H-7,9,11-triaza-cyclohepta[a]naphthalene-5,10-dione
  • 4-dimethylamino-5,10-dioxo-2-phenylimino-5,10-dihydro-2H-benzo[g]quinazoline-1-carboxylic acid amide

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reaction of 2, 3-Dichloro-1, 4-Naphthoquinone with 1-Phenylbiguanide and 2-Guanidinebenzimidazole.
El-Shaieb KM.
J. Chin. Chem. Soc., 54(5), 1353-1358 (2007)
Irena Matulková et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 170, 256-266 (2016-07-29)
Three polymorphic modifications of bis(N-phenylbiguanidium(1+)) oxalate are reported, and their characterization is discussed in this paper. The non-centrosymmetric bis(N-phenylbiguanidium(1+)) oxalate (I), which was obtained from an aqueous solution at 313K, belongs to the monoclinic space group Cc (a=6.2560(2)Å, b=18.6920(3)Å, c=18.2980(5)Å
J P Chen et al.
Brain research, 543(2), 354-357 (1991-03-15)
The serotonin-3 (5-HT3) agonist 1-phenylbiguanide (0.1-1.0 mM in perfusate) caused a robust, dose-dependent enhancement of extracellular dopamine content in nucleus accumbens as measured by in vivo microdialysis. This action was antagonized by co-perfusion of the 5-HT3 antagonists zacopride and GR38032F
Florence Netzer et al.
The European journal of neuroscience, 29(10), 2017-2028 (2009-05-21)
Stimulation of the dorsolateral periaqueductal gray matter (dlPAG) and the B3 cell group inhibits the cardiovagal component of the baroreflex in rats. Our aim was to determine whether the defence reaction induces similar modulatory effects on the cardiac response of
Domitila A Huber et al.
The Journal of physiology, 588(Pt 9), 1515-1525 (2010-03-10)
Adult obese Zucker rats (OZRs) have reduced sympathetic responses to evoked changes in arterial pressure (AP) compared to lean Zucker rats (LZRs). This study examined whether attenuated sympathetic baroreflexes in OZRs may be due to altered sensory or central mechanisms.
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