4,4'-methylenedianiline

Synonyms: "4,4'-diaminodiphenylmethane", "methylenedianiline", "Tonox", "Dianilinomethane", "p,p'-methylenedianiline", "dianilinemethane", "bis(4-aminophenyl)methane", "p,p'-diaminodiphenylmethane", "Epicure DDM", "bis(p-aminophenyl)methane", "Epikure DDM", "4-(4-aminobenzyl)aniline", "4,4-methylenedianiline", "Jeffamine AP-20", "4,4'-diphenylmethanediamine", "diaminodiphenylmethane", "Sumicure M", "Ancamine TL".

Source: 4,4'-methylenedianiline is an industrial chemical used mainly for making polyurethane foams and coating materials, glues, fiber, dyes and rubber.

Identifiers:

IUPAC Name: 4-[(4-aminophenyl)methyl]aniline
CAS Number: 101-77-9
PubChem ID: 7577
InChiKey: YBRVSVVVWCFQMG-UHFFFAOYSA-N
Canonical SMILES: C1=CC(=CC=C1CC2=CC=C(C=C2)N)N

Structural Properties:

Molecular Formula: C₁₃H₁₄N₂
Molecular Weight: 198.269

Pharmacophore Features:

Number of bond donors: 2
Number of bond acceptors: 2
Number of atoms different from hydrogen: 15

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3D structure (.sdf)
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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Harada, Y., 1967. The effect of 4, 4'-methylenedianiline on adrenal corticosterone secretion in the rat. The Tohoku journal of experimental medicine, 91(4), pp.315-322. DOI: https://doi.org/10.1620/tjem.91.315. URL: https://www.jstage.jst.go.jp/article/tjem1920/91/4/91_4_315/_article/-char/ja/.
Yamashita, K., 1963. Adrenal-dependent effect of 4, 4'-methylenedianiline on endometrial carbonic anhydrase. American Journal of Physiology-Legacy Content, 205(1), pp.195-197. DOI: https://doi.org/10.1152/ajplegacy.1963.205.1.195. URL: https://www.physiology.org/doi/abs/10.1152/ajplegacy.1963.205.1.195.
Yamashita, K., 1967. Inhibition by methylenedianiline of testicular 17-oxosteroid secretion stimulated by human chorionic gonadotrophin. Journal of Endocrinology, 37(4), pp.429-432. DOI: 10.1677/joe.0.0370429. URL: http://joe.endocrinology-journals.org/content/37/4/429.short.
Yamashita, K., Nakasone, K. and Kawao, K., 1969. Inhibitory effect of methylenedianiline on testicular 17-oxosteroid secretion produced by pregnant mare serum. The Tohoku journal of experimental medicine, 97(2), pp.175-180. DOI: https://doi.org/10.1620/tjem.97.175. URL: https://www.jstage.jst.go.jp/article/tjem1920/97/2/97_2_175/_article/-char/ja/