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

Methylenebis(chloroaniline)
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 525618

CAS#: 101-14-4

Description: 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

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525618
Name: Methylenebis(chloroaniline)
CAS#: 101-14-4
Chemical Formula: C13H12Cl2N2
Exact Mass: 266.04
Molecular Weight: 267.153
Elemental Analysis: C, 58.45; H, 4.53; Cl, 26.54; N, 10.49

Price and Availability

Size	Price	Availability
25g	USD 250	2 weeks
100g	USD 450	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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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:	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.
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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1: Takeuchi A, Namera A, Sakui N, Yamamuro K, Kawai T, Sumino K. A method for routine analysis of urinary 4,4'-methylenebis (2-chloroaniline) by gas chromatography-electron capture detection. J Occup Health. 2014;56(5):347-50. Epub 2014 Jul 25. PubMed PMID: 25069897.
2: Yoon S, Tanaka H. Formation of N-nitrosamines by chloramination or ozonation of amines listed in Pollutant Release and Transfer Registers (PRTRs). Chemosphere. 2014 Jan;95:88-95. doi: 10.1016/j.chemosphere.2013.07.090. Epub 2013 Sep 5. PubMed PMID: 24011895.
3: Sheshenev AE, Boltukhina EV, White AJ, Hii KK. Methylene-bridged bis(imidazoline)-derived 2-oxopyrimidinium salts as catalysts for asymmetric Michael reactions. Angew Chem Int Ed Engl. 2013 Jul 1;52(27):6988-91. doi: 10.1002/anie.201300614. Epub 2013 May 27. PubMed PMID: 23712675; PubMed Central PMCID: PMC3749446.
4: Lin IS, Fan PL, Chen HI, Loh CH, Shih TS, Liou SH. Rapid and intermediate N-acetylators are less susceptible to oxidative damage among 4,4'-methylenebis(2-chloroaniline) (MBOCA)-exposed workers. Int J Hyg Environ Health. 2013 Jul;216(4):515-20. doi: 10.1016/j.ijheh.2013.02.001. Epub 2013 Mar 13. PubMed PMID: 23491024.
5: Letašiová S, Medve'ová A, Šovčíková A, Dušinská M, Volkovová K, Mosoiu C, Bartonová A. Bladder cancer, a review of the environmental risk factors. Environ Health. 2012 Jun 28;11 Suppl 1:S11. doi: 10.1186/1476-069X-11-S1-S11. Review. PubMed PMID: 22759493; PubMed Central PMCID: PMC3388449.
6: Buszewski B, Olszowy P, Szultka M, Jeżewska A. New approaches to extraction techniques in determination of 4,4'-methylenebis(2-chloroaniline) in air and water solutions. Talanta. 2012 May 15;93:117-21. doi: 10.1016/j.talanta.2012.01.057. Epub 2012 Feb 2. PubMed PMID: 22483886.
7: National Toxicology Program. 4,4'-Methylenebis(2-chloroaniline). Rep Carcinog. 2011;12:262-4. PubMed PMID: 21860478.
8: Keen C, Coldwell M, McNally K, Baldwin P, McAlinden J, Cocker J. A follow up study of occupational exposure to 4,4'-methylene-bis(2-chloroaniline) (MbOCA) and isocyanates in polyurethane manufacture in the UK. Toxicol Lett. 2012 Aug 13;213(1):3-8. doi: 10.1016/j.toxlet.2011.04.003. Epub 2011 Apr 8. PubMed PMID: 21501672.
9: Jeżewska A, Buszewski B. A new method for the determination of 2,2'-dichloro-4,4'-methylenedianiline in workplace air samples by HPLC-DAD. Toxicol Mech Methods. 2011 Sep;21(7):554-60. doi: 10.3109/15376516.2011.571726. Epub 2011 Apr 8. PubMed PMID: 21473712.
10: Dost A, Straughan JK, Sorahan T. Cancer incidence and exposure to 4,4'-methylene-bis-ortho-chloroaniline (MbOCA). Occup Med (Lond). 2009 Sep;59(6):402-5. doi: 10.1093/occmed/kqp093. Epub 2009 Jun 29. PubMed PMID: 19564173.
11: Cocker J, Cain JR, Baldwin P, McNally K, Jones K. A survey of occupational exposure to 4,4'-methylene-bis (2-chloroaniline) (MbOCA) in the UK. Ann Occup Hyg. 2009 Jul;53(5):499-507. doi: 10.1093/annhyg/mep026. Epub 2009 May 15. PubMed PMID: 19447850.
12: Shih WC, Chen MF, Huang CC, Uang SN, Shih TS, Liou SH, Wu KY. Simultaneous analysis of urinary 4,4'-methylenebis(2-chloroaniline) and N-acetyl 4,4'-methylenebis(2-chloroaniline) using solid-phase extraction and liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(24):4073-8. PubMed PMID: 18008389.
13: Chen HI, Liou SH, Ho SF, Wu KY, Sun CW, Chen MF, Cheng LC, Shih TS, Loh CH. Oxidative DNA damage estimated by plasma 8-hydroxydeoxyguanosine (8-OHdG): influence of 4, 4'-methylenebis (2-chloroaniline) exposure and smoking. J Occup Health. 2007 Sep;49(5):389-98. PubMed PMID: 17951971.
14: Cocker J, Jones K, Morton J, Mason HJ. Biomonitoring at the UK Health and Safety Laboratory. Int J Hyg Environ Health. 2007 May;210(3-4):383-6. Epub 2007 Feb 23. PubMed PMID: 17321210.
15: Walraven JM, Doll MA, Hein DW. Identification and characterization of functional rat arylamine N-acetyltransferase 3: comparisons with rat arylamine N-acetyltransferases 1 and 2. J Pharmacol Exp Ther. 2006 Oct;319(1):369-75. Epub 2006 Jul 7. PubMed PMID: 16829624.
16: Robbiano L, Baroni D, Novello L, Brambilla G. Correlation between induction of DNA fragmentation in lung cells from rats and humans and carcinogenic activity. Mutat Res. 2006 Jun 16;605(1-2):94-102. Epub 2006 May 11. PubMed PMID: 16690349.
17: Fairfax R, Porter E. Evaluation of worker exposure to TDI, MOCA, and methylene chloride. J Occup Environ Hyg. 2006 Jun;3(6):D50-3. PubMed PMID: 16621764.
18: Murray EB, Edwards JW. Differential induction of micronuclei in peripheral lymphocytes and exfoliated urothelial cells of workers exposed to 4,4'-methylenebis-(2-chloroaniline) (MOCA) and bitumen fumes. Rev Environ Health. 2005 Jul-Sep;20(3):163-76. PubMed PMID: 16335575.
19: Chen HI, Liou SH, Loh CH, Uang SN, Yu YC, Shih TS. 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.

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Methylenebis(chloroaniline) featured