Benzidine

Details

• Internal ID: 167a7d8e-d1e3-4f99-8192-d3b306b8d979
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Biphenyls and derivatives > Benzidines
• IUPAC Name: 4-(4-aminophenyl)aniline
• SMILES (Canonical): C1=CC(=CC=C1C2=CC=C(C=C2)N)N
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC=C(C=C2)N)N
• InChI: InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
• InChI Key: HFACYLZERDEVSX-UHFFFAOYSA-N
• Popularity: 7,378 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂N₂
• Molecular Weight: 184.24 g/mol
• Exact Mass: 184.100048391 g/mol
• Topological Polar Surface Area (TPSA): 52.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 92-87-5
• 4,4'-Diaminobiphenyl
• p-Diaminodiphenyl
• [1,1'-Biphenyl]-4,4'-diamine
• 4-(4-aminophenyl)aniline
• 4,4'-Bianiline
• 4,4'-Biphenyldiamine
• 4,4'-Diaminodiphenyl
• biphenyl-4,4'-diamine
• 4,4'-Biphenylenediamine
• 4,4'-Diphenylenediamine
• p,p'-Diaminobiphenyl
• p,p-Bianiline
• Fast Corinth Base B
• p,p'-Dianiline
• Benzidin
• Benzidina
• Benzydyna
• p,p'-Bianiline
• C.I. Azoic Diazo Component 112
• (1,1'-Biphenyl)-4,4'-diamine
• Benzioine
• RCRA waste number U021
• 4,4'-Diamino-1,1'-biphenyl
• 1,1'-Biphenyl-4,4'-Diamine
• Benzidine base
• p-Benzidine
• Benzidin [Czech]
• Benzydyna [Polish]
• NCI-C03361
• Benzidina [Italian]
• Biphenyl, 4,4'-diamino-
• CCRIS 71
• benzidine-d8
• NSC 146476
• CI Azoic diazo component 112
• HSDB 948
• C.I. 37225
• EINECS 202-199-1
• MFCD00039765
• UN1885
• Biphenyl,4,4'-diamino-
• RCRA waste no. U021
• BRN 0742770
• CI 37225
• biphenyl -4,4'-ylenediamine
• UNII-2X02101HVF
• AI3-00140
• DTXSID2020137
• CHEBI:80495
• 2X02101HVF
• 4,4'-Benzidine
• NSC-146476
• 4-13-00-00364 (Beilstein Handbook Reference)
• DTXCID80137
• CAS-92-87-5
• Bencidina
• Bensidine
• Benzidene
• Benzidine, 95%
• p,p'-diaminodiphenyl
• [1,4'-diamine
• Biphenyl,4'-diamino-
• BZI (CHRIS Code)
• 4.4'- diaminobiphenyl
• BENZIDINE [MI]
• BENZIDINE [HSDB]
• BENZIDINE [IARC]
• Acetoacet para Phenetidine
• WLN: ZR DR DZ
• 4, 4'-Biphenylenediamine
• Oprea1_312205
• SCHEMBL29021
• YSWG265
• MLS002303016
• Benzidine, analytical standard
• BIDD:GT0832
• CHEMBL15901
• IFLab1_004231
• BIPHENYL,4,4'-DIAMINO
• Benzidine [UN1885] [Poison]
• Benzidine, >=98.0% (N)
• Benzidine; See 1910.1010
• HMS3091M16
• [1,1'-bifenil]-4,4'-diamina
• Benzidine [UN1885] [Poison]
• [4-(4-aminophenyl)-phenyl]-amine
• Tox21_202359
• Tox21_300405
• BBL013163
• NA1885
• NSC146476
• STK317796
• AKOS000118878
• CCG-202856
• LS-1939
• UN 1885
• {[1,} 1'-Biphenyl]-4,4'-diamine
• IDI1_009986
• NCGC00091340-01
• NCGC00091340-02
• NCGC00091340-03
• NCGC00254474-01
• NCGC00259908-01
• 4'-Amino[1,1'-biphenyl]-4-ylamine #
• AS-17227
• SMR000033596
• Benzidine, purum p.a., >=98.0% (N)
• Benzidine 2000 microg/mL in Dichloromethane
• Benzidine, ISOPAC(R), >=98.0% (N)
• 4,4'-Benzidine 10 microg/mL in Acetonitrile
• BENZIDINE, DYES METABOLIZED TO [IARC]
• EN300-18328
