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Sigma-Aldrich

m-Xylylenediamine

99%

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Synonym(s):
1,​3-​Benzenedimethanamine, m-XDA, 1,3-Bis(aminomethyl)benzene, α,α′-Diamino-m-xylene
Linear Formula:
C6H4(CH2NH2)2
CAS Number:
1477-55-0
Molecular Weight:
136.19
Beilstein:
1099911
EC Number:
216-032-5
MDL number:
MFCD00008119
UNSPSC Code:
12352100
PubChem Substance ID:
24902130
NACRES:
NA.22

vapor pressure

15 mmHg ( 145 °C)

Quality Level

100

Assay

99%

refractive index

n20/D 1.571 (lit.)

bp

265 °C/745 mmHg (lit.)

density

1.032 g/mL at 25 °C (lit.)

SMILES string

NCc1cccc(CN)c1

InChI

1S/C8H12N2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6,9-10H2

InChI key

FDLQZKYLHJJBHD-UHFFFAOYSA-N

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Application

m-Xylylenediamine can be used:
  • As a monomer for the synthesis of poly(vinylogous urethane) vitrimers.
  • As a starting material for the synthesis of carbamate-protected multisubstituted bis-guanidine.
  • For the synthesis of polyamides by catalytic dehydrogenation with diols.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1B

Supplementary Hazards

EUH071

WGK

WGK 2

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

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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Direct synthesis of polyamides via catalytic dehydrogenation of diols and diamines.
Zeng H and Guan Z
Journal of the American Chemical Society, 133(5), 1159-1161 (2011)
A versatile one-pot synthesis of 1, 3-substituted guanidines from carbamoyl isothiocyanates.
Linton BR, et al.
The Journal of Organic Chemistry, 65(5), 1566-1568 (2000)
Saverio Cellamare et al.
Bioorganic & medicinal chemistry, 16(9), 4810-4822 (2008-04-15)
A series of N-terminus benzamides of glycine-based symmetric peptides, linked to m-xylylenediamine and 3,4'-oxydianiline spacers, were prepared and tested as inhibitors of beta-amyloid peptide Abeta(1-40) aggregation in vitro. Compounds with good anti-aggregating activity were detected. Polyphenolic amides showed the highest
Yongmei Zhao et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(25), 6621-6629 (2006-06-07)
Polynuclear copper complexes with two or three Cu(BPA) (BPA, bis(2-pyridylmethyl)amine) motifs, [Cu2(mTPXA)Cl4]3 H2O (1), [Cu2(pTPXA)Cl4]3 H2O (2), [Cu3(HPTAB)Cl5]Cl3 H2O (3) (mTPXA = N,N,N',N'-tetra-(2-pyridylmethyl)-m-xylylene diamine; pTPXA = N,N, N',N'-tetra-(2-pyridylmethyl)-p-xylylenediamine; HPTAB = N,N,N',N',N'',N''-hexakis(2-pyridylmethyl)-1,3,5-tris-(aminomethyl)benzene) have been synthesized and characterized. The crystal structures of
K D Rice et al.
Bioorganic & medicinal chemistry letters, 10(20), 2357-2360 (2000-10-31)
The synthesis and optimization of a novel class of reversible and active-site directed dibasic inhibitors of human mast cell tryptase are described. The compounds were shown to be both remarkably potent and selective for tryptase with Ki values for optimized
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