Methylenebis(chloroaniline) | CAS#101-14-4 | Plastic Curing Agent

MedKoo Cat#: 525618 | Name: Methylenebis(chloroaniline)

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aromatic diamine used in the plastics industry as curing agent for epoxy resins and urethane rubbers. It is a curing agent in polyurethane production. It causes bladder, liver, lung, and other neoplasms.

Chemical Structure

Methylenebis(chloroaniline)

CAS#101-14-4

Theoretical Analysis

MedKoo Cat#: 525618

Name: Methylenebis(chloroaniline)

CAS#: 101-14-4

Chemical Formula: C13H12Cl2N2

Exact Mass: 266.0378

Molecular Weight: 267.15

Elemental Analysis: C, 58.45; H, 4.53; Cl, 26.54; N, 10.49

Price and Availability

Size	Price	Availability	Quantity
25g	USD 250.00	2 weeks
100g	USD 450.00	2 weeks

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Synonym

Bisamine; Cuamine; Curalin; Curene; Cyanastat; Methylenebis(chloroaniline)

IUPAC/Chemical Name

4,4'-methylenebis(2-chloroaniline)

InChi Key

IBOFVQJTBBUKMU-UHFFFAOYSA-N

InChi Code

InChI=1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2

SMILES Code

NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl

Appearance

Solid powder

Purity

>90% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Aromatic diamine used in the plastics industry as curing agent for epoxy resins and urethane rubbers.

In vitro activity:

Alterations of the phosphorylation pattern of histones by the carcinogen, 4,4'-methylene-bis(2-chloroaniline) (MOCA) were investigated using rodent spleen cells. Spleen cells were isolated from Sprague-Dawley rats and treated with either 5, 10, 25, or 50 microM MOCA or acetone vehicle controls for 1, 2, 4, or 8 hours. Marked stimulation of histone phosphorylation was observed with the 10 microM MOCA treatment. Reference: J Biochem Toxicol. 1995 Feb;10(1):19-23. https://pubmed.ncbi.nlm.nih.gov/7595928/

In vivo activity:

Male Sprague-Dawley rats were treated with different dosing regimens of MOCA, and DNA was isolated from the liver. Five MOCA adducts were detected in rat liver DNA. Adduct A, which corresponded to N-(deoxyadenosin-8-yl)-4-amino-3-chlorobenzyl alcohol, was the major adduct in rat liver DNA appearing in all treatment groups. Levels of adduct A were higher when MOCA was administered by ip injection versus oral gavage. Reference: Fundam Appl Toxicol. 1996 Mar;30(1):138-44. https://pubmed.ncbi.nlm.nih.gov/8812257/

Preparing Stock Solutions

The following data is based on the product molecular weight 267.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. DeBord DG, Cheever KL, Booth-Jones AD, Swearengin TF, Savage RE Jr. Alterations of histone phosphorylation in rat spleen cells after treatment with the aromatic amine, 4,4'-methylene-bis(2-chloroaniline). J Biochem Toxicol. 1995 Feb;10(1):19-23. PMID: 7595928. 2. Segerbäck D, Kadlubar FF. Characterization of 4,4'-methylenebis(2-chloroaniline)--DNA adducts formed in vivo and in vitro. Carcinogenesis. 1992 Sep;13(9):1587-92. doi: 10.1093/carcin/13.9.1587. PMID: 1394844. 3. Swaminathan S, Frederickson SM, Hatcher JF, Reznikoff CA, Butler MA, Cheever KL, Savage RE Jr. Neoplastic transformation and DNA-binding of 4,4'-methylenebis(2-chloroaniline) in SV40-immortalized human uroepithelial cell lines. Carcinogenesis. 1996 Apr;17(4):857-64. doi: 10.1093/carcin/17.4.857. PMID: 8625501. 4. DeBord DG, Cheever KL, Werren DM, Reid TM, Swearengin TF, Savage RE Jr. Determination of 4,4'-methylene-bis(2-chloroaniline)-DNA adduct formation in rat liver and human uroepithelial cells by the 32P postlabeling assay. Fundam Appl Toxicol. 1996 Mar;30(1):138-44. doi: 10.1006/faat.1996.0050. PMID: 8812257.

In vitro protocol:

In vivo protocol:

1. Swaminathan S, Frederickson SM, Hatcher JF, Reznikoff CA, Butler MA, Cheever KL, Savage RE Jr. Neoplastic transformation and DNA-binding of 4,4'-methylenebis(2-chloroaniline) in SV40-immortalized human uroepithelial cell lines. Carcinogenesis. 1996 Apr;17(4):857-64. doi: 10.1093/carcin/17.4.857. PMID: 8625501. 2. DeBord DG, Cheever KL, Werren DM, Reid TM, Swearengin TF, Savage RE Jr. Determination of 4,4'-methylene-bis(2-chloroaniline)-DNA adduct formation in rat liver and human uroepithelial cells by the 32P postlabeling assay. Fundam Appl Toxicol. 1996 Mar;30(1):138-44. doi: 10.1006/faat.1996.0050. PMID: 8812257.

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Bladder cancer screening and monitoring of 4,4'-methylenebis(2-chloroaniline) exposure among workers in Taiwan. Urology. 2005 Aug;66(2):305-10. PubMed PMID: 16098360. 20: Liu CS, Liou SH, Loh CH, Yu YC, Uang SN, Shih TS, Chen HI. Occupational bladder cancer in a 4,4 -methylenebis(2-chloroaniline) (MBOCA)-exposed worker. Environ Health Perspect. 2005 Jun;113(6):771-4. PubMed PMID: 15929884; PubMed Central PMCID: PMC1257605.