• 4,4'-Benzidine 100 microg/mL in Acetonitrile
• PHENYLBUTAZONE IMPURITY E [EP IMPURITY]
• A844372
• AC-907/25014310
• Q410066
• SR-01000596939
• [1,1'-biphenyl]-4,4'-diamine (ACD/Name 4.0)
• SR-01000596939-1
• W-204254
• Z57901921
• 4'-Amino[1,1'-biphenyl]-4-ylamine (ACD/Name 4.0)
• F1679-0261
• Benzidine (See Benzidine and Dyes Metabolized to Benzidine)
• Benzidine 2000 microg/mL in Dichloromethane Second Source
• BENZIDINE (SEE ALSO BENZIDINEDIHYDROCHLORIDE 531-85-1)
• benzidine; 1,1'-biphenyl-4,4'-diamine; 4,4'-diaminobiphenyl; biphenyl-4,4'-ylenediamine
• Dyes Metabolized to Benzidine (See Benzidine and Dyes Metabolized to Benzidine)
• 26997-10-4
• InChI=1/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9872	98.72%
Caco-2	+	0.9325	93.25%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Lysosomes	0.4524	45.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9882	98.82%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7021	70.21%
P-glycoprotein inhibitior	-	0.9434	94.34%
P-glycoprotein substrate	-	0.9848	98.48%
CYP3A4 substrate	-	0.8748	87.48%
CYP2C9 substrate	-	0.7897	78.97%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.7221	72.21%
CYP2C9 inhibition	+	0.8428	84.28%
CYP2C19 inhibition	+	0.8028	80.28%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	+	0.7308	73.08%
CYP2C8 inhibition	-	0.9536	95.36%
CYP inhibitory promiscuity	+	0.8486	84.86%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.6500	65.00%
Carcinogenicity (trinary)	Danger	0.5280	52.80%
Eye corrosion	+	0.4769	47.69%
Eye irritation	+	0.9960	99.60%
Skin irritation	-	0.8796	87.96%
Skin corrosion	-	0.9583	95.83%
Ames mutagenesis	+	0.6395	63.95%
Human Ether-a-go-go-Related Gene inhibition	-	0.7178	71.78%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	+	0.8875	88.75%
skin sensitisation	+	0.7436	74.36%
Respiratory toxicity	-	0.8778	87.78%
Reproductive toxicity	-	0.9778	97.78%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.5715	57.15%
Acute Oral Toxicity (c)	II	0.7774	77.74%
Estrogen receptor binding	+	0.8918	89.18%
Androgen receptor binding	+	0.8725	87.25%
Thyroid receptor binding	-	0.5121	51.21%
Glucocorticoid receptor binding	-	0.6009	60.09%
Aromatase binding	+	0.8656	86.56%
PPAR gamma	+	0.6692	66.92%
Honey bee toxicity	-	0.9260	92.60%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.9900	99.00%
Fish aquatic toxicity	+	0.9281	92.81%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	7.9 nM; 7.9 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	84.36%	95.48%
CHEMBL1944	P08473	Neprilysin	82.53%	92.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.70%	96.09%
CHEMBL2487	P05067	Beta amyloid A4 protein	81.28%	96.74%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.77%	91.11%
CHEMBL3959	P16083	Quinone reductase 2	80.50%	89.49%

Plants that contains it

• Capsicum annuum
• Typha angustifolia
• Typha orientalis

Cross-Links

• PubChem: 7111
• NPASS: NPC191444
• ChEMBL: CHEMBL15901